AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)

23:11And what for me is now remarkable about that list of projects is that they all existed before these tools made it possible for you to learn how to build something almost instantly or ask it with one question. Hey, can you summarize this very complicated text or this very complicated book for me immediately? Or can I try to do all of these things that were previously impossible to me, but now I'm able to do? Like, can I spin up a, can you make for me like a CAD model of this idea that I might have? Like really capabilities that were truly beyond my reach are now in my reach. And so if those fast projects were possible before with the capabilities we used to have, shouldn't we just see an exponential increase of the number of those types of unreasonably quickly and effectively executed things with what AI has given us?

23:57Lenny Rachitsky:To your point, the hardest part is just remembering to even to try just to be like, oh, yeah, well, let me see if Codex can do this for me. It's just like a new habit, a new thing we have to build in our brain. Tyler Cowen has this statement on his site, which is that you most people underrate the impact of going to someone else and saying, hey, couldn't you what is like the more ambitious version of what you're doing? Or couldn't you try this faster or couldn't you try this at a 10x bigger scale? And in some ways, again, when I think of like what what do PMs do that is incredibly effective now or what can they do that is incredibly effective now?

24:30I think elevating others ambitions or reminding them of what's possible here is a huge part of the product management role. Like when folks say, hey, I think we can get this done in this way or we can get this done by this timeline or maybe this is the first version of it. Part of your job now is to elevate everyone's ambitions and say, actually, isn't the possibility ceiling meaningfully higher? Like, shouldn't we be more ambitious about what we're attempting here or like, couldn't we try this faster? And I think that's a yeah, it's a great place to be. It's a great place to be in terms of what you can build, what's possible, and in terms of, yeah, how exciting the job becomes.

25:08Lenny Rachitsky:That is so interesting. I remember Nick Turley was on the podcast who was maybe had the role before you. I think he's working at Enterprise stuff now. He had this meme internally, is this maximally accelerated? Yes. There's like an emoji, I think, inside the Slack. Is this maximally accelerated? Is this maximally accelerated is totally a OpenAI meme. The other OpenAI meme that Andrew Ambrosino and I love to ask the team is, are you mainlining it yet? Which is, are you using this product all day, every day to get your thing done? And I think that in combination with, are we being as ambitious as possible?

25:45Which is about the scope and the scale of what you're trying to do. is this maximally accelerated? Are we moving as fast as possible on it? And then are you mainlining it yet? Are you using it? And are you bringing all your tastes to bear on whether this thing works and is something that people really want and tightening that feedback loop as much as possible? Those to me are like the three memes of product development that we just have to spread as much as possible now.

26:08Lenny Rachitsky:I love that. That's like the new dogfooding. Instead of dogfooding, you got to mainline it. Yeah, exactly. And that shows so deeply in the tweets. This is mostly how I see your team communicate of just like how obsessed they are with the product and are just constantly asking, what can we do better? What's bugging you now? Here's the thing we're building. It's like, it's very clear how, to your point earlier, that everyone is just the founder of their product. And it's very clear how they act as an external observer. Are there any other memes internally? Those are so interesting. Any others? I don't know.

26:44Yeah, I'm trying to think if there's other good cultural means. Certainly a really important one is like feeling the AGI or just being conscious of AGI coming. There are so many outcomes for what it could look like or how one thinks about it. But a huge part of what puts most people at this company is believing in that mission of AGI being beneficial and trying to do whatever it takes to make that possible, both realization of AGI and ensuring that it is beneficial for humanity. And in building products, another just constant refrain I have to keep in the back of my mind is, are we building for where the models are going to be in two to three months?

27:27You fail if you build for where the models are now. You fail if you build for where you think the models will be in a year. Like both outcomes are equally wrong. And I'm sure many people have talked about this, but both outcomes are really equally wrong. If you're too early, you're wrong. If you build something that was overly focused on a past model's capabilities, you're entirely wrong. The only way to build is two to three months. And having this beam of models are going to get way better. I need to think about the model capability as the center of this product. I need to get out of the way of the model in terms of the product constructs that I create.

28:02How do I ensure that this is right for the model in two to three months time?

28:04Lenny Rachitsky:How do you know what two or three months is like? It's like a challenging understanding, especially while we're on this exponential. Is it like it's just a gut feeling? Is there anything the researchers give you a sense? How does that work? Yeah, certainly communicating really tightly with research on where they think things are going is incredibly important. Like these things aren't entirely like a black box in that you kind of know, hey, we're focused on these particular things. Like we would like models to be better at coding in these specific ways or better writing in these specific ways. So we certainly have focused efforts on making the model better at specific capabilities.

28:42And so knowing where that is and ensuring that product development is as tied as possible to what research has as its agenda and its roadmap is really important.

28:54Lenny Rachitsky:A quote that I'll never forget is when Kevin Weill was on the podcast. He was chief product officer at that time. He said that this is the worst the models will ever be. And it sounds so simple, but it's just like it's hard to just like wrap your head around that, that this is the worst they will ever be. like it's such a cliche almost now to say that but it's it's true it's absurd this is like yeah it's absurd it's truly absurd oh man okay um i want to talk about chat gpt the app briefly uh okay so i have it open right now yes okay so here's what i see in it chat gpt and then there's a drop down and there's chat gpt and codex and then there's this toggle chat and work Tara, what is going on?

29:40Lenny Rachitsky:What are all these things? Help us understand what each of these things are for. And where do you think this goes? Is it going to stay like this? Is there a next step that you're imagining already? Our north star here is that users do not need to make decisions between picking between all these different options. Ideally, there is no toggle here. That you go to the box, you type in your tasks. I would like to build a really awesome app that, I don't know, helps my podcast guests like do research before episodes or something like that. And it will just pick the right harness. It'll pick the right model for you to be able to get that thing done.

