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

1. 0:00 – 3:45

   Sam’s background

   1. SSSam Schillace0:00

      ... 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, like, gravitate in this direction of, like, let's go do unpleasant things and grind our way through the career 'cause, 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- do it as hard as you can. If you get- 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, the work doesn't necessarily have to be hard.

   2. LRLenny Rachitsky0:35

      (instrumental music) Today my guest is Sam Schillace. Sam has an incredible resume that is very hard to summarize succinctly. I'll give it a shot. Currently, he is corporate vice president and deputy chief technology officer at Microsoft, where he leads efforts in the consumer product space, infrastructure, and AI. Sam is most known for basically inventing Google Docs with his company Writely, which was acquired by Google, and became the foundation for what is now Google Workplace, which currently has over one billion active users a month. After joining Google, Sam ended up responsible for many of Google's consumer applications, including parts of Gmail, Maps, Automotive, Groups, Reader and more. He's also founded six startups, was senior vice president of engineering at Box through their IPO. He's also worked at Intuit, Macromedia. He was even a VC at Google Ventures for a time. As you'd suspect, we had a fairly wide-ranging conversation, but the core focus was around innovation. How to think big, how to come up with original ideas, why optimism is so important and powerful, and also a ton of career advice. Sam is hilarious and not what I imagined a corporate vice president at Microsoft would be like, which gives me even more respect for Microsoft. A big thank you to Brett Burson for making this introduction. With that, I bring you Sam Schillace, after a short word from our sponsors. This time of year is prime for career reflection and setting goals for professional growth. I always like to spend this time reflecting on what I accomplished the previous year, what I hope to accomplish the next year, and whether this is the year I look for a new opportunity. That's where today's sponsor, Teal, comes in. Teal provides you with the tools to run an amazing job search, with an AI-powered resume builder, job tracker, cover letter generator, and Chrome extension that integrates with over 40 job boards. Teal is the all-in-one platform you need to run a more streamlined and efficient job search, and stand out in this competitive market. There's a reason nearly one million people have trusted Teal to run their job search. If you're thinking of making a change in the new year, leverage Teal to grow your career on your own terms. Get started for free at tealhq.com/lenny. That's tealhq.com/lenny. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate your growth. Thousands of fast-growing companies like Gusto, Calm, Quora, and Modern Treasury trust Vanta to help build, scale, manage, and demonstrate their security and compliance programs, and get ready for audits in weeks, not months. By offering the most in-demand security and privacy frameworks such as SOC 2, ISO 27001, GDPR, HIPAA, and many more, Vanta helps companies obtain the reports they need to accelerate growth, build efficient compliance processes, mitigate risks to their businesses, and build trust with external stakeholders. Over 5,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC 2 and these other frameworks. For a limited time, Lenny's Podcast listeners get $1,000 off Vanta. Go to vanta.com/lenny. That's V-A-N-T-A dot com slash Lenny to learn more and to claim your discounts. Get started today.

2. 3:45 – 6:45

   The first Google Docs file

   1. LRLenny Rachitsky3:46

      Sam, thank you so much for being here, and welcome to the podcast.

   2. SSSam Schillace3:51

      Thank you. Happy to be here.

   3. LRLenny Rachitsky3:53

      A really fun fact about you is that apparently you have the very first Google Doc, uh, file, I don't know what you call it, the very first Google Doc document saved somewhere from before even Google Docs was a thing. Does it still work in today's Google Docs, and what is in this- this document?

   4. SSSam Schillace4:08

      Yeah. It does actually still work. It's pretty funny. Actually, if I move my camera for a second, you might, if you're on th- on- on, uh, YouTube, you can see the Writely thing in the background. That's- Vant- Writely was the company that did Google Docs. Um, yeah, and like it still works. And it's kind of funny though, 'cause it's like the document of Theseus, right? Like, it's been... So we started off 2005, we wrote this thing in C#, which is little known. In, you know, our own, it was like pre-cloud, so we like had three file servers that we rented that were Windows machines in a data center in Texas with a sys admin in the Philippines running them. So that's like, it started there, like, and then when we moved to Google, we ported everything to Java, we moved all the data over into Bigtable, and we m- we didn't lose anything, like we never lost anybody's stuff. So it's still there, and like moved across, and then like, so that's one backend migration, and there's another one at Spanner, and then like the front end has- has been rewritten twice as well. So it's like, is it really the same document? I don't know. Like, the front and backend have been written. It's not much, it's just me saying something to Steve about, "Is collaboration working? Are we colliding on each other?" 'Cause 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, 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.

   5. LRLenny Rachitsky5:34

      I love that, uh, this- this, uh, philosophical answer of is it still the same Google Doc, considering all the code has been redone.

   6. SSSam Schillace5:42

      Well, The Computer History Museum wants to curate it. Like, I talked to these guys, and they were like, "We'd 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. I can share you into it, but don't- please don't edit it. Like, you know? (laughs) It's like... I don't, like, how do you curate this? Like... so...

   7. LRLenny Rachitsky5:59

      Yeah.

   8. SSSam Schillace5:59

      That's when he-

   9. LRLenny Rachitsky5:59

      I think it needs to be on the blockchain.

   10. SSSam Schillace6:00

       Yeah, I, yeah. If you made the NFT of it, that would be more- more authentic, I think, than the document almost.... is kind of funny.

   11. LRLenny Rachitsky6:07

       That's amazing. And it's amazing that it still works. That's a testament to, I don't know, you/Google.

   12. SSSam Schillace6:12

       Well, I, I'll tell you a quick Google story. Like, we, when we migrated into Google, we were very sneaky about it, and we, like, 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, the new system up. And three days after that, Sergey was in a meeting with me and he's like, "So when are you guys gonna, like, move over to the, to Google infrastructure?" And, and I got to tell him, like, "Oh, yeah. We did it this weekend. No one noticed." 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

3. 6:45 – 10:11

   Disruptive innovation

   1. SSSam Schillace6:45

      about it.

