35: Brie Wolfson - Loving Attention & Ease in Craft

[00:00] A lot of the leaders that I work for, I think they're like fork shaped. Like you hear like T-shaped or something like, or just like broad or just deep on one thing. I think the leaders I like the most can go deep on lots of things. It's almost like vertical slices. Yeah, exactly. And it's just like, they're kind of scouring the land, scouring the land. And then it's just like, shoot, like deep on one really particular thing. And I like that quality in a person. I think it's like fun and interesting. And I like that quality in a leader because it means that kind of nothing can get by them. I think I am a hiker. [00:29] girl. I'm really proud of that. And I'm discerning. I won't hype anything. Yes. [00:36] And I won't lie to you either. I cannot... [00:39] fake it. We're talking a lot about loving attention and taste. And the real, I think the real damning thing is just indifference to everything. And I think I was a little bit that kind of teenager of like, I don't care. I don't care. I don't care. That's like the worst way to live to me. [00:53] Welcome to Dialectic, episode 35, with Brie Wolfson. Where to start on Brie? She wrote a piece recently... [01:01] uh, sort of about Kevin Kelly and sort of about herself called flounder mode. And it's a fun play on Paul Graham's essay founder mode. If you haven't read it and, uh, [01:10] I think it describes Brie well in that she has spent her career – [01:15] to some extent floundering and to other extents doing all kinds of unexpected, brilliant, and compelling things. And I know I relate a bit to her and to Kevin in the way she describes it in that piece as someone who has done a bunch of different things, and that's not necessarily a bad thing. Bree, she spent a bunch of time at Stripe where she worked on organizational culture and systems and planning,

[01:45] and love. [01:46] She went on to Figma where she worked on education, among other things. She started her own agency and helped companies and startups with everything from organizational culture to marketing and storytelling. And now she has two roles. She is the chief marketing officer at Positive Sum, which is known probably most well for both the podcast Invest Like the Best, hosted by Patrick O'Shaughnessy, as well as Colossus, their new publication, which Brie helped launch in the last year. [02:16] Neal Mehta, Matt Wong, Graham Duncan, and more. [02:19] And then Bree's other job, more recently, is head of employee experience at Cursor. She's doing both. I'm not sure how she does it all. And... [02:28] This is a conversation where we talk both about all those things I just mentioned, as well as things that I think are just distinctly Brie. We start with craft. Brie talks about what she calls a finger feel for excellence, this ability to get to the ground level of things, to really feel the quality of things. Obviously, that's something that resonates deeply with this podcast. We also talk about taste, which Brie wrote an amazing piece on. [02:58] and aspire to, but don't always necessarily know how to get to. And Brie is just so eloquent in thinking about and talking about those. We also talk extensively about organizational culture, about her wide ranging career path. She's writing a book for Stripe Press for people early in their career. We talk plenty about marketing and storytelling and words and writing. Brie's also worked with some just truly incredible leaders, people like Patrick Collison, Dylan Field, Michael Truel now at Cursor, and of course, Patrick O'Shaughnessy, who is someone I really look

[03:28] you. [03:28] Yeah, I just, I hope more than anything else that you find this conversation. [03:32] energizing because I think that is something that Brie does perhaps better than anything else. She is so energizing in so many different dimensions, whether it be on the ambition, company building, organizational side, or on some of the more intangible things, talking about how we can actually get to the quality without a name that makes certain things so craftful, so tasteful, so special. Before we get into the conversation, I want to thank Dialectic's presenting partner, Notion. If you missed it last week, [04:02] to Notion support, and I'm so proud to have them as a partner and a tool that I can speak about. Notion is a tool for your life's work. It's an AI-powered workspace that allows you to take [04:13] any of your ideas and expand on them, tinker with them, iterate on them and collaborate. [04:18] around them. I think that last piece is probably the most important if you work with a team or really just any kind of collaborator, even with dialectic, where I'm mostly working solo, being able to, whether it be in the research process as I'm prepping for interviews or afterwards trying to pull out the lessons and ideas that stand out most, being able to have an AI tool to help me synthesize, separate signal from noise and make sense of it all is so powerful. Obviously, [04:43] That is even more significant when you're working with a team or collaborator. And Notion makes it super easy to do that all in the same workspace. You can visit notion.com slash dialectic to learn more. And I hope you build something with Notion. Nothing would make me happier. [04:57] Thank you to Notion for their continued support, and thank you to you for listening.

[05:01] With that, here's my conversation with Bree. [05:04] Brie Wolfson. [05:05] We made it. Thanks for having me, Jackson. Thank you for having me. We're going to start. I actually couldn't find, I was going back, so I hope you actually did say this, but I believe you somewhere said recently, I think you could argue most roles should be craft roles. Hmm. [05:22] Why? And would you have said that 10 years ago? [05:26] First, I'm thinking about did I say that I was like, sounds like something that I would say. I think this is probably a few months ago now. And I think I've refined my thinking on this thing. And we're in the era of the IC. [05:38] That is totally different than a few years ago, which I think means that we're in the era of craft. [05:45] Like you better know your stuff if you're going to be operating today. So I stand by it. Yes. I said it. Good. Yeah. If you hadn't, I think so many other follow up questions I have might fall apart. Um, [05:58] Well, let's start with this. You have a quote. You say turpentine is what is really going on at the one inch altitude. It's not the generic cliched shape of it observed from 10,000 feet. Even the smartest, most thoughtful, best intentioned people won't get it right without the ground level perspective and visceral sense of what is. You talk about this like finger feel for excellence all the time. [06:22] I guess to maybe take that metaphor literally, [06:27] Uh, what are the biggest inputs towards developing that when most of us live lives, at least people in our world live lives that are so digitally intermediated?

[06:38] Yeah, I think probably the most reliable input, if you want to get that finger feel thing, is just time. [06:45] Hmm. On the thing. It's like so unsatisfying in some ways because we want to like shortcut. And I think that's the whole point of it. You cannot shortcut this thing. It's funny hearing those words. I think that was, that must've been from like 2018. Yeah. A while ago. Um, [07:00] before we've started really talking about this as a society. And it still rings really true, and it's still really hard to say. [07:08] to get [07:09] And I think you kind of just know it when you've encountered a person that's got this quality, especially about a particular thing. But, yeah, I think it's just time reps on the thing. [07:20] Thank you. [07:21] Ground level... [07:23] I think when we think of people who are [07:26] spend a lot of time in something and especially approach mastery or leadership or whatever it might be. [07:33] I don't know if everyone's mind goes to being on the ground level. If anything, it's like the more time, the more you rise. [07:39] And we'll talk more about like company leadership later. But like, I'm curious, it seems like you've been around a lot of people who have the like finger feel and the mastery and the like, [07:51] they're not in the ground level in a lot of ways and yet they, they kind of find themselves returning to the ground. Yeah. I'm attracted to those people. Like I, my friends joke that like competence is my kink. Um, I just like people that know how to do shit and it's like, [08:05] You can just tell, like, I'm watching you guys, like, tinkering with all of this equipment. Like, I can tell you, like, know what's going on with this stuff. And you're saying all these words I don't understand. And you're, like, touching all these dials. I can't tell what they do. But to me, that tells me that you're, like, in the details. You're on the ground level. Mm-hmm.

[08:20] And a lot of the leaders that I work for, I like, [08:23] I think they're like fork shaped, like you hear like T-shaped or something like I or yeah, or just like broad or just deep on one thing. I think the leaders I like the most, like. [08:33] can go deep on lots of things. It's almost like vertical slices. Yeah, exactly. And it's just like they're kind of scouring the land, scouring the land, and then it's just like, shoot, like deep on one. [08:42] really particular thing. And I like that quality in a person. I think it's like fun and interesting. And I like that quality in a leader because it means that kind of nothing can get by them. [08:53] Nothing can get by. They're like willing to go deep on just about. [08:57] anything. There's a former guest of mine, Stefan Ongo, who runs Obsidian. He has a post called Don't Delegate Understanding. And he's sort of talking about the ways that so much of modern society is removing friction and tempting you to just be like, ah, somebody else has it kind of figured out. You're talking about almost the... Yeah. If you're a company leader... [09:19] you can structure your company such that like you are briefed on anything or like whatever you're an organizational leader. You're the president of the United States. Like you can live on a brief. Yeah. Um, [09:29] And, you know, [09:31] I think it's more fun to go into the weeds on stuff. So Patrick Collison, Dylan Fields, like Michael Truel, like, [09:39] Something goes by them. They want to know more. They're like deep. They're like in the copy. Pulling them forward. Yeah. They're like... [09:45] my friend Jordan just joined to do recruiting at Cursor and they're like, she's having the time of her life because she's like, this whole leadership team is like on LinkedIn sourcing with me. Like, they don't want to look at the spreadsheet with like the summarized thing. They like want to be on LinkedIn. They want to see the whole back history. They want to see how they frame the descriptions. Like, I understand that kind of learning that like speaks to me versus like, okay,

[10:12] I got the snapshot. Yep, yep. I think you just know something different when you've seen the details. [10:18] Yeah. Yeah. I mean, you started the answer with time earlier and it's like there's no shortcuts to that level of like being in it, feeling it. It's so hard to describe to somebody. [10:29] like what's different if you just read the summary and the spreadsheet versus you read the whole Winton profile. It's one dimensional or not multidimensional. But until you've like [10:40] I don't know, until you've done that thing, until you've gone deep yourself, until you've felt the pattern match that happens when you do the LinkedIn scouring yourself versus you read the spreadsheet, I think it's really hard to make the case for that kind of thing. [10:52] On that note then... [10:54] Let's say you do it enough times to know what that feels like. Can craft be automated at some point? [11:00] Oh, I don't even know what that means. What would it look like for craft to be automated? Maybe my best... [11:06] uh, [11:07] the first thing that comes to mind would be [11:09] from what I've read about Elon, [11:10] Elon will make sure he understands the process, kind of what you're saying. He'll make sure he understands the process first, and then he'll automate it. Yeah, sure, sure. That's maybe an easy plug and play with the sort of robotic manufacturing idea. But in theory, if... [11:24] whatever, Michael and the cursor leadership team have been in the LinkedIn weeds enough. They have started to develop heuristics, maybe like... [11:31] again, can craft the autumn? It's very on the nose and sort of has a strong connotation. But to the extent there are... [11:40] dare I say, shortcuts. Maybe a better way of asking this question would be like, how do these people have time for anything if they are in the weeds on, what does that sequencing look like to go from like, I've really lived on the ground and now I need leverage or scale? Yeah, I'm picturing like Elon walking the factory floor or something. I've of course never seen it myself, but that is

[12:04] looking at all the parts, like touching on the things, seeing all the people. I do think that gets faster over time. Like I like Tammy's definition that I heard. I think it was from Cedric Chin that she talked about in your podcast, which is like taste is unconscious competence. So I think it like takes a while doing conscious competence before you reach what we started off by describing as the finger feel. But you have to kind of go through that process. I'm working [12:34] the product yet. And she's spending a lot of time shadowing SDR calls. And my sense is it's kind of just going to click and then she will be able to move. [12:43] off that. Um, but I think you kind of don't know until, you know, um, [12:48] like, [12:49] Similarly, a management philosophy that I have is to do it before you manage it. That's kind of what I was saying. Yeah. So I don't know if you can automate it necessarily. I think you can shrink the time it takes to get to that unconscious competence state. [13:06] have, I think, observed a pattern where this kind of get it-ness or finger feel is sort of contagious. [13:11] Like once you've had it somewhere, you sort of. You realize that the world is. Yeah. And you kind of. OK, you know that there's like pathways to it. You kind of know what it feels when you have it. So you can kind of like spin up faster on more stuff. I like that. It's funny. Like so many of the things that used to be craft in the world are like I want to talk more in the weeds about it. But like at a super high level, like the last two, three years has been like for people who do kind of things that we do.

[13:41] like [13:42] All of the things that used to be craft, like you can now press a button. Yeah. [13:47] Maybe it's just the ground level thing, but I'm curious, like, what is rattling around in your head as you think about, like, having all of this leverage and all of this, like, so many things that you can, is it about prioritization? Is it about, like... [14:00] disregard efficiency, disregard ambition, and just like choose to do the, have craft and the things that you enjoy. But like, I'm curious how you're feeling about it. [14:08] I think I'm lucky because... [14:11] I'm on Myers-Briggs, like super high P. [14:15] I like the process of doing things more than I like the end state. So in some ways, I'm lucky. I'm not satisfied to hit the button and make the website... [14:24] go poof. That's not exciting to me. So I'm lucky. [14:28] in this era in some ways, because I don't find it very satisfying to just get to the end really fast. Like I want to do things. [14:36] the grinds work. Yeah. So I think I'm sort of like, well, maybe lucky is me. Maybe it's the opposite. Maybe I'm unlucky that I like that work because I'm inefficient. [14:44] or something. But I quite literally just don't and can't. [14:49] work the other way. [14:51] Okay, it's a different question. [14:54] You've... [14:55] Talked a lot about how like... [14:57] you're not really a high volume output person, at least consistency-wise. Substack didn't really work for you. You also have referenced the Seinfeld, it just requires a lot of tonnage. Producing a lot helps you get to the best stuff. Patrick O'Shaughnessy says, if it works, it works fast. And so there's this tension between you're really high bar

[15:20] But also the fact that you like to be in the process, maybe that's actually compatible. And this notion that it's like the classic ceramicist story about the 30 bowls versus the one bowl. How do you square all that? Yeah, yeah. [15:32] I think this is probably the struggle of my life, creatively, is that I'm just a person that has to throw a lot out. [15:40] And it's funny, I wrote two novels, Once Upon a Time, and one of them I wrote between the hours of 5am and 7am in the Stripe Kitchen. [15:50] These were not the conditions for me to write a great novel. Maybe they were. You wrote the novel. I wrote the novel. I finished it. [15:58] Like it got published. I'm not that proud of it. And my mindset during that time was like, I need to be very efficient and I need to maximize the number of words in the draft that makes it to the final page. [16:10] I hate what I came out with. This is Rosie or the other book? The other one. Okay. And that was first or? Second. Okay. [16:16] And I hated that book. I hated writing it. I hated public. Like, I just hated everything about it. [16:23] It's like the scheduled discipline version of creativity. [16:26] I think the schedule I didn't mind so much. It was just the concept that I couldn't do the carving. [16:32] I was like high ratio of words in first draft to words on final draft. It's like measure once, cut once. That was a metric in my head. I was like, no wasted words. Like, I need to shrink this into a short amount of time possible. And I couldn't do this like... [16:48] exploring and like cutting and culling and that I like to do with my work. Um, and this is in between me and being prolific for sure.

[16:59] For sure. But I've just I think I will bump into some challenges like, quote, operating in this like age of sort of like the IC and being prolific and shipping stuff. And it's easy to iterate. This is a this is a personal challenge right now. [17:12] What do you think would cause you to have more tonnage? [17:15] Time. More time. [17:17] You mean output. [17:19] Uh, I, I guess, no, I, yeah, I'm, I'm more asking like, what would cause you to put out more within this existing a lot of time and have it, is there a version of that that would not. [17:29] net out. If you did that a bunch of times, would it just keep feeling like the book? [17:34] I'm not sure. It's funny because I'm I'm working on this book now for a straight press and I sort of been like in and out of working on it. And I'm realizing like how much of a full body experience it is for me to work on something this big. Like I need to be able to hold all the information in my head at once and like write parts of it and reference other parts of it. And if I'm doing too many other things at once, I cannot do that. [17:59] Yes. Work. [18:00] I like lose my own thread. [18:02] Um, [18:03] And I'm struggling with this because I want to be able to pick it up in chunks. [18:07] Like I want to be able to just like whip up this chapter and whip up that chapter and like have everything be discreet enough that. [18:13] It's easy to just whip out more pieces, but I literally can't. It just doesn't work. It breaks. [18:22] I've really benefited from forcing functions and constraints. And there are some people who are like, whatever, the... [18:27] the person who's like the midterm, the finals do at the end of semester. I'm going to do it halfway through. Ben Thompson talked about this with David Perel, where he's like, I don't know if I could write a book. Like I have to publish every day. Yeah. And so I guess as someone who's,

[18:39] Again, more of the like, I'll do it the night before or whatever, like building. One of the reasons the podcast is good for me is like I can show up today prepared or unprepared. Yeah. Whereas writing is a little more. And so I guess maybe one, not to push you, but like. [18:53] What if you had to... [18:54] a draft do you like is the way you get out of the first books sort of like measure ones cut ones is like [19:00] I have this highly rigorously scheduled set of deadlines, but that aren't final, like they're draft deadlines. It was so, it's funny that you're mentioning this. So a couple of weeks ago, the Stripe Press team is like, oh, hey, like, by the way, we forgot to tell you, but this like amazing editor is going to help you work on your book. [19:17] I was like, oh, and that was like my most prolific two weeks because I just like let stuff out that I wouldn't have otherwise. [19:25] Because I was like, okay, I'm going to get to a lot of self-editing too. So I'm sure that there's, I do my filter between like my own head and like what makes the pages like very strong. [19:34] I'm doing a lot of work when it gets translated from my brain into my fingertips, like onto the screen. And is that a good thing? [19:41] I don't know. I think I'm still learning about my creative... [19:45] process. But I something I do know is I know the difference between when I like something that I've produced and when I don't. [19:53] And if I don't like it, I'm happy to put it under the bed. [19:57] Like, I really don't like publishing stuff I don't like. Which is uncommon in the modern era, for sure. Most people default to just, like, rip the tweet. Yeah. I think I've been lucky in my career because I've been doing this a long time, and I've been rewarded enough times for sitting on my hands.