30:18Ideally, the choice here is like not on our users to have to pick between all these different concepts and understand not only what are they trying to do, but understand the limitations and capabilities of our products. So that is certainly where we want to go. So in the near term, picking between ChatGPT and Codex is really a choice for, do you want to stay in sort of like more development-oriented UI or do you want to have the same powering capabilities in the ChatGPT mode? And so if you're a Codex user, keep using Codex. You're not missing out on anything. Like continue using it as much as possible.

30:54But if you're a ChatGPT user who is like, what are these new agentic capabilities? You should probably be in ChatGPT mode. And then when you're in ChatGPT, if you want to have conversations, if you want to search, that's where chat mode is the right thing. It's the same chat mode you know and love with better and better models and newer and newer capabilities every time. But in work mode, that's where under the covers, this is codex. We've removed some of the coding UI. You're not going to see a work tree pop up all of a sudden in work mode, but it is the same power to get things done to, for example, generate like a really complex financial model that's all possible in work mode.

31:36And we see people, especially I mentioned our corporate finance team, use work mode to do incredible, incredible things that were previously either manual or required deep expertise from one person on the team become things that the whole team can be able to execute or just elevate the ambitions of everyone on the team in terms of timeline or capabilities or frontier of what they can get done.

31:58Lenny Rachitsky:Okay, that's really helpful. So there's kind of like these three modes currently. There's like the engineering mode, the chat mode, and then the do knowledge work mode. And the knowledge work mode, it's actually Codex doing all that work, but people may not know what Codex is, may be afraid of it. Is there anything in that work mode that's not just Codex? Because that's actually really interesting. Is there like additional harness tweaks to make it feel a little different? Or is it just the same thing with a little different UI? It's really at the UI level. So work mode and codex mode, if you go to codex and ask it to generate an amazing financial model to price your product or something like that, or like, tell me, predict my revenue for the next six months or something like that, codex will do as good a job as work mode.

32:40It's like really about whilst it's doing so, what kind of UI do you want to see in the chain of thought? What kind of technical detail do you want exposed to you? It's like incredible. It's similarly powerful. And so Codex users aren't missing out on anything by not switching modes. In fact, we do not want them to stay in Codex and do all the stuff you want to do in Codex. And we will show you the appropriate UI based on the things you asked for. Truly, our North Star is to like merge all these things so that users don't have to make any of these decisions. The separation is really more about how can we meet people where they are as much as possible in terms of the products that they use, in terms of their familiarity with concepts and make sure that we are enabling everyone to take advantage of working with agents, which has transformed entirely the way every single developer works, we should do the same thing with KnowledgeWork.

33:29Lenny Rachitsky:It makes sense. There's this like, because things move so fast, like I imagine somebody's like, let's try Codex. This is going to be awesome. And then it takes off and there's 10 million monthly active users. And then they're like, wait, what are we doing here? We got ChatGPT, we got Codex. So it makes sense why these things, you know, like it's not going to feel obvious and perfect for a while because you have to kind of adjust as things work and things don't work. And there's these kind of transition periods of like, OK, cool. Now let's get people moving towards this vision of the super app, let's say.

34:01Lenny Rachitsky:OK. I imagine one of the hardest parts of your job is balancing this hundred billion MAU product, ChatGPT, maybe the most successful consumer product in history. with Codex, which is this new thing and other new things that you guys want to try. How do you think about that? Just, I don't know, just balancing these very innovative, fast-moving teams and products with this like, okay, there's a billion people using this. We can't change this dramatically. Yeah, I think one of the most interesting things here is that one of the goals of launching work in ChatGPT web and launching it in the desktop app and bringing these things together was to look at those billion people who are using chat GPT and bring them more and more of the agent's power.

34:51Like if you think about the first era of AI products as chat, the second era of these products is clearly working with agents and, you know, primarily has been coding agents. We'd like to bring it to more domains, certainly like knowledge work. And that is part of the goal of giving all these billion chat users the power of work. Certainly the product challenge that's on us is how do we not only bring it to them, but make it natural and easy to adopt, make it not a decision they have to explicitly make. We can just help them do the right thing. How do we decomplexify it so they don't need to think about things like harnesses, which feel like crazy concepts for a billion consumers to understand.

35:33So that is primarily the challenge. And then of course, like that third era that might come soon is how do you work with a persistent coworker who is able to get things done with you, maybe collaboratively with other people? And so part of this challenge in the near term is we're introducing agents to a billion people who may not have experienced them yet. How do we do so in the easiest, most natural and most usable way possible? Certainly there's a lot more for us to do to make that happen. But part of this is also a lesson I've had maybe contrasting like pre-AI era or past product experience with this one, which is at previous companies, like Polish was king, getting every UI interaction or getting every little thing completely right was way more important than shipping something early because time didn't make as much of a difference in terms of the outcome.

36:34And so as such, like if every corner wasn't like perfectly polished and everything was wasn't exactly correct, you might as well not ship it. But I think what's been really compelling and interesting about this era and this product experience has been getting the product in the hands of users when you have so much conviction that, hey, it's transformative, like is way better than perfect. And that urgency and that introduction of that product is so important. So we have a lot to do to make it more usable and easier for chat users, certainly, especially for folks who are not maybe even using it for productivity, but using it for like consumer tasks.

37:14But yeah, done is better than perfect. And we have so much more to do. Yeah.

