35: Brie Wolfson - Loving Attention & Ease in Craft

27:03Brie Wolfson:And 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 yeah there's um a subtle but very important shift from like we are building the product to building like we are building the organism that can produce the product or or many products on the ic stuff like the shapes inside of companies seem to be changing maybe back to the tolstoy quote um and i want to talk about culture but like i almost think of culture is sort of like the soft part of companies and called like the primordial ooze right yeah yeah and and there but there's another part which is like the hard the skeleton or the hardware or whatever um and like it seems very clear independently uh of cursor but maybe especially with the example of cursor that like the shape the atomic nature of work inside of companies is changing um 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.

28:15Are we going back to, 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 the individual being the building block again?

28:29Brie Wolfson:I think so. I think so. I think individuals have way more power in organizations now because they can do more wide. Yeah. 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 setup. 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 for me. And like how many other people I think needed to be involved when like really only I needed to be involved.

29:08And you could just ship it.

29:11Brie Wolfson:Yeah. But I had so much like 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. And 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, could you just like, did you, were you thoughtful about what you did and i was like yeah yeah but i like that was hard to deal with honestly like after being brought up in this other you say dependencies kill productivity yes like 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 at work on the note of like different shapes of companies i don't can't remember if you actually worked with them but you were you referenced supercell somewhere and supercell is pretty unique maybe like valve would be kind of similar but they're known for having this like maybe amazon would be a closer tech comp of like not as like super top down way more like there are these cells and like those cells do whatever they want and they produce cool stuff they produce games whatever maybe it's a something kind of unique to game um 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 back to the IC is the atomic thing like are we actually going to live in this world where like you have like Rio is a cell on his all on his own and he just like decides to do stuff and then like reports back yeah so here's my hang up with this setup like I actually if we are going to be all about craft and like I'm like okay my thing is like the words yeah and I actually I don't try that hard on design.

30:58Brie Wolfson:I really like partnering with designers, but it's just like not my thing. My hang up about this world where all the ICs do all the craft work is that we're never going to have the like overlap 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. So I think in this world where everyone does things alone, you sort of like miss out on the, I think the novelty comes from like Venn diagram overlap of like people, two high craft people or like a few coming up with something truly innovative together.

31:34Brie Wolfson:So 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, and now you have every designer being like, whoa, curse is pretty sick. What do you think the balance or how do you, maybe a more specific question, like how are you trying to bring some more of that?

32:10What do you think the balance is to still get the amazing, like you have maybe generalists with specialist spikes or the fork spikes and then there's still the overlap.

32:18Brie Wolfson:I want to, I want to. I'm working on a really fun project right now. And the prompt was like, sort of as you do, it was like, you write the script and the prose and then like baton pass it to design and like they'll do their thing with it. And I was like, no, I don't want to. I want to work with design because I don't like copy on the page can like look a particular way. This isn't a supply chain either. Yeah, 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. It's so good.

32:57Brie Wolfson: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. And I think it would have been hard to pull off without that, like true, like holding hands the whole time mindset. This is like, 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. Like it's sort of like you're making an album and it's like the guitar guy, the guitarist. Yeah. Remember that postal service? Remember that band? And they, they literally did that. But I'm sure there's so many examples.

33:28I get, yeah. It's really easy to be like, let's all get around the table.

33:32Brie Wolfson:Yeah. Yeah. And look and mix things around. Like. Oh, I went down there for our design work. I was going to say. Because I've, I feel better in those rooms about collaboration. I feel this that cursor every day being remote. I would be much more productive and much more integrated if I were in the office. I lament that I'm not. Lack of proximity requires everything to be intentional. Yeah. And intentionality is great, but it doesn't allow for the. Yeah, 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.

34:10Brie Wolfson: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 yeah but this is just the new way this is the new way like it's just fluid can fully remote companies actually be that creative i'm sure i'm sure i mean are you sure um i don't know i have you ever been truly deeply creative in this way we're talking about this collaborative way and maybe it's a spectrum but like i'm 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 doing the creative work not through a screen yeah and for me that's different i don't but like i'm extroverted and i like people and i have a big family and i grew up playing sports teams like i don't know um maybe i'm just a particular way because i was shaped by a particular set of experiences but that's just my feeling yeah the cap cut kids yeah exactly exactly they have a different way of being.

35:08Brie Wolfson:I don't know. 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. And I just, I hate that phrase. I hate that tee up. I hate that whole thing. And I think like Rio has really shape my thinking on this like just don't do that i was gonna say what would you suggest instead um just be like i have a design idea 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 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 that's like not like this dude from marketing is giving me product feedback oh but it said like everyone here is awesome yes yeah trust is one word like i'm not gonna walk into a room with wilson minor and like give him my like design thoughts i'm gonna like stay in my lane and kind of see what he does and then we can like play yeah together yeah so trust is like one word but i'm more like in awe of others like i want their work to flourish like same thing on this versell project these designers are like spectacular they like produce beautiful stuff i want i want them to come to the table with their part um yeah and i don't want to do i'm not a designer but but i want to do like oh what if yeah yeah what if is is is awesome energy um on this still on this note a little bit like as far as I understand, Cursor has like no meetings.

36:57And I assume that's like, it's probably a pointing at something generally shifting of this sort of IC type thing. Like, how do you think like the, back to this hard part, like the skeleton scaffolding part, like how do you think infrastructure around stuff like management, planning, established systems, meetings, like clearly it's in flux or at least like, are we at risk of Chester and fencing it where we're just like, actually, Chris is going to need to have some meetings?

37:26Brie Wolfson:Chris is 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. Yeah. I guess another company truism that everybody's having their own experience of the company. That's probably true for Rio and he should have a lot of time for Deep. Yeah. 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 in the meetings. Yeah. Or jobs. Yeah. Especially on Zoom. And like some of the drudgery of corporate life, like these round the horn updates and like all that stuff.

38:05Brie Wolfson:I think that's a little bit easier to go away. Yeah. There's more automation around that stuff, like the rote stuff. Although I say that and then like a friend just joined a company in 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 just by like organizing the chaos. So I don't know. I'm like, I genuinely am excited 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.

38:42Brie Wolfson: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. Old, old Phil's a little silly, but old on a relative basis. Yes. Yeah. I've been like a friend turned me onto this idea. Like if you are interviewing with a young founder or young company, you should ask the executive like who their mentors are. I thought that was a really good question. And then I was thinking like, who would, who will the CEOs of this generation be mentored by? Like, I wonder if there's new rules and it actually might not be that productive to be mentored by the previous generation.

39:21Some things change a lot and some things don't change.

39:24Brie Wolfson:True, true. But I wonder if that, like, 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 surrounded with are. And this new company, young people leaving it are like, it doesn't matter. And she's like, I know that it matters. And they're just like. Respectfully, you're wrong. Yeah. But I like, I, to me, it's very refreshing and like exciting that they still have that optimism about that. Like if they didn't believe that that was true, it would surely be not true. Like they would surely be tolerant of the politics and yeah, these like weird dynamics.

40:06Brie Wolfson:if they didn't believe that it had to, if they believe that it had to be the case that like companies get political, 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.

40:21You, I know a tweet fairly recently, you referenced the Billie Eilish Vanity Fair video. Oh my God.

40:26Brie Wolfson:I love that video. Specifically, you said about how the speed of company building in the AI era, you're the first person to make that connection. Lol. Which is amazing. I think they're on the eighth one of those for if you want to go watch. 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 goes from 200 ,000 followers to 600 or 6 million. I guess there's a broad point here. And then also maybe it's more specifically like on the infrastructure part, like you help spin up Stripe's planning function.

