OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber

24:45It's like, what is my point of view? who am I building this for and why? And I don't know. I think like as AI becomes more and more, like better and better, for sure there will be an opportunity to always kind of stand out and push. How can you push that even further?

25:01Ian Silber:Yeah, that touches on a conversation I had with the PM of Codex. Asked him just why is AI not good at design? It's actually gotten better since that conversation, which was just like a month or two ago. And he had a number of reasons for it. One is just like, part of great product design is doing something new. And so if it's trained on all the most interesting websites today, it's just like, okay, but that's not interesting anymore. And the other point he made is like, AI researchers aren't innately great at design. And so they may not understand exactly what it takes to train a model to be really good at this.

25:36Ian Silber:Thoughts? What do you think it'll take to get AI to be much, much better at product design? I mean, the new thing is interesting, right? because I think that everything we're doing is trying to design something that hasn't existed before, right? You know, if you look at great products that have come out in the last, you know, 10, 20 years or whatever, right? It's like all of a sudden, you know, take the iPhone, we're designing for multi-touch, and that opened up like this whole new interaction paradigm, and there's no training data for that, right? You have to, you're kind of really trying to understand this new thing, right?

26:12And then you had something like Instagram that was like really embracing the sort of like the fact that everybody had mobile phones. And then Snapchat, I think, is another good example of great design and that it was kind of a maybe people thought strange sort of like interaction design. But it completely like flipped on its head the way people might want to communicate with each other. And to me, that that is like great design. It's like truly understanding, like, I, you know, the people that, like, people have this problem, or there's this unmet need, and I'm going to build it with this in this unique way.

26:50So yeah, I do think that there's that sort of like fresh, new kind of way. And then now with AI, it's like, we're designing, like, how do you talk to something that is, how do you talk to AI with your voice, you know, or how do you use an agent to like carry out tasks for you? It's like, yeah, there isn't a lot of precedent for this. And so I think that, you know, humans are able to kind of do a really good job kind of evaluating, you know, what good is and, you know, or at least kind of like trying a bunch of things and learning along the way with people. And so I don't know. But again, like all this stuff changes really quickly.

27:27It's hard to say. But I think I think there's a lot of reasons why having that human in the loop is going to be so important.

27:34Ian Silber:And kind of following that thread of the human in the loop, when you're hiring designers these days, what's kind of trending up in what you look for, what you think is more and more important in the designers that will be successful today, especially at OpenAI? What's trending down, if anything? This might be a luxury of having a slightly larger team. But if you're, you know, at our scale, you know, but even at a startup or a smaller company, I think this will still be true. I really believe in hiring a well-rounded team that has many different strengths. So I think it's important to have kind of like your handful of or the right ratio of sort of generalists that can kind of do everything.

28:15But, you know, we also hire like incredible visual designers or we have like a really amazing sort of brand team that helps us with kind of like the sort of maybe expression of our brand, both out and in the product or great prototypers or, you know. And so I think that rounding that out or great sort of product thinkers that are a little bit more strategic or people that are like really obsessed over like the very cutting edge of where these things are going. And I haven't found that one designer necessarily checks every single one of those boxes. I think people just naturally are, you know, drawn to certain things.

28:58And I think embracing that when you build a team is actually like, if you have the luxury of doing that, is really valuable. Okay, so that's my broad statement. But then as far as what we look for, we do definitely, I always tell candidates, we do not expect you to have a background in AI. Because again, this is evolving so quickly. but we definitely expect high curiosity about it and, and, and a high aptitude to jumping in and learning how, how, you know, how you're going to use this in your process, how it works and not just how to use in your process, but how, especially for us, like how you're going to create tools to enable more people to use it.

29:40Um, and so it's more about the curiosity, I think, um, is something that like we really push on, uh, or look for. And then, um, definitely prototyping, um, prototyping is something I've always valued in my career. Um, but I just think that, you know, it's become more and more accessible. And so that's something that, uh, I think really does stand out usually when we talk to, to candidates. And then I do think that, But yeah, just like having a point of view on where these things are going or just like any of the tools that people have worked on and really thinking that strategic thinking. I guess the last one on this is like systems thinking is becoming more and more important.

