Description

Brie Wolfson (X) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus, where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review, their new print publication known for superb long form profiles.

Brie also recently joined AI-programming behemoth Cursor as Head of Employee Experience and wrote about the company’s culture. She has worked with craft-oriented software companies throughout her career, including Stripe—where she helped launch Stripe Press and the company’s planning function, among other things—and Figma, where she worked on Education. In her words, she is drawn to companies where the reality is even more impressive than the reputation, and she has publicly and privately worked with a number of the most impressive leaders in Silicon Valley on marketing, culture, and storytelling.

We cover a broad range of Brie’s expertise, including craft, marketing, organizational culture, unlikely career paths, and taste, editing, and writing. This includes how AI is causing companies to become even more oriented around the empowered individual contributor and who the best of them, including company leaders, are focused on an attunement to details that she likens to “finger feel.” We also talk about why she believes marketing should be a kind of truth-telling, closing the gap between reality and perception. She also reflects on the common cultural thread of great companies: a deep-seated desire to be a great company, not just create great products. She talks at length about everything she’s learned from amplifying special people and how she’s navigated the tension in her own desires for fun and breadth and ambition toward greatness.

I hope this conversation inspires you to raise your standards, get to the ground level, and settle into a life of deep attention that produces quality, usefulness, and joy.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. You can read more about why Notion embodies Dialectic’s values and our partnership announcement here. You can find the essay from Notion CEO Ivan Zhao mentioned at the end of the episode here.

Timestamps

0:00: Opening
3:54: Notion
5:04: Intro: Craft, Finger Feel, and Staying Closer to the Ground Level
13:27: Process vs. Output, Quality vs. Speed, and Great Editing
21:44: Craft, Substance, and Truth in Marketing
25:56: Individuals as the Building Block of a Company and Empowered ICs
32:02: Creative Collaboration and In-Person and Remote
36:46: Company Building: What is Changing and What Will Stay the Same
44:25: The Soft Stuff: Great Company Values and Great Culture
52:17: Thinking vs. Doing Cultures, 996 and Difficulty Sitting Still
1:00:37: Morale, Fun, Amplifying Leaders, and Loving Attention
1:11:58: Career Path Advice for Young People
1:19:56: Kevin Kelly, Chasing Greatness, Illegibility, and Ease in One's Craft
1:27:29: Special Talent and Contagious Ambition
1:32:22: Brie's Spike: Charisma, Hard and Soft, Making Things Fun, and Belief
1:43:23: Taste, Appreciation, Generosity, Skill and Soul
1:57:26: Great Editors, Saying No and Getting to Yes, and Being Receptive to Editing
2:05:25: Great Writing: What do You Have the Right to Do that Others Don't?
2:13:55: Grab Bag: Optimism and Pessimism, High and Low, and Closing Maxims
2:30:07: Thanks to Notion

Links & References

Transcript

0:00: Opening

3:54: Notion

5:04: Intro: Craft, Finger Feel, and Staying Closer to the Ground Level

Jackson: Brie Wolfson, we made it.

Brie: Thanks for having me, Jackson.

Jackson: Thank you. We’re going to start. I was going back through your work, and I hope you actually said this, but I believe you said recently, “I think you could argue most roles should be craft roles.” Why? And would you have said that 10 years ago?

Brie: At first, I’m thinking, “Did I say that?” It sounds like something I would say. This was probably a few months ago, and I've refined my thinking on this. We're in the era of the individual contributor, which is totally different than a few years ago. That means we’re in the era of craft. You'd better know your stuff if you’re going to be operating today. So I stand by it. Yes, I said it.

Jackson: Good. If you hadn’t, many of my follow-up questions might fall apart. Let’s start with this quote of yours: “Turpentine is what is really going on at the one-inch altitude. It’s not the generic, cliched shape of it observed from 10,000 feet. Even the smartest, most thoughtful, best-intentioned people won’t get it right without the ground-level perspective and visceral sense of what is.” You talk about this “finger feel” for excellence all the time. Taking that metaphor literally, what are the biggest inputs towards developing that when most of us live lives that are so digitally intermediated?