41:02Like is planning 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

41:15Brie Wolfson: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 that approach more versus like we need to like take these big bets and it's a big chunk and it's gonna 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 a little more obsolete but one function i think it does play as like for these bigger swings that you really want to invest in yeah how do you yeah how do you make sure that the company's carving out time to do that i think great urgent but not or not urgent but important yeah or even if like even just exploratory um i think it'd be really easy to get lost in like little feature wars and um yeah so i think it takes some intention so that's one thing i think planning can do that will like companies won't outgrow 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 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 how are enterprises different than us like what what might we want to do to support that kind of work that is doesn't come naturally like yes doesn't spring almost like a reference point when you're like it's like a i don't know a plot of land when you're out on a boat or something it's like if there's no land anywhere it's like oh yeah but like i mean it was not like an accepted concept to work on planning at Stripe.

42:54Brie Wolfson:Like that was, it was like a risky project because it felt kind of off the culture at the time. Well, this is kind of goes back to what I was saying, which is like, I think that some things don't change and like Stripe and now cursor, like these companies, they're doing, this is why I was laughing at you saying it's like the old way, like Stripe's 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 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.

43:24Brie Wolfson:And it was something like, we're like evolving beyond like the Rube Goldberg machine of spreadsheets. And that is how it felt at that time. Like a Rube Goldberg machine. Cursor does not feel like a Rube Goldberg machine. Like it feels like a multi-armed, like something else, Hydra 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. 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. How does scaling, how do you scale how it feels to build it?

44:02Brie Wolfson:I'm not sure, but maybe these more like nuclear little collaborative pods. Like, I think a really cool thing could be that your like quote team, and maybe this is more like the supercell 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, that feels really fun. I like that. To me. On the soft stuff, on the culture stuff, I think one of your big ideas is that you have to get like out ahead of things before the osmosis stops working. Patrick Collison said a lot of companies end up articulating their values too late.

44:39Maybe first, like what do good companies' values look like and how are they different from individual values? Yeah. I think values seem like something you would actually say or some way you would actually behave.

44:58Brie Wolfson: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? They're just boring. They're so ick. But ick because they don't mean anything. because they're not honest because they're generic yeah any any one of those things like one of the most commonly cited values at stripe was we haven't won yet and that was like the humility 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 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 thing.

45:43Brie Wolfson: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, okay, 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? Cause 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've been like if you didn't have to say that thing first and instead you just got to like brag and stump your chest or something yeah so anyway i think that was like a good value even though we made fun of it a lot you have you you talk all about like the stuff that companies do for the audience of themselves and like what a beautiful kind of definition of culture how does that and there's obviously so many thing machinations inside of like what that means but like how does that incrementally actually produce the desired output of culture.

46:35Brie Wolfson:Yeah. I think like the audience of it self, this is, 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 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. And I think it could be really easy to dismiss all hands like it's like meta work like if we're gonna ship it should be for yeah and 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 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 it would sort of be like why does the sports team have to do the pregame meeting or something like yeah we we treat some of that stuff as rote in a way that 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 yeah thing and she was an extremely talented but by the way that's what we all remember yes you know probably don't remember that many of the goals you scored yes so i like i think i'm also like a locker room girly and i do think that 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 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 and marketing like moves a lot through those channels and they are under invested in oh man especially in a place like san francisco for sure like for sure and that's the true pulse of the company totally this at cursor last week like 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 and like it was totally off-brand like cursor's a little bit more serious and it was like like a really silly moment.

48:48Brie Wolfson:And I think it was really memorable. And I think it made people have like a really good 15 minutes. What is the line between lore or mythology and nostalgia? Oh man. Stream was kind of like anti-nostalgia. Are you anti-nostalgia? No. Okay. I'm like my friend Sam, like ghost of Christmas past. It's actually funny. 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, Remember 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 type things like these.

49:26Brie Wolfson:And often I think they're like not even fully true. But they just like. They're never true. Yeah. No stories are fully true. They like cement a feeling or like 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 adding so many people so quickly to these companies, they're growing so fast. You want to like bring people along with the story of the company. But to me, that's lore. Yes. Or mythology, which is maybe I'm driving like a false dichotomy, but nostalgia is like, I think you're right. And a lot of people are like, nostalgia feels good when you're the person who's there.

50:04It doesn't feel as good. Maybe a better question is like, what is the role for nostalgia in particular?

50:11Brie Wolfson:I don't feel that connected to people who wish they were 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. And maybe that's a little bit what nostalgia is. Like, 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, join us in the future, please.

50:47we talked a little bit about like this Tolstoy thing and like great companies um are no way to know but like is your instinct that all great cultures are like truly original and the like snowflake snowflake sense or are they like permutations or remixes or even something more like an Enneagram or Myers-Briggs where there's like yeah a dozen or so flavors you know

51:11Brie Wolfson: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 idea with this collection of ICs thing that's happening. Surely every page on the Stripes website is an extension of Patrick and John. Based on what I told you about how the cursor website got out, like not so much an extension of the leaders.

51:45But like one could say that's like less finger feel.

51:47Brie Wolfson:Yeah. But one could also say it's actually like an enlightened view from Michael. Yeah, I think so. Or like 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. but I um I think they're I think they're probably all singular any company greater I don't know I try not to say like good or bad they're just like their own way I guess on the note of varieties you this ties to some of what we're talking about earlier which is you've said stripe is very much a thinking culture yeah um as we've clearly exemplified by some of these examples cursor seems more like a doing culture.

52:30Have you slid one way?

52:32Brie Wolfson:Oh yeah. I'm like a chronic over thinker. That's why I was a good fit first, right? Like I love a doc. I love thinking through all the different outcomes. That feels, that's very natural to me. I do that in my personal life. I'm working on becoming more doing oriented. Especially now that it's like a little bit easier with stuff. Like this week I'm working on cursors first, like company pulse survey. and we're like, let's build it in cursor. And I'm 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.

53:11Brie Wolfson:And like, this is the, and it was like, wait, I could just put this in cursor. So anyway, I'm still working on updating my own 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. like it's not a perfect example but i'm sure there are people who if they have to write something are like addicted to chai gbt or like i'm gonna try to get somebody's help and like you have a 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 anything i don't i can't do it i can't do it and then you wait in i think that like the finger feel thing or like the way that 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's so good at what he does.

53:59Brie Wolfson: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 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 yak 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. There's a little bit from, uh, Kari from linear, um, that reminded me of something that I spoke about, about with cursor and I was, uh, with Rio and I was curious to get your opinion.

54:42Uh, 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 pointing at the 996 type stuff. Do you think startups are, and granted, I think you've spent less time at super early stage startups, but you may have worked with some, like are 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 shaping the clay in cursor and like i'm gonna go for a walk yeah like there's no like that yin yang and obviously it's different at a company level but i'm i'm curious or maybe just any reflections broadly on the whole workaholic

55:37Brie Wolfson:kind of aesthetic thing 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 um it's really hard not to be reading or thinking or consuming or tweeting or whatever like it's way harder to not because you feel like you're losing ground 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 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 whatever AirPods in on the walk.

56:17Brie Wolfson: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 to me, like that's the hustle culture feeling to me is I'm not up on it or something. Or yeah, I like, I definitely notice a lot of people who are just like kind of saying stuff in Slack. I don't really know why, but I think it's kind of like receipts, like at my desk kind of behavior. behavior. And like, same thing. I like so many Slack messages are edited. Like people send them and then they tweak them after like that kind of, this is where I noticed this like constant doing, doing, doing, doing, doing.

56:55And it's aesthetic a little bit. Yes.

56:57Brie Wolfson:Yeah. So I definitely am noticing a lot of versions of that. And then it's hard to sit still. And again, like in many ways, I just feel like a benefit of timing. Like, yeah, I lived and worked in a world where this didn't exist. Like my first jobs didn't have Slack. Like I think we use like HipChat or GChat. So I've lived and worked before this. So I had the chance to build some habits around stillness that I 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.

57:37All right. It's just like easier to be at fidgety.

57:40Brie Wolfson:Yeah, for sure. 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. 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 and time for it.

58:12Yeah. Yeah.