30:27important and especially as you're like in our world, it's interesting because we're trying to build, we're building the super intelligence that has all these different capabilities and we need to think more about the underlying primitives that we can build that can kind of build on top of each other. This is something that I think like Notion did really well early on was like, we're going to build these building blocks, right? And then like everything kind of is composable. I think that's becoming really important too, as you think about like, well, we don't want to build all these sort of one-off siloed experiences.

31:07We want to be able to build and ship systems that can build on top of each other so that, you know, when someone goes and uses our product, it feels like one cohesive, simple thing. And the model can reason about how it can pull these things together. So that like idea of like really understanding the system and thinking about that is becoming even more important, especially because it's kind of complex of all the things that it could possibly do.

31:31Ian Silber:This is the fifth podcast in a row I've done where systems thinking has come up as a skill that people are more and more looking for. And it's like so funny. I need a bingo card for systems thinking, but it makes so much sense. And I think it especially makes sense from the designer perspective. If we come back to just why my take on why designers are kind of frustrated and stressed right now is just, there's less time to do design the traditional design process things are just moving like engineers are shipping 5 000 prs a day and so to your point this idea of building blocks and design system language and and just a platform for people to build on feels incredibly important totally it's very hard but i um i i yeah it's like it's funny i've we've had these conversations where i'm like just do less like my encouragement has been do less they're like don't design if you don't have to.

32:23Maybe there's already an existing system or component or something that we can build on top of. Or maybe we don't even need this feature. We actually just need to kind of

32:34extend an existing feature. I think that's an important thing. And part of that is thinking outside of the bounds of what you're working on and thinking across everything, I think, is becoming much more important. And the speed, for sure, I think, is a reason why that's so

32:52Ian Silber:important right now just to follow that thread because that feels like a pretty big change in the design world there used to be this we had a podcast with uh she was head of design club code jenny when and she talked about this and i think it blew a lot of people's minds just there's been this traditional design process prototype mock test use research iterate okay cool ready for engineering build it iterate ship it and now there's just no time for that and so the role in her eyes has just moved to big picture planning and just like steering people in a good direction does that resonate how much is that has changed in the world of a designer i think that a hundred percent we we do work that way it's it depends i think for us it depends on like sort of what stage you're at in the in the uh sort of process or um you know uh how uh maybe how far along the product is.

33:44There are certain features for ChatGPT where we really obsess and we really spend a lot of time. We try a million things and we throw out, you know, we try a hundred things and we throw out 99 and we finally ship one. You know, the, like, or, like, the composers, like, changing every single day and we try many things we throw out. But, or, like, and you can take that for many different things within ChatGPT. and then there are other things like codex where you know I don't know I mean a super app is a good example where we definitely are just like trying stuff really quick I think that we really embrace building in public which is a different way of working but I think that like when you get comfortable with it is actually really gratifying or satisfying because you can try stuff and get instant feedback both internally and externally but yeah I mean, it is moving really fast.

34:44And I think it just depends, right? Like I said, certain things we really sweat the details and we try, you know, and we do tests, we do A-B tests, we'll do user research, and we kind of iterate and evolve a lot. And then other things we take big swings and then we learn quickly. But yeah, I don't know. I think you have to, like, I think the biggest thing is like embracing that the technology might change in like a month or, you know, and maybe a certain interaction or setting or whatever that you needed doesn't need to exist. or now a new one does need to exist or a new capability is there or the latency profile has changed such that you can like rethink this or whatever, all these capabilities are changing or the intelligence has changed.

35:36And so you have to be just like really quick on your feet and maybe not be so precious about it until it's at the point where, okay, this is kind of hardened. Like we don't think that this is necessarily gonna change tomorrow because of the technology. So let's make this the best it can possibly be. you know, like we're thinking a lot about how we should evolve, sort of really think about ChatGPT becoming like deeply embedded in like your personal life and how should the app feel. That's something that we're not going to necessarily design and ship overnight and just like put it out there. We're really thinking about that and we're trying a bunch of different ideas or putting it up on, you know, a whiteboard or, you know, we're doing some design in Figma, we're prototyping it, we're probably going to dog food a bunch of different ideas long before we ever ship something but that's a bigger project right and then there's other things where we're like idea to ship in like you know, four hours

36:37Ian Silber:This all makes sense. Essentially what I'm hearing is you pick your battles and you focus the design effort on the things that will be durable and not change. Exactly yeah, yeah. And it's hard to know what that is. Yeah. Yeah.