   2. LRLenny Rachitsky6:46

      Man, I love these sneaky stories. I'm hoping we hear more. There's a bunch of stuff I want to cover. The first is this broad idea of disruptive innovation. I know that you spend a lot of time thinking about this. Google Docs is a great example of this. It feels like Microsoft increasingly is getting really good at this, just the idea of doing something completely new, oftentimes things that people didn't think were possible. So let me just 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've found to help you and other people think more innovatively, more or- originally?

   3. SSSam Schillace7:18

      It's an interesting question. Like, uh, 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, tribe mates for making a chair. Like, you know, it's like an, uh... 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's threat- 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, we... It's very easy for us to tell stories about why something is right or wrong if we, if we're motivated to. And so I think the... I call these "why not" questions. Uh, people ask these "why not" questions a lot. Like, you know, so a new thing pops up, and if you're not ready to receive it for some reason, like you're not kind of already half 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, with, um, like, Google Docs th- with Writely in the early days about, like, 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, 100 times from journalists. Like, "What if I'm on an airplane? I'm gonna write stuff." I'm like, "I don't know. Like, there'll be connectivity on an airplane soon." Like, you know, which there is. Like... And those are all just "why not" sort- "why not" questions. Uh, the, I think the more interesting ones are the "what if" questions. Like, "What if this does work? What, what if..." Just, like, use, you know, use your imagination. Think about, like, "What, wh- 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. They just, like, look at everything as a problem to be solved. And I think there's something to that. And, um, but I feel like I've missed out more by being pessimistic than I have by, by being t- 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 don't know. That's like... I, I just, I, 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, and explore and find stuff. So, like, disruptive innovation is just... Seems, seems natural to me. But I, 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? 'Cause somebody... Just, you know, everything, right? Everything is like

4. 10:11 – 11:00

   First-principles thinking

   1. SSSam Schillace10:11

      that.

   2. LRLenny Rachitsky10:12

      Along the same lines, I was actually just working on a post around first person- 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-

   3. SSSam Schillace10:22

      Yeah.

   4. LRLenny Rachitsky10:22

      ... that much smarter than you.

   5. SSSam Schillace10:22

      Yeah.

   6. LRLenny Rachitsky10:23

      And there's no reason there isn't a better way.

   7. SSSam Schillace10:25

      Yeah.

   8. LRLenny Rachitsky10:25

      It just happens to be the way it is today.

   9. SSSam Schillace10:26

      Yeah. I, I... One of the other ones that I like to keep in mind is, every new idea looked dumb at first. Unfortunately, the dumb ideas also look dumb at first. It's not a perfect (inaudible) (laughs) but, like, the, but the disruptive, the more disruptive they are, kind of the more dumb you're gonna 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, if it's practical or it's stupid or I don't get it or whatever, like, those are often... See, 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 and threatening, and they can't think of a better criticism for it than it's, you know, it's just

5. 11:00 – 13:17

   Recognizing disruptive ideas

   1. SSSam Schillace11:00

      a toy right now.

   2. LRLenny Rachitsky11:01

      Yeah, I imagine people thought about Google Docs that way initially. It's like, "Oh, this little toy in the browser."

   3. SSSam Schillace11:06

      Yeah. We got all this stuff. I mean, and it... Well, the real interesting thing, though, like I said at the beginning, like, there's a, this... You know, you have this very binary reaction that's possible, right? Like, you either ex- you either understand it, in which case, like, you're super excited about it. Like, "Cool, the world's gonna change in this exciting way." Or you don't and you reject it. And, uh, to the degree that something is really disruptive, that reaction, that binary reaction gets really strong. And so, like, with something like GDocs, we got this thing with GDocs that was really confusing in the early days to me where, like, there's a small group of people that really liked it. Some of them liked it more than we liked it. Like, Nate Torkington over at Writely, like, was this super huge early provi- 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 in 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 what ... Like, that's sort of an in- that's an incremental product. Like that's not really disrupting anything. But if you like, you look at something like ChatGPT where like the entire world is like, "This is amazing," or, "This is terrible," and there's like not a whole lot in between, that's a on, 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.

   4. LRLenny Rachitsky12:33

      That's an awesome framework. Basically if it feels like people, sort of like it's some people, mostly people don't care, some, 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.

   5. SSSam Schillace12:45

      Right. Yeah, actually, weirdly enough, and like it doesn't even, you don't even have to like a- 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, I, who cares, right? Whatever. You know, like it's, it's fine. Like as long as you like, as long as you don't run out of the people who love it, you know, that's

6. 13:17 – 15:46

   Examples of first-principles thinking

   1. SSSam Schillace13:17

      fine.

   2. LRLenny Rachitsky13:18

      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?

   3. SSSam Schillace13:25

      I'm doing it a lo- a lot of it right now, honestly. Like, I mean, th- that's probably the most immediate example. But I could almost point at any product and there's, there's moments like that in there. But I like, right now, you know, there, there's a lot of why not stories, right, around generative AI. So it's expensive, uh, it hallucinates, you know, it, you, you can't necessarily try, it's stochastic, it's random, it doesn't do the same thing twice. Like those are 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 the, you know, what if we can build software around it? You know, what if we can build more complicated programs than what we've been able to build? What if we actually have a reasoning engine that we can use to do meaningful things? 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 wheels, 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, 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. Tesla is a great example, SpaceX is, is a great example where people are like, "That doesn't make any sense." You know? And 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 a car is basically a software product, right? Those are pretty amazing what if questions, right? Of those products.