Brie: The most reliable input if you want to get that finger feel is just time on the thing. It’s unsatisfying in some ways because we want to shortcut it, but that’s the whole point. You cannot shortcut this thing. It’s funny hearing those words. I think that must have been from 2018.

Jackson: 2018.

Brie: A while ago, before we started really talking about this as a society. It still rings true, and it’s still really hard to get. You just know it when you’ve encountered a person who has this quality, especially about a particular thing. It’s just time reps on the ground.

Jackson: Ground level. When we think of people who spend a lot of time in something and approach mastery or leadership, I don’t know if everyone’s mind goes to being on the ground level. If anything, the more time, the more you rise. We’ll talk more about company leadership later, but I’m curious. It seems like you’ve been around a lot of people who have the finger feel and the mastery. They’re not at the ground level in a lot of ways, and yet they find themselves returning to the ground.

Brie: I’m attracted to those people. My friends joke that competence is my kink. I just like people who know how to do shit. You can just tell. I’m watching you guys tinkering with all of this equipment. I can tell you know what’s going on. You’re saying words I don’t understand and touching dials I can’t identify, but that tells me you’re in the details. You’re on the ground level. A lot of the leaders I work for are fork-shaped. You hear about T-shaped people, or just broad or deep on one thing. The leaders I like the most can go deep on lots of things.

Jackson: It’s almost like vertical slices.

Brie: Exactly. They’re scouring the land, and then they swoop deep on one really particular thing.

I like that quality in a person; it’s fun and interesting. I like that quality in a leader because it means nothing can get by them. They’re willing to go deep on just about anything.

Jackson: A former guest of mine, Steph Ango, who runs Obsidian, has a post called “Don’t Delegate Understanding.” He talks about the ways modern society removes friction and tempts you to let somebody else figure things out.

Brie: If you’re a company leader, you can structure your company such that you are briefed on anything. If you’re an organizational leader or the President of the United States, you can live on a—

Jackson: Brief.

Brie: Yeah. And I think it’s more fun to go into the weeds on stuff. Patrick Collison, Dylan Field, Michael Truell—if something goes by them, they want to know more. They’re deep in the copy, pulling it forward. My friend Jordan just joined to do recruiting at Cursor, and she’s having the time of her life. She told me, “This whole leadership team is on LinkedIn sourcing with me.” They don’t want to look at the spreadsheet with the summary. They want to be on LinkedIn. They want to see the whole back history. They want to see how they frame the descriptions. I understand that kind of learning. That speaks to me. It’s different than just getting the—

Jackson: Snapshot.

Brie: Yep. I think you just know something different when you’ve seen the—

Jackson: Details. You started the answer earlier. There are no shortcuts to that level of being in it, feeling it.

Brie: It’s so hard to describe to somebody what’s different if you just read the summary in the spreadsheet versus reading the whole LinkedIn profile.

Jackson: It’s one-dimensional.

Brie: Multidimensional. Until you’ve done that thing, until you’ve gone deep yourself and felt the pattern match that happens when you do the LinkedIn scouring yourself, it’s really hard to make the case for that kind of thing.

Jackson: On that note, let’s say you do it enough times to know what that feels like. Can craft be automated at some point?

Brie: I don’t even know what that means. What would it look like for craft to be automated?

Jackson: The first thing that comes to mind is what I’ve read about Elon Musk. He will make sure he understands the process first, and then he’ll automate it. That’s maybe an easy plug-and-play example with the robotic manufacturing idea. But in theory, if Michael and the Cursor leadership team have been in the LinkedIn weeds enough, they have started to develop heuristics. Maybe a better way of asking this question is: How do these people have time for anything if they are in the weeds? What does that sequencing look like to go from “I really lived on the ground” to where they are now?

Brie: I’m picturing Elon walking the factory floor. I’ve never seen it myself, but that is very vivid imagery to me: looking at all the parts, touching the things, seeing all the people. I think that gets faster over time. I like Tammy’s definition from Cedric Chin on your podcast: taste is unconscious competence. It takes a while of doing conscious competence before you reach what we started by describing as the “finger feel.” You have to go through that process. I’m working with a company leader now who feels like she doesn’t quite get the product yet. She’s spending a lot of time shadowing SDR calls. My sense is it’s just going to click, and then she will be able to move off that. But you don’t know until you know. Similarly, a management philosophy I have is to do it before you manage it.