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37:58Ian Silber:Mercury is a fintech company, not an FDIC insured bank. Banking services provided through Choice Financial Group and Column NA members FDIC. So I asked a bunch of people that know you well what to talk to you about. And Joel Lowenstein, who happens to be the head of design at Anthropic is a good friend of years, which I love. And he said what he imagines the hardest part of your job is, is balancing the needs of the existing billion monthly active users of ChatGPT with the need to innovate and push and iterate and invent. And so I'm just curious how you just think about that. How do you find that balance knowing you have to cater to both sides?

38:37That's a great question. And it's a really fun part of the way we work. I think that we have vastly different audiences, like really, really different. I've never worked in this kind of quite a spread. You know, at Instagram, I spent eight years working at Instagram. We had a billion user or billions of users, maybe. I don't actually know what they're at now, but it was a lot of people. But the product was pretty simple and it was sort of, you know, a couple ways that you use it. We did think about like creators and, you know, larger accounts that have special needs, but this is like vastly different where you have someone who's, you know, using this to help them come up with the recipe to eat tonight or, you know, brainstorm their next haircut or something like that.

39:27And then there's somebody who's like transforming the way they're doing farming for their, you know, they're like, you know, helping to automate their farm in Japan or something, right? And it's just like the broadest spectrum ever. Generally, what we've seen is that we believe in this idea of this sort of capability overhang, where the product, you know, like vast majority of the people are getting a sliver of the true value that they could out of the bottle. That's not necessarily a bad thing. They're still getting tons of value. But we found that we make sure to focus on creating an extremely simple, streamlined experience for many, many people.

40:21And then we put all of the cutting-edge stuff. We also make sure to give that and make sure that's really accessible for the people that care. The challenge, of course, is not necessarily over-indexing and putting something that people might not understand in front of a billion users. But generally what we've seen is we can experiment early with the people that really care, and that's where we have our desktop app and we have Codex, and now ChatGP work is kind of stepping into a much broader audience, which we're really excited about. And eventually what we know, and we think about this a lot in design, is like things will truly become like for billions of users when they don't have to like think about a switch or a mode or anything like that.

41:08And so we know that like eventually it has to kind of get distilled into that main experience. But it is like a really fun thing to balance. And we have to think about like people that are using this for free every day to people that are paying us hundreds of dollars and lots of different needs. It's just a matter of sort of balancing. And as a designer, it does add a lot of complexity for sure to think to you really have to have empathy for every sort of different type of user. But it makes it fun for sure.

41:39Ian Silber:That is such a mind blowing point you're making about the spectrum of usage of ChatGPT and Codex. I didn't think about it that way. Like, is there has there been a product that has such a wide spectrum from just like what's this rash on my finger to building Salesforce? Yeah. And it makes it really hard to, you know, because a lot of it's so funny, like one of the big challenges we're always thinking about is this like blank box problem. Right. And people talk about this all the time. It's like, is chat really the final frontier? It's a terminal. It's, you know, glorified terminal. It is like some critique that that I think these chatbots get.

42:17And then it's like, OK, so how do you design something that can kind of shape shift into anything? You know, it's like maybe someone is coming here for image generation for fun or, you know, they're trying to generate a PowerPoint or, you know, so having this adaptable interface is like a really interesting design challenge. And it's like sort of uncharted territory because it can really like shape shift into many different tools. And it's this like incredible, so many different things and trying to figure out how to present that. And then thinking about, you know, we think a lot about like a novice user, someone who's sort of brand new to this experience, that we want to help them understand how this can add value to their lives or to their sort of professional work or whatever capacity they're using this in.

