Lenny's Podcast: Product | Career | Growth
00:56:40 · Lenny Rachitsky, Ian Silber
[00:56:40] S0: That 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 a Codex thread? What's the mechanic of doing this at night? [00:56:49] S1: ChatGPT Work has been incredible because it now runs fully in the cloud. And so the idea is you can just be anywhere and talk to chat and have it really spend the time and come back with a really great artifact. So I've found that it's been really fun to just be like, "Hey, we're working on whatever this thing is." Whether it's helped me think through it or sometimes I will just have some ideas that I would love to see quickly visualized before I even take it further and it will just help me play with it and try it and stuff. And so that's been really fun. The fact that it's so accessible. I might not even be near a computer or I can, I don't know, just have that flexibility I think is really fun. [00:57:43] S0: Awesome. Okay, I'm going to take us to another corner, Fail Corner. [00:57:47] S1: Yeah. [00:57:48] S0: So the reason I do this, a lot of people, 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 in success. What's a story of a time you failed in your career and what did you learn from that?
00:58:12 · Ian Silber
[00:58:12] S1: I mean, there are so many times I think that even at OpenAI, I think that I've found that I've had to learn every step of the way. When I first joined, I remember not really even fully understanding how I wanted to build a design team and not understanding how to hire or whatever. I sort of felt like I was failing every day, but just quickly trying to adjust and learn. I don't know. I mean that's maybe kind of a cop-out answer, but really just feeling like every day I'm learning on the go. I feel that my whole career has been that way in that I have never really planned any one step in quickly learning from your mistakes. I've shipped plenty of things that did not work out. And I've also shipped things that have worked out, but many times you try something and it's kind of a failure. And at Instagram we had flops and then we'd quickly move on. I mean, I worked on IGTV, which was a huge flop, and then we shipped Reels. I mean, that's a good example because we just kind of baked in some wrong assumptions and we held onto a few constraints. But then we learned from that quickly and we were like, "Okay, actually let's change that." And then we sort of redid it and then it became a really successful product. And so I've seen that many cases of... And I think that's helped harden me to the critique and feedback of things because sometimes you get it wrong. Sometimes you try something and sometimes it is just about having to put it out in the world and work through it and get the feedback and iterate. And I think that more importantly is not what you shipped one time, but how you react and how you fix forward and how you continue to iterate and listen to your users.
01:00:34 · Lenny Rachitsky, Ian Silber
[01:00:34] S0: That's a very common theme in this corner is just people's careers are like, it's mostly failure along the way. [01:00:39] S1: Yeah, definitely. [01:00:41] S0: And so I think that's helpful for people to hear. [01:00:43] S1: Yeah. [01:00:44] S0: Okay. Before we get to our very exciting Lightning Round, is there anything else you wanted to share that we haven't covered? [01:00:50] S1: If I could distill it's like I hope that this is just a really fun time to build stuff. And I hope that we as designers can be really adaptive and focus on making really great stuff. And that I think that designers are just like... I think great companies are seeking designers and seeking great design, and I've found that to be really true. There are probably 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. [01:01:31] S0: I completely agree. I'm very bullish on design. [01:01:33] S1: Yes. [01:01:34] S0: Well, Ian, with that, we reached our very exciting Lightning Round. I've got five questions for you. Are you ready? [01:01:34] S1: Okay. Yes. [01:01:40] S0: All right, here we go. What are two or three books that you find yourself recommending most to other people?
01:01:40 · Lenny Rachitsky, Ian Silber
[01:01:40] S0: All right, here we go. What are two or three books that you find yourself recommending most to other people? [01:01:47] S1: It's funny, I'm not a big, big book recommender. I think when people ask me, I do get asked about books for design, and I haven't found that many that really have stuck with me purely design. Although I will say I do love the Design of Everyday Things. I think that's such a classic. [01:02:07] S0: That's the one. [01:02:11] S1: Yeah, it's not a unique recommendation, but it is just kind of a classic of thinking about how we think how I think about design. [01:02:20] S0: You have to read it if you're in tech or not even in tech. [01:02:22] S1: Yeah. [01:02:24] S0: Awesome. Anything else there or should we keep moving? [01:02:27] S1: We can keep moving. Yeah. [01:02:28] S0: Let's do it. Favorite recent movie or TV show that you have really enjoyed? [01:02:33] S1: Okay. So I have one that actually is not a movie or TV show, but I'm in New York. I just saw a Broadway show called Maybe Happy Ending. [01:02:43] S0: Yes, I've seen it. Love it so much. [01:02:44] S1: You saw it? [01:02:44] S0: Yes. [01:02:47] S1: Oh, you saw it. Okay. Yeah. It was so unique. And of course it kind of hit home a little bit because it's about these super intelligent humanoid robots. But the production was incredible. The set design, everything about it I though was so unique, which was I thought... Yeah, so if you have the chance to see it, I though it was really, really good. I also just saw The Invite, which was I thought... Have you seen it?
01:02:47 · Ian Silber, Lenny Rachitsky
[01:02:47] S1: Oh, you saw it. Okay. Yeah. It was so unique. And of course it kind of hit home a little bit because it's about these super intelligent humanoid robots. But the production was incredible. The set design, everything about it I though was so unique, which was I thought... Yeah, so if you have the chance to see it, I though it was really, really good. I also just saw The Invite, which was I thought... Have you seen it? [01:03:23] S0: Yes, also love it. It's so simple, but so good. [01:03:29] S1: That's what I loved about it is it's so simple. It actually is like a play and it's just four people in one kind of beautiful apartment and the set design's amazing. But the writing, everything about it was incredible and it's just kind of a wild ride. And knowing nothing about it, I thought it was incredible. [01:03:52] S0: Excellent taste, sir. I love both those so much. And The Invite just came out. It's in theaters right now. [01:03:57] S1: Yeah. [01:03:58] S0: Next question. Favorite product you've recently discovered that you really love?
01:03:58 · Lenny Rachitsky, Ian Silber
[01:03:58] S0: Next question. Favorite product you've recently discovered that you really love? [01:04:02] S1: I feel kind of like a typical Silicon Valley person recommending this one or something, but I did finally switch to an EV after having many cars for a long time. I got a Rivian and I don't know, I do respect the design a lot of just how they've really made it just all of the... I think of probably Tesla's similar, but there's a lot of assumptions that how operating a car should work or have gone away. You just walk up to it unlocks. It's like you don't have to turn on and off the car. And it's cool to see that evolving. Of course I love... Waymos are probably, if I could own a Waymo right now, that is the most magical experience in the world. And I'm waiting on bated breath for that to be broadly accessible for everybody. [01:05:03] S0: Do you have a favorite life motto that you find yourself coming back to in work or in life? [01:05:07] S1: Not necessarily, other than I think trying to sum up how I felt about all of this is have fun with it and just try stuff. And 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 I don't know, be flexible and adaptable. But yeah, it's not quite a life motto, more of a vibe of just trying to have fun with it and build great stuff.