Jackson: That’s kind of what I was saying with Elon.

Brie: [00:07:57] I don’t know if you can automate it necessarily. I think you can shrink the time it takes to get to that unconscious competence state. I also have observed a pattern where this “get-it-ness” or “finger feel” is contagious. Once you’ve had it somewhere…

Brie: You realize that the world is…

Brie: [00:08:11] Yeah. You know that there are pathways to it. You know what it feels like when you have it, so you can spin up faster on more stuff.

Jackson: [00:08:20] I like that.

13:27: Process vs. Output, Quality vs. Speed, and Great Editing

Jackson: It’s funny, so many of the things that used to be craft in the world… I want to talk more in the weeds about it, but at a super high level, the last two or three years have been different for people who do what we do. All of the things that used to be craft, you can now press a—

Brie: Button.

Jackson: Yeah. Maybe it’s just a ground-level thing, but I’m curious what is rattling around in your head as you think about having all of this leverage. Is it about prioritization? Is it about disregarding efficiency and ambition to just have craft in the things that you enjoy? I’m curious how you’re feeling about it.

Brie: I think I’m lucky because I’m super high P on Myers-Briggs. I like the process of doing things more than I like the end state. I’m not satisfied to hit the button and make the website go poof. That’s not exciting to me. I’m lucky in this era because I don’t find it satisfying to just get to the end really fast. I want to do the grunt work. Maybe “lucky” is the opposite—maybe I’m unlucky that I like that work because I’m inefficient. But I quite literally can’t work the other way.

Jackson: [00:10:08] Different question. You’ve talked a lot about how you’re not really a high-volume output person, at least consistency-wise. Substack didn’t really work for you. You’ve also referenced Seinfeld—it just requires a lot of tonnage. Producing a lot helps you get to the best stuff. Patrick O’Shaughnessy says if it works, it works fast. There’s this tension between your really high bar and the fact that you like to be in the process. Maybe that’s actually compatible. And this notion of the classic ceramicist story about the thirty bowls versus the one bowl. How do you square all that?

Brie: [00:10:44] The struggle of my life creatively is that I’m just a person that has to throw a lot out. I wrote two novels once upon a time. One of them I wrote between the hours of 5:00 AM and 7:00 AM in the Stripe kitchen. These were not the conditions for me to write a great novel.

Jackson: [00:10:51] You wrote the novel?

Brie: [00:10:52] I wrote the novel. I finished it, and it got published. I’m not that proud of it. My mindset during that time was that I needed to be very efficient and maximize the number of words in the draft that made it to the final page.

Jackson: [00:11:07] Is this Rosie or the other book?

Brie: [00:11:08] The other one.

Jackson: [00:11:08] Was that first or second?

Brie: [00:11:09] Second. I hated that book. I hated writing it. I hated everything about it.

Jackson: [00:11:16] It’s the scheduled, disciplined version of creativity.

Brie: [00:11:20] I didn’t mind the schedule so much. It was just the concept that I couldn’t do the carving. I wanted a high ratio of words in the first draft to words on the final draft.

Jackson: [00:11:31] Measure once, cut once.

Brie: [00:11:33] That was the metric in my head: no wasted words. I needed to shrink this into as short an amount of time as possible. I couldn’t do the exploring, cutting, and culling that I like to do with my work. This stands between me and being prolific, for sure. I think I will bump into some challenges operating in this age of the IC, being prolific, and shipping stuff where it’s easy to iterate. This is a personal challenge right now.

Jackson: [00:12:07] What do you think would cause you to have more tonnage?

Brie: [00:12:10] More time?

Jackson: [00:12:13] Output, I guess. What would cause you to put out more within this existing allotted time? Is there a version of that where, if you did it a bunch of times, it wouldn’t just keep feeling like the book?