[20:13] Do you think that a really amazing editor makes you more likely to sort of just... [20:18] blob everything on the page? Or are you filtering more? I was telling Jeremy that he's made me a much lazier writer because he's such a good editor. That's cool. It is cool. It is cool. And to the [20:31] I think the, sorry to interrupt you, but I think the best version of creativity instinctively to me is probably actually like your max. It's sort of like the right drunk at it's sober, but between two people, it's like. [20:42] You were maximally unfiltered, and then it gets shaped over time. Yeah, I think so. I mean, I love being edited by Jeremy. He's an incredible... [20:50] editor, he sort of like understands the person on the other side, and he's just got away with words. So you're like, [20:56] wow, that would have taken me a while to come up with this turn of phrase. Like, thank you so much. And like, I do like that process. Like Michael and I at Cursor were jamming on something recently and he was looking over my shoulder and he was like, oh, you use like the actual thesaurus. Like you go to thesaurus.com. Like, what is up with you, girl? And I was like, I do go to thesaurus. I like that process of like, I just like it. I like doing that work. Yeah. [21:21] It's inside of all that, everything you just said is like, is actually making writing a little more collaborative or multiplayer, which is, it's very, usually very single player, I think. Yeah, yeah. [21:30] Yeah, I mean, all of my writing has seen, like, many hands and eyes before, like, [21:34] It's gone out. [21:35] But I'm very careful with when I send my drafts out and I kind of know what I want to get at each phase. [21:43] I think, obviously, we've been talking about craft and so much of what you do is craft, but you're also...

[21:49] Maybe whether, I don't know how much you like the term, but like you are a marketer and I think you're known as a marketer and you're known as an excellent marketer in a, maybe a world also that like isn't always the most thoughtful about marketing. Yeah. When does marketing like emerge naturally or at least naturally? [22:07] in this sort of compelling way out of craft versus something else. And like – [22:15] Why is maybe maybe the more important question is like, why is marketing? It's rooted in craft and substance. So important. [22:22] My general philosophy on marketing is people read bullshit pretty easily. [22:27] Fast. [22:29] So if you're going to bullshit, people will think you're bullshit. And like a good way not to bullshit is to just like tell the truth about what you're doing. And if there's. [22:37] Nothing interesting, but... [22:38] There, there's like nothing interesting. [22:40] there. So I think one of the reasons I like working for like craft focused companies is just like there is a story there. There's like something to say. It's not like lipstick on pings, like hand weavy stuff. There's just more. [22:53] substance. We were talking about this a little bit last night, sort of closing the gap between what is true and what is perceived about a company. I like when there's a rich [23:03] Or like a wide space. Yes. There's like a lot for me to do. So much potential. Yeah. Like I don't, I would never work for like an overhyped brand. That's like my nightmare. I always want to work for something underrated. And like clearly I've worked for very like highly rated brands. [23:17] brands like Stripe and Figma and Cursor. And also they're highly rated. They're highly rated. And yes, I believe they are still underrated. Like I think Patrick and Michael and Dylan are known as like incredible leaders. I think there's even more incredible stuff.

[23:31] there. And to me, that's like a very exciting space. And to take it back to craft, like if there was no story, if there was no great leader, it [23:39] if there was no [23:41] great craft, there's no story to tell, there's no work for me to do. That's boring. That's not intuitive because when people think about great marketing companies, they have Red Bull or Coca-Cola. [23:51] they don't even make the product. Yeah, fair. Maybe to put it another way, you were talking about Harold Ross, and you were like, he actually got the form right before he got the content right, and he was so obsessed about this. It feels like Silicon Valley, maybe to your point, is actually like, [24:08] All substance, no style, typically. [24:12] Like, is there a right balance in that? Like maybe, maybe, maybe a more important question is how can there be craft in both style and substance? [24:20] Yeah, I mean, I think now marketing is thought of as more of a discipline approach. [24:24] on its own. Like I've seen, I think we've seen enough examples of it working that we like want to hone that as its own. [24:30] craft. Like, it's not just... [24:32] telling the product story. Like there's something else to do in that conversation. Bringing the marketing team the night before or whatever. Yeah. [24:38] So I think we've like started to honor marketing as a craft more. I also think there's just noisier. [24:45] So it's a little harder to cut across. Sure. There's something like another thing you said is like all sub stacks look the same. And like there's something about tech that like because, again, there's so much substance. Yeah. It's like, yeah, like the style, like or even like the MySpace to Facebook thing. It's like just make it look fine. Did you have a Tumblr? Are you like? I did, but not like I wasn't super deep.

[25:08] The first way I ever coded was to update my AOL profile. [25:15] Yeah, I think I've always had an intuition that... Okay, another thing I like about marketing is you have to simultaneously be understood and known and also cut across at the same time. You're doing two opposite things at once. You want someone to understand, to see truth, but you also want to be noticed. Yeah. [25:31] And those really are pulling at each other. Yes. I think they are in tension. I'm like... [25:37] Like. [25:39] Red Bull is crazy. It's like really eye catching, but there's something known about it. [25:46] Like it feels like familiar to something. Yes. Yes. And I think I just enjoy that. I enjoy that. [25:53] space. [25:55] I like that. You brought up ICs. [25:58] earlier, um, [26:00] And I think much of this craft thing to me is sort of revolving around, or at least a huge implication of it, is what's going to happen to companies and organizations. [26:10] And I think as much as you're known for the craft marketing stuff, you're known for working with organizations and helping them grow and figure out what culture means and all these types of things. [26:20] So many places, Stripe, Figma, Cursor, et cetera. Before we get too in the weeds, though, our friend Tammy asks, what do all of these incredible organizations have in common? [26:31] This is actually a harder question than you would think it'd be to answer. When I started all this consulting work, I had that Tolstoy quote in my head, happy families are all alike and unhappy families are different. I was like, every company should work the Stripe way. And then I met Figma and I was like, nope, this company does not work the Stripe way and they are certainly excellent. So I think I'll have a cheating answer. I think the only thing these companies have in common is that they want to be great.

[26:53] Like they aspire to be great companies themselves. They are like turned inward on like understanding that they want the organization to be great. [27:02] And. [27:03] I think that's almost not that intuitive. Like, you know, you want to build a great product. You know, you want like customers to enjoy your work. I think it like takes sort of like an enlightened leader to understand, like, I want a great company. So I think wanting to be great, like wanting your people to be great. [27:20] Yeah, there's... [27:22] A subtle but very important shift from like... [27:26] we are building the product to building, like we are building the organism that can produce the product or, or, or many products on the IC stuff. Like, [27:33] the shapes inside of companies seem to be changing. Maybe back to the Tolstoy quote. And I want to talk about culture, but like, [27:40] I almost think of culture as sort of like the soft part of companies and called like the primordial lose. Right. Yeah. And, and there, but there's another part, which is like the hard, the skeleton or the hardware or whatever. Um, and like, [27:54] it seems very clear that, [27:56] independently of Cursor, but maybe especially with the example of Cursor, that like the shape, the atomic nature of work inside of companies is changing. [28:06] In a world where like most roles at a company are craft roles to go back to that first thing. And there's all this leverage and speed for the individual, um, um, [28:15] Are we going back to... [28:18] I think you have some quote where you say like a company going from the individual is the building block of the company to the org or the team being the building block of the company. Like, are we going back to,

[28:28] The individual being the building block again? I think so. [28:30] I think so. I think individuals have way more power in organizations now because they can do more work. [28:36] Yeah. [28:38] And so what do I mean by this? Like a recent project I took on at Cursor was to update the careers page. It's super simple. There's like, it's just like a few lines of copy on like a pretty blank text. It like integrates with Ashby, but it's like a simple project. [28:52] Set up. [28:53] My job was like the words. And I learned through this project that I had such a learned helplessness around like approvals and like having other people see stuff and like do stuff. [29:02] for me and like how many other people I think needed to be involved when like, [29:06] Really, only I needed to be involved. And you could just ship it. Yeah. But I had so much like... [29:13] anxiety about that, that I literally could not do it. Like, I can't tell you how many pings I sent. Like, is this copy approved? And it was, everyone was just like, ignore. [29:23] I'm like, but like, is it approved? Like it's going to go out like like many, many people see this page every day. I looked at the analytics. Does anybody else want to look? And everyone's just like. [29:32] "Were you thoughtful about what you did?" And I was like, "Yeah." - Trust you. - Yeah, but that was hard to deal with, honestly. [29:39] like after being brought up in this other kind of... You say dependencies kill productivity. Yes. Yeah. And I just, I could knock it out in my own way. I was just like left and right. Like I could have walked up to anybody sitting at their desk and be like, will you approve this copy, please? But like I could have, and I should have just gotten it out. But I like, I think this is a new way of thinking.

[29:59] At work. [30:00] - On the note of different shapes of companies, I can't remember if you actually worked with them, but you referenced Supercell somewhere. And Supercell's pretty unique. Maybe Valve would be kind of similar. But they're known for having this, maybe Amazon would be a closer tech comp of not as super top down, way more like there are these cells and those cells do whatever they want and they produce cool stuff, they produce games, whatever. Maybe it's something kind of unique to game. [30:27] Reading or thinking about that, I was thinking of Cursor and I was thinking about my conversation with Rio and like the way he works. Like... [30:35] Back to the IC is the atomic thing. Are we actually going to live in this world where you have... Rio is a cell all on his own, and he just decides to do stuff and then reports back? Yeah. So here's my hang-up with this setup. I actually... [30:50] if we are going to be [30:51] "all about craft." And I'm like, "Okay, my thing is the words." And I actually, I don't try that hard on design. I really like partnering with designers, but it's just not my thing. My hanging about this world [31:03] where all the ICs do all the craft work, is that we're never going to have the overlap. [31:07] moment where I'm like, okay. And I had this a lot on straight press. It was like, okay, these are the words on the page, but like, how should the page look and how should the book render? And like that collaboration is actually the Avengers for making an awesome book. Yes. [31:20] So I think in this world where everyone does things alone, you sort of like miss out. [31:24] I think the novelty comes from Venn diagram overlaps of two high craftspers.

[31:30] people or like a few coming up with something truly innovative together. So I, I worry in this world of like, I see only, we sort of miss out on these moments of collaboration. I talked with Rio about this because on the other, I think he's, and a lot of people are coming at the standpoint of like, he's like a designer and he's like, Google has visual designers and interaction designers and like everyone's like locked in their lane and like we can't, I should never publish some code. And so like you have that on one end, obviously, which is, I think a lot of, [31:59] And now you have every designer being like, whoa, curse is pretty sick. Yeah. Um, [32:03] What do you think the balance or how do you maybe it may be a more specific question like how are you trying to bring some more of that are you what do you think the balance is to still get the amazing like you've maybe generalist with specialist spikes or the fork spikes and then there's still the overlap. I want to I want to I'm working on a really fun project right now and. [32:23] The prompt was like, sort of as you do, it was like... [32:27] You write the script and the prose and then like baton pass it to design and like they'll do their thing with it. [32:34] And I was like, no. [32:36] I don't want to. I want to work with design because... [32:40] I don't like copy on the page will can like look a particular supply chain either. Yeah. [32:45] Yeah. And a very design oriented and vibey company. They got that right away and they were like, sick, happy to play this way, both hands on the baton the whole way through. [32:56] It's so good. I'm like, I'm so proud of what's going to come out on this. And to me, that was like true words, visuals, collaboration.

[33:04] And I think it would have been hard to pull off without that like true, like holding hands the whole time mindset. [33:10] This is like... [33:12] I mean, the first place my mind goes, and I know you, at least at the time, had written extensively about the way that COVID and remote work was shaping things. It's sort of like you're making an album, and it's like the guitarist sends you this track. Yeah, remember Postal Service? Remember that band? And they literally did that. But I'm sure there's so many examples. Yeah, it's really easy to be like, let's all get around the table. Yeah. [33:32] Yeah. And look and mix things around. Yeah. [33:36] Oh, I went down there for our design work. I was going to say. Because I feel better in those rooms about... [33:43] collaboration. I feel this at Cursor every day being remote. [33:47] I would be much more productive and much more integrated if I were in the office. I lament that I'm not. [33:52] Lack of proximity requires everything to be intentional. Yeah. [33:56] And intentionality is great, but it doesn't allow for the... [34:00] It totally. It's so funny. I was just with a friend who's starting a new job. This is her first like AI native company, too. And she was saying, if I ask someone if they'll schedule a meeting, they ignore me. [34:10] And if I walk over to their desk and interrupt them, we'll have the meeting. And she's like, I don't get it. But this is just the new way. This is the new way. [34:19] Like it's just fluid. Can fully remote companies actually be that creative? I'm sure. [34:24] I'm sure. I mean, are you sure? [34:28] I don't know. I... [34:30] Have you ever been truly, deeply creative in this way we're talking about, this collaborative way?

[34:36] And maybe it's a spectrum, but like, it's too hard to say if like the output would be better. I don't have the counterfactual. I just know how I feel. [34:45] doing the creative work, not through a screen. And for me, that's different. I don't, [34:50] But I'm extroverted and I like people and I have a big family and I grew up playing sports teams. I don't know. Maybe I'm just a particular way because I was shaped by a particular set of experiences. But that's just my feeling. [35:03] Yeah, the CapCut kids. Yeah, exactly. Exactly. They have a different way of being. I don't know. [35:08] Um, you know, it's funny. I was thinking about as you were saying all this, one of like my pet peeve phrases at work is someone's like, I'm not a marketer, but I'm not a designer. But that's like the thing you say when you're trying to intrude on somebody's work. Like, I'm not a designer, but I'm going to tell you my design opinion. Um, and I just I hate that phrase. I hate that tee up. I hate that whole thing. And I think like Rio has really shaped my thinking on this. Like, just don't do that. [35:39] Just be like, I have a design idea. [35:42] No hedging. This is how the design is hitting me or something. Like a phrase I use a lot when I'm editing is like, this hits my ear funny. That is what I mean. I suspect these type of companies that you tend to work at, [35:53] One of the things that built taking building organism and the culture really seriously empowers and obviously the talent bar and all these things is like a baseline level of trust. [36:02] That's like not like this dude from marketing is giving me product feedback. Oh, but it said like everyone here is awesome. Yes. Yes.

[36:10] Yeah, trust is one word. I'm not going to walk into a room with Wilson Minor and give him my design thoughts. I'm going to stay in my lane and kind of see what he does. And then we can play together. So trust is one word, but I'm more in awe. [36:27] Like I want their work to flourish. Like same thing on this Vercel project. These designers are like spectacular. They like produce beautiful stuff. I want I want them to come to the table with their part. [36:40] Yeah. And I don't want to do, I'm not a designer, but, but I want to do like, Ooh, what if? Yeah. Yeah. Ooh, what if is, is, is awesome energy. Um, [36:50] Still on this note a little bit, as far as I understand, Cursor has no meanings. And I assume that's probably pointing at something generally shifting of this sort of IC type thing. How do you think... [37:06] Back to this hard part, like the skeleton scaffolding part. How do you think infrastructure around stuff like management, planning, established systems, meetings, clearly it's in flux? Are we at risk of Chester and fencing it where we're just like, actually, Kirsten's going to need to have some meetings? Kirsten having no meetings is an extreme exaggeration. They're certainly not. I think Rio told me he has one meeting a week, which maybe is a Rio thing, but... [37:34] Yeah, I guess another company truism that everybody's having their own experience of the

[37:41] company. That's probably true for Rio and he should have a lot of time for Deep. Yeah. Yeah. Yeah. Yeah. It depends on the person. I don't know. I don't know. I think what almost certainly will be true is fewer people. [37:54] In the meetings. Yeah. [37:56] Yeah. And like some of the drudgery of corporate life, like these round the horn updates and like. [38:04] all that stuff. I think that's a little bit easier to go away. There's more automation around that stuff, like the rote. [38:11] Stuff. [38:12] Although I say that and then like a friend just joined a company and what I think people would call like a quote meta role. There was like a lot of skepticism about like project management. Why do we need a whole role for that? And she's adding a ton of value. Yeah. [38:25] just by like organizing the chaos. So, [38:29] I don't know. I'm like, I genuinely am excited. [38:32] to see like what the new shape of company will be. I do think it's changing. And I like, I want to be a part of that. It's probably why you have two jobs. Yeah. But I do feel like an anthropologist in this way. Like I, I feel I have studied company culture in the, in like the old way and now I'm going to old and yeah. Yeah. Old, old Phil's a little silly, but old on a relative basis. Yes. [38:56] Yeah, I've been, like... [38:58] A friend turned me on to this idea, like if you are interviewing with a young founder or a young company, you should ask the executive who their mentors are. I thought that was a really good question. And then I was thinking, who will the CEOs of this generation be mentored by?