   4. LRLenny Rachitsky14:49

      Yeah. So then this work on understanding what first principles actually looks like when you're thinking from first principles. The steps are essentially figure out what you want to do, figure out the levers that keep you from achieving that thing and then to basically question every assumption that stands in the way of making this possible. So I think Elon's a great ex- like the classic example, like you can't talk about first principles thinking without quoting Elon, telling stories of Elon, but essentially it's just, okay, how much would it cost to make this if we were to start over and not ...

   5. SSSam Schillace15:15

      That's I mean the, the why not? There are actually problems you need to pay attention to eventually to build stuff. But it's, once you have the what if, right, like the what, like just to pick on SpaceX for a second, right? Like if you have the what if of like if I could make, you know, weight to space cost, you know, payload to space cost a lot less, what if? Like okay that's amazing, that's an amazing world, let's see if we can work on that problem. And then now you have the all the why nots. Why not? Why isn't it as, as cheap as it could be? And you just 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.

7. 15:46 – 19:47

   The power of optimism

   1. SSSam Schillace15:46

   2. LRLenny Rachitsky15:46

      This connects to something else that I know you're big on, which is optimism. Being optimistic. There's this feeling a- that pessimism, you're always, you're often right. 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. Can you just talk about why you think that's important and how you approach that?

   3. SSSam Schillace16:06

      It's funny. Like it's a choice. Like I'm not an o- I'm not an optimistic person by nature. Like I'm 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. 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, you can be optimistic to the point of being careless and causing harm for sure. But like you know I think it's a, it's a, like maybe a better way to say it is growth mindset, right? Where like you want to look at the possibilities rather than the limitations and like suspend some disbelief and, and just kind of work on these problems. I, I, that's just 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 over my career, I wish I had been more open-minded and more p- more optimistic and more willing to try things and more, 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 I, it's kind of funny like when I came out here, like I was premed, I dropped out of school, I came out to be a computer scientist sort of with my friend. I didn't think of it that way. I came out to have a job at Ashton Tate with a friend of mine and spent 10 years like not understanding that I was actually in a career and thinking that this was a temporary thing where I had to go back and like go back to med school and get my degree 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 that's constantly growing and constantly inventing things and constantly, you know, coming up with these new ideas. And actually the best posture in that world is to be creative and curious and open and optimistic and try things and stuff like that. The other, the other thing I'll say about optimism too is like kind of related to doing these disruptive things like Gdocs, 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 that's a sort of fundamental thing of you're gonna 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 ma- you know, if it's, you know, in the very early story of G Docs, when I had the idea for Writely, like my two co-founders who were both deep domain experts in both app building and word processors, were like, "The browser's never gonna support this. It's a bad idea. Let'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, you know, wrong in that, like, the world was gonna change and evolve. And we would never have done the first experiment if it had been a long and costly thing to do, right? So like, the fact that our tools were sharp and we could, 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'll be like, "Uh, even that's not worth it. Like two days is a waste of time." So there's, like, always a little bit of a leap of faith, and then you kinda want to make those as consumable as, as possible. Like you wanna be able to try things out quickly and learn things, you know, and, and do these experiments. No, I, lots of people have said that before, but I think it kind of, all those pieces connect for me, you know, in this idea of being optimistic and open to trying stuff. 'Cause stuff always is different. You're always wrong about products. That'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.

8. 19:47 – 21:53

   Sam’s motto: Get to the edge of something and fuck around

   1. SSSam Schillace19:47

   2. LRLenny Rachitsky19:47

      Awesome. There's a few threads I wanna follow there. But tha- this is also, uh, a tool that I found came up a- 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 gonna work." And exactly as you just described, you often find out it, you're completely wrong when you actually try it out. And you have this quote, I think, in one of your newsletter posts, talking about building Google Docs. You describe it as just fuck around.

   3. SSSam Schillace20:12

      Yeah. Kind of.

   4. LRLenny Rachitsky20:13

      Get to the edge of something and fuck around.

   5. SSSam Schillace20:15

      Yeah.

   6. LRLenny Rachitsky20:15

      That's the strategy.

   7. SSSam Schillace20:16

      Yeah. Get to the edges and, like, get your tools as sharp as you can get them to be. Make it so that you can try lots of cheap experiments, right? Like, and just mess around and see what happens. Like see what pops out. And just be, try to be observant. 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, "I, you know what, I hate this. I'm doing four experiments a day 'cause I have to do it, 'cause 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. 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, well how far can I get with this." Like, "Oh, it's not working. Well why isn't it working? Well that's kind of interesting. Like what broke here?" We've done stuff like that on some of the things, the projects I've got going in Microsoft, um, right now. Like we've got a chatbot thing we've been working on for a while, 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 y- 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. Don't know why. Like it just makes them smarter. It's like that was kind of one of these nice little, like, bits of discovery where 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 was like, "Well let's, let's try to like give them a whiteboard just like a person and like see if they cooperate better." And it, and it turns out they really do. So I think another example of

9. 21:53 – 24:31

   User value and laziness

   1. SSSam Schillace21:53

      that mindset.

   2. LRLenny Rachitsky21:54

      Along this thread, I was gonna ask about this earlier, but there's a lot of technologies people get optimistic about. Crypto comes to mind. Not that there's, 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 winter time. Is there anything you've learned that gives you a signal that, "Let's keep working. I'm gonna stay optimistic about this thing"?

   3. SSSam Schillace22:15

      I spent a lot of time really thinking hard about crypto, and like whether I was just reacting to it 'cause it threatened some part of my identity or whatever. And I, I, I never kind of, I never came down to the, 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, "Well what if this works, like how valuable is it?" For, uh, crypto I was always like, "Well what if it works? Like, then I have to run opsec on my fi- 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 about user value. Users are lazy, right? We're all lazy. We don't really care that much at the end of the day. No one's gonna 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, like they care about, you know, making their life easier. W- 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 gonna work. You know, it's not gon- it doesn't matter. Shove all the marketing dollars into it you want, you can write all the articles you want, but like you know, it, 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.