Brie: [00:12:45] I’m not sure. It’s funny because I’m working on this book now for Stripe Press, and I’ve been in and out of working on it. I’m realizing how much of a full-body experience it is for me to work on something this big. I need to be able to hold all the information in my head at once, write parts of it, and reference other parts of it. If I’m doing too many other things at once, I cannot do that work. I lose my own thread. I’m struggling with this because I want to be able to pick it up in chunks. I want to be able to whip up this chapter and that chapter and have everything be discrete enough that it’s easy to whip out more pieces. But I literally can’t. It doesn’t work. It breaks.

Jackson: [00:13:16] I’ve really benefited from forcing functions and constraints. Some people say, “The finals are due at the end of the semester; I’m going to do it halfway through.” Ben Thompson talked about this with David Perel, saying, “I don’t know if I could write a book. I have to publish every day.” As someone who is more of a “do it the night before” person, one of the reasons the podcast is good for me is that I can show up today prepared or unprepared. Writing is a little more complex. Not to push you, but what if you had a draft due? Is the way you get out of the “measure once, cut once” mindset to have a highly rigorous, scheduled set of deadlines that aren’t final—that are just drafts?

Brie: [00:14:01] It’s funny you mention deadlines. A couple of weeks ago, the Stripe Press team told me, “By the way, we forgot to tell you, but this amazing editor is going to help you work on your book.” That was my most prolific two weeks because I just let stuff out that I wouldn’t have otherwise. I knew I was going to get help.

Jackson: [00:14:21] You do a lot of self-editing, too.

Brie: [00:14:24] I do. My filter between my own head and what makes the page is very strong. I’m doing a lot of work when it gets translated from my brain into my fingertips and onto the screen.

Jackson: [00:14:35] Is that a good thing?

Brie: [00:14:36] I don’t know. I think I’m still learning about my creative process. Something I do know is the difference between when I like something I’ve produced and when I don’t. If I don’t like it, I’m happy to put it under the bed. I really don’t like publishing stuff I don’t like.

Jackson: [00:14:55] That is uncommon in the modern era. Most people default to just ripping the tweet.

Brie: [00:15:01] I think I’ve been lucky in my career because I’ve been doing this a long time. I’ve been rewarded enough times for sitting on my hands.

Jackson: [00:15:08] Do you think a really amazing editor makes you more likely to just blob everything onto the page, or are you filtering more?

Brie: [00:15:17] I was telling Jeremy that he’s made me a much lazier writer because he’s such a good editor.

Jackson: [00:15:21] That’s cool.

Brie: [00:15:23] It is cool.

Jackson: [00:15:43] I think the best version of creativity is like “write drunk, edit sober,” but between two people. You are maximally unfiltered, and then it gets shaped over time.

Brie: [00:15:56] I think so. I love being edited by Jeremy. He is an incredible editor. He understands the person on the other side, and he has a way with words. You think, “Wow, that would have taken me a while to come up with this turn of phrase.” Thank you so much. I do like that process. Michael and I at Cursor were jamming on something recently, and he was looking over my shoulder. He said, “Oh, you use the actual thesaurus? You go to Thesaurus.com? What is up with you, girl?” I told him I go to the thesaurus. I like that process. I like doing that work.

Jackson: [00:16:15] Everything you just said is actually making writing a little more collaborative or multiplayer. Usually, it is very single-player.

Brie: [00:16:24] All of my writing has seen many hands and eyes before it’s gone out. But I’m very careful with when I send my drafts out, and I know what I want to get at each phase.

21:44: Craft, Substance, and Truth in Marketing

Jackson: [00:17:07] We’ve been talking about craft, and so much of what you do is craft. However, you are also known as an excellent marketer in a world that isn’t always the most thoughtful about marketing. When does marketing emerge naturally in this compelling way out of craft versus something else? Why is marketing rooted in craft and substance?

Brie: [00:17:32] My general philosophy on marketing is that people read bullshit pretty fast. If you bullshit, people will think you’re bullshit. A good way not to bullshit is to just tell the truth about what you’re doing. If there’s nothing interesting there, there’s nothing interesting there. One of the reasons I like working for craft-focused companies is that there is a story there. There’s something to say. It’s not lipstick on pigs or hand-wavy stuff. There’s just more substance. We were talking about this last night, sort of closing the gap between what is true and what is perceived about a company. I like it when there’s a rich or wide space.

