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 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 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.