[39:14] Like, I wonder if there's new rules and it actually might not be that productive to be mentored by the previous generation. [39:21] Some things change a lot and some things don't change. True. True. But I wonder if that like... [39:27] *sigh* [39:28] A friend is another friend is thinking about a role, a leadership role. And she, I think, reasonably wants to know who the other leaders she'll be. [39:38] surrounded with R. And this new company, young people leading it are like, it doesn't matter. And she's like, [39:45] I know that it matters. And they're just like... Respectfully or wrong. Yeah, but I like... [39:51] to me it's very refreshing and like exciting that they still have that optimism [39:55] about that. Like, [39:57] If they didn't believe that that was true, it would surely be not true. [40:00] like, [40:01] They would surely be tolerant of the politics and, yeah, these, like, weird dynamics if they didn't believe that it had to – if they believed that it had to be the case that, like, companies get political. Yeah. [40:11] They probably just are like, okay. So anyway, I was thinking that maybe there's some path dependence, like to believing you can run a political org or whatever. [40:20] You, uh... [40:22] I know a tweet fairly recently, you referenced the Billie Eilish vanity fair video. I love that video. Specifically, he said about how the speed of company building in the AI era, you're the first person to make that connection, um, which is amazing. I think on the eighth, one of those for, if you want to go watch, uh, it's like starts when she's 15 and maybe what's so telling about the video is she's gone from 15 to 16 and you're like, you're staring up the slope of compounding. It's like, she has goes from 200,000 followers to 600 or 6 million. Um, um,

[40:51] I guess there's a broad point here. And then also maybe more specifically, like on the infrastructure part, like you help, [40:58] spin up stripes planning function. Um, [41:01] like is planning... [41:04] a thing in this world like your point about billy is like everything feels like it's like this one year is infinite amount of time nothing is the same yeah like it's pure oh my gosh i was so naive like [41:15] I'm not sure. I think it would be nice if companies could be more iterative. And I think if you can move faster, you can trust them. [41:24] that approach more. [41:25] versus like we need to like take these big bets and it's a big chunk and it's going to take three months of work and all this coordination. Like I think if you have less coordination, faster to do things like maybe planning or like at least on long time horizons becomes like – [41:39] a little more obsolete, [41:41] But one function I think it does play is like for these bigger swings that you really want to invest in. [41:47] Yeah, how do you... [41:49] How do you make sure that the company is carving out time to do that? I think great. Urgent, but not urgent, but important. Yeah. Or even if like even just exploratory. [41:58] I think it'd be really easy to get lost in little feature wars and... [42:03] Yes, I think it takes some intention. So that's one thing I think planning can do. [42:07] that will like companies will not grow. And the other thing is maybe like holding a mirror so that it's like you're kind of shifting inertia in some ways. So like [42:17] One thing that like cursor is thinking about a lot right now is like, they're certainly their own best user as like a startup developer where they're like not their own best user as like a enterprise developer. So like, could planning help us like, okay, like,

[42:31] how are enterprises different than us? What might we want to do to support that kind of [42:36] work that doesn't come naturally. It doesn't spring forth. It's almost like a reference point when you're like, it's like a, I don't know, a plot of land where you're out on a boat or something. It's like, if there's no land anywhere, it's like... [42:46] - Whoa. - Yeah, but like, [42:49] I mean, it was not like an accepted concept to work on planning at Stripe. [42:54] Like that was it was like a risky project because it felt kind of off the culture. [42:58] at the time. Well, this kind of goes back to what I was saying, which is like, [43:01] I think that [43:03] Some things don't change. Yeah. And like Stripe and now Cursor, like these companies, they're doing... [43:08] this is why I was laughing at you saying it's like the old way, like Stripe is still one of the most like innovative companies in the world. And so like, maybe it turns out like on a long enough time horizon, people realize like, [43:17] Some long-term planning is really good. It's funny. I think I still remember Patrick's email to the company when we rolled out planning. And it was something like we're evolving beyond the Rube Goldberg machine of spreadsheets. [43:29] And that is how it felt at that time, like a Rube Goldberg machine. Cursor does not feel like a Rube Goldberg machine. [43:36] machine. Like it feels like a multi-armed like something else Hydra. [43:41] or something. So I think that's what I mean by old way. Like it was going slower. Like you're like watching the marble slide down the thing. Cursor doesn't feel like that. [43:51] You have a line where you say, if you believe, like I do, that what we build is a function of how it feels to build it. [43:58] How does scaling, how do you scale how it feels to build it?

[44:03] I'm not sure, but maybe these more like nuclear little collaborative pods, like... [44:08] I think a really cool thing could be that your, like, quote team, and maybe this is more like the super sell way, your quote team is actually, like, a very diverse set of people. My team is not a bunch of other marketers. Yeah, it's the Avengers. Yeah. Yeah. [44:21] That feels really fun. I like that. To me. [44:25] on the soft stuff, on the colder stuff. Yeah. [44:26] I think one of your big ideas is that you have to get out ahead of things before the osmosis stops working. Patrick Collison said a lot of companies end up articulating their values too late. Maybe first, what do good companies' values look like and how are they different from individual products? [44:45] Values. [44:46] Thank you. [44:48] Yeah. [44:50] I think values seem like something you would actually say. [44:54] Or some way you would actually behave differently. [44:58] I keep a doc of all values I've ever encountered from any company. And I was just taking a spin through it the other day, and I was like, wow, a lot of these suck. Why do they suck? [45:09] They're just boring. They're so ick. [45:12] But ick because they don't mean anything, ick because they're not honest, ick because they're generic. Yeah, any one of those things, like... [45:21] one of the most commonly cited values at Stripe was we haven't won yet. And that was like the humility. [45:27] Yeah. One, but we were winning. So it was like this like cheeky, funny thing you would say. Be like, I, we haven't won yet, but I closed this massive deal. We've won like eight championships in a row. And it was like the way to say like, we're still humble, but like now I will brag to you about this.

[45:42] thing. [45:43] And then I was like, wait, that like actually kind of did make us more humble because nobody bragged about anything without saying first, like, OK, I know I'm bragging, but it was a filtration system or something. Yeah. And it like it sort of makes you think, like, am I bragging? Because if I am going to brag, I got to say this other thing first to like be on the vibe. And I just I wonder what the culture might have been like if you didn't have to say that thing first. And instead, you just got to like brag and some of your stuff. [46:09] chest or something. Yeah. [46:11] So anyway, I think that was like a good value, even though we made fun of it a lot. [46:16] You talk all about the stuff that companies do for the audience of themselves. And what a beautiful kind of definition of culture. How does that... [46:27] And there's obviously so many machinations inside of what that means, but how does that incrementally actually produce the desired output of culture? Yeah, I think the audience of itself, this is... [46:38] I think this is a little bit what we were talking about, like companies that want to be great companies themselves. Yeah. And I think one mechanism where this kind of thing becomes clear is like, [46:47] all hands or like internal comms, like how does the leader like address the company? To me, I think it's like a privilege to see your colleagues work. [46:59] And I think it could be really easy to dismiss all hands like... [47:02] it's like meta work. Like if we're going to ship, it should be for. Yeah. And. And. [47:09] I think a really good all hands is amazing because there's there is some stuff that you can say to your colleagues that you can't say to the outside world yet.

[47:16] Maybe. And so like, it's a privilege to have the inside scoop or to like understand something more about like someone's sense of humor or like how might they design their slides or something. [47:27] It would sort of be like, why does the sports team have to do the pregame meeting or something? Yeah. We treat some of that stuff as rote in a way that... [47:35] I think if the context were different, might be perceived as more foundational. My friend, who's like a really talented lawyer, and we played soccer together in college, she always is like, I like the bus and I like the locker room. Like, that's her thing. And she was an extremely talented player. But by the way, that's what we all remember. Yes. You probably don't remember that many of the goals you scored. Yes. So I think I'm also like a locker room girly, and I do think that... [48:02] impacts like how the work gets out into the world. And I think in general, also people sort of underestimate brand and marketing, just like what your employees say when they're like, [48:12] to their spouse or when they're out for dinner with their friends or like when they're talking to their random uncle. Like I actually think brand [48:18] and marketing moves a lot through those channels and they are under-invested in. Oh, man. Especially in a place like San Francisco. For sure. For sure. That's the true pulse of the company. Totally. At Cursor last week, like... [48:33] one of the a newer leader on the team he like had the company in stitches like laughing about whatever something silly i know people were talking about that when they went home yeah and like it was totally off-brand like cursors a little bit more [48:45] serious. And it was like a really silly moment. And I think it was really memorable. And I think it made people have like a really good 15 minutes.

[48:53] What is the line between lore or mythology and nostalgia? Oh, man. [49:00] This trend was kind of like anti-nostalgia. [49:02] Are you anti-nostalgia? No. Okay. I'm like my friends and I'm like Ghost of Christmas Pass. [49:08] It's actually another friend was texting me this morning, like they're getting their new office set up and he's like, it's chaos, like all the furniture is in pieces. And I'm just like this part. Yeah. In five years, we're going to talk about this on a podcast. I know it. But I think these are like maybe core memory. [49:24] Type things like these. And often I think they're like not even fully true. [49:29] And they're never true. Yeah. No stories are fully true. They like cement a... [49:34] feeling. [49:35] Or like... [49:36] they help you make a feeling legible or like how you got this way. So I think the mythology is important. I also think now that we're, [49:46] adding so many people so quickly to these companies, they're growing so fast. You want to bring people along with the story of the company. But to me, that's lore or mythology, which is [49:55] Maybe I'm driving a false dichotomy, but nostalgia is like, I think you're right. A lot of people are like... [50:02] Nostalgia feels good when you're the person who's there. It doesn't feel as good. Maybe a better question is, like, what is the role for nostalgia in particular? [50:10] I don't. [50:11] feel that connected, [50:14] to people who wish they were... [50:17] at a different time or place. Like you can always tell you when someone's telling a story and they're like, I wish it was still like that. The good old days. Yeah. Yeah.

[50:23] Yeah. Um, and maybe that's a little bit what nostalgia is. Like I, [50:28] I don't think this guy will be like, wish he was still at the phase where they were like, like furniture was in chaos. But those moments were great. Yeah. And I feel like you can always tell when you're talking to someone and they're just like, it used to be another way and I want to be in that way. And you're just like, catch up. [50:43] Join us in the future, please. [50:47] We talked a little bit about this Tolstoy thing and great companies. [50:53] arc- [50:55] No way to know. But, like, is your instinct that... [50:57] all great cultures are like truly original in the like snowflake sense? Or are they like [51:03] permutations or remixes or even something more like an Enneagram or Myers-Briggs where there's like... [51:08] a dozen or so flavors. [51:11] I think I'm evolving out of this theory, but one that I used to consider is that great companies are extensions of their leaders. I think I might be evolving out of this theory. [51:22] idea [51:23] with this collection of ICs. [51:26] thing that's happening. [51:27] Um, [51:29] Like surely every page on the website is an extension of Patrick and John, like based on what I told you about how the cursor [51:36] website got out like, yeah, [51:39] Not so much an extension of the... [51:41] leaders. Um, [51:44] But one could say that's less finger feel, but one could also say it's actually an enlightened view from Michael. Yeah, I think so. Or maybe you can say it's just a little more indirect because he's so prescriptive about who gets hired, and he trusts them so much that it is an extension of him because he picks who's hired, who does the work, who gets on the landing page. I don't know.

[52:05] I think they're... [52:08] I think they're probably all singular, any company. Greater, I don't know. I try not to say good or bad. They're just their own way. Yeah. [52:17] I guess on the note of varieties, this ties to some of what we were talking about earlier, which is you've said Stripe is very much a thinking culture. Yeah. As we've clearly exemplified by some of these examples, Cursor seems more like a doing culture. Have you slid one way? [52:32] Oh, yeah. I'm like a chronic over thinker. That's why I was a good fit first, right? I love a doc. [52:38] I love thinking through all the different outcomes. That feels that's very natural to me. I do that in my personal life. [52:46] life, I'm working on becoming more doing oriented, especially now that it's like a little bit easier with stuff like, yeah, this week, I'm working on [52:55] Cursors first, like company pulse survey. And we're like, let's build it in Cursor. And then like, okay, who's going to help me build it in Cursor? I'm just like, well, can't you build it in Cursor? And I'm still working on that. Like, you know, I wrote the doc that was like, these are the questions and this is the vibe. And like, this is the, and it was like, wait, I could just [53:14] put this in cursor. So anyway, I'm still working on updating my own, um, [53:18] Thinking on that, I have a feeling I will find this satisfying, like once I get over the hump, but I'm still writing briefs over here. We all have different kinds of humps. [53:27] it's not a perfect example, but I'm sure there are people who, if they have to write something or like addicted to HIV, or like, I'm going to try to get somebody's help. I'm like, you have a,

[53:36] you have the finger feel for that, right? Like this is new. You don't have the finger feel. It's like, I don't know. I'm doing video podcasts. Like how do I do any, I don't know. I can't do it. I can't do it. And then, [53:46] You weighed in. I think they're like... [53:49] The finger feel thing or like the way doing will help is you still have to start at the end, though. You kind of have to know. This is why I think Rio is so... [53:57] good at what he does. He like, he has a loose conception of what the thing at the end is, and he can like poke and prod the clay the right way to like, get close to that thing. I think if you go into the project, not like, [54:08] having any idea of where it's going to end up, you would just like get lost in a chat GPT chat infinite forever. And you like can't like the work becomes the act shave of talking to chat GPT, you're like not really moving towards an end. So anyway, for me, like the brief sort of helps with that process of like getting to the end of the thing. [54:29] There's a little bit from, uh, Kari from linear, um, that, um, [54:36] reminded me of something that I spoke about with RIO, and I was curious to get your opinion. Kari says, before PMF, hiring a lot of people or working super hard might not actually work that well. To get to PMF, I think you need reflection and clarity. What I see is that companies are trying to imitate success. Successful companies are busy, therefore I should be busy. Successful companies hire fast, therefore I should hire fast. They get the causation and correlation wrong, but what you really need is to get the product right. And he's kind of [55:05] pointing at the 996 type stuff. Um,

[55:09] Do you think startups are... [55:12] and granted, I think you've spent less time at super early stage startups, but you may have worked with some like our startups over weighted to sort of mimicking the aesthetics of the grind set thing rather than one of the things Rio spoke to me about is like, he has two sort of modes. He's like, [55:25] Shaping the clay in cursor and like, I'm going to go for a walk. Yeah. Like there's not like that yin yang. And obviously it's different at a company level, but I'm curious, or maybe just any reflections probably on the whole workaholic kind of aesthetic thing. [55:39] I'm not sure. I'm not sure. I something I'm noticing it myself and in other people is it's really hard to sit still right now. It's really hard to sit still. [55:51] Um... [55:52] it's really hard not to be reading or thinking or consuming or tweeting or whatever. Like it's way harder to, [55:58] Not. [55:58] Because you feel like you're losing ground? [56:00] Maybe or like there's just infinite things or like whatever amount of time you have, there's like something in that unit of time that can like fill. [56:08] That like if you've got like one puzzle piece of a hole of time in your day, there's like a TikTok reel or a tweet or a blog post or like the AirPods in on the wall. [56:17] That is a part of like hustle culture. I feel the most like I'm always like behind on reading or I like didn't see the latest or. [56:24] to me, like that's the hustle culture feeling to me is I'm not up on it. [56:29] Yeah. Or something. [56:32] Or, yeah, I, like, I definitely notice a lot of people who are just, like, kind of saying stuff in Slack. I, like, don't really know why, but I think it's kind of, like, receipts, like, at my desk kind of behavior.

[56:43] And, like, same thing. I, like, so many Slack messages are edited, like, literally. [56:48] People send them in and they tweak them after like that kind of, this is where I noticed this like constant doing, doing, doing, doing, doing. And it's aesthetic a little bit. [56:57] Yeah, so I definitely am noticing a lot of versions of, [57:01] of that, and that it's hard to sit still. And [57:05] Again, like in many ways, I just feel like a benefit of timing, like, [57:09] Yeah, I lived and worked in a world where this didn't exist. Like, my first jobs didn't have Slack, like... [57:16] I think we use like hip chat or G chat. Um, um, [57:20] So I've lived and worked before this, so I had the chance to build some habits around stillness that I... [57:26] still rely on. But because I know that they work for me, I think it'd be harder to train yourself up that like stillness or going for walks works. But I know it works and it's still, I still forget. All right. It's just like easier to be at fidgety. Yeah, for sure. [57:41] Okay. [57:42] One of the things that stood out to me, you talk about funding culture specifically. You have to literally and actively fund a great culture. Steve Jobs funded the last 1%. It can never be the best version unless you fund it. Find a boss or a place that will fund the last 20%. Yeah. Yeah. [57:58] Um, [58:00] Maybe it's a false question, but like, do you think companies don't fund culture because they don't know how or because they don't want to sacrifice the capital in time for it?