58:13Brie Wolfson: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 for your work is becoming more of a thing. So I'm excited about that. I think it's like means that the internal work like 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, the first thing you do is shift to the internal version and see if your colleagues are into it.

58:51Brie Wolfson:It's like a test flight for the whole company. Yes, and old-world versions of this are you talk about your intentions and planning, or you write the doc, or you give the all-hands presentation about what you're going to do. um 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 react g's they get that 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 i wonder how that will evolve 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 um 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 so a huge part of the this team's job is to like get people pumped about enterprise and they have to like explain why it's cool yeah 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 the average engineer to like work on the enterprise product to unblock the da da da.

1:00:07Brie Wolfson:And that's like all internal marketing work. And I think one way you can think about that is like negatively, like people have to do these like internal press tours to get their work done. And one way you can think about it is positively because you're like building more cohesion. Yes, selling vision. Yeah, and you're excited about each other's work that you yourself can't do alone. So anyway, that's the version I'm excited for. That's like, yeah, taking care of the internal audience. I think it might be a little related. I want to talk a little bit about leadership and great organization and cultures.

1:00:44You 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.

1:01:00Brie Wolfson:Yeah. Maybe speaking of even just selling things internally with your team, what is morale and where does it come from? Yeah, the word I would use maybe instead is just having fun. I think Devin 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 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, like giving it, I'm like creating some morale. It's like above the baseline. Yeah. And just genuine enthusiasm is, yeah. And I think you can manufacture it. I think you can manufacture it.

1:01:42Brie Wolfson:Maybe this comes from my background doing sports. But 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, gonna have to get someone pumped to like, make a change that's gonna like, be a huge deal for NVIDIA. And he's gonna have to like, tell that story and convince somebody else that that is sick and fun and awesome and rocks. And like, 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 gonna like, check off your whatever.

1:02:17the other part of that tweet i have to observe is a sense of destiny yes interestingly though it actually seems that like you think about it and are sort of drawn to both of those things maybe we might talk about like greatness a little bit later but like you are both very clearly having fun and very interested in having fun and also not just like fun is the only point only vibes like actually we're trying to like and and when i think of morale it's actually both of those things yes smashed together which don't necessarily always go together yeah one of

1:02:55Brie Wolfson:my earliest memories in childhood is 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 okay girls do we love to win or hate to lose and every single person said love to win and i said hate to lose 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 competitive i hate to lose i also love to win so like that environment is fun yeah to me again maybe i'm just lucky because i'm wired this but by the way i I should know, like most hate to lose people don't have that much fun.

1:03:37Brie Wolfson:Yeah, yeah. But I'm just wired. The right mix. I'm just wired this way. Like again, locker room stuff. We talked a bit about them a bit earlier, but like you've worked with a bunch of amazing leaders, the Collisons, Claire, Hughes Johnson at Stripe as well, Dylan Field, Patrick, Michael now, and other folks at Cursor, Patrick O'Shaughnessy. um what about people like this makes someone like you want to magnify them and the cultures they build oh man i've gotten so much more out of those relationships than you described and they got out of their relationship with me um i think like ultimately the reason i wanted to do great work for these people is like they funded me doing great work like my story at stripe was i was just like 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 gonna work on this weird project to like integrate this team that we 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 um and i feel indebted to them forever 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.

1:05:04Brie Wolfson:And I was like, wow, I have like a new chance to like do something awesome. I like really want to. Um, okay. Let's take away the stripe people. Yeah. You've also like, yeah, I'm sure you've gotten an amazing amount from all these people you've worked with since, but you're all like, they're hiring you for a reason. Yeah. Why are they hiring me? Um, I think they probably feel that I see something in them too. 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 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.

1:05:54Brie Wolfson:I want to, I want, I've, all those people that you just described, I think are incredible human beings. I like 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. Like, I think my natural view of, and I admire someone and I will only work for people that I admire. My natural lens on them is Skinny Mirror. So everything they say, I'm like, like, how do we make that sound awesome?

1:06:29Brie Wolfson: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 being inspired or being excited or being moved to act or think or whatever. hmm yeah there's uh i was listening to the only time i ever listened to him uh dac shepherd who has this podcast and he was interviewing adam grant the psychologist and adam's observation of dac was that he's like you have inverse charisma that's why you're such a good podcast 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 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 my infinite energy is to like how people like say more awesome stuff.

1:07:21Brie Wolfson:So like, yeah, if any of them say something to me in like a private room, I'm like, let's write a blog post about it. Like, I think that's really interesting. Like, I think we should like let more people in on this thing that like I got private access to. So anyway, I think that's like always my lens on stuff. Refract great people out. 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.

1:07:57Once 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? 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 a looks good to me culture. He looked down at his coffee for a moment. Quote, I'm afraid I'm never gonna 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.

1:08:35Of 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. you've talked about this feeling of being a part of something in so many places going back to the all-american soccer days um or startups or whatever it might be um yeah what is it like a very kind of basic or foundational but what what is it about these groups that moves you so much

1:09:04Brie Wolfson:do you feel you've ever been excellent at anything like a taste of it i think i bounced off it it's also like quite elusive 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 sort of like the gaze of someone else. Like I always would play better when I knew my coach was like daggers on me. 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, okay, better get my ass in gear. So I'm motivated by that kind of like loving attention. I think like someone who wants me to succeed.

1:09:51Brie Wolfson:So anyway, I like think these environments where people are like, I have a loving gaze on your work. I think this could be better. It's, it will, it would be impossible for me to generate that push on my own. I think, I think this surprised a lot of people when I say it, like still, when I write, I imagine Patrick reading my stuff, Coulson. and like I wonder what he's going to think of it still like I have not been in a room with him in almost a decade 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 it's 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 amazing.

1:10:36Brie Wolfson:Like how, like all these people I sent the draft of the careers page to who are like, wording's not quite it. Um, 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. You use the, you use that phrase loving attention several times, but the first time you used it, I thought I first heard 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 there are people who love attention, but what you are seeking is this very specific kind of attention.

1:11:14Yeah.

1:11:14Brie Wolfson:I want someone who feels invested in making my stuff 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, 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, those typos are Easter eggs for you. But like, a lot of people see the type of, I'm not going to bug them. Yes. Excuse me. Yes. Um, so anyway, I just like, I like that kind of, yeah, this, 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.

1:11:54Brie Wolfson:And like, I love that. I love it. 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 uh you're writing a book for people early in their career and you've had quite this winding path um 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 in the path. I don't think that works for everyone. But it worked for me because I got to do stuff where no one would say no because a lot of people just didn't care.

1:12:38Brie Wolfson:But I know a lot of people who just did the latter and it was great for them. But you also pick things up in the crannies and mean people care about the crannies. That's true. Yeah, I do think I've had a particular nose for the type of problems in the crannies. I think you don't want to be in obscurity. 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. Yeah, yeah. Or could be made to be important. Yeah, I think I have a particular temperament for that because I like zero to one. To me, that's like the most fun phase.

1:13:10Brie Wolfson:And often if too many people are, too many cooks in the kitchen, they're like, it can't really flourish. 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 i'll hit it and many people have great career paths that way too i think you were talking to uh perel you said it's hard to have a finger feel for things if you i mean it was paki 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 for the people who do relate to you yeah and see brie and they're like man what an amazing opportunity to have that path like with the benefit of hindsight how do you how do you how do you square the finger feels so important and also i yeah you capture the so well in flounder mode and and yet 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?

1:14:17I'm smirking about this a little bit because I, there's this thing

1:14:23Brie Wolfson: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, yeah, story. People want the story. And maybe it was, it's probably six or seven years ago. I think it was when I was applying for Figma. I like wrote this document to a company that was like, I want to be your head of storytelling. telling. You were early. Yeah. And they basically were like, that's cute. No. And I was, I like, felt very ashamed after that. 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.

1:15:00Yeah.