   4. LRLenny Rachitsky23:34

      Yeah. So I think the lesson there is truly understand if the value is real-

   5. SSSam Schillace23:38

      Right.

   6. LRLenny Rachitsky23:39

      ... versus like, this sounds really cool.

   7. SSSam Schillace23:40

      Right.

   8. LRLenny Rachitsky23:40

      Or you think a lot of, like would you want it-

   9. SSSam Schillace23:42

      Right.

   10. LRLenny Rachitsky23:42

       ... I think is a nice exercise there.

   11. SSSam Schillace23:43

       We pick on poor Elon, but like you know, I feel like with a lot of his products, at least he o- or you know, he's got lots of other issues, but like he articulates clear user value even in the beginning when he's hyping things up. Like Teslas, 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 gonna put a lot of batteries in these things. They're gonna really be real cars. They're gonna have real range. We're gonna 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 'cause the fuel is cheaper. Like he's solving all of the end user problems for me. Like that at least makes sense, even if you don't believe that he's gonna do it-... or, you know, believe in the way he did it. Like, at least the end user value proposition makes sense,

10. 24:31 – 28:36

    People are lazy (and what to do about it)

    1. SSSam Schillace24:31

       right?

    2. LRLenny Rachitsky24:32

       You have this other, uh, great quote in your newsletter, "People are lazy. Look beyond cool to, on how much easier a new tool or tech makes someone's life. Convenience always wins."

    3. SSSam Schillace24:40

       Yep.

    4. LRLenny Rachitsky24:41

       Can you talk about that, just this realization people are just lazy and that's the key?

    5. SSSam Schillace24:44

       Yeah. Well, that, I mean, that is the thing. Like I think w- we... I, I think as product builders, you know, it hard to not love what you're doing. Like you build a product 'cause you love it. You build it 'cause you understand some problem. You know, you build it 'cause 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, but just kind of in general is like people are just lazy about stuff, and like don't care about anything other than it making their life better. The thing that's complicated with that is there's two things about it that I think are interesting that, that follow from that principle. One is like I think products almost follow these like thermodynamic 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? And I think ChatGBT 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, and it's sort of kind of adding a little bit of value and kind of slowly lu- you know, lumbering along, or maybe it's gonna collapse under its weight. That- that's the, that's kind of the, the, y- you know, one thing I, like about the, the users are, 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 will be like, "Entropy's not real. Look, it go- runs backwards all the time on the, on earth. Like life gets more complicated. Like, what, what is, 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 entro- in entropy all the time. We're just making use of some of it. And I think the same thing is kind of true about user laziness where like people are like this tiny thing that I'm focusing on, this feature that I added is better, therefore users should adopt it. But you forget all the stuff around it. 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. 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 i- uh, Writely at the beginning, we didn't even ask for an email address 'cause 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 abou- after about two minutes of typing, if you were still there, we'd very gently just say, "Please give us your email address. No password, no anything. Just give us your email address so we can send you a URL of this document in case you care about it later, 'cause 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 fric- 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 amou- number of seconds you have, you know, is, is not many, like 15 seconds, 30 seconds, right? To convince somebody that there's some value there, they're not gonna like hang out and grind their way through a bunch of high friction stuff to sign up for your thing, like your, you know... So like that's the other part of it is 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, right? So it has to make your life a lot better and hopefully a really a lot better, like 10X better than what you spend to use it.

    6. LRLenny Rachitsky28:10

       What I think of as you're describing this is, uh, Excel, Microsoft Excel had a billion toolbars and buttons and options, which allowed Google Docs essentially to come in with a much simpler experience (laughs) . Now you're on the other side of that, which is I never... I didn't think about.

    7. SSSam Schillace28:25

       Yeah, it's a really funny place to be. Like, you know, I did... I... Like, and it's funny to be at Microsoft 'cause I'm kind of the enemy, right? (laughs) It's like I'm the guy who like messed them up a little bit. So there's, there's some

11. 28:36 – 31:06

    Building Google Docs

    1. SSSam Schillace28:36

       friction around that. Yeah, I mean, I think there are similar trade-offs to be made right now, by the way, with AI. I think there's similar opportunities, but we made this choice with... So it's a little hard to remember, right? 'Cause 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? It had to be shipped around. It had to be bought and installed. It was like hard to, 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 a thousand 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? So we made this trade-off. We're like, "Look, we're easy to use. We're zero install. You don't have to ever deal with it. 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 to deal with file system, fire- file servers. But, you know, we're gonna take away most of the features 'cause 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 where you get all these complaints about people who wanted, who wanted word count, which I felt was a really weird... I thought that was gonna 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. We just had like these basic documents, but page count or word count came in. Of course, it was students 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 th- there was this dance with Microsoft that we deliberately made this trade-off. Like we were... And, and I think it's kind of... It's almost like a, a classic innovator's dilemma model, right? Like we took this, you know, you had 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. We just kind of chipped away from the bottom like, you know, the, the innovators doing that. And then, 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 gonna 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. Like it's, you know, um, we have all the users now, but (laughs) they have all the money. (laughs) Like we have all the money I guess

12. 31:06 – 37:15

    The evolution of Google Docs

    1. SSSam Schillace31:06

       now.

    2. LRLenny Rachitsky31:07

       I want to spend more time on Google Docs and the story there. A couple of questions. How long did it take from starting on it to feeling like it's working, like whatever you consider product market fit?