43:15And then we also want to like get out of the way of people that, you know, use this every single day and they use this as like a real workhorse tool. and so designing for that spectrum is something we have to think about a lot um but yeah it's

43:29Ian Silber:all a world of spectrums i guess there's a comment that kevin wheel your former chief product officer made on the podcast that has really stuck with me which is uh to your point people always diss this idea of just like it's just like a chat box why hasn't it ever changed from that even though it has but still it's kind of this chat box chat bot and he made this really good point that what is an interface that is very good at spanning a wide spectrum of intelligence it's actually just talking. If you think about humans, we talk to people of low IQ to very high IQ. We can all just talk to each other.

44:01Ian Silber:And it's actually a really good interface for packaging something that is increasingly smarter and smarter and smarter. Yeah, and I think we're seeing what's been really fun design space for us is, you know, there's two things we think about. One is like, how can we help you express your intent better, right? Like, we don't want you to have to think about being a perfect prompt engineer, but like, how do we even, one, teach you that, oh, this is something that the model can help me with, and then how do we make sure that we get, we sort of best understand what you want. And so, like, you know, we recently shipped some features where if you ask sort of an open-ended question, it can follow up with, you know, some follow-up questions that you can, like, just tap through an answer versus having to type everything out, right?

44:48Or another good example is, you know, so then once you actually ask it to do something, there's the chat transcript doesn't need to be purely text, right? We've seen these now evolve so far from what it was with when ChatGP just launched. You know, it's no longer just a pure chatbot. It actually has many features within that, right? So a good example is what we call writing blocks. You ask it to write you a letter or an email, and it now contains that email in sort of a block that you can directly manipulate, and you can type with it, and you can brainstorm, and you can edit little bits and parts of it.

45:25You can copy just that. And that has made that interaction much better, and we're seeing the same thing with image generation and creating special tools for that kind of mode. And I think that's where the UI is going to start to really continue to evolve is how do we make, if you come at this and you're a designer, maybe chat should be a T should actually really look differently, look different or have different affordances. Or you're, you know, a data scientist or, you know, you're using this to run your home, you know, like your personal life. Maybe it should really kind of work or look differently.

46:01So like understanding the context and giving you different affordances based on that is something that we're thinking a lot about.

46:08Ian Silber:In terms of the vision and future of where all this goes, I know this is always evolving. But is there kind of a sense of what the future of ChatGPT codex is? I know there's this idea of a super app. You talked about voice, this personal assistant idea. What's like a way you think about where this goes long term? I think that it will start to become more and more adaptive to, you know, all of the context of your life. I think proactivity is a big, untapped kind of part of the experience that we're really excited to think about. we're starting to see this with ChatGPD work now where it actually has pretty good suggestions based on your calendar or your Slack or these different sort of inputs and external kind of context.

47:01I think that's going to become more and more important or kind of shift the way you use it. I think voice, we just have a step change in the model that just feels much more natural. and again like you know I can only imagine how that's going to feel in two three years this will just get better and better I think people I do love interacting with chat GPT especially voice in like just I want to just kind of like really quickly say something and and then I think like its ability to kind of go sort of like not just from asking questions but actually doing things for you that's all going to change and hopefully all of this gets simpler as we do it too right When we think of the super app, I think eventually we really think of the idea of, especially for our broad consumer base, we do think that there should be sort of this one universal input that you can ask that knows when it needs to answer really quickly or it should be chatty or whether it should go and go off and do work for you.

48:04And so that's a big, like, excitement that we can get to is how can we continue to simplify the experience such that you shouldn't have to think about how this works. You shouldn't have to think about what model you're on or what sort of speed you're using. You know, that goes back to the balancing the different kind of, you know, personas and user needs. Like, of course, we want to expose that for the right people. But then we want to make sure that we can get a default experience that works great for most people. But yeah, I think it's going to be really proactive. I do think that we're going to get much richer input through voice and richer visual outputs that are more interactive.

48:45I think that you'll start to build more durable workflows with ChatGPT that you can use over and over. Right now, a lot of times it feels like you're coming and starting from scratch each time. And we want to really make this kind of the tool that you can use to help you with whatever sort of task you have.