1:15:00Brie Wolfson:And then 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. Like if I, 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, yeah, get us to print a fricking book and get it on Amazon and like all this stuff to like earn the right to just like tell stories about the authors.

1:15:35Brie Wolfson:But I had to do 90 % of that, the other work. Now I think I can just, 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. But now I think there might be. Maybe a generalized lesson here is like you're allowed to dabble if you like find enough ways to move bricks or whatever. Yeah. I'm preparing like a section on this in the book. I think 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 role?

1:16:17Brie Wolfson:Yeah. 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. I like signed all my renewals. So it was like, sure, spring her on to this other thing. But like, you have to know why you're at the company. If you're 22, like that, advice isn't that helpful because you got to get in the door first. Like, do you have any broad thoughts on like the person who sort of feels like a generalist or like it doesn't, they're not, they're not, um, if their craft isn't necessarily that obvious, they might have a craftful approach to things.

1:16:50Brie Wolfson:I'm curious about like how this will, yeah, how these careers will pan out soon. Like really common hiring advice. Like if you just wanted horsepower, it was like hire somebody who's done a couple of years at McKinsey. I actually wonder if that meme is like still 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 so i don't i like i think there's more expectation for people to be able to produce their own output um whereas I think I spent the early part of my career being like glue for people who had like great ideas, but like couldn't really get them done.

1:17:41Yeah. On the output front, how important is, especially pre having the job, you've been pretty public. You've been relatively public in the last relative period of time. I don't know if you always were.

1:17:55Brie Wolfson:Yeah. Like I think the, if you're 23, like the obvious thing is you got to get a Twitter following or whatever, like share your projects and go viral like what's your advice on that part i i put out a call for the book like if you have questions that you hope the book will answer what are they yeah and the question i get the most is do i need to be twitter famous yeah um no you don't need to be 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.

1:18:32Well, it's otherwise illegible. Your career broadly is illegible, but it's especially illegible if you don't even see the specs of it.

1:18:40Brie Wolfson:Twitter famous is like the wrong way to describe it. I think it's really useful to publish your work. I think it's good to get it to completion. I think it's good to like put it on the internet where other people can see it. Like, I think that - Have something to point to. Yes. And also like just have - 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 share a record of like, what have you like?

1:19:14Brie Wolfson: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 have the record. When it's also not necessarily like an endless stream of noise. Yeah. I think like you have gotten a lot out of like being online I meet a lot of people I like my Twitter feed I think a lot of people don't like theirs I like mine so anyway I get a lot out of being online but I talk to a lot of founders they're like ugh like I have to like 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 like medium of expression on the fodder mode note a quote i think somewhere along the way the message about what it feels like to be great has become a bit forverted kevin says in that piece and everywhere that greatness is overrated you seem to be chasing greatness still um can flounderers be great um i am i think i'm not chasing greatness in the way that Kevin describes it.

1:20:22I agree. Um, I don't, I don't care

1:20:26Brie Wolfson:to like run a company. I don't need like history books to admire me. Like that is not the kind of greatness I'm looking for. I just want to like feel at ease in my craft. And I think that is a lifelong, that will be a lifelong pursuit for me. I want to push you slightly. Cause I think you are both doing that and you, you, I mean, you were 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 is it really just you want to be like it is in your craft you're like not on the list of people i call when i'm having like anxiety swirls about everything like this being illegible has like plagued me throughout my career like you did an amazing job capturing that piece oh thank you but like imagine me at like 27 sending this like email to the ceo of like an actual company being like i want to be your like head of storytelling and then like laughing me out of the room like that was like that did not happen in a confident place like i was like i'm gonna like shoot my shot on this thing i'm gonna like be bold and like put myself on the page we also weren't laughing you out of the room i suspect it was a little bit about the legibility more so than you fool.

1:21:42Brie Wolfson:It was respectful, but it was like, oh, like I... They weren't ready. They actually, it was too illegible. Yeah. You were actually totally onto something, but it wasn't... Yeah, but I'm like, 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. 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?

1:22:15Brie Wolfson:He was like, does not compute. So I, to me at ease in my craft is like, I know my, 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. Um, because I don't want it to be magic. I want to be like real. Yeah, yeah. So I'm like still on a journey with this thing. There's a, the thing that most stands out about Kevin, the way you convey Kevin in that piece is this demeanor or this disposition of abundance. It's kind of what we were saying about the bouncing off thing.

1:22:56Like 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.

1:23:07Brie Wolfson:Yes. That, I mean, honestly sounds a little bit like what you were just kind of describing.

1:23:16You also though 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. When do you feel this at the end of that piece, Kevin talks, or maybe you talk about like the wellbeing bottomless, like what a beautiful imagery. That was all him. When do you feel that abundance and how do you try to get back to it.

1:23:38Brie Wolfson:Yeah. It's funny. You're like tying my whole life together. After I graduated college and soccer was over, my, I was in a pit of despair that I would never be so good at anything again. Like truly, truly, truly. You were really, really great at that. And I was obsessed with it. Like 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, yeah, it was awesome to be an all American, but there was like many stages above me that I, that I thought about.

1:24:16Brie Wolfson:Um, and I think I've done this now enough times where I like have to pass the torch and start over that it's like, 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 I don't know winding down Constellate I like usually I trick myself into thinking like this is the magnum opus like Constellate is like what it all laddered into like a piece of software that like helps companies do great work and I had truly zero product vision but I was like this is its final form and then like I joined Patrick O'Shaughnessy.

1:24:57Brie Wolfson:I'm like, yes, like helping founders plus media, like this is its final 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 sad. But now I've done this enough times where I'm like, yes, I'm going to try to like be the very best. Like, I think it'd be so lame to go into these projects and be like, it could be okay. I don't want to write an okay book. Yeah. That would be so lame.

1:25:28That's the abundance is like what Kevin is doing. Kevin doesn't seem to have that this needs to be the opus. No. And yet it's all great.

1:25:36Brie Wolfson:I know. Yeah. Which is so powerful. This doesn't have to be like the best walk across China that anybody's ever done. And also I'm not going to phone it in. Yes. Yeah. 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. Yeah. And like, what is even like the best book about great operators? Like, it doesn't matter. It's just like my best book. 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. It's just like hate to lose competitive person.

1:26:08Brie Wolfson:But like, I think I will be happier when I trust myself to produce excellent work and to like understand 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. Willpower is overrated. Maybe. Yeah, I'm just, but yeah, I don't want to be afraid of my work. I want it to like, I want it to come out more joyfully. 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. One more from Kevin or on Kevin.

1:26:47His range is wide, but all his work somehow rhymes. What are the dominant rhymes for you in your work?

1:26:58Brie Wolfson:Definitely excellent people around me and like for an audience of other excellent people. That matters to me a lot. Optimism, I hope. Like I always want to paint the picture of the future is going to be better than it is now. And maybe like a touch of something unexpected. I hope these would be like very generous terms to describe my work, but that's what I aspire to, yeah. 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. What do they say about their best employees and the best early talent?

1:27:43Brie Wolfson:Yeah.