37:20Lenny Rachitsky:I remember when this app first launched, there was a lot of comments about the confusion and seeing how quickly the team iterated and respond to the feedback is exactly what I'm hearing here is get it out, figure out what the hell's, what's not working, how people are using it, iterate quickly. Feels like that's the model now. And of course, there are things that you can continue to iterate and get that feedback prior to launching. And there's a lot that we can and should always do better. But iterating as quickly as possible and listening to the right signals is regardless of whether that's pre-launch, post-launch, ideally pre-launch is the key thing.

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39:07Lenny Rachitsky:The I.O. card is issued by Patriot Bank and a member FDIC pursuant to a license for MasterCard International Incorporated. Something I've noticed on Twitter is there's definitely been this vibe shift from Claude Code to Codex in the past few months. used to be everyone was cloud code this cloud code that more recently it just feels like people are leaning now towards codex at least on twitter which is a bubble but it's where a lot of tech people are i'm curious what's shifted internally in the past i don't know three to six months other than tara joining and shaping up the ship uh is there anything that you can share that's just like okay we figured this thing out we shifted this we cut this thing what what helped shift the vibes and help Codex become as successful as it is becoming?

39:53You know, I think there's like this phrase, which is before enlightenment, carry water, chop wood, post-enlightenment, carry water, chop wood sort of thing. And actually with the Codex app, the team who initially got it up and running and were working on it were super, again, user-focused, tight iteration loop, really dog-fooded the thing, like mainlined the app. as much as possible to get everything right. Folks started to realize that was happening externally and on Twitter, and users started to really notice. But the team was always really focused on users, really focused on that iteration.

40:35And it was merely the, to some extent, like the market catching up that was the change. And that process has not changed internally. Everyone still constantly uses the app. everyone who's building it, obviously, as a developer, using it for development and is constantly fixing not only their own problems, but trying to listen to other people in the company's problems and user problems. Actually, what's sort of remarkable is that the mode of operating hasn't changed. It's always been the same thing I had mentioned earlier. Like, are we elevating our ambition sufficiently? Are we maximally accelerating progress?

41:11And are we great that users and folks on Twitter have noticed, but that operation, like that full credit to the team, like that hasn't changed.

41:24Lenny Rachitsky:What's really interesting about this answer is it's the very human part of it. It's you, it's Andrew, it's Tebow, it's the team just like being obsessed with the customer, the product. And it's not like AI was the answer. It's the humans that made the difference. Yeah, I'll give the team deserves like full credit here. Everyone on the team is incredibly thoughtful and independent and to the point of like there are you know many founders at openai like almost everyone on that team like the desktop team especially like acts like founders and cares about every piece and every detail and when they notice an area that should be better they go build it very independently and get the thing up and running and if it doesn't test well internally like people aren't using it if people don't find it useful They'll iterate on it and then finally like ship it externally.

42:15But that loop is full credit to like people on the team and individuals for making that happen.

42:20Lenny Rachitsky:Something you touched on is this idea of roles overlapping, this idea of like, you know, engineers are doing a PME work. You're doing probably shipping prototypes and building, maybe shipping to production. I don't know. Just it feels like that also creates a lot of challenges. I hear from a lot of people like, what is my job now as a designer? What am I responsible for? What am I not responsible for as a marketer? What am I doing? Is that something you notice? Is that something that you're dealing with? Just any thoughts along those lines? I think the thing I've always liked the most about working at startups, and sometimes I've started at a startup that actually grew into a large company, but largely primarily working at startups, is that there are very few boundaries around your role, that everything and nothing is your responsibility.

43:04Ultimately, you're accountable for success. actually like Stripe was very, very much this way where there are no boundaries around what a engineer could do versus a product manager could do versus a designer could do. Everyone could do anything. And so actually it kind of feels like I've always really loved that mentality. And now finally capability is catching up to that. But the thing I really care about is that someone needs to look after or have core accountability for, is this product being used by users? Is it something that people want? Is it high quality? Is it effective? And whether that person is like an engineer or a designer or a PM or whomever, like someone is the DRI.

43:48And then whatever work needs to be done to make that possible, you know, certainly people can pick it up based on their affinity based on their capability. But I like a team that doesn't really mind what the boundaries are between individual roles, but everyone's just sort of focused on making the outcome happen. The converse of this is I also really love like the craft aspects of like being a PM. Like there are so many aspects to PM craft that I know folks like Shreyas or maybe Marty Kagan or Shashir, Like all these people have really a spouse that I think are wonderful. And sometimes maybe some of these questions come from, wait, I so love the craft of my domain by taking this more fluid approach to teamwork and collaboration to get something done.

44:36Do I lose out on getting better and polishing my craft? And I truly don't have an answer for that question. I think it's like something we're all experiencing together, which is some pieces of our craft are actually getting abstracted by models being able to do it really effectively, maybe better than than individuals can. And your craft moves from being able to do that very specific task you did in the past to now applying it to some other part of the product or the discipline. But yeah, that is still a question I'm thinking about, which is how do I balance my desire to be part of a team and use these tools and feel so compelled by how effective one can be now with all these products, with my love of like the, yeah, it's really fun handwriting code for an engineer all the time.

45:26And one doesn't really do that anymore.

45:27Lenny Rachitsky:Yeah, that's where I was going to go. It's just like unbelievable how different the engineering role is now. Yeah. It's like you used to write code all day. That was your job. It was no longer your job. Yeah. And that happened so quickly. I see people mourn like the flow state of writing code manually yourself versus now what one does. But I think it is a, yeah, it's a tough transition. Yeah. And, you know, some people love it, some people don't. And that's a whole other topic. Kind of along those lines, something I'd like to ask people at the frontier of AI is, where do you think human brains will continue to be valuable in the future?