49:04Ian Silber:This all sounds wonderful. I can't wait. Just kind of zooming out a little bit. And then I want to talk a little bit to designers again. But you're in this epic role right now. I imagine there's a lot of surprises as you entered OpenAI and took on this role. What's something you wish you'd known? What's something you wish you could whisper into Ian of day one to give you some advice? I mean, so many things. I think, you know, the first one is like, recognizing that we're really early. And instead, like, I actually was pretty intimidated coming to open AI, if I'm being honest. You know, I remember like, okay, interviewing, oh, no, I gotta like, you know, GPT-4 had kind of recently come out.

49:49And GPT, like, I, you know, I was like, what is all this stuff? Like I was using it and I was using the stuff, but I didn't feel like I had a true understanding of it. And to be honest, you know, I still have so much to learn. So that idea of like, you are early, we're figuring this out. Like that, I think I would want to hear. And the other thing like that I found, you know, and for me, this is more of like a personal thing. It's less about AI or anything, but I stepped into a really different role. You know, most of my career I've managed, I definitely managed before, but never like a scale that's growing so fast.

50:29And, and then at a company that is like, so different, you know, that the role was just every day was something new. And for a long time, I felt like I'm kind of like bad at this, or, you know, I don't know what I'm doing. and then I went and talked to friends that had led really large design teams or were in a similar transition as me and they all felt exactly the same or the problems that I had were not unique. And so this is, I guess, yeah, more personal advice. It's like, I think at any stage of your career, there's that feeling of imposter syndrome and like, what am I doing? I don't know how to do this.

51:13Finding people you can talk to that are going through similar things, you'll find that there's usually a lot of shared kind of challenges and struggles and having that sort of, whether it's a mentor or just like a buddy that is like impartial and out of it as was really helpful to me. And, you know, finding that community, I think has been helpful. So yeah, so like that, and then understanding that this is all so new

51:35Ian Silber:and evolving really quickly. That is extremely helpful to hear. Elena Verna had this really great post. I don't know if you know her. she's had a growth of lovable right now uh she had this great post called stop the ai confidence theater where she just kind of like all these people just keep posting all these things they've done with ai and all the ways it's changed her life and it's just they're killing it figured all out and really it's like very few people like very few of these things are actually that great and working and and it's just like stop stop pretending like this is actually you figured it all out i think it's much better to be humble about it be like wow yeah i don't know this is like changing quickly and like i'm just gonna embrace it and see where it goes yeah and that connects to what you said was a core component of people that are doing well right now people that are curious and just kind of poking around and trying to try these things and try them again because maybe it didn't work now it didn't work before it now works now a hundred percent yeah it's like being kind of like yeah every every model every new every new feature it's like the people that are poking around at those edges i found are just having such a blast doing it you And this connects to something else Kevin Wheel, former CPO at OpenAI, said on the podcast, which has always stuck with me, which is the model we have today is the worst the model will ever be.

52:48Exactly. I mean, that goes back to like when, you know, we, yeah, I mean, a new model comes out, what, every week? I don't know, every day? Like, if you count all the labs and everything, it's like, it's changing so quickly and everyone gets better. and I don't know. It's like, yeah, I always try to remind myself. It's like, you know, it must be like what, like, I don't know, building or designing in like early days of computers when like componentry was like really evolving really quickly and there were these drastic step changes and, you know, like you would hit these limitations and all of a sudden those limitations were gone.

53:33You know, I think it's the same, right? It's like these things just change and what was totally broken yesterday and now actually just kind of works.

53:41Ian Silber:So maybe to start to close out the conversation, say a designer is listening to this and they're in that bucket of overwhelmed, anxious, struggling, stressed, feeling uncertain about their future. What's one suggestion you have for them to help them move out of that state and into a better place? Just recognizing that it's a totally rational feeling and it's a great time to just try to explore and see what if I tried working, what if I tried, you know, rethinking about the tooling or what if I just embraced like, oh, maybe I should prototype more. Let me try, you know, try using these tools. But again, like recognizing that maybe it helps to hear that I think that we're all still so early and it's still changing and just kind of embracing that, like, just have fun with it and see where it goes.