1:27:48Brie Wolfson:It's like the main thing that they say is like, they're just so good. They're just so good. i'm like but why and i don't know they're just so good i'm trying to like is that get itness 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 itness um and lots of people have words for it but they're not quite right and yeah i think what they're saying is like they generally can just like move through space and like get things done um like a knife cutting butter yes yes and i'm like are they like persnickety or not persnickety they're all over the map like are they like 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 some flame keepers or something like they just they just is that innate like is that um is that obvious when they're 20 i think so yeah i think so um and I still think that you can it can be cultivated like or grown or compounded or something yeah yeah and this is why I got so obsessed with talent like I had a couple jobs before Stripe um 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 but like the job I had before that was at a startup that was we're 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 like and i was like in the window and i was like yeah i was but like i was like really not trying all right sometimes you got to feel it you got to be next to it it's a finger feel again yeah so i don't know things really changed for me at work where I started to like want to be good 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 so yeah I think it can be cultivated I think a lot of actually people that I talk to who are I would like consider a 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 I think what's that Steve Jobs quote like basically keep looking yes but yeah follow the romantic sense yes I like did talk to a lot of people who like yeah they were not in the right container at first and they knew it 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 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 yeah and 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 was happening at work I just didn't really I think it's broadly true no maybe no no definitely is most people do not work eight hours a day and they're watching I don't know if they're watching you're watching like yeah um things don't take that much time yeah i had never seen like i'd never seen like a hive like hive mind like really buzzy buzzy workplace so i was like yeah i'll just like that's what i do at work yeah like not that much and it took me getting to the place where other people were doing that but i don't think i 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 the fastest hundred meter dash after Usain Bolt is the guy who raised him.

1:31:38Yes. Like this is just so clear. Like this is how we work.

1:31:43Brie Wolfson:Yes. Yes. So everyone might have a different Usain Bolt. Like 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. 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, Oh, 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, okay, now I'm like alive at work.

1:32:19Brie Wolfson:So anyway, you can, you might find it in unlikely places. you seem to move between 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 not a secret yeah everybody knows um which is funny yeah we were even talking about this at dinner last night like am i type a or type b like it's kind of hard to know um it does it does resonate i don't think about holding both because that's just how i am um but they like maybe you allow yourself to be both whether it's consciously or unconsciously whereas i think people you i almost wonder if we like sort ourselves i'm i'm this way and so i gotta yeah yeah and i like being around creatives it's almost necessary yeah that makes a lot of sense yeah for the two the worlds you like to inhabit yeah and i don't just mean creative like people who do art like any kinds of people who make stuff bring new stuff into the world so i think you need to yeah you need to exude a certain quality um for like to be welcome in those places yeah like 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 i know that's not the right place i could read a room i was thinking about like what is your spike um and we've talked about a lot of the things you're good at and a lot of the sort of patterns my best um sense of it i think comes from a few quotes where um 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 what is the there's this ambiguity.

1:34:40People 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. You talked about helping people tell their stories, being this empowering force next to us. But why is we talking about that? Working with ambition and joy. You referred to Harold Ross of The New Yorker as excitable. And so my best point at it is this, it's a charisma specifically around being excitable. Why is being excitable a virtue?

1:35:16Brie Wolfson:That resonates. That's a really nice compliment. I hope that that's true. It's a virtue because like, I don't know, stuff could just be a drag. So it could just be a drag or it could be fun and like exciting and like interesting and um morale a little bit yeah and captivating and I think a lot of the stuff like seen through a new lens of like But what's like the fun version of it is like it actually like shifts the work in the right It actually shifts the work in the right direction. It's not like lipstick on it like actually Changes something about it. It's funny. I was like on a three-way call with two girlfriends recently and mom was putting her newborn down for a nap.

1:36:00Brie Wolfson:And she was like, do you think she's going to stay down? And the other girl was like, honey, I don't think so. And I was like, he's totally going to stay asleep. He's going to 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 miracles. I think I am a hype girl. I'm really proud of that. And I'm discerning. I won't hype anything. Yes. And I like won't lie to you either. I like, I cannot fake it. You believe it. Yes, I do believe the hype. I do believe it. I'm sorry, I'm saying I believe you.

1:36:32People around you believe your hype, which is so critical.

1:36:35Brie Wolfson:Well, I believe it. Yeah, and I think that's my only 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 fake it. 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 like 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 like lose. And I was like, I don't care.

1:37:04Brie Wolfson:And then I like started to believe it. And then I was like the third best salesperson in North America after. But like I. You can sell anything you believe in. That's true for anybody. Yeah. So I link. And I link. I seek to believe. I'm not like. Yes. I want to. I think that's like really fun. I want to find the awesome things about people. Like you said, like, what did I say? Well, I like people tell me things and I like to hear them. Like, yeah, I want to 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.

1:37:35Brie Wolfson:Like, I want you to look good. So I think people feel that in me and also that I'm not, yeah, not fake. Like, oftentimes someone will, like, try something on and be like, no, let's try it again. Yes, yes, yes. So I think that energy is, like, 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 um i think most people want it to be some version of fun um so anyway i like try to i try to bring it i don't always but i try what does it mean to be an api to x maybe this is a little bit we're talking about like like being legible to two different things at the same time it's like connect two things that shouldn't be connected um and a lot of that yeah i think i'm very comfortable in that place like oh i like want to put these two wires but like you really gotta stretch them i'm very willing to do that that's great it's a great mental image you you tweeted a i think a napkin drawn good at talking matrix um that it's sort of like good at talking on the on the whatever the y-axis or something and then competent or good at doing.

1:38:49It was good at doing on the other axis. And one of the good at talking but not good at doing is the yapper. Yeah. And the top right is the good one. You're definitely in the top right. How did you get there?

1:39:04Brie Wolfson:I think people just generally like having me around. Well, not everybody. Like the right setups. So I think I just get to learn from a lot of really good people. 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 yet. I think writing is kind of being a professional thinker. There's a lot of output though. Yeah, I guess I like getting stuff done. Sometimes I make checklists to just check things off. This is also like the picking up the crevices thing. Yeah, that's fair. I do get stuff done. I think I just like to. I think I just like to there's this I think it was on a podcast maybe with Paki or Perel you talked about Steve Jobs wanting to like know how the parts of the thing work I love that story and you said I have that with people and I have that with ideas what do you love about people and ideas it's like an infinite puzzle and everything is different yeah it's an infinite game you cannot understand people you cannot like wrangle ideas and i i'm definitely not the smartest people in most rooms but i'm like i think i am like one of the most willing to ask questions maybe you feel like you have some of this yeah um and to me that's like a very satisfying way to live and i have like no shame about being dumber than others one last thing on that kind of career advice bit uh you were talking to Barrett Brooks and you said, I just, I finally realized I just want cool people to think I'm cool.

1:40:48Brie Wolfson:Patrick O'Shaughnessy helped me get to that insight. It's beautiful. And what you followed that up by saying was I had the clue. I just wasn't listening. Yes. Evergreen. Um, you, I think you even talked to you about it, like sort of maybe some of the aspects of this feel like fundamentally unrigorous or like female gendered or like vibe queen or whatever. Um, I think we all have this in so many aspects of our life, not just career path, but like to people who like, do you have advice for people to get better at listening to the clues or seeing clues? That's a really good question. I'm still, I'm still working on getting better at this.

1:41:29Brie Wolfson:Um, I think it's related to this quietness and like stillness thing we talked about earlier i think it's like thinking when everything is quiet um like when i make a career decision one thing i'll do is like go on like a like a tour of like all my friends and sometimes i'm like maybe it'd be better if i just went into an empty room um i i think that's like part of listening better is just like trying to make everything else quiet so i can hear but it's really hard to do like we're surrounded by smart people and there's a lot of writing on everything and people have opinions on this or that and they're smart and like it seems silly not to like hear from them but i think i'm like still on a journey of learning to trust myself 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 on your own um like if no matter what was happening when i was 22 or whenever 23 whenever i joined stripe like that was the right career decision i think the thing like competing with it at the time was like to stay working at dandelion chocolates and like being a soccer coach and it was like i think maybe that could have been like more fun or like quote listening to myself.

1:42:52Brie Wolfson:But like that was the right step for me to take. So anyway, I'm like, it's hard to know when to listen and when to not. But I think at least like documenting or hearing what the signs are. So at least you have some record of what's going on inside. 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, stillness is something.

1:43:24We've made it well over an hour and a half without talking about taste, but we have to.

1:43:29Brie Wolfson: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. 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, 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.

1:44:08To pursue it is to appreciate ourselves, each other, and the stuff we're 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. It's telling that you say appreciate things more, not judge things more.