    3. SSSam Schillace31:17

       Almost immediately, honestly. Like it- it was weird. Like the, 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, 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 that JavaScript was out there. And like we had done word processors in the past, this team, and like for a long time. In fact, like w- my co-founder Steve, the other person on that document, like wrote this thing called Full Write 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. Like there's 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 'cause there's no presence or anything like that, and there's no collision detection or anything like that. So like, so pretty quickly we were like, oh, that's kind of cool. Like, that feels good as a development team to have like these shared documents, not have to send stuff around and not like... So that's cool. So let's build that out. But like, oh, bummer, like collaboration's a problem, like we'll have to go fix that. And like naively like figured out that like that's a problem. And it took forever to, to get that working out. It was really, really hard at 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, because the browsers... The logical document of a, you know, of 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 blank paragraph with a singleton BR tag and IE would do it with an open closed paragraph tag. And so like, you know, even the tree doesn't match, and like so it's a really hard merge problem. So that turned out to be like a gnarly hard problem to, 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, um, like I think if we'd gotten it in the other order, we might not have done it. Like it's a good ex- 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 could collaborate on would be. Because if we understood how hard the collaboration piece would have been first, without understanding that value, we might have been like, "Eh, 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 it's a, I think it's a good little counter-example of like that optimistic, pessimistic perspective we were talking about. Like, you know, 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.

    4. LRLenny Rachitsky34:16

       That is really interesting actually, that you need to be pulled to the what if getting you so excited that you're gonna spend however many years it took you to solve that problem-

    5. SSSam Schillace34:25

       Yeah.

    6. LRLenny Rachitsky34:26

       ... because you s- because you are so excited about this what if.

    7. SSSam Schillace34:29

       Yeah. Yeah.

    8. LRLenny Rachitsky34:30

       I think that's a really good point.

    9. SSSam Schillace34:30

       And that, that's what, I mean, I've spent a lot of time... It, it's kind of funny, like GDocs, I keep expecting people to just be like, "All right, Grandpa, stop talking about GDocs. It's been a long time." Like, so it has been a long time, it's been 17 years and like, but it's still very relevant. It's got a couple of 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, well, why did that work? Like, what worked about that? Like, what lessons can I draw from it? Like, it was, it was, there was a lot of energy around it, positive and negative. I, the first week I was at my, at, uh, 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 re- 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 had contracted earn-outs, and like, you know. So like that was like another one of these, like, interesting lessons of like sometimes the opposition is en- 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 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, or what. I'm not sure what. But like we'll keep, 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 good, really innovative good products is mi- 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 and be- best practices of doing iteration and user testing and user interviews and really listening and, you know, 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 k- some kinds of pushback are, are good pushback and some are, 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- and like I'm gonna go there because the world doesn't care :if it's gonna push back. But you also have to be really flexible about feedback. Like, you might not be, you probably aren't gonna be right about a bunch of it. And so like you have to, like, blend these two things together somehow. Like, you know, it's like a samurai sword that's like hard on the back but softer on the edge so it doesn't break and like it's or bad, other way around thing. But like, you know, it's like there's this hard thing you have to do as an entrepreneur, and I think it's like the real core of building really great products is like f- finding that balance and really listening to those- those signals, being open to

13. 37:15 – 39:52

    Finding product-market fit

    1. SSSam Schillace37:15

       it.

    2. LRLenny Rachitsky37:15

       And also knowing how long to commit to it versus it's 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?

    3. SSSam Schillace37:30

       It depends on what market we're talking about. Like, I- I've been continually surprised at the adoption of GDocs. 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 was 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 G- at the time, 37signals was kind of like the cool company and we were 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, like, let's go advertise on Google and see how much it costs to, like, 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, it got us noticed. We were like, I think, like, one of the first 10 articles at TechCrunch, like Michael Arrington. Like, there's another funny Brightly story is that, like, we had, I had a breakfast with Michael Arrington at Buck's in that era where he was, like, trying to decide... He had this, like, spreadsheet idea he wanted to work on and he was trying to decide if he should go do that and, like, maybe join forces with us 'cause we were cool or if he should, like, continue to work on this blog thing he had going called TechCrunch (laughs) . I'm like... So I might be res- partially responsible for TechCrunch 'cause we turned him down and said, "You should go do TechCrunch instead." (laughs) You know, every time I would bump into him, I would laugh about that with him. But, like, when that, when we got noticed, like, we really got noticed. There was just this period where we were, like, the hot thing for, you know, a couple of months, like, where every VC wanted to talk to us and everyone's trying to figure it out. 'Cause I think we were, 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 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 gonna go?" With, you know... So, like, we- 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? 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 it's collaboration? Well, you get to spend a bunch of energy on offline, which was miserable, which never turned out to matter that much, you know. Now, that team

14. 39:52 – 44:57

    The future of documents

    1. SSSam Schillace39:52

       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 wood pulp and ink pressed by, you know, metal type, right? Like, we're building linear documents that are fixed, that are static. So, like, one of the things we've been doing with these- these chatbot things is they're also, they also serve as documents. I say bots are docs all the time. And so you'll like, you'll do these things where, like, you... I do this all the time where, like, we'll interview... Have one that will create a new one as a, it has a, you know, separate identity as a separate document. And then you tell it, like, "I'm gonna 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 'cause it's conversational. But at the same time, you've been building all these, like, semantically encoded virtual synthetic memories in this, in this vector 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, what is this? If I change this, what if I change that? Summarize this part of it." So you can start to interact with it. That's still, 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 gonna happen is, you know, just like it seems... Well, in the early days of GDocs, like people would- 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, if you get handed a device that's not connected to the- 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 gonna 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 in an intelligent way, have it converse with me, whether that's a device or a- a piece of- of- of gooey, you know, UX somewhere, I- I think that's, like, it's gonna feel anachronistic. It's gonna feel really weird. There's like that scene in one of the early Star Trek movies where, like, Scotty tries to talk to the mouse, right? He's like, "Computer, like, make the trans-" You know, like, and he's like, he's pissed off because he can't talk to the computer. Like, we're all gonna be like that in, like, five years, I think, about and it's gonna seem really weird that we have these applications that, like, I- you know, I can't collaborate with the application. Like, why can't I collaborate with the application? It's like- it's like the application's locked on a file server just like the pre-GDocs days. Like, why can't I just, like, interact with it and have it configure itself the way I want it to configure itself, and, like, show me the data the way I wanna 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 gonna change radically in the next few years.