46:08Lenny Rachitsky:It's impossible to predict long term. Will we need humans, hopefully? But I'd say in the next, I don't know, next couple years, just like, where do you think human brains will continue to be most valuable? I think humans will continue to be the most valuable as a certainly as a like an entity of accountability. So who ultimately owns the outcome here? In some ways, you can think of your agent that you're working with as like your your report. ultimately who owns like what's what was the end product was it high quality was it the thing that you wanted it to do and say like that that will certainly remain a person at least at least for now and especially in industries and places that are highly regulated or require like a direct human interface like that that makes a ton of sense to me i think the human brain is also really valuable for expression.

47:00I'd mentioned earlier that analogy of software is not like real estate. It is more like a film where you could put money and a great film does not come out. Like the greatest films are not the ones with the biggest budgets. And given that there's a certain artistry and opinionation and expression in building software where you feel like there is some authorship by a person or a group of people. And that part remains to me so human. Like what you choose to build and how it feels, feels like such a such a human question. I also think the human brain continues to be valuable in like how we care for each other and relate to one another.

47:40That piece of my work has remained so human and remained actually become more important than ever. The part where you talk to other people on your team and collectively figure out how you can be enthusiastic about a area, how you learn and work together, how you elevate each other's ambitions. All of that feels and remains such a human thing to do. Yeah, I think the human brain will continue to be so valuable in that regard. That said, I can't predict what will happen with the models. But those pieces feel to me to be incredibly, incredibly human.

48:18Lenny Rachitsky:I love that answer. There's this idea that you talked about, this idea of this overhang of what AI is capable of and what we're actually doing with it. People are always like it feels like one of the biggest gaps is like, OK, what should I do with it? I'm curious, what are some ways that you use AI in your work that may inspire people like, oh, wow, I didn't think about using it that like there's kind of two buckets here. One is just like what's like the most how your PM job has changed most thanks to AI that you're just like, OK, now I use AI for this stuff. And then what's like is there any like super interesting creative uses of AI recently that you're like, oh, yeah, I should try this.

48:55One of the most exciting ways that I use AI in work is actually build sites all the time now. I don't know if you've tried building sites. I haven't.

49:05Lenny Rachitsky:Talk about sites. Sites is a really fun, amazing product. You can basically build a site, certainly in work as a presentational artifact, but I also build sites for literally anything. I built a site for the team as a game where we all played a game together using a site because sites have a database. You can build a site. I actually built a site because I went on a backpacking trip recently. I built a site of the route that like tracked the elevation of everywhere we were going. Everyone on our trip like inputted all their food. It was like super fast and effective. Sites kind of realized the dream of like malleable personal software that Alan Kay, you know, flagged in the 60s of like the true personal computer is one that has personal software.

49:48In some ways, sites are like the tangible way to make that possible. We had all once dreamed of like making personal software and certainly people with tools like Notion, et cetera, try with all these blocks to configure what that could be. But with a site, it is literally a prompt. I literally with a prompt say like build me this exact tool that I need to get this thing done. And it just does it. They're shareable. They can use like an auto update. You can use like internal data to build a dashboard, for example, with lots of metrics. and rather than like painstakingly laboring over some sort of like slide deck a site is just a way more dynamic surface for presentation how do you use a site do you have to do anything special you tell it make create a site in codex be like create a site that um is a i don't know isn't mafia game

50:38Lenny Rachitsky:for my team and it will just do it and like like i'm thinking capital s site but doesn't matter imagine it just knows what sites are so it's yeah because it used to be here's a here's some source code, go figure out where to deploy it. Yeah. And what you're saying here is it just hosts it for you and immediately you can use it. You can choose whether it's public, you can choose whether it's with your team or choose whether it's private to you. They're great. They've the easy reach of building a site all the time has changed what my day to day looks like, which often in previous worlds used to look like creating lots of artifacts like dachshunds, cheats and whatever it might be.

51:13Now I just make sites all the time.

51:16Lenny Rachitsky:And you could do that through, I imagine, work or can you do it through all the surfaces? Codex, work, chat, GPT chat? You can do it through work. You can do it through Codex. You can do it in the web. You can do it on mobile. You can do it anywhere. I just kicked off a create a site about Tara Seishon. Great. Is that your pronounce your last name, by the way? I haven't asked you. Tara Seishon, like station. Seishon. Okay, cool. Okay, cool. Sites. Okay. Any other quick tips while we're on this topic for people? That was a great tip because I don't think a lot of people know about sites. That's very useful.

51:47Yeah, sites are awesome. The other thing I really love is using visualize in Codex. Have you used slash visualize?

51:53Lenny Rachitsky:No. Oh, slash visualize is incredibly exciting. Ask, you can just do slash visualize, visualize my chat UBT usage until now or something like that. And it will pull in like all the things that you've done and create like an amazing visualization for it. The number of times that I've been thinking about how do I not only pull in a bunch of charts and data, but present them in a way that is understandable and useful for the story I'm trying to tell has been infinite. And Visualize makes that incredibly simple. It is like surprisingly delightful to use Visualize. It's just like, it's just, these are such good examples of there's so much power here we don't even know about or understand.

52:31Lenny Rachitsky:And that's the challenge you have here. Help us know all these things. That's why podcasts like this are also useful. Can't put it all in the product. I'm going to go in a totally different direction. I want to talk about writing. I asked Brie Wolfson, who knows you well, what to ask you. Funny enough, she suggested questions for the previous podcast conversation I did with Adam Ward from Cursor. So she said, okay, you should ask her about writing slash thinking. A Tara brief is iconic. Help us understand just what makes your writing, your briefs iconic? And any tips that might be helpful for people that are maybe trying to get better at writing and writing documents?