1:44:32Brie Wolfson:Yes. Can you say a little more about that? Yeah. The best example I have is coffee. 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 like so into coffee. Like if you look over there, there's like a whole setup. There's like scales and like temperature, like all this stuff. He's like a scientist and he dials in every factor. And like every morning we do this whole ritual together every day where we make coffee and we like talk about if we like it. It's such, we have so much going on.

1:45:05Brie Wolfson:It's like, it'd be so much easier to just like get, get it from the gas station, but it's just like a lovely ritual. 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.

1:45:35Brie Wolfson:Yeah, it like, it, yeah, it makes me feel like things are like precious and like choices and that I can make them too and I can like exert more influence on like my experience of the world or yeah or like I think more about people I think more about people yeah yeah there's a few few sort of themes in that thing in the 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, well, you say, I think I'm a good consumer somewhere.

1:46:18Not in that piece. And then you've also used the word connoisseur. And specifically how being a good connoisseur actually makes the output better. Great connoisseurs don't hoard. Who don't hoard, I should say, make your great curators. And the thing that came to me here was like, it's actually a form of generosity. both in two ways, which is 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. What do you see in your favorite and particularly the most generous consumers and curators?

1:47:00Brie Wolfson:Just like honestly spending time talking about stuff. Like that connoisseurship thing comes from Fran Lebowitz. And she says like the reasons art was so good in the seventies is because the audience was so good. People were really paying attention and they were critiquing and they were pushing their creators. Like, I hope that like when a, I don't know, someone makes a TV show, like they like imagine like me and my friends at brunch, like talking about all the choices. Yes. And like, yes. Loving attention. Yes. Loving attention. Just recently like this, Rosalia released a new album. Have you listened to it yet?

1:47:38Brie Wolfson: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 do you hear when those drums came in like her voice like 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 like live tweeting all day i'm like sorry meetings are canceled like i gotta i gotta text about this um and i like i love her art i 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.

1:48:16You're not a musician. And yet, this goes back to what we were saying earlier. I'm not a designer, but you're kind of doing it. Which is like, 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.

1:48:30Brie Wolfson:Yes, gabbing about it at brunch with the girlfriends. there's something i think you talk about a bit in the piece or at least point out which is like taste is kind of this external and internal thing together um there's an external sensibility or even recognition um maybe closer to like the correctness and then there's like listening to what's going on inside you uh does great taste require both i think so because i think it's actually um 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 porting over something else she's like coming up with their own things happening in there yeah like I think I framed it in the piece as some kind of alchemy and I do 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 fashion needs to adhere to to like look good and probably has to do with proportions and colors materials yeah yeah and some things and like there's ways to break that in a way that's like tasteful and not um but i think it just yeah it takes loving attention to get there well i think maybe you already given me my answer but i had another question about like why curiosity alone doesn't make for tastefulness and maybe it's this, maybe it's that curiosity can be, 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.

1:50:04Brie Wolfson:I think I use the word metabolize a lot and this is why. It's like you want to do some work on it. Like I think it's related, like if I just to the Rosalia did LGTM, like I could text a friend, like love this album, or I could be like, 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 who has most shepherded your taste oh man a lot of people like really a lot um give us three definitely Tammy um my friend Charlton Lamb and my friend Matt Coleman what is there anything that stands out about when you think of those people and the way that's happened for you or what what what about their taste is so wonderful to me these people are like the ultimate polymaths yeah like 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 you can't really have taste great taste in lots of things which i i almost not i'm not sure i agree with it's hard to i mean like i think like truly great.

1:51:14Brie Wolfson:Otherwise it'd be so exhausting. But like, I think what Tammy can do and, and Charlton 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 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, 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, yeah, yeah, yeah.

1:51:48Brie Wolfson:Or like, so anyway, I just like this polymathic, like helps you push in question and like more informed ways. Those things improve my taste because they're often like opening new doors. Like I actually don't have a great command of black history, but I did like Beyonce's album. So like getting into conversation with Charlton and Matt about like, It's deeper to go. Yeah. And that's like a whole new door for me. Yeah. Maybe to try to compress 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.

1:52:31Brie Wolfson:You're picking out all my heroes in this conversation. It's all bangers. He's talking about his students. Yeah. Taste honors someone's standards of quality, but also the distinctive way the world bounces off a person. I think it's you. And finally, you briefly referenced this. When we recognize true taste, we are recognizing that alchemic combination of skill and soul. Yeah.

1:52:58Brie Wolfson:That taste piece had a great editor for what it's worth. I was going to ask about that. Yeah. Um, yeah. What, maybe like what examples come to mind when you think about craft and taste coming together or skill and soul coming together? Like, yeah, I mean, everything, anything that's good. We recognize soullessness so fast. Are you sure? Do you, you do? Is the world getting, is the world getting worse at that? Is that, is that a false fear? People are very worried about slop yeah almost to the point where it's like we're like yeah okay i'll take that nudge i don't know do you think people like are eating mcdonald's and think it's like good food i think digital it's harder like there's a materiality physical world thing that's just like fundamentally more scarce yeah i've eaten mcdonald's and thought it was good i don't mean like good like does it taste good yeah i mean like is it skill and soul yeah yeah um but like i don't know we were just talking last night about how we know some people who write very well and like they don't totally write it like and by the way does that mean it's less soulful i don't think so no but so maybe that illustrates your point but i do wonder um and even even the soul piece like do you and i feel soul with rosalia in a way that other person might be like this is craft there's a lot of craft here but like yeah i don't know yeah is in the eye of the beholder not all the time i think there's like a lot of universally recognized yeah this special combination history would also i mean like christopher alexander go down the list like the quality of the name like history would indicate like people are pretty good at sniffing this i think so um maybe we'll get better at it 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 like i don't think anything i see on tiktok is like good 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 and 2021 he just made his first movie and one of the things that always stood out was like this actually has a lot of soul for a one minute video this guy Baron Ryan um I think you're right I I think the fear I think I maybe talked about this a little bit with Nadia but like the fear is you just like you don't even get the chance because you're just like mind numbed yes Mark Zuckerberg's got you in his yeah or you like don't want to like I think it's like I think it's challenging to read Moby Dick yeah yeah um I mean there's like a lot in there like I had I had to have like a friend like walk me through a chapter by chapter to like I I don't know why.

1:55:48Brie Wolfson: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 or something. But anyway, I feel up to the challenge of soulful and craftful things. Can I say one more thing about George Saunders that's just striking me as you say? That's when he says his students arrive already wonderful. Imagine being George Saunders, one of the most accomplished writers, and this like room of like, I don't know, 18 year olds like shows up and you believe that they are already perfect. Like what a generous belief.

1:56:27Brie Wolfson:How cool is that? I suspect he has this unbelievably refined ability to see people and see their magic or whatever, their light. 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. Like you can be at peak craft and like believe someone unshaped is like has arrived already perfect. That's like, and yeah, your job is to like make them more themselves. Like what a beautiful way to like approach someone who's a student to you. Yes. So anyway, like I, yeah, I hope to move through the world more like that.

1:57:08Brie Wolfson: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. 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. It's the optimism and so much of the stuff we were talking about earlier. One connection I think on, I want to talk a little bit about taste and editing. 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.

1:57:42that's a little extra um and speaking of saunders like he's he's got this pn thing and i think you you've talked about that both in the literal editing sets but also as this amazing template or sort of like what it feels like to actually like taste more um how do you edit towards

1:58:01Brie Wolfson:ineffability 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 and the main way it comes out is he says no to stuff. And a thing that we're working on together is like, how do you get it to yes? Like, it's actually less interesting, like that it's no, like you need to know what dials exist so that we can like 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.

1:58:35Brie Wolfson:It's not good enough. 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 yeah there's just lots to work on there to like help understand how to get a ts and i think this like taste like one of my most fashionable friends throughout 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, yeah, you need, I'm like picturing like a air, like a cockpit.