[58:10] Yeah. [58:13] Yeah, it's the audience of yourself thing. It's like whether you value that audience or not. Yeah. I do think this concept of like internal product market fit. [58:23] for your work is becoming more of a [58:26] Thing. [58:28] So I'm excited about that. I think it's like... [58:31] means that the internal work starts to look important. - Can you say a little bit more about that? - Yeah, so one feature at Cursor and a lot of other friends who are at more AI native startups now, [58:42] The first thing you do is like shipped to the internal version and see if your colleagues are into it. [58:48] And. [58:51] Like a test flight for the whole company. Yes. And like old world versions of this are like, you sort of like talk about your intentions and planning, or you like write the doc, or you give the all hands presentation about what you're going to do. [59:02] But this is like a little bit faster and more iterative and there's more responsiveness. Like I think people legitimately judge the validity of their ideas by like how many Slack reacties they get. [59:11] That... [59:12] Might be really good at a place that cursor really bad elsewhere. Yeah. Yeah. Which is important. Maybe like I would guess that Slack was using an internal version of Slack. Yeah, sure. Like. Sure. Sure. [59:22] I wonder how that will evolve later. [59:25] Yeah, I wonder how much of it is just a product and building like a specific type of tool that you yourself use versus something more meta. But now think about it not for just product stuff. So maybe, okay, like a new enterprise engineering team is like emerging in Cursor. It's like a little bit, as we talked about before, that's like different than that. Right, right, right. So a huge part of...

[59:45] that this team's job is to like get people pumped about enterprise and they have to like [59:50] Explain why it's cool. That's probably try to find a way to live it a little bit too. And like in a bottoms up culture where people mostly decide what they work on without some tops down planning process, they're going to have to convince people. [1:00:02] the average engineer to like work on the enterprise product to unblock the da da da. And that's like all internal marketing work. And, [1:00:11] I think one way you can think about that is negatively. People have to do these internal press tours to get their work done. And one way you can think about it is positively because you're building more cohesion. Yes. Selling vision. Yeah, and you're excited about each other's work that you yourself can't do. [1:00:29] alone. So anyway, that's the version I'm excited for. That's like, yeah, taking care of the internal [1:00:34] audience. [1:00:36] I think it might be a little related. I want to talk a little bit about leadership and great organizations and cultures. You retweeted Nabeel, former friend of the pod, former guest Nabeel Qureshi had tweeted, "Napoleon's observation on war that morale is 75% of winning is one of the most important lessons for startup CEOs. Morale should be understood broadly here. It's something like a sense of destiny." [1:01:01] maybe speaking of even just selling things internally with your team, what is morale and where does it come from? [1:01:08] I've... [1:01:09] Yeah, the word I would use maybe instead is just having fun. I think Devin like sent me this tweet recently that was like, you can't compete with somebody having fun in all caps. And I think that that's...

[1:01:21] True. For some reason, when I think of morale, I think of a little bit like you wouldn't otherwise be excited, but I'm like... [1:01:28] Hi. [1:01:29] I'm creating some morale. It's like above the baseline. Yeah. [1:01:34] Just genuine enthusiasm is... [1:01:37] Yeah. And I think you can manufacture it. I think you can manufacture it. Maybe this comes from my background doing sports, but... [1:01:46] So anyway, that's the thing I think is just like getting people pumped to do the thing. Like, I'm just thinking of this enterprise guy again. And he's just like going to have to get someone pumped to like make a change that's going to like [1:01:57] be a huge deal for NVIDIA. And he's going to have to like tell that story and convince somebody else that that is sick and fun and awesome and rocks. And like, you know, [1:02:06] If he can successfully do that, like that work will go better than like it came down from this top down planning process and you're going to like check off your whatever. [1:02:16] The other part of that tweet I have to observe is a sense of destiny. Yes. Yes. [1:02:23] Interestingly, though, it actually seems that you... [1:02:27] think about it and are sort of drawn to both of those things. Mm-hmm. [1:02:31] Maybe we might talk about greatness a little bit later, but you are both... [1:02:37] very clearly having fun and very interested in having fun. [1:02:41] And also not just like... [1:02:44] Fun is the only point, only vibes. Like, actually, we're trying to, like... And when I think of morale, it's actually both of those things. Yes. Smashed together, which don't necessarily always go together. One of my earliest memories in childhood is...

[1:02:58] I was playing soccer. I remember our team was the orange team. And for some, I think I was probably in kindergarten. And for some reason, the coach was like, OK, girls, do we love to win or hate to lose? And every single person said love to win. And I said hate to lose. [1:03:11] That's one of my earliest memories. And I was like, I'm so different than everybody else. So I'm like I'm inherently like very. [1:03:22] competitive. I hate to lose. I also love to win. So like that environment is fun. Yeah. [1:03:29] To me, again, maybe I'm just lucky because I'm wired this way. [1:03:32] But by the way, I should know, like most hate to lose people don't have that much fun. Yeah. Yeah. [1:03:38] Yeah, but I'm just wired. I'm just wired this way. Like, again, locker room stuff. [1:03:44] So [1:03:45] we talked a bit about them a bit earlier, but like, [1:03:49] you've worked with a bunch of amazing leaders, the Collisons, uh, Claire, he was Johnson at Stripe as well. Dylan field, Patrick, Michael now, and other folks at cursor, Patrick, O'Shaughnessy. Um, um, [1:04:01] What about people like this makes someone like you want to magnify them? [1:04:09] and the cultures they build. Oh man, I've gotten so much more out of those relationships than you described than they got out of their relationship with. [1:04:16] me. [1:04:17] Um, [1:04:18] I think... [1:04:19] Like, ultimately... [1:04:21] The reason I wanted to do great work for these people [1:04:23] people is like, they funded me doing great work. Like my story at Stripe was I was just like,

[1:04:31] a person on the account management team. And then someone, I think it was, I forget if it was Claire or Patrick had sort of like plucked me up and was like, you're going to work on this weird project to like integrate this team that we, um, [1:04:42] acquired. And that sort of like set me up to like do my first leadership facing work and do my first like weird off the org chart project. You broke off the dependency or whatever. Yeah. [1:04:52] Yeah. And... [1:04:55] I feel indebted to them forever. [1:04:57] for just like, I don't know, seeing me in a sea of, it wasn't that many people at the time. But anyway, I just like felt seen in that work. And I was like, wow, I have like a new chance to like do something awesome. I like really want to. Okay, let's take away the Stripe people. Yeah. [1:05:12] You've also, like... [1:05:14] Yeah, I'm sure you've gotten an amazing amount from all these people you've worked with since, but they're hiring you for a reason. Yeah, why are they hiring me? I think they probably feel that I see something in them too. Mm-hmm. [1:05:25] And like, I respect and admire them. Like kind of what we were saying before about how I think of my job as a marketer to sort of close the gap between like what is and what's true. And like what the world knows about someone is like, I believe there's more in them. Like, that's actually that was my real question, which is. [1:05:43] I have a sense of why they're choosing to work with you. I'm curious why you're choosing them. And I think it's that you're seeing this. That's what my original question was like. This magnification desire is like there's something here that can be amplified. Yes. I want to. I want. [1:05:56] I've all those people that you just described, I think are incredible human beings. I think more of their stuff out in the world is better for the world. And I want to help them do that. That's genuine in me. Patrick O'Shaughnessy calls it the skinny mirror, which I love, where he's like, you hold a mirror up to someone, but it's like always the one that like makes them like look really good when they're doing their fit check.

[1:06:26] So everything they say, I'm like... [1:06:27] Like, how do we make that sound awesome? And like, let other people know. And like, you should write about that. And like, let's talk about that more. And like, say that a different way so more people get it. Like, that is an instinct within me. I want to like refract these great people out. And I want more people to benefit. What I benefit from them is just like... [1:06:43] being inspired or being excited or being moved to act or think or whatever. Hmm. [1:06:48] Yeah, I was listening to, the only time I ever listened to him, Dak Shepard, who has this podcast, and he was interviewing Adam Grant, the psychologist, and Adam's observation of Dak was that [1:06:58] He's like, you have inverse charisma. That's why you're such a good podcast host, is you make other people charismatic. That's funny. I'm like, what an amazing trait. And it's like, not exactly the same thing, but it's a similar... [1:07:09] Yeah, I think all these people, again, they're doing great on their own. They're perfectly charming and wise and thoughtful. And I just like... [1:07:15] My infinite energy is to like... [1:07:18] how people like say more awesome stuff. So like, [1:07:22] If any of them say something to me in a private room, I'm like, let's write a blog post about it. I think that's really interesting. I think we should let more people in on this thing that I got private access to. I think that's always my lens on stuff. Refract great people out. [1:07:38] One last thing on this. You were writing in the COVID era about the sort of lack of momentum that can show up in work. You say, but I do think work can be a source of real meaning in life, but we'll only ever get out what we put in. And in the case of work life, it's kind of a collective decision. Once your neighbor starts signing off of Slack at 3.30 consistently, it's hard not to do the same. If your closest collaborators don't turn stuff around quickly, why would you?

[1:08:07] A separate place you said, "A few months ago, someone complained to me that the new, very hot stuff startup they were at had an LGTM culture, or looks good to me culture. He looked down at his coffee for a moment. [1:08:19] Quote, I'm afraid I'm never going to see my best work again. And then this is you in a different place. Again, call me masochistic, but I have to admit that it felt good to care about anything that much and to be around people who I know cared that much, too. Of course, I believe you can love something without it having to hurt. But I've never truly loved anything that didn't move me to my core. Yeah. [1:08:43] Thank you. [1:08:44] You've talked about this feeling... [1:08:46] of being a part of something in so many places, going back to the [1:08:49] all American soccer days, um, or startups or whatever it might be. Um, [1:08:54] What is it about these groups that moves you so much? [1:09:04] Do you feel like you've ever been excellent at anything? [1:09:07] Like a taste of it? I think I bounced off it. [1:09:12] It's also like quite elusive. Yeah. [1:09:15] to me, but even being close to that sun is like very, it's like electrifying. And I'm not good at generating that on my own. Like it takes [1:09:27] sort of like the gaze of someone else, like... [1:09:30] I always would play better when I knew my coach was like daggers on me. Like, yeah, like I wouldn't want to go for the ball. I was like too lazy to make the run. And if I felt her presence, I'd be like, OK, I better get my ass in gear. So I'm motivated by that kind of.

[1:09:46] like loving attention. [1:09:48] I think like someone who wants me to succeed. So anyway, I think these environments where people are like, I have a loving gaze. [1:09:55] on your work, I think this could be better. It would be impossible for me to generate that push on my own. [1:10:03] I think this surprised a lot of people when I say it. Like, still, when I write, I imagine Patrick reading my stuff, Coulson. [1:10:09] And I wonder what he's going to think of it still. [1:10:11] I have not been in a room with him in almost a decade. [1:10:15] And like here I am still like I crave his like loving attention on my stuff. I wonder what he will think of my work. And I think this is like to me, that is like a core motivator is like people I admire their gaze on my stuff, like imagining how they'll tune it better. And I think like being in groups of people who will give each other that kind of loving attention is like. [1:10:35] Amazing. [1:10:37] Like all these people I sent the draft of the careers page to who are like, wording's not quite it. [1:10:43] And that like that was so motivating to me, like I wanted to work it until it was perfect for them. So it just means a lot. [1:10:50] you use the, you use that phrase loving attention several times, but the first time you used it, I [1:10:54] thought I first heard [1:10:55] like loving space attention. And what a profound inverse. It's loving attention. It's both. Attention is, of course, but I think my recognition from you is... [1:11:09] There are people who love attention, but what you are seeking is this very specific kind of attention. Yeah, I want someone who feels invested in making my stuff work.

[1:11:17] better. And I think that's, to me, that's what's so damning about LGTM. It was like, skimmed it, seems fine. Like, reliably, when I post something on the internet, [1:11:27] Stripes will DM me a typo. And I'm like, I fucking love these people. Like they actually read it. That's how I know. I'm like, [1:11:35] Those type of art Easter eggs for you. But I love it. When a lot of people see the type of art, I'm not going to bug them. [1:11:40] Yes. Excuse me? Yes. Yes. [1:11:42] So anyway, I just like I like that kind of. [1:11:45] Yeah, I think this is related to the funding thing. It's like, I'm going to take time to tell this person it has a typo or like, I didn't love this turn of phrase. And like, I love that. I love it. [1:11:57] I want to talk about your career path. You say there's just all this work that lives in the crannies that doesn't seem like it should be owned by anyone in particular. So why not me? You're writing a book for people early in their career. Yeah. [1:12:12] And you've had quite this winding path, um... [1:12:15] that's probably not necessarily the most obvious template. How much weight do you put into that line, of sort of picking up the things in the crannies, [1:12:26] in the path. [1:12:28] I don't think that works for everyone. [1:12:31] But it worked for me. [1:12:33] Because I got to do stuff that where no one would say no, because nobody, a lot of people just didn't care. But I know a lot of people who just like did the ladder. [1:12:41] And it was great for. But you also pick things up in the crannies and mean people care about the crannies. That's true. That's true. Yeah, I do think I've had like a particular nose for the type of problems in the crannies. I think you don't want to be in obscurity.

[1:12:55] You have a nose going back to something we talked about earlier. You have a nose for things that are not currently important, but will someday be important. [1:13:01] Yeah. [1:13:02] - Yeah. - Or could be made to be important. - Yeah, I think I have a particular temperament for that, because I like zero to one. [1:13:08] To me, that's like the most fun phase. And often if too many people are, too many cooks in the kitchen, they're like, it can't really flourish. Right. [1:13:17] And I also have like a I'm also totally fine giving away my Legos. Not everybody is. I'm like happy to pass my work on. So I think I have like a particular temperament for this kind of that flavor of work. I think many more people want more sort of like structure, validation, show me a goal. I'll like. [1:13:34] I'll hit it. And many people have great career paths that way too. I think you were talking to Perel. You said it's hard to have a finger feel for things. If you, I mean, it was a packy. It's hard to have a finger feel feel for things. If you don't have a lot of reps on it and it's hard to have a lot of reps. If you do many things, it's true. Um, again, revolving around a similar thing here, but given that conversation we had about craft, like, [1:13:54] For the people who do relate to you and see Bree, and they're like, man, what an amazing opportunity to have that path. [1:14:01] with the benefit of hindsight, how do you square the... [1:14:05] Finger feel is so important. And also, you capture the still wall in flounder mode, and yet... [1:14:10] I think it's still easy to sit there being like, if Kevin Kelly can do it, that's cool. But like, how am I going to develop skills? I'm smirking about this a little bit because... [1:14:20] I... [1:14:21] there's this thing happening in the world right now where there's like a real enthusiasm for people who can tell stories. And like, that's the word people are using, like,

[1:14:30] yeah, story. People want the story. [1:14:33] And [1:14:34] maybe it was probably six or seven years ago. I think it was when [1:14:37] I was applying for Figma. I wrote this document to a company that was like, I want to be your head of storytelling. [1:14:42] You were early. Yeah. Yeah. [1:14:44] And, [1:14:45] They basically were like... [1:14:47] That's cute. No. And I was I like felt very ashamed after that. [1:14:53] I was like, oh, yeah, that's a fake word. That's like I went to the big boy table and like or the adult table and they told me to go sit back. Yeah. And I was like, oh, like, why did I do that? I don't think I could have gotten reps enough reps on this thing to have it be a full time job. And now I actually do feel like I have the opportunity to do it. Like I've basically had to do ups on the side so that I could do storytelling stuff sometimes. This is the crannies. It's like, yeah. [1:15:17] Like if I think if I wasn't like a fantastic, like get shit done person, Stripe Press would have never landed on my plate. Like I had to do all. Yes, I had to do all. I had to be the person that could like. [1:15:27] Yeah, get us to print a freaking book and get it on Amazon and, like, all this stuff to, like, earn the right to just, like... [1:15:34] tell stories about the authors, but I had to do 90% of that. The other work now I think I can just [1:15:39] Today, I think there's like permission for Brie to spend full time just on the story stuff. But I think I generally had that self awareness that like I had to pay my dues with the ops stuff like there just wasn't enough company work in story. Right. But now I think there might be. [1:15:56] Maybe a generalized lesson here is, like, you're allowed to dabble if you, like...

[1:16:02] find enough ways to move bricks or whatever. Yeah, I'm preparing like a section on this in the book. I think [1:16:09] operators underestimate this. Like the first question all managers are talking about when it's time to like pick up another job is like, how are they doing at the core? [1:16:17] Yeah. [1:16:18] Like the reason I got to do that project I described at Stripe where I helped the acquired teams is because like my account management book was doing great. [1:16:25] I signed all my renewals. So I was like, sure, spring her on to this other thing. But you have to know why you're at the company. If you're 22, like... [1:16:34] that advice isn't that helpful, because you've got to get in the door first. [1:16:39] Do you have any broad thoughts on the person who sort of feels like a generalist or they're not... [1:16:45] Their craft isn't necessarily that obvious. They might have a craftful approach to things. [1:16:50] I'm curious about how this will... [1:16:54] how these careers will pan out soon. [1:16:59] Really common hiring advice, like if you just wanted horsepower, it was like hire someone who's done a couple of years at McKinsey. I actually wonder if that meme is like still. [1:17:06] around like if we value these generalists my sense is generalists now have to be able to produce output like they should be able to like cursorify the company pulse survey on their own they shouldn't like need someone else's time to do something like that so yeah and that would be the version where the generalist is like more valuable than ever yes [1:17:23] So, [1:17:24] I don't... I like... [1:17:26] I think there's more expectation for people to be able to produce their own [1:17:30] output. Whereas I think I spent the early part of my career being like glue for people who had like

[1:17:37] great ideas, but like couldn't really get them [1:17:40] Done. [1:17:41] - Yeah. On the output front, how important is, especially pre-having the job, [1:17:46] Um, you've been pretty public. You've been relatively public in the last year. [1:17:52] relative period of time. I don't know if you always were. Like, [1:17:57] I think if you're 23, the obvious thing is you've got to get a Twitter following or whatever. Oh my gosh. Share your projects and go viral. [1:18:04] What's your advice on that part? [1:18:05] I [1:18:07] I put out a call for the book, like if you have questions that you hope the book will answer. [1:18:12] What are they? Yeah. And the question I get the most is, do I need to be Twitter famous? Yeah. No. No. [1:18:18] You don't need to be. It doesn't hurt. It doesn't hurt, but you do not need to be Twitter famous, period. I think what people are, they're like sort of anti-pattern matching. They only pattern match on the people who like are Twitter famous. Yes. Well, it's otherwise illegible. Your career broadly is illegible, but it's especially illegible if you don't even see the specs of it. Yes. Twitter famous is like the wrong way to describe it. I think it's really useful to publish your work. [1:18:47] I think it's good to get it to completion. I think it's good to put it on the internet where other people can see it. [1:18:53] I think that... Have something to point to. Yes. And also, like... [1:18:57] Just have... [1:19:00] Were we talking about this the other day? Like the reason you go on the book tour is because like the thinking has been codified. It's like a little bit about that you have the book, but it's also like, okay, my ideas are baked. Yes. On this, I think it's pretty good to like...