    2. LRLenny Rachitsky42:46

       I wanna follow that thread. Before I do, I found the first TechCrunch post about you guys. Starts with, "Imagine Word, but as an AJAX browser application on a screen."

    3. SSSam Schillace42:53

       Oh yeah, there we go. (laughs) Yeah, AJAX. Wasn't even JavaScript, it was AJAX.

    4. LRLenny Rachitsky42:58

       AJAX, so hot back then.

    5. SSSam Schillace42:59

       It's also funny too, 'cause like I'll talk to young front end developers these days, and I'm like, "I don't wanna scare you too much, but like, jQuery didn't even exist when I wrote this thing." You know? Because it was like bare metal in the DOM, and there were bugs. Like when I went to Google, like I had to write this, um, little network stack at the bottom of, of the JavaScript that like i- in, in theory, XML HTTP, you could interrupt, you could have multiple requests in flight and you can interrupt them and discard them and stuff. But the stack at the time was really buggy in, I think it was IE. And so I wrote this little, like, network queue that would, like, keep track of whether there were requests in flight and, like, kill them in a way that didn't break everything. And, you know, it was hard to do, like, 'cause 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 s- with their formatting. Like, there was some bug in the JavaScript compiler of the time that, like, white space mattered. And so I wound up, like, checking it in broken, got the readability badge, and immediately fixed it. And so, like, that was another one of our little, our little hacks to get this working.

    6. LRLenny Rachitsky44:06

       I love it. This episode is brought to you by Ahrefs. Many of you already know Ahrefs as one of the top tools for search engine optimization. It's used by thousands of SEOs and companies like IBM, Adidas, and eBay. What you may not know is that there's a free version that was made with small website owners in mind. It's called Ahrefs Webmaster Tools. It's free, and it can help you bring more traffic to your website. Ahrefs Webmaster Tools will show you keywords that you rank for and backlinks that you can get. It also performs automated site audits to find what issues prevent your website from ranking higher on Google. Every detected issue comes with a detailed explanation and advice on how to fix it. Visit ahrefs.com/awt, set up a free account, connect your website, and start improving it. That's A-H-R-E-F-S dot com slash A-W-T.

15. 44:57 – 47:58

    The value of playing with technology

    1. LRLenny Rachitsky44:57

       There's often this criticism as an engineer, you just wanna work on interesting things and work on the technology before you find a problem that it's solving. It feels like with this example, it was you just think this is a cool technology, let's see what happens. Do you have any, uh, I don't know, learnings or advice for when it's actually fine, "Let's just play with this tech, be at the edges," you said, "and maybe it'll lead somewhere," versus, like, you should probably try to avoid that and first focus on a problem?

    2. SSSam Schillace45:22

       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, 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, um, 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 the sy- So like right now, we're doing these multi-agent systems. We're trying to figure out how m- much independent work they can do without a person holding their hand. And so, a nice domain to test that out in is programming, 'cause you don't have a whole lot of, like, you know, 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 VI 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, 'cause it's, it's a thing you could expect a reasonably competent programmer to do mostly independently. And so, like, 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, 'cause we already have VI, like, doesn't matter. 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, that's valuable. Like, that would be a valuable thing to have. Now, it's kind of interesting too, 'cause, 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. 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, like, when there, when there's a problem somewhere, it goes and figures out what the problem is, and then 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, 'cause we don't trust it. But, um, you know, like, it's, like, very helpful as an assistant, 'cause 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, so... But it's starting to produce interesting stuff, right? 'Cause we have these north stars that we aim things at. And I think that's maybe a good antidote to this. 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." Like, you know, "I wonder if I can build this thing and grind away at that for a week and see how close I can get, see what I learn about why it's hard." Um, that- that's probably better than just like, "Let me poke at JavaScript

16. 47:58 – 49:21

    Taking risks and embracing failure

    1. SSSam Schillace47:58

       for a while." (laughs)

    2. LRLenny Rachitsky47:58

       It's also different, I think, at a bigger company where you need to achieve something versus I think as a, just an engineer out of college, just playing around, like, you know, go for it, right? It's just like, what's the worst thing that could happen?

    3. SSSam Schillace48:09

       Even the early days of Writely, like, the very f- I mean, we had a goal from the beginning. The beginning was like, "Can I write a word processor in a browser?" Like, that was literally the problem statement, right? It was like, "I have content editable, I have AJAX or JavaScript. 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. So...I don't know. Like, I think that's, I li- I like playing around with... I think a lot of the good product ideas, most of the good product ideas actually come up from engineering. So I, I think there's a lot to be said for, you know, get familiar with tools. Particularly like weird esoteric combinations of tools can also, often be useful. Like, if you understand two or three things... So like, I'm at, at Google, like I was one of only two people in the company who had, uh, code readability, which is like the right to, to check in code in this language, in both a backend language, which is the monitoring language, Org Mode, 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, like, that broad perspective sometimes. So...

    4. LRLenny Rachitsky49:15

       Sam, the Renaissance man-

    5. SSSam Schillace49:17

       Yeah.

    6. LRLenny Rachitsky49:17

       ... of all languages.

    7. SSSam Schillace49:18

       ADD are more like it, but yeah- (laughs)

    8. LRLenny Rachitsky49:20

       (laughs) .

    9. SSSam Schillace49:20

       ... I'm good at a bunch of

17. 49:21 – 53:48

    Thinking in the future

    1. SSSam Schillace49:21

       new things.

    2. LRLenny Rachitsky49:22

       I wanted to follow this thread a little further around being good at these what if questions. It feels like you've built this, or maybe you were born with this skill of thinking in the future. Thinking about what's possible, thinking about where things are going. Is there anything that you could recommend to people listening to get better at this skill? 'Cause for a lot of product people, this is really important to figure out where could we be going and let's work back.