54:36And I think maybe another thing I would say is really try to focus on the output, the outcome, right? At the end of the day, we're not here to build tool, like processes. We're not here to like build or token max or something like that. We're here to make great software that people love or great products or whatever it is you do. But that's the thing that really matters. And if you focus on that, you know, I think that you'll hopefully find that, you know, these tools can help you do that. But you still have a huge role in that as the person that's kind of steering and directing it.

55:17Ian Silber:So along those lines, I'm going to take us to a couple of recurring corners of the podcast. The first corner is AI corner. the question is just what's one way that you have found ai to be really useful in your job that maybe might inspire someone to use say uh jgbt or codex i was like a designer designer i mean nowadays i spend less time in the pixels um but i really do use it to kind of help me think through broader ideas um or maybe like you know i'll have an idea at night or something and then I'll just like quickly type it in and have it like prototype something. And it'll give me like an idea that I can go and talk to the team about and help visualize something.

55:59And so that's like a part of the design process. It's like early ideas or we're riffing through something. And I found that ChatGPT, whether it's ChatGPT work or Codex can like really kind of help me visualize that. That's been something that's been really fun. And then like there's more of the operation side, you know, it's like I have it now, like checking and making sure that like important Slack messages that I need to follow up with are summarized and giving me context before sort of like, you know, important meetings or for recruiting or for all like every part of my process, I use this to kind of augment the work that I do.

56:39Ian Silber:It makes sense. On the prototyping piece, just to give someone a tip on how to do this, are you opening up on your phone and firing off just like a codex thread? What's like the mechanic of doing this? Chat2T work has been incredible because it now runs fully in the cloud, right? And so the idea is you can kind of just be anywhere and sort of like talk to chat and have it like really spend the time and come back with like a really great artifact. So I found that it's been really fun to just be like, hey, you know, we're working on, you know, whatever this thing is. like whether it's helped me think through it or, you know, yeah, sometimes I will just have like some ideas that I would love to see, like quickly visualize before I even like take it further.

57:26And it will just like kind of help me like play with it and try it and stuff. And so that's been really fun. The fact that it's so accessible, right? Like I might not even be near a computer or I can, you know, I don't know, just kind of like have that flexibility. I think it's really fun. Awesome.

57:44Ian Silber:Okay, I'm going to take us to another corner, fail corner. Yeah. So the reason I do this, a lot of people, awesome, awesome people like yourself come on the podcast and all people hear is all the amazing things they've done, all the ways they've been really successful. And they don't hear all the times things didn't work out. And I feel like that's very important for people to hear. It's not always up into the right and success. What's a story of a time you failed in your career and what did you learn from that? I mean, there are so many times I think that, I mean, even at OpenAI, it's like I think that I've found that I've had to learn every step of the way, right?

58:25You know, when I first joined, I remember, you know, not really even like fully understanding like how I wanted to build a design team and, you know, not understanding how to hire or whatever. I mean, just I sort of felt like I was kind of failing every day, but just kind of like quickly trying to adjust and learn. I think that that, I don't know. I mean, that's like maybe kind of a cop out answer, but like really just feeling like every day I'm kind of like learning on the go. I feel that my whole career has sort of been that way and that I have never really kind of like planned like any one step.

59:09and sort of like quickly learning from your mistakes. I've shipped plenty of things that did not work out. And I've also shipped things that, you know, have worked out. But like most many times I've shipped or, you know, you try something and it's kind of a failure. And, you know, at Instagram we had flops and then we, you know, we'd like quickly move on. I mean, I worked on IGTV, which was like a huge flop. And then we shipped reels. and Reels was like, I mean, that's a good example because we just kind of baked in some wrong assumptions and we held on to a few constraints. But then we learned from that quickly and we were like, okay, actually, let's change that.