1:59:09Brie Wolfson:Like you need to have all these knobs and you like know what to turn, when to like get it to yes. You can't just be like, 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 to get to something really special. Yeah. Figma taught me a lot about like design thinking that was part of what was real 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 you and i think that's mostly the journey of yeah virgil abloh talked about three percent better three percent 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 well Well, you mentioned earlier, you mentioned both of them, Jeremy Stern at Colossus and that editor for this piece.

2:00:04What was so special? What made them or makes them great editors?

2:00:09Brie Wolfson:They keep you in it. Jeremy certainly has a distinctive voice when he is writing that he does not impose on me when he's editing my work, which 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. Um, so I think of that as like very generous and like they often see work when it's not perfect and like the, yeah, enthusiasm to keep going. Like they never say anything is bad. Yeah. It's part coach, part like evaluator. Speaking of hands on the dials, they, they know exactly how to get a TS. yes um and it's really rare but every now and then there's like something that i do want to hold on to and 100 of the time they just say okay i like that i think we talked about this but maybe worth hitting a lot again how do you you you have this amazing desire to be edited and a comfort with being critiqued and edited like is that an eight can you get better at that oh yeah i've like had critics my whole life this is like the this is one of the things i learned the most from being an athlete um but 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 critiqued like yeah if i make a bad pass i know it's bad right um if you like hit the wrong note you know it's bad yeah nobody's opinion yeah so it's like a little easier to stomach like it's pretty clear what the rules are.

2:01:51Brie Wolfson: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. And this is another thing I learned at Figma, like critique is a huge part of the design process. It's like, there's no such design process without it. So I think having mechanisms that like build this in like we all look at this work together and talk about what we like and don't like um that feels very normal to me now i think a lot of people have not had that personal attack totally um or like another version of this is watching tape in sports where you just go back and you you watch yourself doing stuff and you're like why it's a way of being though it's it's it's assumed yes it's not a special yes we watch tape yes and yeah exactly it's not like a punishment is just sort of part of the craft.

2:02:45Brie Wolfson: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 listened to any because I, yeah. But anyway, I feel like it's like a comfort with like being in the critique space. My last thing on this, our mutual friend Molly Mielke McCarthy tweeted this yesterday. It's actually a little harsh, but I thought of you in a good way, I promise.

2:03:22She says, in Silicon Valley, quote, tastemaker 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.

2:03:37Brie Wolfson:That's funny. This is decidedly not you. Back to the earlier point about being someone who can talk and have taste, but also does a lot. 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. Yeah, why do you think it's harsh?

2:03:59Maybe 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.

2:04:21Brie Wolfson: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, they're like, will this resonate with another community? Yeah. 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. Which I don't think is what Molly's talking about when she's talking about the tastemaker. No. 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. the influencer is a famous one.

2:04:56Brie Wolfson:They're like deploying taste. I think she's saying that we call people tastemakers who aren't actual. I see. I see. I see. I see. That makes sense to me. But yeah, I mean, I mostly don't stand to gain anything. 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. Like, do you think this is good or something? But I don't think, yeah, I don't think people refer to me as that.

2:05:25We are, we are well in, um, 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. One of the first thoughts I had on the writing front is just, you already brought up like, we, it seems like we're really in the storytelling era, which is cool. It's a, it's a time for, for Brie Wolfson's, um, what makes writing clever?

2:05:48Brie Wolfson:Clever. That's a good word. Um, 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 so yeah I think like if it's good writing and it's keeping your attention there's probably a degree of clever you've talked about how so much of modern writing lacks editing especially on the internet and social media um and what editing sort of does is like it's like who is this for and what will they get from this yes um you've also said self-editing is a real virtue um as we i think we talked about uh how does editing like i think you use this thing it was like close the distance between the writer and the reader yeah yeah i think like morgan haunchell 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 i think that's another good way to produce good writing so i don't think this is the only way like closing the gap um he also i think like one shots it like he 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 writer um but he's self-editing the whole writing process also yeah yeah i think i think this was also fran lebowitz or maybe it's tina brown yikes he says like good writing knows its place i think that's more of what this is like you know that meme on twitter that's like nobody and then it's like then it's blank and then it's like me and then it's something i think a lot of writing is that it's like 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 so i think it like knew its place in this it's not like i'm rolling up to the function and lobbing a take yeah like it's like i've been in 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 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 like the longest deepest most intimate treatment look like that was like an answer to something that knew its place i think um so anyway i'm trying to like respond to like what I'm feeling in the world.

2:08:15Brie Wolfson:It's not just random. Yeah. Yeah. You, 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. Maybe it relates to last thing or profiles broadly, but like, should we aim for our writing to be less competitive as a general rule? Maybe this is more like Kevin's stuff of like, don't be the best, be the only. Yeah. Like, I think with the Colossus stuff, we often like ask ourselves, like, what do we have the right to do that others don't?

2:09:01Brie Wolfson: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 generally, we haven't run into this yet because we were mostly staying in the investor and founder pool. But I think we would really question ourselves if there was someone like truly outside of our network we like did not understand or know, like that we didn't feel like we like had the right to cover. Like that comes up a lot. Yeah, yeah. What makes Jeremy so good at writing?

2:09:31That's about editing.

2:09:32Brie Wolfson:Oh man, I don't know. He's another one of these people. He knows everything. He's read everything. Maybe a better question is like what goes into having such a strong voice? I think he has like, 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 experienced this. I still definitely do. Like when I sat down to write, I assume this like other, 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 or like describe it in like weird ways that like feel technically correct, but like no human would ever say.

2:10:14Brie Wolfson:Jeremy, I think allows himself to like say the human words, which I don't, it should be easier, but it's actually harder. Yeah. What do we love so much about numbered lists? Oh my God, I don't know. It's funny. It's like 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 it does some of the work too of like it's just like so easy for your brain to just like ratchet up the ratchet down the taste numbers yeah what's the best essay you've ever read oh man 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 and reality has a surprising amount of detail I like think about those things a lot why um I think they taught me something I actually did not know before and then it was like that Bader Meinhof thing where I was like now I see it everywhere 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.

2:11:34Brie Wolfson: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, I quite knew it. 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 the world as a museum of passion projects. It was, and I was like, wait a second. Is this true? Because if it's true. 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? is this kevin i'm familiar with the name but i don't know if i read it it's 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 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 somewhere I'm very conscious of like, I feel taste is the conversation is ruined.

2:12:34Yes, yes, yes, yes, yes. You love to talk through things and 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?

2:12:47Brie Wolfson:They're looping for me. And I think writing, thinking gets a lot of praise. Talking, thinking less so. yeah yeah why is talking thinking 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 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 you know professional magazine I'm like should I credit them like anyway like the lines are blurring.

2:13:19Brie Wolfson:I think the talking is like, is it your idea? 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. So that's all your own original ideas. If it's just writing thinking. What does talking do for you? That writing that you're cycling through? I'm like so attuned to like the glint in the eye on a thing. So I throw a lot of stuff out and then And 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. Yeah. Yeah. He's so amazing at that.

2:13:54Brie Wolfson:Yeah. Unbelievable. Okay. My last string of things. Forgive me. You said her name last night. And I don't know. 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. and you're being tuned into the details to like tweak them to get it there. But if you do it the, I guess not the opposite, but if you do it in the context of pessimism, it's like no fun. It's the same thing. It's like all no, no yes. You want more yes. Yeah, something came up. I can't remember who was an interview.

2:14:36Maybe it was with Henrik Carlson, which is like, we want less, not that, more maybe this.