Jackson: [00:17:59] Space.

Brie: [00:17:59] Yes. There’s a lot for me to do. So much potential. I would never work for an over-hyped brand. That’s my nightmare. I always want to work for something underrated. Clearly, I’ve worked for highly rated brands like Stripe, Figma, and Cursor.

Jackson: [00:18:14] And they’re also highly rated.

Brie: [00:18:15] They are highly rated, and yes, I believe they are still underrated. Patrick, Michael, and Dylan are known as incredible leaders, but I think there’s even more incredible stuff there. To me, that’s a very exciting space. To take it back to craft: if there was no great leader and no great craft, there would be no story to tell. There’s no work for me to do. That’s boring.

Jackson: [00:18:40] That’s not intuitive. When people think about great marketing companies, they think of Red Bull or Coca-Cola, and they don’t even make the product.

Brie: [00:18:47] Yeah.

Jackson: [00:18:48] Fair. Put another way, you were talking about Harold Ross and how he actually got the form right before he got the content right. He was obsessed with this. It feels like Silicon Valley is actually all substance, no style, typically. Is there a right balance in that? Maybe a more important question is: how can there be craft in both style and substance?

Brie: [00:19:32] Marketing is thought of as more of a discipline on its own now. We’ve seen enough examples of it working that we want to hone that as its own craft. It’s not just telling the product story; there’s something else to do in that marketing team the night before. So anyway, I think we’ve started to honor marketing as a craft more. I also think it’s just noisier, so it’s a little harder to cut across.

Jackson: [00:19:41] Sure. Another thing you said is that all Substacks look the same. There’s something about tech because, again, there’s so much substance. Or even the MySpace to Facebook thing. It’s just, “Make it look fine.”

Brie: [00:19:58] Did you have a Tumblr?

Jackson: [00:20:00] I did, but I wasn’t super deep.

Brie: [00:20:03] The first way I ever coded was to update my AOL profile. I think I’ve always had an intuition that—okay, another thing I like about marketing is that you have to simultaneously be understood and known, and also cut across at the same time. You’re doing two opposite things at once. You want someone to understand and see truth, but you also want to be noticed.

Jackson: [00:20:26] And those really are pulling at each other.

Brie: [00:20:29] Yes, I think they are in tension. Red Bull is crazy. It’s really eye-catching, but there’s something known about it. It feels familiar.

Jackson: [00:20:42] It’s tethered to something.

Brie: [00:20:43] Yes. And I just enjoy that.

Jackson: [00:20:48] I like that.

25:56: Individuals as the Building Block of a Company and Empowered ICs

Jackson: You brought up ICs earlier. Much of this craft conversation revolves around what is going to happen to companies and organizations. You are known for the craft and marketing stuff, but you are also known for working with organizations and helping them grow and figure out what culture means. You have worked with Stripe, Figma, Cursor, et cetera. Before we get too in the weeds, our friend Tammy asks: what do all of these incredible organizations have in common?

Brie: [00:21:38] This is actually a harder question than you would think. When I started this consulting work, I had that Tolstoy quote in my head: “Happy families are all alike, and unhappy families are different.” I thought every company should work the Stripe way. Then I met Figma and realized this company does not work the Stripe way, and they are certainly excellent. I have a cheating answer. The only thing these companies have in common is that they want to be great. They aspire to be great companies themselves. They are turned inward on understanding that they want the organization to be great. That is not intuitive. You know you want to build a great product. You know you want customers to enjoy your work. It takes an enlightened leader to understand, “I want a great company.” It is about wanting to be great—wanting your people to be great.

Jackson: [00:22:13] There is a subtle but very important shift from building the product to building the organism that can produce the product. Regarding the IC stuff, the shapes inside of companies seem to be changing. I want to talk about culture, but I almost think of culture as the soft part of companies.

Brie: [00:22:41] Called the primordial ooze.

Jackson: [00:23:01] Exactly. But there is another part, which is the skeleton or the hardware. It seems very clear, especially with the example of Cursor, that the atomic nature of work inside companies is changing. In a world where most roles are craft roles and there is all this leverage and speed for the individual, are we going back to the individual being the building block? You have a quote where you say a company goes from the individual as the building block to the team being the building block. Are we going back to the individual?