[1:19:12] share a record of like, what have you like? It's an artifact that, yeah, yeah, yeah, yeah. I don't think that means you have to be like famous, but I think if someone goes clicking around about you, it's probably useful to pass a record. Well, it's also not necessarily like an endless stream of noise. Yeah. [1:19:26] I think like you have gotten a lot out of like being online. [1:19:31] I meet a lot of people... [1:19:33] I [1:19:35] Like, I like my Twitter feed. I think a lot of people don't like theirs. I like mine. Um... [1:19:40] So anyway, I get a lot out of being online, but I talk to a lot of founders that are like, ugh, I have to tweet every day. I'm like, just don't really bother. If you don't want to, yeah, don't do it. So anyway, I think it is some people's... [1:19:53] medium of expression. [1:19:56] On the Fodder Mode note... [1:19:59] I think somewhere along the way, the message about what it feels like to be great has become a bit perverted. [1:20:04] Kevin says in that piece and everywhere, their greatness is overrated. [1:20:10] you seem to be chasing greatness still. Um, [1:20:14] Can flounders be great? [1:20:18] I am. I think I'm not chasing greatness in the way that Kevin describes it. I agree. [1:20:23] Um, I don't, [1:20:25] I don't care to run a company. I don't need history books to admire me. That is not the kind of greatness I'm looking for. I just want to feel at ease in my craft. And I think that is a lifelong... That will be a lifelong pursuit for me. Yeah. [1:20:41] I want to push you slightly because I think you are both doing that and you, I mean, you are like an all-American soccer player. You've like done, you've been exceptional in many ways consistently. And granted, maybe it's not perfectly intrinsically motivated or whatever. You've done a bunch of different things rather than one thing, but like.

[1:20:59] Is it really just you want to be like, it is in your craft? [1:21:02] Thank you. [1:21:03] You're not on the list of people I call when I'm having anxiety swirls about everything. This... [1:21:10] Being eligible has, like, plagued me throughout my career. [1:21:15] You did an amazing job of capturing that piece, by the way. Oh, thank you. But imagine me at 27, sending this email to the CEO of an actual company, being like, I want to be your head of storytelling, and then laughing me out of the room, like, [1:21:29] That did not happen in a confident place. I was like, I'm going to shoot my shot on this thing, and I'm going to be bold and put myself on the page. We also weren't laughing you out of the room. I suspect it was a little bit about the illegibility more so than you fool. It was respectful, but it was like, oh, I... [1:21:45] They weren't ready. They actually, it was too illegible. Yeah. It was, it was, you were actually totally onto something, but it wasn't. Yeah, but I'm like, I, it wasn't, none of us was surrounded in confidence. I was like supremely self-conscious about that whole event. And I think if I was like truly at ease in my craft, I'd be like, oh, they just like don't see it yet. This is the Kevin, this is when the comments bounce off of Kevin because he just doesn't care. Yeah. He's like, I can't even, I don't even, he's like, I don't even understand what you mean by like, does an audience have to validate you? [1:22:15] It was like, does not compute. So I, to me, at ease in my craft is like, I know my... [1:22:22] I know my value. Like, people say this, people are always like, just call it Brie Magic. I would never call my work Brie Magic. And, like, I think they're saying something kind, but to me it's, like, dismissive.

[1:22:34] because [1:22:35] I don't want it to be magic. Yeah. I want it to be like real. Yeah. Yeah. So I'm like still on a journey with this thing. [1:22:45] There's a, the thing that most stands out about Kevin, the way you convey Kevin in that piece, um, is this demeanor or this disposition of abundance. It's kind of what we were saying about the bouncing off thing. Like, um, what I'm talking about is taking your interests seriously enough to have the courage to stay moving. You can give stuff away. You can abandon things. You can tolerate failure because you know that tomorrow there is more. Yes. That, I mean, honestly, sounds a little bit like what you were just kind of describing. Um, yeah. [1:23:15] you [1:23:16] Also, though, I have like what you were just saying. You've talked about like feeling at this stage in your life, in your career, like some doors are closed. Yeah. Um... [1:23:24] When do you feel this... At the end of that piece, Kevin talks, or maybe you talk about the well-being bottomless. What a beautiful imagery. That was all him. When do you feel that abundance and how do you try to get back to it? Yeah, it's funny. You're tying my whole life together. After I graduated college and soccer was over, my... [1:23:45] I was in a pit of despair that I would never be so good at anything again. [1:23:49] Truly, truly, truly. You were really, really great at that. And I was obsessed with it. [1:23:54] I would get to practice early and practice my touch. Like I would go home and like do planks while I watch TV. Like I was obsessed. Like I really put it in the time to be great. And I like was great. I like a division three school and everyone else on my team like went on to D1 schools. So like.

[1:24:10] Yeah, it was awesome to be an all-American, but there was like many stages above me that I... [1:24:14] that I had thought about. Um, [1:24:17] And I think I've done this now enough. [1:24:20] times where I like have to pass the torch and start over that it's like, [1:24:26] That feels fun and exciting. I know I will do it again. Like, this is the main thing writing the novel taught me. It was like, I could do a huge thing by myself, but like, [1:24:35] Winding down Constellate. Usually I trick myself into thinking this is the magnum opus. Constellate is what it all laddered into, a piece of software that helps companies do great work. And I had truly zero product. [1:24:51] vision, but I was like, this is its final form. And then like I joined Patrick O'Shaughnessy. I'm like, yes, like helping founders plus media, like this is its final form. [1:25:01] form. And then I like ram something up and I give it away. And I'm just like on this, this book, I'm like, this is my magnum opus. This will be like, all the things I've ever thought about, like how to do great work is like going to be in this book. And then when they're done, it's like, [1:25:14] Sad. [1:25:16] But now I've done this enough times where I'm like, yes, I'm going to try to like, [1:25:20] Be the very best. Like, I think it'd be so lame to go into these projects and be like... [1:25:23] It could be okay. [1:25:25] I don't want to write an okay book. Yeah. That would be so lame. That's the abundance is like what Kevin is doing. Kevin doesn't seem to have... [1:25:32] that [1:25:33] This needs to be the opus. And yet it's all great. I know. Yeah. This doesn't have to be like the best walk across China that anybody's ever seen.

[1:25:41] done. Also, I'm not going to phone it in. Yes. So I think I'm trying, like when I say at ease in my craft, like I think of Kevin as at ease in his craft. Like he trusts himself that like his version will be beautiful. And like what is even like [1:25:55] the best book about great operators. Like it doesn't matter. It's just like my best book. [1:26:00] That's what I have to do. This is Kevin's most famous line. Don't be the best, be the only. Yes. But that's like very hard to channel. I just like hate to lose competitive person. But like, I think I will be happier when I trust myself to produce. [1:26:13] excellent work and to like understand [1:26:16] my own like worth and value and all that stuff. And like trust the process instead of like white knuckle so much on the way. Like I'm afraid of this book. Well, power is overrated. Maybe. Yeah. I'm just, but yeah, I don't want to be afraid of my work. I want it to like, [1:26:31] I wanted to... [1:26:32] come out more joyfully. [1:26:35] And I think I'm always like fighting that a little bit to like nudge it and like make it perfect. And yeah, I think I would like like a little more ease in the process. [1:26:45] One more from Kevin or on Kevin. His range is wide, but all his work somehow rhymes. Mm-hmm. [1:26:52] What are the dominant rhymes for you and your work? [1:26:55] Thank you.

[1:26:58] Definitely excellent people. [1:27:00] around me and like for an audience of other excellent, [1:27:04] people that matters to me a lot. Um, [1:27:08] Optimism, I hope. [1:27:10] Like, I always want to paint the picture of the future is going to be better than it is now. [1:27:18] And maybe like a touch of something unexpected. [1:27:21] Um, [1:27:23] I hope these would be like very generous terms to describe my work, but that's what I aspire to. [1:27:28] Uh, [1:27:30] Tammy, something else Tammy mentioned to talk to you about. She said you've talked to lots of great talent spotters for the book. I have. [1:27:37] What do they say about their best employees and the best early talent? [1:27:43] Yeah. [1:27:48] It's like the main thing that they say is like, they're just so good. They're just so good. [1:27:52] I'm like, but why? I don't know. They're just so good. [1:27:56] I'm trying to like... Is that get-it-ness? Maybe. That was actually, yeah. Jackson's referring to like... I tweeted yesterday. I'm like looking for a word for like a general sense of get-it-ness. [1:28:07] And lots of people have words for it, but... [1:28:10] They're not quite... [1:28:11] Right. I mean, I think what they're saying is like they generally can just like move through space and like get things done. Like a knife cutting butter. Yes. [1:28:21] Yes. And I'm like, are they like... [1:28:24] persnickety or not persnickety, they're all over the map. Like, are they like, [1:28:28] like really thinky or really dewy. They're all over the map, but it's just like, it just, maybe they're like momentum sources or like flame keepers or something. Like they just...

[1:28:37] Is that obvious when they're 20? [1:28:41] I think so. Yeah. I think so. And I still think it can be... [1:28:47] cultivated, like [1:28:48] Or grown or compounded or something, yeah. Yeah, and this is why I got so obsessed with talent. I had a couple jobs before, Stripe. [1:28:55] But I had my real, like, both intellectual awakening and, like, agentic awakening at Stripe, where it was, like, everybody's really good, and I wanted to be really good in that context. [1:29:05] the job I had before that was at a startup that was weird. The office was on church street in San Francisco and we have like a storefront as our office. And like someone once caught me watching the good wife, like at work, like in this, like, like a user came in and they're like, where you're just like watching the good wife on your laptop. And I was like in the window. And I was like, [1:29:27] Yeah, I was. But I was like, really not. [1:29:32] trying. [1:29:34] Sometimes you got to feel it. You got to be next to it. It's a finger feel again. So, I don't know. Things really change for me at [1:29:40] work where I started to like want to be good. [1:29:43] there and like, I don't know, I had a clearer picture of like how you could or what it would look like or, um, yeah. [1:29:51] So, yeah, I think it can be cultivated. I think a lot of actually people that I talk to who are, I would like... [1:29:56] consider great talent they had a couple early jobs where they didn't quite feel it they were bouncing around yeah they like they knew they weren't doing that good of a job they were like in kind of this is the hope this is the optimistic case is like you don't have to be boy genius when you're 18 or 20 and like yes have only ever won yes yeah i think what's that steve jobs quote like basically keep looking yes but yeah follow the romantic scent yes i like did talk to a lot of

[1:30:21] Yeah, they were not in the right container at first, and they knew it. [1:30:25] Yeah. Like they were also watching The Good Wife at work or whatever. Yeah. The question is, do you let the container sort of like suppress you or do you find a way to the... Yeah. It's funny. At that time, I wouldn't have said I was super ambitious like at work because I was just sort of... [1:30:39] Yeah, I'm doing what I remember having a thought like, what do people do all day from nine to five every day? I had no idea. I was like, certainly everybody else is also watching. No way. People are working for eight hours. I was like, they're also watching The Good Wife. Like, that's what I thought. [1:30:52] was happening at work. I just didn't really... I think that's broadly true. No, maybe. No, no, no. It definitely is. Most people do not work eight hours a day. And they're watching the good five. I don't know if they're watching. You're watching... Like, yeah. Um... [1:31:05] Things don't take that much time. [1:31:07] Yeah. I had never seen like, I'd never seen like a hive, like hive minds, like really buzzy, buzzy. [1:31:14] workplace. So I was like, yeah, I'll just like, that's what I do at work. Like not that much. And it took me getting to the place where other people were doing that. But I don't think I, it was obvious to me that I wanted that to myself. I think like one of the most beautiful metaphors for this is just like, [1:31:32] The fastest 100-meter dash ever. [1:31:35] after Usain Bolt, is the guy who raised him. Yes. Like, this is just so clear. Like, this is how we work. Yes. [1:31:43] Yes. So and [1:31:46] That like you're used. [1:31:47] Everyone might have a different Usain Bolt. [1:31:50] Like.

[1:31:51] So certain cultures might work for you or not. Like one of these like great talents I was talking about, one of her first, like one of the first places she was working where she was like not effective and not a fit was in a lawn company. [1:32:02] And like surely you would expect that like that kind of environment would like juice any ambitious person up. But it like wasn't a fit for her. She was like, I guess I just like won't be that good at work. But like her environment was the intensity of an Elon Musk company. And it wasn't until she like found the next job that she was like, OK, now I'm like alive at work. So anyway, you can. [1:32:20] You might find it in unlikely places. [1:32:24] You seem to move between... [1:32:27] like hard and soft or like yin and yang uh tammy one more time she said brie is creative but she's also kind of ruthless uh and so like there's this to the yin yang there's like vibes but a lot of ambition there's like very intuitive but also into like tracking and systems there's this like super high bar for intangible things well i was gonna ask if it resonates it sounds like it resonates a little bit like how do you hold both of those things it's funny it does resonate i think the first time tammy said that to me i was like tammy that's my best kept secret and she was like it's [1:32:56] not a secret. Yeah, everybody knows, which is funny. Yeah, we were even talking about this at dinner last night, like, [1:33:03] Am I type A or type B? It's kind of hard to know. It does resonate. I don't think about holding both because that's just how I am. [1:33:14] But they like... [1:33:18] Maybe you allow yourself to be both. [1:33:19] Whether it's consciously or unconsciously, whereas I think...

[1:33:23] People... [1:33:25] I almost wonder if we sort ourselves. I'm this way, and so I got to – yeah. [1:33:31] Yeah, and I like being around... [1:33:34] Creatives. [1:33:36] It's almost necessary. Yeah. [1:33:38] That makes a lot of sense. Yeah. For the worlds you like to inhabit. Yeah. And I don't just mean creative, like people who do art. [1:33:45] any kinds of people who make stuff, bring new stuff into the world. So I think you need to, yeah, you need to. [1:33:52] exude a certain quality. [1:33:55] Um, [1:33:56] for like to be welcome in those places. Yeah. Like, [1:34:01] Yeah, if I was like walking into a creative brainstorming being like, get that timeline, even though that is like low grade, what's going on in my head? Like, I know that's not the right thing. [1:34:09] I know that's not the right place. I could read a room. [1:34:13] I was thinking about like, what is your spike? [1:34:15] Um, [1:34:17] And we've talked about a lot of the things you're good at and a lot of the sort of patterns. My best... [1:34:22] sense of it, I think, comes from a few quotes where you say, it had become hard to explain what I was good at, most importantly to myself. And then the people who become legendary in their interests never feel they have arrived. That's from the Kevin piece. It's like, [1:34:37] What is the, there's this, there's this ambiguity. [1:34:39] People love to tell me things and I like hearing them. That's one thing you said. I want to be an active metabolizer. And then finally, I became the person you asked to have a coffee with when you wanted to quit your job and do something weird.

[1:34:53] You talked about helping people tell their stories, being this empowering force next to Special Minds. We talked about that. Working with ambition and joy. Yeah. [1:35:00] You referred to Harold Ross of The New Yorker as excitable. And so my best point at it is this... [1:35:09] It's a charisma specifically around being excitable. Yes. Um... [1:35:14] Why is being excitable a virtue? [1:35:16] That resonates. That's a really nice compliment. I hope that that's true. Um, [1:35:22] It's a virtue because like... [1:35:25] I don't know, stuff could just be a drag. [1:35:28] So it could just be a drag or it could be fun and like exciting and like interesting and... [1:35:34] Back to morale a little bit. Yeah, and captivating. And I think a lot of the stuff, like, seen through a new lens of, like, blah, blah, blah, it's, like, the fun version of it. It's, like, it actually, like... [1:35:46] shifts the work in the right... It actually shifts the work. Yes. In the right direction. It's not like lipstick on it. Like actually... Yes. [1:35:53] changes something about it's funny i was like on a three-way call with two girlfriends recently and one was putting her newborn down for a nap and he she was like do you think she's gonna stay down and the other girl was like honey i don't think so and i was like he's totally gonna stay asleep he's gonna stay asleep forever and they're like oh brie's just a hype girl but then he stayed asleep and i was like i willed it into if you believe in magic magic happens you believe in [1:36:16] girl. I'm really proud of that. And I'm discerning. I won't hype anything. Yes. [1:36:23] And I won't lie to you either. I cannot...