2:14:43Brie Wolfson:Yes, yes, yes, yes. I love that. I love that. Like, you never, like, okay, imagine you're, like, editing a blog post, and it's, like, it was supposed to ship two days ago, but we're, like, 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 of fixing all the details? Why would I? Keep it, yeah, it's about momentum preservation. Yes, exactly. You're, like, this, like, is so close to great. Like, just a few tweaks, and it's, like, going to be great. that's the energy you want to like bring to fixing stuff and it's like this word it's not doing it for me like this whole paragraph i'm not sure like in the context of like this could be awesome is really fun to fix otherwise not so much you said you were star star struck by kevin kelly oh man are you star struck by anyone else or have you been um definitely i like totally what's that thing you have uh when you like get weird in front of celebrities if i like pass one on the street in New York.

2:15:38Brie Wolfson:I'm like, no chill at all. Across the board. Yeah. Here goes the dog. Um, but who, for some reason lately I've like really 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 and off times. Uh, any further realizations on like what causes the magnet to be on? It's funny. The magnet on thing actually is first came from like friends and periods of dating where Magnon is just like, the hotties are knocking. But I think it just comes from confidence. But I think confidence is not in a vacuum.

2:16:20Brie Wolfson:You're like starting to get some 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. who else is doing this and maybe what else could be done? I think this like story movement is a vote to fund weird ideas, basically. Like hopefully we'll get this kind of story studio type thing spun up at cursor and the pitch on it was six stunts a year. 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?

2:17:02Brie Wolfson:and it's like, not really. But anyway, so I think this work is getting funded more now. Taste is a good dinner party topic because everyone's got a thought on it, something you said. Yeah. What are other good dinner party topics? I'm gonna take any weasel word or suitcase word, whatever they're called.

2:17:23Brie Wolfson:Or, I mean, anything that's like mean-y. Anything, everyone's got it. One of them, everyone has an opinion on, yeah. And 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. Maybe part of what you were just saying, but like what we have other buzzy words, like agency that I don't think are this. Oh my God. But agency is 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.

2:17:57Brie Wolfson:Good question. I could do a notes on marketing. right now probably i think everyone's got a really different definition for that all right we'll have to we'll have to wait and see uh patrick o'shaughnessy told me to ask you how do your friends decide where to work where to work

2:18:21Brie Wolfson:it's funny most of my friends are in silicon valley so i think they're a ground they're probably ground level on what the hot stuff is and i think it's talking to other friends 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 like where are the hotties at like where are the smart people at you mentioned Tina Brown a bunch or I did we didn't get to talk about it a lot one of my favorite ideas is high low so many ways those people I mentioned Tammy, Matt, Charlton, my tastemakers all high low you said or I think she said the uncanny valley between high and low route is very wide.

2:19:04How do you know when you've made it to safety? You made it out of the chasm on either side.

2:19:13Brie Wolfson:I don't know. 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're talking about, Vanny Fair, and you have the example of like whatever, Or cultural affairs or like political geopolitics and Brittany or whatever. Just so many of the best things, 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.

2:19:46Brie Wolfson:Yeah, for sure. I actually think like one of the mysteries of like marketing and taste and all this stuff, like every now and then I know when something's going to hit. I mostly don't. i mostly don't and i think most people mostly don't like maybe there's a few like the mischiefs or the mystery like maybe they have 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 he's like obsessive about youtube like it's basketball yes yes um so i mean like maybe there's something there for those people but i generally don't No.

2:20:22Yeah. You have a scrapbook of pride in a brag document.

2:20:26Brie Wolfson:Yeah. Any highlights in there that come to mind? It's honestly, this is why the insight about like, just wanting cool people to think I'm cool. It's like mostly compliments from people I think are cool. As it probably should be. Yeah. I don't think that's the way to like build your internal flame source, but that's mostly what's in there. it's good to live a relational life i think yeah i think that's a nice way to put that yeah 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 yeah it's like one description of my writing like a long time ago was cinematic and i was like then shouldn't it just be a movie so i think it missed like or 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 bigger in the magazine and like give that visual peek so yeah I think it does sometimes miss the I mean obviously it misses the visual stuff but on the flip side it allows you to paint a mental picture my friends Nick and Devin they're like really into right now how like stuff on the web doesn't have any sounds um not real os yeah there you go um i'm interested in that um but i don't know i like i think it's its own thing i don't think too much about what it misses what do you love about matisse um i don't know it just is pleasing to my eye i think it's because of sharp contrast yeah that's all i need to say uh you said graham duncan's concept of grip quite literally changed your life yeah why it's i now i see it everywhere that would be another good candidate for an essay that 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 on this seeing the water yes it's seeing the water and 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 um and it's getting in my way because i I can't bring the loose quality that like makes me happy.

2:22:40Brie Wolfson:And more than any other person in the world, Patrick O'Shaughnessy has like, like loosened my grip on things. 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, he has a leg grip on everything. 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. It's empowering. yeah to me the happy place is the lighter grip place like my all my problems using your craft right exactly all my problems are related to grip so anyway now that i can see the water on grip it's just the dog we um you have a few maxims or like little lines on your website um that are all great uh have a real friend in the generation above and below you oh yeah what do you look for in intergenerational friends?

2:23:34Brie Wolfson:That's a good question. I'm thinking of one. My best friend in the generation above me is this woman named Leslie Berlin.

2:23:45Most notably, at least recently, for the Steve Jobs archive stuff. Yeah, amazing. Makes something wonderful.

2:23:51Brie Wolfson:And she's just, she's an amazing woman. And I think the main criteria for her is like, it's i think it's like fun to hear like the problems facing someone like my age and yet she like still has wisdom that feels relevant to me like she doesn't um she's not dismissive of like 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 everyone wants to help ask for what you need oh yeah how have you gotten better at asking just being more specific weren't you saying this the other day you were like yeah don't ask like if you send an email that's like can I pick your brain or like can you catch up who wants to do that who's got the time to help yeah and there's an abundance in helping that's the thing I think I'm working through it's like yeah you don't get one shot necessarily doesn't everybody like to be thought of of like in the room where it happens it's actually generous yeah yeah yeah when for this like very brief moment in my life where I had this startup like many people later were like i was like sad you didn't ask me and i 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 um everything will be different in six months totally true in startup life yeah especially now that i have an infant she's like a new person every day it's amazing She's been, like having an infant and moving out of California where there's seasons has like changed the conception of time for sure.

2:25:52The deeper you go, the better it gets.

2:25:55Brie Wolfson:This insight also preceded all the taste stuff. And I wrote this after actually, I like thought there was a bunch of people I didn't like. And then I was like 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. and now whenever someone feels like some flavor of enemy, to me, the antidote 100 % of the time is just to go hang out. It's a life's work to bridge the inside 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.

2:26:43Brie Wolfson:and I don't have the kindest inner voice at all times. And it made me think, what a waste. So I'm just like trying to, yeah, like quiet down that voice and like let more of the inside come out. It's always better. But I don't know why everyone has a lot of fear around that. 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. It comes to mind. Yeah. Good question.

2:27:22Brie Wolfson:My mom gave me all the joyful stuff. And I think she had a complicated relationship with like too much joy and too much excitement. But she gave me that, 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 for sure. For sure. One last thing. Your dog's going to kill me. You tweeted this the other day to be of use.

2:28:05Brie Wolfson:Oh yeah. Just a little excerpt from it. 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 omphras for wine or oil, hoppy vases that held corn, are put in museums, but you know that they were made to be used. The pitcher cries for water to carry and a person for work that is real. why is work that is real worth it 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 gonna get anything he's like is it useful um 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 he just reminds me every day like the main like point of a life is to like 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 yeah this is our thing 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 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.

2:29:59Brie Wolfson:So yeah, mostly that's a note to self as well. Thank you, Brie. This is all I got. Jackson, have fun. Oh, what a gift. Oh, thank you. 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 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 rear view window.

2:30:40We think schemorphically, we think in the context of the past. And effectively, Ivan's thinking about how first and foremost organizations and then eventually economies are going to change thanks to 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 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 we are able to collaborate faster and all have so much more leverage.

2:31:13One 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. Thanks again. See you next time.