Brie: [00:23:27] I think so. Individuals have way more power in organizations now because they can do more.

Jackson: [00:23:34] Wide?

Brie: [00:23:35] Yeah. A recent project I took on at Cursor was to update the Careers page. It is super simple: just a few lines of copy on a pretty blank text that integrates with Ashby. My job was the words. I learned through this project that I had such a learned helplessness around approvals and having other people see stuff and do stuff for me. I thought many other people needed to be involved, when really only I needed to be involved.

Jackson: [00:24:05] And you could just ship it.

Brie: [00:24:07] Yeah. But I had so much…

Jackson: [00:24:11] Anxiety.

Brie: [00:24:12] I literally could not do it. I can’t tell you how many pings I sent asking, “Is this copy approved?” Everyone just ignored me. I asked, “But is it approved? It’s going to go out. Many people see this page every day. I looked at the analytics. Does anybody else want to look?” Everyone just asked, “Were you thoughtful about what you did?” I said, “Yeah, I trust you.” That was hard to deal with, honestly, after being brought up in this other kind of environment.

Jackson: [00:24:39] You say dependencies kill productivity.

Brie: [00:25:03] Yes. Dependencies kill productivity. I could not get out of my own way. I could have walked up to anybody sitting at their desk and asked, “Will you approve this copy, please?” I could have, and I should have just gotten it out. I think this is a new way of thinking at work.

Jackson: [00:25:20] On the note of different shapes of companies, I can’t remember if you actually worked with them, but you referenced Supercell somewhere. Supercell is pretty unique. Valve would be similar, but they’re known for having this structure. Amazon would be a closer tech comp. It’s not as super top-down. There are these cells that do whatever they want and produce stuff like games. Thinking about that, I was thinking of Cursor and my conversation with Ryo and the way he works. Back to the IC as the atomic thing. Are we actually going to live in this world where you have Ryo as a cell all on his own? He just decides to do stuff and then reports back?

Brie: [00:25:42] Here’s my hang up with this setup. If we are going to be all about craft, my thing is the…

Jackson: [00:25:52] Words.

Brie: [00:25:52] I don’t try that hard on design. I really like partnering with designers, but it’s just 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 overlap moment. I had this a lot on Stripe Press. It was like, “Okay, these are the words on the page, but how should the page look and how should the book render?” That collaboration is…

Jackson: [00:26:14] Actually, we have the Avengers for making an awesome book.

Brie: [00:26:16] Yes. In this world where everyone does things alone, you sort of miss out on the novelty that comes from Venn diagram overlaps of two high-craft people coming up with something truly innovative together. I worry in this world of IC-only, we sort of miss out on these moments of collaboration.

Jackson: [00:27:04] I talked with Ryo about this. A lot of people are coming from the standpoint that Google has visual designers and interaction designers, and everyone is locked in their lane. They think we should never publish some code. Now you have every designer saying, “Whoa, Cursor is pretty sick.”

32:02: Creative Collaboration and In-Person and Remote

Jackson: What do you think the balance is? As you’ve been at Cursor, are you trying to bring some more of that in? How do you maintain the balance to still get the amazing generalists with specialist spikes, while still having the overlap?

Brie: [00:27:18] I want to. I’m working on a really fun project right now. The prompt was, “You write the script and the prose, then baton pass it to design, and they’ll do their thing with it.” I said, “No. I don’t want to. I want to work with design because copy on the page can look a particular way.”

Jackson: [00:27:50] It’s not a supply chain, either.

Brie: [00:27:51] Yeah. A very design-oriented and vibey company, got that right away. They were like, “Sick. Happy to play this way. Both hands on the baton the whole way through.” It’s so good. I’m so proud of what’s going to come out on this. To me, that was true words-visuals collaboration. I think it would have been hard to pull off without that true “holding hands the whole time” mindset.

Jackson: [00:28:17] I know you have written extensively about the way Covid and remote work was shaping things. It’s s sort of like making an album and the guitar guy sends in his track.

Brie: [00:28:29] Yeah, remember Postal Service? They literally did that.