[1:36:26] Fake it. You believe it. Yeah. I do believe the hype. I do believe it. I'm like, I'm sorry. I'm saying I believe you. People around you believe your hype. [1:36:34] which is so critical. Well, I believe it. Yeah, and I think that's my only... [1:36:38] bar for this, or at least my only criteria for this stuff. Do I believe it? And I won't work on it if I don't believe it, which is why I picked these great people to work for. I have to believe in it. I don't want to... [1:36:49] In fact, I got that in my very first performance review at Google. I was in sales and I didn't believe this. It's funny. It was video. I didn't believe in video. And I was like, I'm not going to pitch this until I believe it. And they're like, okay, well then you're just going to lose. And I was like, I don't care. [1:37:04] And then I started to believe it. And then I was the third best salesperson in North America after. You can sell anything you believe in. That's true for anybody. Yeah. So I seek to believe. I'm not like, I want to. I think that's really fun. I want to find the awesome things about people. Like you said, what did I say? People tell me things and I like to hear them. Yeah, I want to. [1:37:27] get into it. Like, I want the skinny mirror. I want you to look good in your clothes. Like, I don't want to talk shit behind your back about how you look fat. Like, I want you to look good. So I think people feel that. [1:37:38] in me and also that I'm not fake. Like oftentimes someone will like try something on and be like, no, let's try it again. Yes, yes, yes. [1:37:47] So I think that energy is like... [1:37:50] contagious too. Actually, someone just sent me a really nice note that like something they learned from working for me was like to make it fun. I think most people want it to be some version of

[1:38:01] fun um so anyway i like try to i try to bring it i don't always but i try [1:38:07] What does it mean to be an API to X? [1:38:11] Maybe this is a little bit we're talking about, like... [1:38:14] being legible to two different things at the same time is like connect to things that shouldn't be connected. Yeah. [1:38:20] And a lot of that. Yeah, I think I'm very comfortable in that. [1:38:25] place like [1:38:26] I want to put these two wires, but you really got to stretch them. I'm very willing to do that. That's great. It's a great mental image. You tweeted, I think, a napkin-drawn good at talking matrix. [1:38:41] That it's sort of like, good at talking on the... [1:38:45] whatever the y-axis or something and then competent or good at doing. It was good at doing on the other axis. Um, and one of the, the, the good at talking, but not good at doing is the yapper. Um, and the top right is, is the good one. Um, [1:38:59] You're definitely in the top right. How did you get there? [1:39:04] I think people just generally like having me around... [1:39:08] Well, not everybody. Like... [1:39:10] The right... [1:39:11] setups. [1:39:14] So I think I just get to learn from a lot of really good people. [1:39:17] And then I get to just copy what they do. I actually, we talked about this before, I don't think I'm great at doing things. [1:39:24] I think writing is kind of being a professional thinker. There's a lot of output, though. [1:39:30] Yeah, I like and I guess I like getting stuff done. Sometimes I make checklists to just check things off. It's also like the picking up the crevices thing. Yeah. Like, yeah. Yeah. OK, I do. Yeah, that's fair. I do get stuff. I do get stuff done. I think I just like to.

[1:39:46] I think I just like to. [1:39:48] There's this... [1:39:50] I think it was on a podcast, maybe with Paki or Perel. You talked about Steve Jobs wanting to know how the parts of the thing work. Yeah, I love that story. And you said, I have that with people and I have that with ideas. Yes. Yes. [1:40:03] What do you love about people and ideas? [1:40:06] It's like an infinite puzzle, and everything is different. Like, you can... Yeah, it's an infinite game. There's no... [1:40:12] You cannot understand people. You cannot, like, wrangle ideas. [1:40:19] I'm definitely not the smartest people in most rooms, but I think I am like one of the most willing to ask questions. Maybe you feel like you have some of this. Really? Yeah. Yeah. [1:40:28] And to me, that's a very satisfying way. [1:40:31] to live. And I have no shame about being dumber than others. [1:40:36] Thank you. [1:40:38] One last thing on the career advice bit. [1:40:41] You were talking to Barrett Brooks and you said, I just I finally realized I just want cool people to think I'm cool. [1:40:48] Patrick O'Shaughnessy helped me get to that insight. It's beautiful. Yeah. And what you follow that up by saying was I had the clue. I just wasn't listening. Yes. Evergreen. [1:40:59] I think you even talked, too, about it. Maybe some of the aspects of this feel fundamentally unrigorous or female-gendered or vibe-queened or whatever. [1:41:10] I think we all have this in so many aspects of our life, not just career path, but two people who...

[1:41:16] Do you have advice for people to... [1:41:20] get better at listening to the clues, seeing clues. [1:41:25] That's a really good question. I'm still I'm still working on getting better at this. I think it's related to this quietness and like stillness thing. [1:41:34] we talked about earlier. I think it's like, [1:41:36] Thinking when everything is quiet. [1:41:39] like, like, [1:41:41] When I make a career decision, one thing I'll do is go on a tour of all my friends. And sometimes I'm like... [1:41:48] Maybe it'd be better if I just went into an empty room. [1:41:53] Um... [1:41:54] I think that's like part of listening better is just like trying to make everything else. [1:42:00] Quiet. [1:42:01] so I can hear. [1:42:03] But it's really hard to do. Like, we're surrounded by smart people and... [1:42:07] There's a lot of writing on everything and people have opinions on this or that and they're smart. [1:42:12] And, like, it seems silly not to... [1:42:14] Like. [1:42:15] hear from them. But I think I'm still on the journey of learning to trust myself. [1:42:19] a little more. And I think to like make decisions in the direction of yourself, you also have to believe that like you have what it takes. [1:42:27] on your own. [1:42:30] Like. [1:42:32] If... [1:42:33] no matter what was happening when I was 22 or whenever 23, whenever I joined Stripe, like that was the right career decision. [1:42:40] I think the thing like competing with it at the time was like to stay working at Dandelion Chocolates. [1:42:45] And like, [1:42:46] being a soccer coach. And it was like, I think maybe that could have been like more fun or like quote, listening to myself. Um,

[1:42:52] But that was the right step for me to take. So anyway, I'm like... [1:42:57] it's hard to know when to listen and when to not, but I think at least like, [1:43:01] documenting or hearing what the signs are. So at least you have some record of what's going on inside. You have this, you have this image of like, I think in the context of writing, which obviously applies here, but like putting the microphone close to yourself. Yes. The other thing I think about metaphor I try to lean on is like, it's like, you got to let the snow globe settle. It's like, I'm viscerally shaking this thing, looking for answers. It's like, yes, stillness is something. Um, [1:43:24] We've made it well over an hour and a half without talking about taste, but we have to. I thought you were just using craft as a stand-in. I think they're very related, but I think they're a little different. Um, [1:43:36] And I think obviously like taste is such an input to craft. I think that you've written a lot of great things, but you have, if people are going to read one thing, I hope it is notes on taste, which is just so wonderful and very influential to me. It certainly precedes a lot of the discourse and whatever else. I want to just pull out a few things because we could spend, [1:43:54] And I think you kind of have spent lots of time talking about this with people. First, you say taste is something we can and should try to cultivate, not because taste itself is a virtue per se, but because I found a taste filled life to be a richer one. [1:44:08] To pursue it is to appreciate ourselves, each other, and the stuff we are surrounded by a whole lot more. Appreciation is a form of taste. Creation is another. Those who create tasteful things are almost always deep appreciators, though. Finally, taste cannot sublimate. It can only bloom. Mm-hmm.

[1:44:28] It's telling that you say appreciate things more, not judge things more. Yes. Can you say a little more about that? Yeah. [1:44:35] The best example I have is coffee. [1:44:38] I like to say that my husband ruined my life by getting me into coffee because I used to be able to just drink it from the gas station. And that was fine with me. But he's so into coffee. If you look over there, there's a whole setup. There's scales and temperature, all this stuff. He's a scientist, and he dials in every factor. And every morning, we do this whole ritual together every day where we make coffee and we talk about it if we like it. It's such... [1:45:03] We have so much going on. It would be so much easier to just get it from the gas station, but it's just like a lovely... [1:45:11] And anyway, I just, like, notice. And, like, now I know where – I always know where the beans are roasted because, like, we like African blends. So just, like – I don't know. It just makes me think a little bit more deeply about, like, what's going on? Where did these beans come from? That same, like, Steve Jobs taking things apart or, like, John Collison's, like, World is a Museum of Passion Projects. Like, it just makes me think more about, like, how things came to be. A deeper state of attention, I think you also call it. Yeah. It, like – it – [1:45:38] Yeah, it makes me feel like things are like precious and like choices and that I can make them. [1:45:45] And I can exert more influence on my experience of the world or... [1:45:51] Yeah. Or like, I think more about people. [1:45:54] I think more about people. Yeah. Yeah. There's a few, a few sort of themes in that.

[1:45:59] thing in that essay that all point to this. Like, um, there's the quote from Tina Brown about noticing things. You can't teach someone to noticing things, listening to what's going on inside you. We were just talking about what I like and why emphasis on that and why. Another theme is, um, [1:46:16] Well, you say, I think I'm a good consumer somewhere, not in that piece. And then you've also used the word connoisseur, like, um, and specifically how being a good connoisseur actually makes the output better. Um, great connoisseurs don't hoard, uh, who, who don't hoard, I should say, make your great curators. And the thing that came to me here was like. [1:46:36] it's actually a form of generosity, both in two ways, which is, um, um, [1:46:43] Generous in consumption in the way that maybe it makes the thing better, a receptive audience. And generosity on the other side, which is if you're not hoarding it, if you're curating, you're generous. [1:46:53] What do you see in your favorite... [1:46:55] and particularly the most generous consumers and curators. [1:47:00] Thank you. [1:47:00] Just like honestly spending time talking about it. [1:47:03] stuff. [1:47:04] Like that connoisseurship thing comes from Fran Leibovitz. And she says like the reasons art was so good in the 70s is because the audience was so good. [1:47:13] good. People were really paying attention and they were critiquing and they were pushing their creators. Like, [1:47:20] I hope that when someone makes a TV show, they imagine me and my friends at brunch talking about all the choices.

[1:47:31] just loving attention yes loving attention um just recently like this rosalia released a new album have you listened to it yet unbelievable like it's so good she's on another level but like just my friends and i are like every track are like the transition like this like you hear when those drums came in like her voice like [1:47:48] yeah, loving attention on her work. Like, I trust that she worked very hard to, like, create something amazing. And I'm, like, appreciating. I'm, like, live tweeting all day. I'm, like, sorry, meetings are canceled. Like, I got a text about this. Yeah. [1:48:03] And I like, I love her art. [1:48:05] And it's so fun to pay attention to it and talk about it and learn from it and get excited about it. I'm not a musician. I'm enjoying beholding her art. [1:48:16] You're not a musician. [1:48:18] And yet, this goes back to what we were saying earlier. I'm not a designer, but... [1:48:22] you're kind of doing it, which is like, [1:48:23] You're not a musician, but you are engaging with it in a way that I think she would appreciate, which is that it's loving attention. Yes, gabbing about it at brunch with the girlfriends. [1:48:33] There's something I think you talk about a bit in the piece, or at least point out, which is like... [1:48:39] Taste is kind of this external and internal thing together. There's an external sensibility or even recognition [1:48:46] maybe closer to like the correctness. And then there's like listening to what's going on inside you. Uh, [1:48:53] Does great taste require both? [1:48:55] I think so. Because I think it's actually Anna Mitchell who gave me this term of like a true original. Where if you think about the person who has like the best taste in fashion, it's not like she's just...

[1:49:06] porting over something else [1:49:08] She's like coming up with their own spin on it. Something's happening in there. Yeah. Like, I think I framed it in the piece as some kind of alchemy, and I do... [1:49:16] believe that that's kind of the quality of it it's like or i think there's another quote in there that's like in accordance with the good and the true it's like yes there are some like laws of physics that like [1:49:26] fashion needs to adhere to to like look good and probably has to do with proportions and color materials. Yeah. Yeah. And [1:49:33] Some things and like there's ways to break that in a way that's like taste, [1:49:37] fall and not. [1:49:39] Um, but I think it just, yeah, it takes loving attention to get there. I think maybe you already given me my answer, but I had another question about like, [1:49:48] why curiosity alone doesn't make for tastefulness. And maybe it's this, maybe it's that curiosity can be, [1:49:56] I don't know if it's only external, but it actually can be internally driven, but it doesn't give the thing the time to sort of percolate inside you or whatever. I think I use the word metabolize a lot, and this is... [1:50:07] Why? It's like you want you want to do some work. [1:50:10] on it. Like, I think it's related, like, if I just, to the Rosalia, did the LGTM, like, I could text a friend, like, love this album. Or I could be like, [1:50:20] Like, here's all the sounds I heard and all the cool noises and transitions and whatever. Like, those things are very different. Those things are different. [1:50:28] Who has most shepherded your taste? Oh, man, a lot of people. Like, really a lot. Give us three. Three. [1:50:35] Ah, definitely Tammy.

[1:50:38] my friend Charlton Lamb [1:50:40] And my friend, Matt Coleman. [1:50:43] Is there anything that stands out about when you think of those people and the way that's happened for you? [1:50:48] Or what about their taste is so wonderful? [1:50:52] To me, these people are like the ultimate polymaths. Yeah. Like, [1:50:57] Tammy knows everything. She reads everything. This runs against something you say in the piece, though, which is that you sort of imply that most people... [1:51:03] You can't really have great taste in lots of things. [1:51:07] Which I almost not, I'm not sure I agree with. It's hard to, I mean, like, I think like truly great. Otherwise it'd be so exhausting. But like, I think what Tammy can do and Charles and Matt, all these three people are this way. They read and know everything. And that means that they know how to like exert pressure. [1:51:25] on a thing in a particular way. Like they can draw from math or pop culture or literature or history to like push on an idea. It's like the fork thing a little bit. Yeah. It's like you need the broads. Yeah. It's like, if you, [1:51:39] let's go back to music. Like if you listen to Beyonce's album with an awareness of black history, like something else, something unlocks for you. Yeah. Um, or like, [1:51:49] So anyway, I just like this polymathic like helps you push in question and like more informed people. [1:51:55] ways, um, [1:51:58] Those things... [1:51:59] improve my taste because they're often like opening new [1:52:03] I actually don't have a great command of black history, but I did like Beyonce's album. So getting into conversation with Charlton and Matt about... It's deeper to go. Yeah. And that's a whole new door for me. Yeah. Maybe to try to...

[1:52:18] compressed taste and craft on the nose slightly. You're talking about George Saunders in the piece a lot. At this level, good writing is assumed. The goal is to help them acquire the technical means to become defiantly and joyfully themselves. You're picking out all my heroes in this conversation. It's all banners. He's talking about his students. Taste honors someone's standards of quality, but also the distinctive way the world bounces off a person. I think it's you. [1:52:48] we recognize true taste we are recognizing that alchemic combination of skill and soul yeah [1:52:56] Um... [1:52:58] That taste piece had a great editor for what it's worth. I was going to ask about that. Yeah. [1:53:03] Yeah, what? [1:53:05] Maybe like what examples come to mind when you think about craft and taste coming together or skill and soul coming together? [1:53:11] Yeah, I mean everything, anything that's good. [1:53:16] We recognize soullessness so fast. [1:53:19] Are you sure? [1:53:21] You do. [1:53:22] Is the world getting worse at that? Is that a false fear? People are very worried about slop. Yeah. [1:53:30] Almost to the point where it's like... Yeah, okay. I'll take that. No. [1:53:36] I don't know. Do you think people like are eating McDonald's and think it's like [1:53:40] Good food. [1:53:43] I think digital, it's harder, like... [1:53:46] There's a materiality, physical world thing that's just like fundamentally more scarce. Yeah.