53:12I really strongly believe that I do two types of writing at work. One is writing as thinking, and the other is writing as reporting. Writing as thinking is me writing a brief about why we should build a certain product or why we should take a certain strategy or why maybe a spicy take. But writing as reporting is things like, oh, I'm summarizing the status of what our team has been up to this week and I'm sending over a report about it. Or this is our plan for this particular launch or announcement or something like that. Writing as reporting, I happily automate or I use the models all the time to make that as simple as it can be.

53:49But writing as thinking is something I never will automate. I really strongly believe that the at least for me the act of going through and outlining something turning it into some level of prose cutting it and editing it continuing to iterate on it is one of the most important steps for me to get my ideas in line I think most people actually will paint with a really broad brush like I will never use them use the models for writing or I I always use the models for writing. And actually to me, like both those broad brushes are wrong. I think you should use the models as much as possible for writing as reporting.

54:29And in as much as you think with writing, as I really do, and I think a lot of people do, you should not use it. You shouldn't replace your thinking with it. But my briefs in the past, because I write so much as a way of thinking, is that I will write a, I will like go into a hole, write a brief for a new idea or a product, spend a ton of time refining that particular idea, shop it around with people and have them attack the ideas in it as much as possible and poke holes, make it stronger, and then take it to the next person and do the same thing. And so at Stripe, this is something I did many, many, many, many times over, whether that was like to kick off a new product area or to suggest a big change in direction or to analyze a problem and suggest like a path forward.

55:20And Stripe is incredibly oriented as a writing culture. And there are many people like Jeff Weinstein who are also very into writing and sharing briefs at Stripe. Stripe is one of the few places where like a brief will go viral inside the company. And so writing as thinking there is really prized. And that's where I did like the majority of that writing work. At OpenAI, I think I still write as thinking all the time. But the shareable artifact here is not really a long doc or a sort of proof of work in that way. partially because times have changed and a long doc is not a signal that you thought through something because you could easily produce a long doc that indicates that you haven't.

56:11And so actually the point, maybe one of the biggest changes I've experienced personally in my day to day, which has been a big, maybe jarring change, is I used to think in a document and then do some translation of that into a presentational artifact. And that would be my indication that I had thought through a problem and this is what we're going to do and the team moves in that direction. And now I am way more on mocks, not docs or prototypes, not docs. And if I have something that people can try and interact with or even better, I have like results where we tried this, we ran an AB, here's like the results.

56:45This is why I think we should like go in this direction. That is a way better communication tool than like the doc itself. And so I still write hundreds of docs all the time, but I do it for me. And I no longer do it for other people, really. Like that no longer is the best way to talk and communicate. That is probably the biggest change I've experienced personally in this era versus the previous era.

57:10Lenny Rachitsky:That is so interesting. I really liked your tip of getting tons of feedback on a doc. Like, you know, it sounds obvious, but, you know, you can get to an iconic doc slash brief by just cheating almost and getting lots of feedback on it as you're iterating. Yes. To make it stronger and stronger and stronger versus like, cool, here it is first time and it's really going to be amazing. I honestly had a manager who told me that the right thing to always do is write a doc to 70 % completion and then take it to the people that you need buy-in from and get it from 70 % to 100%. And that still is like a thing that I do all the time because very few great people want to interact with like a perfectly polished, finished idea, like a perfectly polished idea.

57:51Their new ideas just like bounce off of it versus something that has more crags and more rough edges that they too can polish with you together. And I think that bringing people into the process that way, where a doc is an underlying artifact for that, is one of the best ways to collaborate that I found.

58:08Lenny Rachitsky:How do you think about AI brain rot and starting to over rely on AI? That's just a challenge everybody's going to have. Why not use this magic to help look at something? And then we start to lose our ability to read long documents. Is there anything you do that you are trying to avoid that? Yeah, I think this writing is thinking discipline is one of the main pieces that I employ in my day to day to make sure I'm not overly atrophying my thinking abilities. I think I will, again, outsource all writing is reporting as much as possible to the model. But writing is thinking I have to do myself. And I have this personal belief that if I'm going to make someone read my document, I have to at least read it first that number of times.

58:57Or I think about this in meetings, too, that if I'm going to call a meeting with a set of people, I need to have prepped the collective amount of time that people are going to spend in that meeting before the meeting. And so when it comes to keeping my thinking sharp, I do that writing for the document myself first and make sure I've invested the collective amount of time I expect people to read it, at least in writing it and producing it. And I don't really rely on the model either for polishing my prose, which I don't think it really does. or especially not in like generating the first version.

59:31But I do, of course, have the model help me a lot when it's like summarization or like translation of content from one format to the other all the time.

59:41Lenny Rachitsky:So what I'm hearing is write the idea, the brief, the plan yourself as a human, write it yourself. Don't start with AI. And even don't use it to improve on the writing. Just keep that all human. Yeah, at least for me, I start myself and I end myself. I might use AI in the middle to research specific elements or drop in some data or go pull some data or help me. Or push back on some ideas. Yeah, push back on some ideas. But start yourself, end yourself with a piece of writing, and that doesn't deteriorate your thinking. Okay. One last question. I want to ask you about Sutter Hill. You had this very unusual career step.

1:00:21Lenny Rachitsky:You went to your PM, PM founder person, and then just like, okay, EIR at Sutter Hill Ventures, which is an iconic VC. People can look it up. A lot of amazing companies came out of Sutter Hill. It has a very unique way of approaching founding where basically they incubate companies. Snowflake is an example. What was that? What was that about? What did you learn from that experience? Sutter Hill is an iconic firm and is intentionally a very illegible firm. Like if you go to the Sutter Hill website, you will see nothing on the website. It is a firm that doesn't operate loudly. It tries to operate as under the radar as possible, as modestly as possible, yet is somehow responsible for some of the most iconic successes that Silicon Valley has seen.