59:53And then we sort of redid it and then it became a really successful product. And I've seen that many cases of like, and I think that's helped harden me to the sort of critique and feedback of things because you know sometimes you get it wrong sometimes you try something and sometimes it is just about having to like put it out in the world and work through it and um and get the feedback and iterate and i think that that's like the most more importantly is not sort of what you shipped one time but how you react and how you um you know how you kind of like fix forward and how you continue to iterate and listen to listen to your users it's a very

1:00:34Ian Silber:common theme in this corner is just people's careers are like it's mostly failure along the way yeah definitely and so i think that's helpful for people to hear yeah uh okay before we get to a very exciting lightning round is there anything else you wanted to share that we haven't covered if i could distill it it's like i hope that this is just like a really fun time to build stuff build stuff and i hope that we you know as designers can be really adaptive and focus on making really fun, making really great stuff. And I, and I, and that I think that designers are just like, hope, you know, I think, I think great companies are seeking designers and seeking great, great design.

1:01:18And I've found that to be really true. There probably are going to be a bunch of companies that will be left behind because they haven't shifted. But I think that there's plenty of room for amazing, great design. And that's going to be more true than ever.

1:01:30Ian Silber:I completely agree. I'm very bullish on design. Yes. Well, Ian, with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready? Okay. Yes. All right. Here we go. What are two or three books that you find yourself recommending most to other people? I'm not like, you know, it's funny. I'm not like a big, big book recommender. I think like when people ask me, I do get asked about like books for design and I haven't found that many that really have stuck with me, like purely design. Although I will say I do love the design of everyday things. I think that's like such a classic.

1:02:07Ian Silber:That's the one. That's the one. It's not like, yeah, it's not a unique recommendation. But it is just kind of a classic of thinking about how we think about design. You have to read it if you're in tech or not in tech. Yeah. Awesome. Anything else there or should we keep moving? We can keep moving, yeah. Let's do it. favorite recent movie or TV show that you have really enjoyed? Okay. So I have one that actually is not a movie or TV show, but it's a, I'm in New York. I just saw a Broadway show called Maybe Happy Ending. Yes. I've seen it. Love it so much. Oh, you saw it. Okay. Yeah. It was so unique.

1:02:50Right. And of course it kind of hit home a little bit because it's about these like super intelligent humanoid robots and like, you know, but the production was incredible. The set design, everything about it, I thought was like so unique, which was, I thought, yeah. So if you have the chance to see it, I thought it was really, really good. I also just saw the invite, which was, I thought, have you seen it?

1:03:23Ian Silber:Yes, also love it. It's so simple, but so good. That's what I loved about it is it's like so simple. It's like, it actually is like a play, you know, and it's just four people in one kind of beautiful apartment and the set design is amazing. But like the writing, everything about it was like incredible and it's just kind of a wild ride. And knowing nothing about it, I thought it was incredible. Excellent taste, sir. I love both those so much. And the invite just came out. It's in theaters right now. Yeah. Next question. Favorite product you've recently discovered that you really love? I feel kind of like a typical Silicon Valley person recommending this one or something.

1:04:07But I did finally switch to an EV after having many cars for a long time. I got a Rivian. and I don't know, they just, I do respect the design a lot of just kind of how they've really made it. Just all of the, like, I think if, you know, probably Tesla's similar, but like there's a lot of assumptions that how operating a car should work have gone away. You just walk up to it and it unlocks, you know? It's like, you just like, you don't have to like turn on and off the car and it's cool to see like that evolving. Of course, I love, you know, at Waymo's are probably if I could like own a Waymo right now, that is the most magical experience in the world.

1:04:56And I'm waiting on bated breath for that to be broadly accessible for everybody.

1:05:02Ian Silber:Do you have a favorite life model you find yourself coming back to in work or in life? Not necessarily, other than I think like kind of trying to sum up like how I felt about all of this is like have fun with it. and like just try stuff. And, you know, I think don't feel like, I've never felt like you have to fit into a specific box and know that it's perfectly all right to be very fluid about the way you work or the way you think about things and, you know, be flexible and adaptable. But yeah, it's not quite a life motto, more of a vibe of just trying to like have fun with it and build great stuff.

1:05:42Ian Silber:I should shift this question to what's just like the vibe that's been helpful to you because I love that. It's very Sam Altman in terms of just you can just build stuff. Exactly. Yeah. Okay. Last question. Something I love about your career history. If you look at your LinkedIn, you were a designer at Groupon. I love that you were at Groupon and now you're heading design for essentially super intelligence. What's something you learned at Groupon that is maybe helpful these days building super intelligent AI? I love that. Groupon was a really fun company. Andrew Mason was like a really incredible CEO and just that he brought such character to the product.