[1:53:51] I've eaten McDonald's and thought it was good. No, I don't mean like, does it taste good? Yeah. I mean like, is it skill and soul? Yeah, yeah. But like... [1:54:02] I don't know, we were just talking last night about how we know some people who write very well, and they don't totally write it. And by the way, does that mean it's less soulful? I don't think so. No. Maybe that illustrates your point, but I do wonder... [1:54:17] Um, [1:54:18] And even the soul piece, like, do you and I feel soul with Rosalia in a way that other person might be like, this is crap. There's a lot of crap here, but like, eh. [1:54:27] I don't know. Probably. [1:54:28] Yeah, is in the eye of the beholder. [1:54:31] Not all the time. I think there's a lot of universally recognized... [1:54:35] Yeah, this special combination. History would also, I mean, like Christopher Alexander, go down the list. Like the quality of that name, like history would indicate like [1:54:43] People are pretty good at sniffing us. I think so. Um... [1:54:48] Maybe we'll get better at it. [1:54:50] That would be nice. Because there's so much slop. Like, I think actually the real risk is that, like, slop is, it's, like, better at hijacking our brains. I think that's the real problem here. Yeah. Yeah. [1:55:02] I don't think anything I see on TikTok is like good. [1:55:06] But like I can spend a lot of time on it by accident. I saw my first feature film directed by a TikToker that I had like watched in 2020, 2021. He just made his first movie. And one of the things that always stood out was like, [1:55:17] this actually had a lot of soul for a one minute video. This guy, Bear Ryan, um,

[1:55:22] I think you're right. I think the fear, I think I maybe talked about this a little bit with Nadia, but like the fear is you just like, [1:55:28] You didn't get the chance because you're just like mind numbed. Yes. Mark Zuckerberg's got you in his. Yeah. Or you like don't. [1:55:34] want to like, I think it's like, [1:55:37] I think it's challenging to read Moby Dick. Yeah. Yeah. I mean, there's like a lot. [1:55:42] in there. I had to have a friend walk me through it chapter by chapter. I don't know why. Great. What a gift, by the way. Yeah. And I don't know why I wanted to read it, but I just did. But I was struggling. So anyway, it would have been much easier to watch Real Housewives. [1:55:58] or something. But anyway, I feel up to the challenge [1:56:02] of, yeah, like soulful and craftful things. [1:56:06] Can I say one more thing about George Saunders that's like just strikes me as you say this when he says like his students arrive already wonderful. Imagine being George Saunders, like one of the most accomplished writers and this like. [1:56:17] room of like... [1:56:18] I don't know, 18 year olds like shows up and you believe that they are already perfect. Like what a generous. [1:56:26] Belief. [1:56:27] How cool is that? I suspect he... [1:56:30] has. [1:56:32] this unbelievably refined ability to see people and see their magic or whatever, their light. [1:56:40] But I think this is why... By the way, I don't think he's being nice. No, me either. I don't think he's being nice. But this is why he's one of my heroes. You can be at peak craft and believe someone unshaped has arrived already perfect. That's like...

[1:56:53] And yeah, your job is to like make them more themselves. Like what a beautiful. [1:56:59] way to like approach someone who's a student. Yes. [1:57:03] To you. Yes. [1:57:05] Yeah, I hope to move through the world more like that. Like we're talking like we're talking a lot about loving attention and taste. And the real I think the real damning thing is just indifference to everything. And I think I was a little bit that kind of teenager of like, I don't care. I don't care. I don't care. That's like the worst way to live to me. [1:57:23] It's the optimism and so much of the stuff we were talking about earlier. [1:57:27] One connection I think on, I want to talk a little bit about taste and editing. Um, [1:57:33] You say, but taste gets you to the thing that's more than just correct. Taste hits different. It intrigues. It compels. It moves. It enchants. It fascinates. It seduces. That's a little extra. Amazing. And speaking of Saunders, like he's got this PN thing. And I think you've talked about that both in the literal editing sense, but also as this amazing template or sort of like what it feels like to actually like. [1:57:54] taste more. [1:57:57] How do you edit towards... [1:58:01] Yeah, it's I'm glad you're asking this because I'm actually I'm working with a leader right now and I think he's got amazing taste. [1:58:08] And the main way it comes out is he says no to stuff. [1:58:11] And. [1:58:12] a thing that we're working on together is like, how do you get it to yes? [1:58:16] Like, it's actually less interesting, like... [1:58:18] That's no. [1:58:19] Like you need to know what dials exist so that we can like, [1:58:22] get it to yes. Like that's the happy place. Steve Jobs was really amazing at saying no, and also had a few awesome yeses. Yes. And like, you have to know what dials you have. Like, it's no fun to like be the person reviewing tweets and just being like, it's not good enough. It's not good enough.

[1:58:36] like a true leader is like, okay, this is how we make it good enough. And there's a lot in there. There's like content, there's skill, there's language, there's like... [1:58:44] Yeah, there's just lots to work on there to like help understand how to get a TS. And I think this like taste. [1:58:49] Like one of my most fashionable friends now in her 30s, throughout her 20s, she wore some like ratchet stuff. But she was trying. Like she was playing. She got a lot of no. Yeah. She got a lot of no's. And now she's like dialed to the yes place. Anyway, I think you just need to like... [1:59:06] I'm picturing like a cockpit. You need to have all these knobs and you know what to turn when to get it to yes. You can't just be like... [1:59:15] No. Well, pure correctness without taste is like the minimalism slop thing. And to your point, like you actually have to go kind of maybe why you have to be willing to take a risk. Yes. To get to something really special. Yeah. Figma taught me a lot about like design thinking. That was part of what was real. Yeah. [1:59:31] really fun about being there, like a lot of people who had been trained in that mindset. And one thing that early designers do is you copy paste something and then you change one thing about it to make it more. [1:59:40] you. And I think that's mostly the journey of, yeah. Virgil, I will talk about 3% better, 3% different. Yeah. And just like, it's like, Oh, like remake this movie poster that you've seen the movie ever. It's like a lot of copy paste tweak. It's a great slope into agency and creativity. Yeah. Yeah. Yeah. Um, [1:59:57] Well, you mentioned earlier, you mentioned both of them, Jeremy Stern at Colossus and that editor for this piece. What was so special? What made them or makes them great editors?

[2:00:09] They keep you in it. [2:00:12] Um, um, [2:00:14] Jeremy certainly has a distinctive voice when he's writing that he does not impose on me when he's editing my work, which... [2:00:23] I think of as an incredible skill. Like he's peek at his craft and then he's like letting me do it my way. He's amplifying. He's not. Yeah. Yes. [2:00:32] So I think of that as like very... [2:00:34] generous and like they often see work when it's not [2:00:37] perfect and like [2:00:39] The enthusiasm to keep going. They never say anything as bad. Yeah, it's part coach, part coach. [2:00:47] Yes, speaking of hands on the dials, they know exactly how to get a TS. [2:00:54] And it's really... [2:00:56] rare but every now and then there's like something that i do want to hold on to and 100 of the time [2:01:02] Thank you. [2:01:03] Hmm. [2:01:04] Hmm. I like that. I think we talked about this, but maybe we're hitting again. How do you, you, you have this amazing desire to be edited. Hmm. [2:01:14] Uh, [2:01:15] in a comfort with being critiqued and edited. Like, is that innate? Can you get better at that? [2:01:20] Oh, yeah. I've had critics my whole life. This is one of the things I learned the most from being an athlete. But... [2:01:29] And my friends who played music growing up, like seriously, they have this too, where there is an objective rightness. So it's like a little bit easier to be critique. Like, yeah, if I make a bad pass.

[2:01:40] I know it's bad. Right. Um, if you like hit the wrong note, you know, it's bad. Nobody's opinion. Yeah. So it's like a little easier to stomach. Like it's pretty clear what the rules are. So anyway, I've just had people critiquing me my whole life. And now, so now when these things are more nebulous, what's, what's the right word to use here? What's the right color? How should this look? I think I like already have a comfort with the language of critique. Yeah. Um, and this is another thing I learned at Figma. Like [2:02:07] Critique is a huge part of the design process. It's like there's no such design process without it. [2:02:12] So I think having mechanisms that like, [2:02:15] build this in. Like we all look at this work together and talk about what we like and don't like. Um, [2:02:21] That feels very normal to me now. I think a lot of people have not had that. It's not a personal attack. Totally. Or like another version of this is watching tape in sports where you just go back and you watch yourself doing stuff and you're like, why? It's a way of being, though. It's assumed. It's not a special. Yes. We watch tape every time. Yes. And yeah, exactly. It's not like a punishment. It's just sort of part of the... [2:02:45] And I had this at Google when I was working in sales. They would film us doing our pitches. And this is where I learned, like, if I have an earring in, I'll play with it. So I don't wear earrings anymore because I don't want to, like, fidget. But, like, until you've seen yourself in a meeting, like. So you've heard yourself on a podcast? Yeah. I never listen to any because I, yeah. But anyway, this, I feel like it's like a comfort with. [2:03:06] Like being in the critique space. [2:03:10] My last thing on this, uh,

[2:03:12] Our mutual friend Molly Malky McCarthy tweeted this yesterday, uh, [2:03:16] It's actually a little harsh, but I thought of you in a good way, I promise. She says, in Silicon Valley, quote, tastemaker. [2:03:25] is the consolation title given to people who somehow maintain proximity to power without ever building anything of their own. There's another word for that elsewhere influencer, but no one seems to talk about that. That's funny. Um, this is decidedly not you, um, back to the earlier point about being someone who can talk and, uh, have taste, but also does a lot. Um, [2:03:47] What do you think of tastemakers who do not deploy their taste to use language from our friend Tammy? Yeah, that's Tammy's words. [2:03:55] Yeah, why do you think it's harsh? [2:03:57] Um... [2:03:59] Maybe harsh is the wrong phrase. I guess I mean it's poignant and very opinionated. I'm not sure I fully agree with her or Tammy on the deployed taste thing. I also think it gets a little bit subtle, which is like, or there's nuance, which is, what is a curator? Is a curator deploying your taste? Am I deploying my taste? All I do is talk and curate people. [2:04:21] The way this is hitting me is actually more of the API thing. I think when people are doing like a taste check with me, [2:04:27] They're like... [2:04:28] Will this resonate? [2:04:29] with another community. [2:04:31] Yeah. Um, [2:04:33] I think that's valuable. Yeah. I think that's like deploying taste. Because I'm like, yeah, if we tune in this knob, I think it will land better. [2:04:40] Which I don't think is what Molly's talking about when she's talking about the tastemaker either.

[2:04:44] But I think the difference between like an influencer, as Molly's describing it, and this like tastemaker is the tastemakers in the wings. They're never famous. [2:04:54] The influencer is a famous one. They're like deploying taste for all their own games. I think she's saying that we call people tastemakers who aren't actual. I see. Yeah. I see. That makes sense to me. Yeah. But yeah, I mean, I mostly don't stand to gain anything. [2:05:06] I doubt many, maybe they do, but I would be kind of surprised if people refer to you as a tastemaker, even though you clearly are. They're referring to you by the things you've actually done, which is maybe the point. Yeah, I don't think, a lot of people will, like, ask me for my take on something. [2:05:19] Like, do you think this is good or something? Yeah, yeah, yeah. But I don't think people refer to me as that. [2:05:24] I [2:05:25] We are well in on multiple hours. I have two sections left. One is a quick one on writing and then a final one, which is just a bunch of miscellaneous things we can run through. [2:05:36] One of the first thoughts I had on the writing front is just, you already brought up, it seems like we're really in the storytelling era, which is cool. It's a time for Brie Wolfson's. What makes writing clever? [2:05:48] Clever. That's a good word. Um, [2:05:52] Yeah, there's another George Saunders-ism. Like, good writing is only that you want to read the next sentence. And I think clever has an element of, like, surprise in it. And I think you can be lulled to sleep really easily with most stuff. [2:06:06] So, yeah, I think, like, if it's good writing and it's keeping your attention, there's probably a degree of clever. [2:06:12] You've talked about [2:06:14] how so much of modern writing lacks editing, especially on the internet and social media. Um,

[2:06:19] And what editing sort of does is like, it's like, who is this for and what will they get from this? Yes. [2:06:24] You've also said self-editing is a real virtue, as I think we talked about. [2:06:29] How does editing like... [2:06:31] I think he used this thing. It was like close the distance between the writer and the reader. Yeah. [2:06:36] Yeah, I think like Morgan Hounsville or something, he would say that he doesn't think of his audience at all. I think like a lot of people say like they're writing for themselves. [2:06:44] I think that's another good way to produce [2:06:46] Good writing. So I don't think this is the only way, like, closing the gap. [2:06:50] um he also i think like one shots it like yeah he's talking about how he just like he'll edit it as he's going and he's just like when it's done it's done yeah he i mean he's also like a prac a very practiced yeah [2:07:00] writer. [2:07:01] But he's self-editing the whole writing process also. [2:07:06] Yeah, I think... [2:07:07] I think this was also Fran Lebowitz, or maybe it was Tina Brown, yikes. [2:07:11] who sounds like good writing knows its place, I think that's [2:07:14] more of what this is like you know that meme on twitter that's like nobody and then it's like [2:07:19] Then it's blank. And then it's like me. And then it's something. I think a lot of writing is that. [2:07:23] It's like... [2:07:25] I think why the taste piece struck so much is because people were talking about it already. It was like sort of like an answer to what I was hearing. It wasn't like random. [2:07:33] Ah. So I think it, like, knew its place in the sense... It's not like I'm rolling up to the function and lobbing a take in. Yeah. Like, it's like, I've been in the context, and I'm listening. Yeah. And I think this is what's hitting so much about the Colossus stuff. Like, I...

[2:07:49] I can see the meme that's like nobody. And then it's like, here's like 20,000 words on Josh Kushner. But I actually think we're like craving more depth on stuff like that felt true to me that was going on in the culture. It was like everything short form, everything clippy, like what is actually the longest, deepest, most intimate. [2:08:05] treatment look like, that was like an answer to something that knew its place, I think. So anyway, I'm trying to like... [2:08:13] respond to like what I'm feeling in the world. It's not just random. Yeah. [2:08:18] Yeah. [2:08:19] You... [2:08:20] Speaking of the Josh profile and the Colossus ones, you've talked about the New Yorker and how much you love their profiles and this chain of obsession and how exclusives are so interesting because they kind of make you like, like not compete, whether that's being obscure or being timeless or whatever. Yeah. [2:08:37] Maybe it relates to the last thing or profiles broadly, but like, should we aim for our writing to be less competitive? [2:08:44] There's a general rule. [2:08:47] Maybe this is more like... [2:08:49] Kevin's stuff of like, don't be the best, be the only. [2:08:52] Why? [2:08:53] I think with the Colossus stuff, we often... [2:08:57] like ask ourselves, like, [2:08:58] What do we have the right to do that others? [2:09:01] don't, it's not like to make it better or anything. It's just like, what do we know about this person? Or like, how do we experience them? That's like, what makes us special? Like what makes us earn the right to do this work? And I, [2:09:12] Generally, we haven't [2:09:13] run into this yet because we were mostly staying in the investor and founder pool. But I think we would really question ourselves. There was someone like truly outside of our network. We like did not understand or know like,

[2:09:22] that we didn't feel like we had the right... [2:09:24] to cover like that comes up a lot. Yeah. Yeah. [2:09:29] What makes Jeremy so good at writing? That's about editing. Oh, man. I don't know. He's another one of these people. He knows everything. He's read everything. [2:09:36] Um, you're very, maybe a better question is like what goes into having such a strong voice. Hmm. [2:09:43] I think he has like... [2:09:45] Thank you. [2:09:47] I wonder how he would respond to this, but he reads to me as very confident in his voice. Like he will. I don't know if you experience this. I still definitely do. Like when I sat down to write, like I assume this like other like I call it teacher voice persona. Like even if I'm like writing a diary entry, I'm like, why am I like all of a sudden assume like words I wouldn't normally use like or like describe it in like weird ways? [2:10:10] ways that like feel technically correct, but like no human would ever say. Jeremy, I think allows himself to like say the human, uh, [2:10:18] words, which I don't, it should be easier, but it's actually harder. Yeah. [2:10:22] So [2:10:23] What do we love so much about numbered lists? Oh, my God. I don't know. It's the best way to go viral on the internet. On this last cursor piece, Jeremy was like, you know, I really don't love listicle generally, but like, I think we can make it work with this one. But yeah, I think it's just easy to scan. Yeah. [2:10:46] It does some of the work, too, of like... [2:10:49] It's just like so easy for your brain to just like ratchet up the ratchet down the taste numbers. Yeah.

[2:10:57] What's the best essay you've ever read? [2:10:59] Oh, man. [2:11:02] I mean, really so many, but I think probably there's a recency effect here. But maybe the one that lives the most, the two that probably live the most rent free in my head at the moment is Nadia's Basic as a Virtue. [2:11:13] And reality has a surprising amount of detail. I think about those things a lot. Why? I think they... [2:11:21] taught me something I actually did not know before. [2:11:24] And then it was like that Bader Meinhof thing where I was like, now I see it everywhere. We were saying like, now, you know, I was so anti-Marina when I was like living in the mission and 22 years old. And now every time I go to the Marina, I'm like, Nadia was right the whole time. But it like reached me before I was quite... [2:11:39] It was ahead of you. It was out ahead of you. It was out ahead of me. And so is reality has a surprising amount of detail. That was like before this insight about [2:11:47] the world is a museum of passion projects. It was, and I was like, wait a second. Is this, [2:11:51] true because if it's true um john salvatier what an incredible essay yeah it's so good and also you know what geeks moths and sociopaths do you know that one this is kevin [2:12:04] I'm familiar with the name, but I don't know if I read it. [2:12:09] so good. It's basically about how movements get started. And it's like first the true believers, and then it's like the people who just glom on, but they don't really have an impact on it. And then it's like the sociopaths come and try to commercialize it and make it suck. [2:12:22] But I think maybe I have read this. I think because of the work that I do, which is often trying to like find a little dim flame,

[2:12:28] Somewhere I'm very conscious of like, I feel taste is the conversation is ruined. Yes, yes, yes, yes, yes. You love to talk through things. You also love to write. I can relate, I think, by talking. What are the pros and cons between thinking, writing, thinking and talking, thinking? They're looping for me. [2:12:48] And I think writing thinking gets a lot of praise. Talking thinking less so. Yeah. [2:12:53] Yeah, while I was talking, thinking. [2:12:55] It's funny. I've actually been thinking a lot about this now that instead of like just writing on my own personal blog, I'm like writing for a magazine that like has just like a different standard of like. [2:13:07] I don't know if ethics is the right word, but like in the taste piece, like I would happily just like copy and paste someone's words and put it in there. Like in this professional magazine, I'm like, should I credit them? Like anyway, like the lines are blurring. I think the talking is like, is it your idea? [2:13:22] That's why people don't like the talking thinking. Like the writing thinking, everybody knows it's all your stuff. Because it's just you and the paper. You're allowed to, you're, ah, hmm. So that's all your own original ideas. Yeah. If it's just writing thinking. What does talking do for you? The writing, that you're cycling through. I'm like so attuned to like the glint in the eye on a thing. [2:13:43] Um, so I throw a lot of stuff out and then I'm like, that's the phrase. Patrick O'Shaughnessy is actually great at that, too. He's like waiting to hear what gets echoed back. [2:13:52] Yeah, he's so amazing at that. Yeah. Unbelievable. [2:13:55] Okay. My last string of things. Forgive me. You said her name last night. E-E-K-E. Eka. Eka from Stripe on critique. Why is it so good to be a micro pessimist and a macro optimist? I think because generally you think about the ways that it will go right.