1:01:06And they have this very unusual incubation model, which Mike Spizer, who is one of the amazing partners there, started and has rolled out success after success. I think the thing that was most iconic to me about Sutter Hill is that people look at finding product market fit as a dark art or building like a tens of billion dollar company as a dark art. Like, oh, it's luck. Oh, it's chance. Oh, it's all these like things that must come together. Yet Mike Spicer has done it multiple times. And so there is there is like clearly a way to do it. There's clearly a roadmap for making that possible. There is a set of things one can do to get this repeatedly.

1:01:47It's not just luck. It's not just a dark arch. There is a there is a playbook, as it were. And that playbook lives inside of the firm Sutter Hill. And they have figured out how to be right a lot in terms of like calling shots and making bets. And they've learned how to be right a lot in terms of the daily compounding things that one does to create a successful company. Whether that's how you set up your enterprise sales team, how you position your product, how you like build the initial founding team. The recruiting at Sutter Hill is like an unparalleled excellent thing. They have a secret tool called Reticle where they have a map of, you know, everyone that they've interacted with and the 10 best people that those people have interacted with that helps them be so, so effective at this.

1:02:36So I went to Sutter Hill because in some way my career has been about how do I try to find product market fit as many times as possible, whether that was as a founder or in starting new products at Stripe or in like joining a startup like Watershed. And so Sutter Hill is a place where they've figured out how to find product market fit on B2B products. And I wanted to learn what I could from them.

1:02:56Lenny Rachitsky:What'd you learn? What's one thing you took away from that experience other than they know how to do it? They definitely know how to do it. I think one thing that was very surprising to me that I learned there is that product market fit is sure important, but actually I really underrated product marketing fit. The idea that the way you talk about the product and the way you market it can proceed actually even building the product. It should probably come from some sort of bringing together of understanding the technology deeply and then understanding the enterprise sales process. And then that product marketing fit, that narrative, that positioning is actually even before you build a product experience, the right thing to test.

1:03:35So you should go pitch 100 people, figure out how to refine that pitch as much as possible, get the marketing narrative of why this thing is transformative right. And then and only then go commit the, OK, this is exactly the product shape. And Mike Spicer is like unbeatable at this art. Previously, I'd always kind of underrated PMM work. I was like, oh, it's whatever. Like it's the glue between these functions. It's fine. And then I realized how transformative that work done excellently is to a company's outcome. And in fact, can be the element that makes a company successful.

1:04:12Lenny Rachitsky:I so agree with that. Positioning. We talk a lot about that on this podcast. okay i'm gonna show you what uh sites got created real quick it was running while we were talking check this out look at this oh man i was like as like make it more awesome and it made it more awesome multi-product beautiful look at this this is like a design look at you got quotes big conviction small teams it's true the buyer how do you feel about this being your website your new website i do think that the picture of me at maybe 19 years old at the top is really funny but yeah otherwise i love love the site okay it's looking good i think that was that's my that was my badge photo from stripe oh wow amazing i love that it built i already unshared it but i love that it built the whole like little thing it's around your head so cute uh tara is there anything else that you wanted to share anything else you want to uh touch on before we get to a very exciting lightning round yeah one thing that we've been thinking about a lot in product building especially with chat GPT work in this new era, is how knowledge work and coding are actually fundamentally different.

1:05:17And one of the surprising things we learned as a part of that is that coding is so output oriented that when you ask it to do a coding task, you can verify whether it did the task correctly or well via tests. You can try it out and see if it works. There is a way to validate it based on the output. But knowledge work is different in that I can't simply look at the deck in the end and see the numbers. Oh, it's like 90 % success or whatever in the deck and actually believe that. I really need to think about the process and the inputs and the reasoning and how it went along the way. And so in terms of how that looks in the product, like a lot of work that we have done and have to continue to do is continue to adapt the product to knowledge work, which means way more focus on making ChatGPT your collaborator, allowing you to see all the in-progress work, see its citations and inputs, help you go on the journey with the model to get to that end output such that you know in the end, oh, wait, this thing is right.

1:06:21This thing is good. This thing is useful. And that shows up certainly in the UX of the product quite a bit, but also should show up in things like the reasoning in the chain of thought. Like, should you see more citations along the way, for example, of how it got to that end state in that data. Is the surface of a thread which is so suited to coding the right place for you to see all of that for knowledge work as well? There's so many big, important product questions. And so as we think of maybe bringing in human collaborators into your work, we also need to think about how we can make the model more of a collaborator with you as you get things done together.

1:06:57Lenny Rachitsky:That is such a good point. imagining an exec meeting where you're trying to pitch the exec on here's what the plan is here's the six here's what i think we should be doing so much of that is helping them see here's the work i did to get there here's all the steps and and so it makes sense that you need the ai to show you that same sort of uh work that it did the proof of work essentially versus engineering we're like okay i don't need to know all of the little architectural decisions you made just what does it look like? Is it passing all the tests that we have? So that is a really good point, just how different those two models are.

1:07:34Lenny Rachitsky:And also there's like the context. Does it have the context it needs to do the thing that you want it to do? Does it know, does it, can it see your email? Can it see all your Notion docs? Such a good point. So I see the challenge in your job. You make all this work as one product. Tricky, tricky. Amazing. Anything else before we get to a very exciting lightning round? Yeah, let's jump into it. With that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready? Yes. What are two or three books that you find yourself recommending most to other people? One book I really recommend to people is Barbarian Days by William Finnegan.