    3. SSSam Schillace49:45

       This is a really interesting question. And I'm like, I, I may actually write... I've been thinking about writing a book that's from some of my Sunday letters, and this is m- maybe the frame of it. So I'm curious to see how flamed I get by, from saying this. It'll 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 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 the stupid toy." Like, you know, whatever, "It's not real computing. Go, go learn a mainframe," or whatever. And my attitude was like, "Out of the way, old man." Like just like, "You're irrelevant. I'm gonna 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, Okay Doomer. That one, the professor actually put it up there. 'Cause the, the, like this 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 the re- 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, and to fail, honestly. 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 out 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, so like and 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, at these elite schools, they're hard to get into. I went to Michigan 'cause, quote, "You're kind of smart. Michigan's a good school. You live nearby. Go apply to that one." Like, you know, nothing, 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, those students like, I didn't do sports and I didn't do extracurricular. I was just like a weird nerd that, you know, happened to be good at math. And so I think there's that as well. Like, if you're highly curated where you've spent a lot of your life thinking, "Everything I do has to have a reason and an output," it's very hard to just mess around and do something that might, you know, lead down a surprising path, right? So that's the curationist 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, uh, it was like the faculty ghetto for this small university my dad taught at. And like we just ran wild. It was like on, on the estate of the widow of, of Dodge Motor, founder of Dodge Motors, where we had like couple hundred acres of swamp and fields to run around. And we did hair-raisingly dangerous things that my parents 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, making a fool of yourself. Like, having bad ideas. I send, like, stupid emails to Satya at Microsoft all the time where I'm just like, "I don't know what the hell he thinks of me at this point," 'cause I send him all these goofy ideas. I think he actually, like, gets it and he's like, he likes it 'cause 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. I'm like, "Yeah, that was a dumb idea. Sorry about that." You know, like, "I, I've decided that wasn't a very good one." But I think like, you know, I, you just have t- like you cannot dance if you can't, if you're, you know, afraid to embarrass yourself or 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, I'll iterate on it." I have this personal motto which is like, "From error comes virtue." 'Cause I'm a maker. I make stuff and I fuck it up all the time. Like, I'm, I'm, I have 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, I, it's a, a 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. It's like, "Virtue from

18. 53:48 – 1:01:20

    Finding joy in your work

    1. SSSam Schillace53:48

       error."

    2. LRLenny Rachitsky53:49

       Amazing. On this topic of failing, I think a lot of people hear this advice and they're like, "Yeah, okay. I need to fail more." It's hard to do and oftentimes your performance is, as a comp- at a company is, is negatively impacted. Is, and it feels like for you, it was just having f- you've done it enough times where you're, "Fine. Okay, it's gonna be fine. I launched this thing. No one cares. I email Satya this thing, he ignores it or he doesn't..." Like, "It's gonna be okay." Is that maybe the key to this or is there anything else that you've done to allow you to be okay with failure?

    3. SSSam Schillace54:17

       I think there's this... I feel like you can have a linear return on your effort if you manage things in a, in a linear way, which is I think that managing, you know, tightly managing, "Okay, nothing's gonna be surprising. I'm gonna be within this boundary. I'm gonna like kind of slowly accrete value. I'm gonna play this game," whatever. Like, you can have a nice linear, boring return to your career and you'll climb the ladder and it takes 30-... years, or whatever. I don't have the patience for that. And I think the way you get extraordinary returns is you do extraordinary things, right? You get, you know, you have to have, you have to take bigger risks, and, and, you know, have kind of more, I don't know, more, more interesting shots to have this kind of extraordinary result in your career. I, I, I feel like I always tell people, like, I think, I mean, I, I, I, I pitch this because I've observed myself and thought about, like, what has been successful in my career. It's, uh, not every- it's not a thing everybody can do. Like, I'm just kind of like this. I, I'm, I never really fully grew up. I'm kind of this weirdo. I still feel, I'm 57 now. I feel like I'm about 17, like I'm still very mature and like, like to mess around with stuff and, 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 'cause 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 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, 'cause, 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, if there's a thing like that, and do the hell out of it, right? Like, do the, do it as hard as you can. If you get, 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, that work doesn't necessarily have to be hard. It often is, but it doesn't have to be. And the best case is that it isn't. The most impact you'll ever have is where you're in that mode, where 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, right? Like, I think that's the, that's the career thing that makes sense to me. I, and, and at least that's what I've done.

    4. LRLenny Rachitsky56:42

       Mm-hmm.

    5. SSSam Schillace56:43

       You know? Who knows? Like, it, it's all luck sometimes. So it's hard to replicate, 'cause every- everybody has a different path.

    6. LRLenny Rachitsky56:50

       Amazing. I love that advice. (clears throat) It's exactly where I was gonna take our conversation, so I love that you took us there. It makes me think of, uh, I'm reading, uh, Charlie Munger's Almanack, 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-

    7. SSSam Schillace57:09

       Right.

    8. LRLenny Rachitsky57:10

       Like, make one bet a year. But when you find that, go, go for it. Don't, like, buy a little bit at a time. And, uh, I love that that's exactly what you're saying.

    9. SSSam Schillace57:18

       Sometimes things don't make sense either. Like, I'll, I'll, so I'll lean over and, like, show you for, if people with the video, that's an instrument I made. Um, 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, this is e- virtue from error right there. Like, I dug this piece of wood out of the forest. It had been sitting in the forest f- for 80 years, trying to not rot, and doing a pretty good job of it, 'cause 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, the arch of it's a little bit too high, so it's a little hard to play, um, 'cause the pick hits the top, because the strings get a little bit close 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. 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 the, like, I don't know, sometimes I don't even understand why I do stuff. Like, you just do it 'cause you do it, 'cause it makes some sense to you.