[2:14:15] And you're being tuned into the details to like tweak them to get it there. But if you do it the... [2:14:23] I guess not the opposite, but if you do it in the context of pessimism, it's like, [2:14:26] No fun. It's the same thing. It's like, I'll know. [2:14:29] No, yes. You want more, yes. [2:14:41] Not that. Or maybe this. Yes, yes, yes, yes. I love that. I love that. Like, you never, like... [2:14:47] Okay, imagine you're like editing a blog post. [2:14:51] And it's like, [2:14:52] It was supposed to ship two days ago, but we're still revving the words. If someone was like, this blog post is going nowhere, no one's going to read it, what's the point? [2:14:59] fixing all the details. Why would I? Yeah, it's about momentum preservation. Yes, exactly. You're like, this is so close to great. Just a few tweaks and it's going to be great. That's the energy you want to bring to fixing stuff. This word is not doing it for me. This whole paragraph, I'm not sure. In the context of this could be awesome is really fun to fix. Yeah. [2:15:22] Otherwise, not so much. [2:15:24] You said you were star struck by Kevin Kelly. Oh, man. Are you star struck by anyone else? [2:15:29] Where have you been? [2:15:31] Um, definitely. I like totally... What's that thing you have when you, like, get weird in front of celebrities? If I, like, pass one on the street in New York, I'm, like, no chill at all. All across the board? Yeah, here goes the dog. Um, but who... [2:15:45] For some reason lately, I've, like, really...

[2:15:48] set my mind on like meeting Tina Brown. I think I'd be freaked out in front of her version. All right. We got to make it happen. Yeah. Yeah. Yeah. You've talked about magnet on times. Oh, my God. Off times. Well, uh, any further realizations on like what causes the magnet to be on? [2:16:03] It's funny. The Magnan thing actually is first came from like a friends and periods of dating where Magnan is just like, yeah, the hotties are, are knocking. Um, [2:16:15] But I think it just comes from confidence. But I think confidence is not in a vacuum. You're starting to get some... [2:16:23] Momentum. You said it takes a ridiculous person to fund something like Stripe Press. Yes. Back to funding culture, partially at least. And Colossus. And Colossus. [2:16:33] who else is doing this and maybe what else could be done. [2:16:37] I think this like story movement is a vote to fund weird ideas, basically like, like, [2:16:44] Hopefully we'll get this kind of story studio type thing spun up at Curseur. And the pitch on it was six stunts a year. [2:16:52] Um, so this is like a few thought through like big, weird ideas. Like that's the pitch. And that kind of thing is resonating. And it's just like, okay, can we like write out what a stunt is? And it's like, not really, um, [2:17:04] But anyway, so I think this work is getting funded more now. [2:17:09] Taste is a good dinner party topic because everyone's got a thought on it. Some of you said. Yeah. What are other good dinner party topics? I'm going to take any weasel word or suitcase word, whatever they're called.

[2:17:22] Thank you. [2:17:23] Or, I mean, anything that's mean-y. [2:17:27] Anything. Everyone's got it. Something everyone has an opinion on. Yeah. [2:17:30] Um... [2:17:32] Sontag said to snare a sensibility in words is on the same note, especially one that is alive and powerful. One must be tentative and nimble. And she's talking about camp. She's talking about taste. [2:17:42] Maybe part of what you were just saying, but like what we have other buzzy words like agency that I don't think. But agency like a little clearer, at least. Maybe it's like I'm curious if there are other immediate words that come to mind. Maybe if you were going to do notes on X in 2028, what it might be on. [2:17:57] Good question. [2:17:59] I could do a notes on marketing. [2:18:02] Right now, probably. I think everyone's got a really different definition for that. All right. We'll have to wait and see. [2:18:11] Patrick O'Shaughnessy told me to ask you, how do your friends decide where to work? [2:18:15] Where to work? Mm-hmm. [2:18:20] That's funny. Most of my friends are in Silicon Valley. [2:18:25] So I think they're probably ground level on what the hot stuff is. And I think it's talking to other friends. [2:18:32] I think it's, again, in the dating era of life, we used to say, like, where are the hotties at? This is, like, for work. It's generalized. Yeah, it's like, where are the hotties at? Like, where are the smart people at? [2:18:44] You mentioned Tina Brown a bunch, or I did. Um, [2:18:47] We didn't get to talk about it a lot. One of my favorite ideas is high-low. Yeah, it's the best. So many ways. Those people I mentioned, Tammy, Matt, Charlton, my tastemakers, all high-low. You said...

[2:18:59] or I think she said the uncanny valley between high and low route is very wide. Mm-hmm. [2:19:04] How do you know when you've made it? [2:19:06] to safety. You made it out of the chasm on either side. [2:19:13] I don't know. [2:19:15] Do you have an idea? I don't know either. I mean, I think one of the things that's important maybe is just to think about it and recognize like high and low can come together, which is maybe the core point you said with Danny Fair. And you have the example of like whatever cultural fair or like political... [2:19:30] geopolitics and Brittany or whatever. [2:19:33] Just so many of the best things... [2:19:36] They hold both? Yeah. But yeah, I don't know. I think it's more of a, you know, this is back to the taste thing. You have to know when you see it. Like, it's in the uncanny valley. You know when it's in the uncanny valley. Yeah, for sure. Yeah. [2:19:47] I actually think, like, one of the mysteries of, like... [2:19:50] marketing and taste and all this stuff, like every now and then I know when something's going to hit, [2:19:55] I mostly don't. [2:19:57] I mostly don't. And I think most people mostly don't. Like maybe there's a few, like the mischiefs or the mischiefs, like maybe they... [2:20:04] It's more mechanical, though. Yeah. To some extent for mischief, which is one of the reasons I think Gabe and those guys are, like, done with it. Yeah. Mr. Beast is extremely mechanical. He's, like... [2:20:13] obsessive about YouTube like it's basketball. Yes. Yes. So maybe there's something there for those people, but I generally don't. [2:20:21] No. Yeah. Yeah. [2:20:23] You have a scrapbook of pride and a brag document. Yeah. Any highlights in there that come to mind?

[2:20:29] And it's honestly, this is why the insight about like just wanting cool people to think I'm cool is like mostly compliments. [2:20:37] from people I think are cool. As it probably should be. [2:20:41] Yeah, I don't think that's the way to build your internal flame source, but that's mostly what's in there. [2:20:49] It's good to live a relational life, I think. Yeah. I think that's a nice way to put that. Yeah. [2:20:57] What types of things, maybe we talked about this kind of with the talking thing, but what types of things does writing as a medium miss? [2:21:02] Mm-hmm. [2:21:04] Yeah, one description of my writing a long time ago was cinematic. And I was like, then shouldn't it just be a movie? So I think it missed... [2:21:14] I guess this could also be thought of as an asset that it's like there are no visuals. But this is actually one of like the founding ideas for Colossus was photography to like make that medium. [2:21:25] bigger in the magazine and like give that visual peek. So yeah, I think it does sometimes miss the, [2:21:31] I mean, obviously it misses the visual stuff, but on the flip side, it allows you to paint a mental. [2:21:36] Picture? [2:21:38] My friends, Nick and Devin, they're like really into right now how like stuff on the web doesn't have any sounds. [2:21:44] Not real OS. Yeah, there you go. I'm interested in that. [2:21:48] Um... [2:21:49] But I don't know. I think it's its own... [2:21:52] thing. [2:21:53] I don't think too much about what it misses. What do you love about Matisse? [2:21:58] I don't know. It just is pleasing to my eye. I think it's because of sharp contrast.

[2:22:04] Yeah. That's all I need to say. You said Graham Duncan's concept of grip quite literally changed your life. Yeah. Why? Now I see it everywhere. That would be another good candidate for... [2:22:14] And I say that [2:22:15] Um, I think about a lot, um, because now I, it's one of those things that becoming self-aware about it, like what is my grip? [2:22:22] On this... Seeing the water. Yes. [2:22:25] It's seeing the water and, [2:22:26] Almost always like you're we're you're probably getting a more sense of my temperament from this conversation. Almost always my grip is too tight. [2:22:34] Um, [2:22:35] And it's. [2:22:36] getting in my way because I can't bring the loose quality that like makes me happy. And more than any other person in the world, Patrick O'Shaughnessy has like, like loosened my grip on things and, [2:22:47] So it like helps me get to joyful faster. Wow. And he, you know him, he's like also intense and competitive, but he has a light grip on everything. [2:22:56] Mm-hmm. [2:22:56] And it just makes him, he's so much more fluid and flexible without sacrificing like any power or effectiveness. And anyway, it's just like. [2:23:07] It's empowering. [2:23:08] To me, the happy place is the lighter grip place. Like all my problems are related to grip. So anyway, now that I can see the water on grip. [2:23:19] just the dog. We, um, [2:23:21] you have a few maxims or like little lines on your website, um, that are all great. Uh, [2:23:26] Have a real friend in the generation above and below you? Oh, yeah. [2:23:30] What do you look for in intergenerational friends? [2:23:33] And [2:23:34] That's a good question. I'm thinking of one. My, like, my best friend in the generation above me is this woman named Leslie Berlin. Um, and,

[2:23:43] And. [2:23:44] I like most notably, at least recently for the Steve jobs archive stuff. Yeah. Yeah. Make something wonderful. Um, and she's just, she's amazing. [2:23:54] woman. And I think the main criteria for her is like, it's, [2:24:00] I think it's like fun to hear like the problems facing someone, [2:24:03] like my age and yet she like still has wisdom that feels relevant to me. Like she doesn't, um, [2:24:11] She's not dismissive of, like... [2:24:13] my experience, um, because I'm like younger or like it wasn't like that when she was coming up. It's the best, one of the best traits in an older person. Yes. And I think the same is true from a younger person. Like my, um, my sister is much younger than me. She's like very squarely Gen Z. Um, and like, I think a younger generation too can look at the generation above it and think it's like old news and doesn't have anything to offer. So anyway, I think it's that it's like respect for what's coming before or after. Mm-hmm. [2:24:41] Everyone wants to help. Ask for what you need. Oh, yeah. How have you gotten better at asking? Just being more specific. [2:24:49] Weren't you saying this the other day, you were like... [2:24:51] Yeah, don't ask... [2:24:53] If you send an email, that's like, can I pick your brain? Or can you catch up? Who wants to do that? Who's got the time? People want to help. Yeah. And there's an abundance in helping. That's the thing I think I'm working through. It's like, you don't get one shot necessarily. Or doesn't everybody like to be thought of in the room where it happens? Yeah. It's actually generous. Yeah. When, for this very brief moment in my life where I had this...

[2:25:16] startup like many people later were like I was like sad you didn't ask me [2:25:21] And I, they were on a list and I was like, I would never ask these people for money. So anyway, that like broke my brain a little bit. Oh, yeah. [2:25:32] Everything will be different in six months. Totally. True in startup life. Yeah, especially now that I have an infant. [2:25:38] She's like a new person every day. It's amazing. She's been... [2:25:44] Like having an infant and moving out of California where there are seasons has like changed the conception of time for sure. [2:25:52] The deeper you go, the better it gets. This insight also preceded all the tastes. [2:25:58] stuff. [2:25:59] Um, [2:26:00] And, you know, [2:26:01] I wrote this after, actually. I thought there was a bunch of people I didn't like, and then I was forced to hang out with them for a weekend, and I was like, oh, I like them. People are hard to hate, close up. Yeah. Yeah. [2:26:12] Um, and now whenever like someone feels like some flavor of enemy, um, [2:26:17] To me, the antidote 100% of the time is just to go hang out. [2:26:23] It's a life's work to bridge the inside of [2:26:25] You and the outside you. This came from... Is it going? It's going okay, I would say. But a therapist friend told me that she has seen people survive anything but a cruel inner voice. Yes. [2:26:43] And I don't have the kindest inner voice at all times. And it made me think, what a waste.

[2:26:51] So I'm just trying to quiet down that voice and let more of the inside come out. It's always better. [2:26:59] Um, but I don't know why everyone has a lot of fear around that. Hmm. Uh, you had a complicated home life growing up. I'm curious if there is one thing from each of your parents that you hope to embody for your daughter. Um, [2:27:14] Mm-hmm. [2:27:14] It comes to mind. Yeah. [2:27:17] Good question. [2:27:21] My mom gave me all the joyful stuff. [2:27:26] And I think she had a complicated relationship with... [2:27:30] like too much joy and too much excitement. But she gave me that. [2:27:36] That I like, I treasure, I want my daughter to like have fun with things. And my dad gave me the hardworking side. Like he gave me the like, it's that hard and soft a little bit. Yeah. And like I being able to have them both at once, like once I truly like can integrate and enjoy them both, like that will be, and I hope my daughter has those things. [2:27:57] For sure. [2:27:58] for sure. Uh, one last thing, your dog's going to kill me. Um, you tweeted this the other day to be of use. Oh yeah. Just a little excerpt from it. Uh, the work of the world is common as mud botched. It smears the hands crumbles to dust, but the thing worth doing well done has a shape that satisfies clean and evident Greek on for us for wine or oil, hoppy vases that held corn are put

[2:28:28] Okay. [2:28:34] Why is work that is real worth it? [2:28:37] So [2:28:38] This is basically like why I married my husband. He like teaches me this every single day. Like there is not a thing in this house he would not repair. Everything he wears is like old and patched up. Like every time we're going to get anything, he's like, is it useful? And like, especially now with an infant, there's like all these like single use products and everything's being marketed to you and all this stuff like that. [2:29:01] He just reminds me every day, like, the main, like... [2:29:04] point of a life is to like [2:29:07] I don't know, put in more than what you get out and like use your hands and like recycle. And like, he just he's very good like that. He like reminds me that like, I don't know, humans are sort of. [2:29:20] Yeah, this is our thing. [2:29:22] Like we are tool users and we like can fix and problem solve and like be useful. And like a joyful life is more around these things than the other things. But yeah, I love that poem. And I think I tweet it probably like once a year because I'm just like trying to remind myself. It's very easy to get caught up in the stuff that's not that. [2:29:44] But that's why I like that line about like, it's mud. Like it's kind of like down in there. Yeah. Yeah. And it's like, I don't, when I see mud, it's like the main thing I want to do is like not go near it. Yeah. But this reminds me like, oh, that is the stuff. It's the whole thing. Yeah. That's the whole thing. So yeah, mostly that's a note to self as well.

[2:30:02] Thank you, Bree. This is all I got. Jackson, have fun. What a gift. Thank you. [2:30:06] Once again, I'd like to thank Notion for presenting Dialectic. One of my favorite things I read over the holiday break was a little Twitter essay written by Ivan Zhao, co-founder and CEO of Notion. It's titled Steam, Steel, and Infinite Minds. In it, he walks through how new technologies have developed. [2:30:23] fundamentally reshaped how we work and build things over the course of the 20th century. And now we have a new kind of magical material, AI. Ivan references an amazing Marshall McLuhan line in the essay where he talks about how we tend to drive to the future via the rearview window. We think [2:30:41] Schemorphically, we think in the context of the past and effectively, I've been thinking about how first and foremost organizations and then eventually economies are going to change thanks to. [2:30:52] Abundant intelligence. When coordination and collaboration are assisted by all kinds of intelligent agents, how is the actual work going to change? I think it's clear that [2:31:02] Over at Notion, they're thinking a lot about this in terms of how we're going to work together. And I love how he thinks about both what we're going to get and what we might lose as... [2:31:10] We are able to collaborate faster and all have so much more leverage. One of the things I've been impressed with Notion about is how they've been really thoughtful about focusing on the quality of the actual work and reducing friction and taking away busy work. And to be clear, there are going to be a lot of trade-offs. Ivan's really thoughtful about the ways that as we gain speed and leverage, we might lose things. But I was really impressed to see him thinking about it in this way. And I hope you give it a read and check out Notion if you haven't.

[2:31:36] Thanks again. See you next time.