1:08:10I don't know if you've read it. It's about a life of a man who is a New Yorker reporter, but how he fell in love with surfing as his passion. The thing I took away from the book is that one can be deeply passionate and dedicated and have something be your life purpose without you being good at it. And it is about the art of like falling in love with surfing and his striving for excellence and perfection whilst knowing that he will like never reach it. It is such a compelling and transformative story for how I think one should continue to live our lives. I really, really love that book. Another book that I might recommend as a book that people should read.

1:08:55I really love Anna Karenina. I've been rereading the classics lately. And I love Anna Karenina because it's like a book of layers. And I think that a huge part of what we're going to have to do in this new era is like transform ourselves or like take ourselves on a journey to do different things than what we were used to. And when I think about that book. I think about when I was 13 and I read it, I understood basically the plot. When I read it at like 17, I understood the European history dynamics and like the class warfare. And then when I read it at 30, I was like, oh, this is like a story about like a woman and humans.

1:09:32And it just reminds me of like growth and that it is possible to look at the same thing through multiple different lenses as you continue to grow, which I think is kind of the challenge that's ahead all of us, ahead for all of us as we consider our careers as well.

1:09:46Lenny Rachitsky:It's interesting on both these, like I could connect to AI in the time we're living in now too. I also recently read Anna Karenina. What did you think? Earlier this year, amazing. I've never read it before. I saw it on a book list of like, here's what the smartest people in the world have read. And it's like a whole list of books. And that was one that I hadn't read. So I'm like, I got to read that. Yeah, it was amazing. Someone gave away the ending, which kind of made it less like surprising. I don't want to give anything away, no spoilers. and I also felt like it was very long but now I'm reading The Power Broker which has set the new precedent for a long been reading it for half my life at this point I love The Power Broker another thing I highly recommend to people is if anyone follows the substack like Simon Hazel's substack where he does a slow read of important books so he did one of War and Peace and he's doing one of Wolf Hall I think or he did one of Wolf Hall which is the Hilary Mantel book like take it chapter by chapter And that's like the only way to read something like The Power Broker or War of Peace or even Anna Karenina.

1:10:46It's like chapter by chapter.

1:10:47Lenny Rachitsky:Speaking of that, there's someone, I forget who, told me this. There's a 99 Press Invisible book club breakdown of The Power Broker where it's 13 episodes, an hour to each. And they go through a couple chapters of the book, one at a time, and talk about it. And they have special guests like Pete Buttigieg and AOC and folks that lived in that area. And they talk about every, you know, the story. And it was so it's so fun to read and listen to their analysis of it. And then they have Robert Caro come on a couple of times. Whoa, that's amazing. Yeah. Hot tip. OK, we'll keep going with our very lightning round.

1:11:22Lenny Rachitsky:Favorite recent movie or TV show you've really enjoyed if you've had time to watch anything? Of course, I watched The Odyssey. I found it to be an incredible, incredible film. It is about AI as or my hot take is that it's about AI or Christopher Nolan's view on how AI transforms society. um which i i loved and i highly recommend watching the odyssey he is like the he's just an incredible director and has bridged artistry and commercial success in a way that i think no other modern director has like done i also recently watched the film rashomon which is the akira kurosawa film um that did for the first time did that technique of telling a story through multiple people's perspectives where you never know what was true in the end.

1:12:08Like that technique in film was pioneered by Kurosawa. And it reminds me what one can do under constraints. That film was made in like the 50s. It was black and white. They're like, you know, there's a guy holding the camera and yet it is so perfect. And it is such a tasteful, innovative, amazing example of creativity. and what I'm reminded of watching that film is like I have a hundred times the power and tools that he had making that film in my iPhone. And like, what's my excuse for not elevating my ambitions and making better stuff?

1:12:42Lenny Rachitsky:All comes back, ambition. On the Odyssey, I'm still trying to get tickets. It's so hard. I slept on it and now it's like impossible for like a month. There's no seats anywhere. Kevin Kwok got us tickets at 10 p.m. at the Metreon earlier this week. It was so good. Next time, call me. i mean oh man i have like bots running on it i have a person working on it i have a friend we're all trying to find it's amazing you're gonna love it and i can't wait to hear what you think after you see it if you agree with me that it is about ai and the collapse of morality okay no spoilers uh hopefully by the time this comes out i have seen it but if not if anyone has hookups please tell me and i'm trying to do like the imax full power matron sort of thing.

1:13:24Lenny Rachitsky:Yeah. Okay. Next question. Favorite or interesting AI product that you've recently discovered? If ideally not open AI product, but you can also go there if you want. Ooh. I mean, of course, my favorite AI product is China TVT and using cool sites and visualize stuff in codex, which is amazing. But outside of open AI products, my favorite AI products are or products that my friends make for me because now actually people can do that. I think that's so cool. I'm such a huge fan of like the cozy software movement where you like make software tools for like five of your friends and you guys use it together.

1:14:01And so I have a friend named Sebastian who made a really cool AI app that turns anything into a podcast and puts it in your like a little podcast app for you. And he also made a really great private social network for our friends and it's called Gats. It is exactly what I think the future should be, which is people should make software that exactly meets their and their friends needs.

1:14:26Lenny Rachitsky:What does Gats stand for? Is that some inside joke? It is not, or at least if it is an inside joke, I don't know it, but it is the place that I, it's like private Twitter maybe for like a group of, a small group of friends. And I learned the most interesting things on that product. It's like a WhatsApp but not. Yes, Exactly. The podcast app is so interesting, but I feel like the version that I would love is it's actually like podcasts in your feed of podcasts. Yeah. And then just new episodes get added of things you want to read or whatever. Yeah, that's what it does. It drops it in your Apple podcast feed.