    10. LRLenny Rachitsky58:25

        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, feed their family.

    11. SSSam Schillace58:33

        I know, I realize what I'm saying is very privileged, and I, like, I'm sorry about that, but, like, from some perspective.

    12. LRLenny Rachitsky58:38

        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 excited about this work"? Is, do you recommend try to get out of that as soon as you can? Is it enjoy it as much as you can, get the most out of it?

    13. SSSam Schillace58:52

        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, 'cause 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 I'm kind of a programmer, but not real. Like, I'm (laughs) this weird, weird non-linear person, that, like, only barely fits into the programming world. But, like, you know, it's okay. Like, uh, it took me a long time to figure out that I could do that, that I could, th- that I could be comfortable with that part of myself. And, like, I'm fortunate enough now that I've done enough things, and 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... So it's like, it is kind of privileged f- you know, advice, and it's not something everybody can do at every stage in their career. Certainly earlier stages, you often have to make compromises. But I still think it's worth paying attention to, right? When you're working, like, what makes you happy? What is the stuff that you feel guilty for getting away with? What, like, when I started managing people, I couldn't understand why people were paying me and I wasn't writing code, 'cause all of my energy was attached to, like, I can produce a lot of lines of code every day. And then it, and, you know, 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, 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 gonna pay me for talking to people all day.... you know, 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, 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 and a- 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, you can do these pivots.

19. 1:01:20 – 1:02:34

    Just do the best you can

    1. SSSam Schillace1:01:21

    2. LRLenny Rachitsky1:01:21

       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're in just try to en- enjoy it and do the best version of that job you can, because you'll enjoy it more, I- 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 at being a waitress at this place. I'm just going to do the best at greeting people entering the Apple store."

    3. SSSam Schillace1:01:45

       Absolutely. Yeah, I think that's absolutely right. Like I- 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 com- the most comfortable with, right? Um, you know, that like where you really have high impact. I don't know. I- I tend to be very... Like it's kind of a joke 'cause 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 with just a ridiculous amount of intensity, for better or for worse. Um, 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 (laughs) the people around me are probably less happy, but like stuff happens. Anyways, I get

20. 1:02:34 – 1:09:27

    The transformational power of AI

    1. SSSam Schillace1:02:34

       things done.

    2. LRLenny Rachitsky1:02:35

       Speaking of getting things done and being intense and working on 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 somewhere that I have here that I think are cool. One is, "AI isn't a feature of your product, your product is a feature of AI."

    3. SSSam Schillace1:03:01

       I love that one, yeah.

    4. LRLenny Rachitsky1:03:03

       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."

    5. SSSam Schillace1:03:14

       Yeah, I think both of those are- are really, are really true. Like I... So I'm like what I'm working on is I... Most of the industry right now is focused on, when you talk about somebody who's working in AI, it's somebody who's creating models, right? It's somebody who's figuring out how to do some new open source model or somebody who's doing some new training or make some model bigger. And like T- 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- I'm a, 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- on GPT-4 with Microsoft in like September of last year, like my immed- my immediate reaction to it after like 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 like stochastic peer function that just like takes a- 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 outs. And- And so like that just kind of started me down this rabbit hole of thinking about building a semantic kernel, which we built, and then building Infinite Chatbot, which was next, and these other projects we've been working on. And like more I think about this stuff, the more I do think like those two quotes are- are- are good quotes. Like I think what's going to happen over time, I- 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- pixels are expensive to produce now. Like they take programmers and they take lots of infrastructure and like putting a pixel in front of the user is a harder... 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 hard, being hard to distribute information 25 years ago. But like 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. 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? Like so those pixels got really free but... And that similar things are happening in- 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 ifs. 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 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? If you have all of those things, you're just going to spend a lot of time talking to that agent. Like w- it's like if- you know, what would you do if you imagine you're like the richest person in the world, you've got 100 of the best people working for you and a chief of staff and they're tireless and they never fight with each other, they do everything you want, like with that staff supporting you, like what are you doing with software? Like how much time are you... What are you doing when you're sitting in front of a screen? Well, you're probably communicating intention and you're probably consuming some in- either entertainment or some of the products of that intent. And- 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- I think that's kind of where we're headed, I- I think, in the world of software at least, um-... you know, things are gonna 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, 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 gonna get interesting. Like, that's a new device." Now we gotta go do a whole bunch of engineering before they actually are, like, as useful as they are today, right? So like, I think, I, I get it. Like, I think software is going to change radically now. I this, I had the same feeling when I sh- when I, when we started doing... This is go- going back to gdocs again, it's another lesson. Like, it's another one of these category shifts. Like, the second we got G- Brightly up on its feet and when 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 gonna 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, you know, how you deal with replication, how you do security, like, all kinds of hard pro- all the, 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 qui- 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 yep, software's gonna totally change. Like, these businesses are gonna totally change. It might take 10 years to like really work through all of it but like, yep, like door open, new room, like new game, like fill in bla- start coloring in the blanks, right? Like, you know, let's go. So I, I, that's- that's where I, 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 ways. So like, we're gonna 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 that are gonna pop out, and you know, there's just a whole lot of stuff to get that to be real the way there was with the, all of the last transformations. But, I think this is a, just a giant category shift. Like I- I- I don't th- I think it's just incontrovertible that, that it is. Uh, it's kind of funny, like when, um, Gemini came out, all the press take was like, "Oh, it's not that different from GPT-4. I guess we're done with AI now. We can go back to bed." (laughs) 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 we could have had on that, I think that was like the dumbest one, honestly. Like, you know, I, I don't think it's, eh, like, you could say many things about either company. You could say many things about the science, but like, guess there's nothing here to see is not one of

21. 1:09:27 – 1:13:07

    Advice for approaching AI

    1. SSSam Schillace1:09:27

       them.

Episode duration: 1:27:50