1:06:28You know, it was like kind of a brand-led product.

1:06:35And, you know, like we had – there was like a comedy team. There was like a writer team, but they were like all comedians basically. And the product really did not take itself seriously, at least in its early couple years. It was like – it didn't take itself seriously. And I think that the brand really stuck out, right? You weren't signing up for Groupon because, I mean, of course, the daily deal was great. You were getting like 50 % off something. But people loved that email because it was like really well written and it was funny and it had character. And I thought that like early on the company did a really good job with brand and sort of embracing that side of things.

1:07:21and I think the other thing if I were to carry that forward is I found that every company that I've worked for has such unique DNA and the way you have to work kind of maybe changes a little bit based on that right because so I you know Groupon was run one way you know then I went to Instagram which was like this very design and creativity focused and Kevin's you know Kevin incredible designer and he sort of saw himself or like worked in that way with us which was really cool and it just created a different way of working and then you have like sam altman who's like a completely different way of operating and he's like uh you know i think you know and then an opening i'd be in a research lab and so learning that companies have these really different dnas and understanding how to sort of embrace them and kind of leverage that to your, like, or help kind of like empower that or like, I guess, lean into that has been something that I've learned a lot from moving around and getting the opportunity to work at very, very different companies.

1:08:26Ian Silber:And also just to add to that, it's also important to realize you're not going to change that. You're not going to like come in and change that culture because that's very hard, especially if it's very founder oriented. I think it's about finding like, oh, wow, like at OpenAI, you know yeah sure like we spent more time at instagram we definitely moved slower and i would say that we um we changed the product less and that actually worked really well for most stages of of instagram uh but i don't think that that would work in in the current stage of where we're at with open ai and that way of working of course i bring a lot to that and i think like you know at Instagram, we had this motto, like, do the simple thing first.

1:09:10And we always use that. We really embrace that. I've tried to carry that through to the way I think about building product at OpenAI. But that's not the only way I think of working. You know, sometimes it's actually not necessarily the right way to think about it. Sometimes we actually do throw some things out that we're still experimenting with. And so just being really, I found that having to be flexible and not necessarily trying to change it,

1:09:34Ian Silber:but trying to kind of like help round it out maybe. Ian, what an incredible place you have in the world right now just being on the inside of such cool technology, such cutting edge stuff that's happening. And I feel very fortunate that you found time to chat with us and share what you're seeing, where things are heading. Two final questions. Where do you want to point people if you want to plug anything? And how can listeners be useful to you? Where do I want to point people? I mean, I think that please, you know, I guess use, you know, have fun with the stuff we're making with ChatGPT and Codex and fire away feedback and thoughts.

1:10:13I'm on Twitter. I love to talk with designers about all sort of stages or not just designers, engineers, PMs, whatever. That's probably where I'm most sort of reachable and accessible. and you know how can you yeah I think to be useful again it's like I love when when people do show off the way they're kind of working and how that's kind of shifting and that's like a great way for us to learn how we can we can build better products both like internally at OpenAI but just as a as a design community like maybe showcasing a little bit more of our process because it is becoming a little bit more opaque like well how is it working just I think sharing that is like such a gift to the community.

1:11:00So doing more of that.

1:11:01Ian Silber:Also pointing people to your website, which I have here now. And I think my face is probably changing colors because the site has all these crazy colors. So if you go to iansilber.com, you could see this insane website. It's a personal website. Yeah, that's a deep dive into all of my past work. You can see there. And the trick is you'll have to discover the Easter egg where there's a game involved. That's right. See if you can set the high score. Yeah, the high scores are out of control. I don't know what's happening. Someone's found a cheat code. Ian, thank you so much for being here. Thank you so much for doing this.

1:11:36This was awesome. Super fun. Same. Bye, everyone.

1:11:41Ian Silber: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 lenny'spodcast.com. See you in the next episode.