1:15:00Oh, amazing. I want this. It's great.

1:15:03Lenny Rachitsky:Help me subscribe to this. For sure. Okay. Amazing. Okay. Two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life? Ooh, my life motto that I come back to all the time in work is actually Toni Morrison's three takes on work. Let me, like, pull it up really quickly. Amazing. Okay, it's four things. It's from her essay, The Work You Do, The Person You Are. The first one is, whatever the work is, do it well, not for the boss, but for yourself. The second is, you make the job. It doesn't make you. The third is, your real life is with your family.

1:15:40and the fourth is you are not the work you do you are the person that you are

1:15:45Lenny Rachitsky:i got tingles wow so good and i think that's what you have pinned to your um your twitter profile yes i remember seeing that so cool okay uh maybe we'll show that on screen as you're talking about that i love that uh i love that's a great way to remember something just stick it to the top of your twitter because every time i go to twitter oh there it is again uh okay final question uh You were a Thiel fellow back in the day. Thiel fellow, Thiel or Thiel? Thiel. Thiel, yeah. What an alumni group. Holy moly. So it's such a great idea and program. Any story from that time that might be fun to share?

1:16:21Lenny Rachitsky:Something that's like, oh, wow, that was crazy. I don't know. Any other Thiel fellow that you're proud of? Any other? What was the interview like? I don't know. Anything along those lines? Yeah, the Thiel fellowship was an inflection point in my life. I wouldn't be where I am without it. It maybe to the point of like, there are key moments where you can tell people to elevate their ambitions and they do, and that changes them. Like that was a moment where someone came to me and elevated my ambitions and said, no, you can do this. You don't have to, you know, take the path that you were on. And truly, I'm eternally grateful for them being able to do that.

1:16:54One of the Teal fellows that I get to work with all the time now is Ari Weinstein, who founded a company called Sky that was acquired by OpenAI. and prior to this he founded and worked at Apple for a while because they acquired his previous company. Ari is just one of the most creative thinkers I've ever seen and is truly the expert on what are all the cool things you can do on a Mac. And so Ari leads a lot of our computer use stuff at OpenAI and he's like shipped a whole bunch of great things for computer use. But yeah his his creativity and his like joy and what he does and his love of his craft really inspires me and like Ari is a cool guy um but I'm trying to think what it's like a good story from that time that feels uh as you think about it I'll explain the Teal Fellowship for people that

1:17:47Lenny Rachitsky:don't know this and correct me if I'm wrong basically Peter Teal is like a people shouldn't go to college instead they should just try building something that they want and and you get$100 ,000 to not do college and instead just go follow your ambition. Is that roughly correct? Yeah, that is. That is exactly right. And you're with 19 other people at the time. It was like 20 people every year because it's 20 under 20. And how many years did it go on for? Is it still going? I think it's still going, but I think it was like the constrained at the 20 number for like the first four or five years or something like that.

1:18:21Yeah, I think a really crazy thing that happened my year is that I was the second every year of the fellowship. They decided to make it all a documentary on CNBC. And so our whole my pitch for the fellowship, getting up on stage and presenting the idea I was going to do, all of that is unfortunately live on YouTube. So if you really want to see me as a 19 year old doing something embarrassing, it's there. Of course, one of the most amazing and successful people who came out of that batch of the fellowship is Dylan Field, who is not only an incredible talent, but also like a very kind person. And yeah, feel very lucky to be able to work with those folks.

1:19:03Lenny Rachitsky:Amazing. Yeah, it's interesting that Dylan's like the guy, I think everyone thinks of when they think of Teal Phillips. Yeah, yeah. What a brand. Okay, Tara, this was incredible. Is there anything you want to plug, anything you want to point people to? And how can listeners be useful to you? Anything I want to plug and point people to, maybe they should use the ChatGPT desktop app. They should use ChatGPT in the web and try work. It's like, unfortunately, a little toggle. They can toggle over to it and try out work. Ask it to do some cool thing. Ask it to build a site about you, maybe to start or ask it to make a little visualize block of your ChatGPT usage.

1:19:39It's a really cool way to start like experiencing the power of this stuff very intimately. And the list of use cases they can do from that, you know, are infinite. And I'm happy. Here's a better idea.

1:19:54Lenny Rachitsky:Here's a better idea. Ask it to build a site to tell you what you could do with work. Great. That will work. Solve all the problems. Okay. I interrupted you. I apologize. What else were you going to add or say? Yeah, my main plug is, yeah, go down with the TryTubT app, go use it on web. Even more transformatively, go try it on mobile, then take like a long subway ride or something like that or a muni ride. And when you pop out after having no service, the thing is done for you. That's the part that feels super duper magical. You're not like wandering around with your laptop open the entire time.

1:20:28You've finally got these things running in the cloud doing real work.

1:20:31Lenny Rachitsky:Yeah, that last piece I was going to bring up, but that's, I think, a really underappreciated element of the product today on mobile. And it's most, that's just a mobile only feature, the cloud piece. No, it's everywhere. It's everywhere. Okay, so amazing. So on your mobile app, you can go to JGBT, toggle work, ask it to do some work. And you don't need to actually have the, it's not running locally, it's running in the cloud. It'll go keep doing work until it's done and then you could chat to it. So like it feels like really simple, but that's a massively powerful thing. OK, anything else, Tara, before we let you go?

1:21:07No, that's it.

1:21:08Lenny Rachitsky:OK, thanks, Tara. This was awesome. Thank you so much for doing this. Such a pleasure. What a journey since the fellowship back in back in the day. I'll talk about that more in the intro. Yeah. All right. Well, thanks for being here. Thank you. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com.

1:21:40Lenny Rachitsky:See you in the next episode.