Jackson: [00:28:34] I’m sure there are so many examples. It’s really easy to say, “Let’s all get around the table and look and mix things around.”

Brie: [00:28:53] Oh, I went down there for our design work because I feel better in those rooms about collaboration. I feel this at 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.

Jackson: [00:29:10]

Lack of proximity requires everything to be intentional.

Brie: [00:29:13] Totally.

Jackson: [00:29:13] Intentionality is great, but it doesn’t allow for the…

Brie: [00:29:17] Totally. It’s so funny. I was just with a friend who is starting a new job at her first AI-native company. She said, “If I ask someone if they’ll schedule a meeting, they ignore me. If I walk over to their desk and interrupt them, we’ll have the meeting.” She said, “I don’t get it.” But this is just the new way. It’s fluid.

Jackson: [00:29:38] Can fully remote companies actually be that creative? I’m sure, but are you sure? Have you ever been truly, deeply creative in this collaborative way?

Brie: [00:29:56] It’s too hard to say if 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. For me, that’s different. I’m extroverted, I like people, I have a big family, and I grew up playing on sports teams. Maybe I’m just a particular way because I was shaped by a particular set of experiences, but that’s just my feeling.

Jackson: [00:30:20] The CapCut kids.

Brie: [00:30:22] Exactly. They have a different way of being. One of my pet peeve phrases at work is when someone says, “I’m not a marketer, but…” or “I’m not a designer, but…” That’s 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.” I hate that phrase. I hate that tee-up. I hate that whole thing. I think Ryo has really shaped my thinking on this. Just don’t do that.

Jackson: [00:30:55] What would you suggest instead?

Brie: [00:30:56] Just say, “I have a design idea.” Or, “This is how the design is hitting me.” A phrase I use a lot when I’m editing is, “This hits my ear funny.” That is what I mean.

Jackson: [00:31:07] I suspect at the type of companies you tend to work at, taking building the organism and the culture really seriously empowers a baseline level of trust. It’s not like, “This dude from marketing is giving me product feedback.” Instead, everyone here is awesome.

Brie: [00:31:27] Trust is one word. I’m not going to walk into a room with Wilson Miner and give him my design thoughts. I’m going to stay in my lane, see what he does, and then we can play together. Trust is one word, but I’m more in awe of others. I want their work to flourish. On this Vercel project, the designers are spectacular. They produce beautiful stuff. I want them to come to the table with their part. I’m not a designer, but I want to say, “Ooh, what if?”

36:46: Company Building: What is Changing and What Will Stay the Same

Jackson: [00:32:03] “What if?” is awesome energy. Still on this note, as far as I understand, Cursor has no meetings. I assume that points to a general shifting toward an individual contributor model. Back to the hard part—the skeleton and scaffolding. How do you think about infrastructure around management, planning, established systems, and meetings? Clearly it’s in flux. Are we at risk of Chesterton Fencing it, where we realize Cursor actually needs to have some meetings?

Brie: [00:32:43] Cursor having no meetings is an extreme exaggeration. There are certainly meetings.

Jackson: [00:32:47] Ryo told me he has one meeting a week, which maybe is just a Ryo thing.

Brie: [00:32:53] That’s another company truism: everybody is having their own experience of the company. That’s probably true for Ryo, and he should have a lot of time for deep work.

Jackson: [00:33:02] It depends on the person.

Brie: [00:33:04] I don’t know. I think what almost certainly will be true is fewer people in the meetings. That helps, especially on Zoom. Some of the drudgery of corporate life, like round-the-horn updates, is easier to let go of. There’s more automation around the rote stuff. Although, a friend just joined a company in what people would call a “meta” role. There was a lot of skepticism about project management—why do we need a whole role for that?—but she’s adding a ton of value just by organizing the chaos. I’m genuinely excited to see what the new shape of the company will be. I do think it’s changing, and I want to be a part of that.

Jackson: [00:33:57] It’s probably why you have two jobs.

Brie: [00:33:59] I feel like an anthropologist in this way. I feel I have studied company culture in the old way, and now I’m going to…

Jackson: [00:34:08] “Old” feels a little silly, but old on a relative basis.

Brie: [00:34:13] A friend turned me onto this idea: if you are interviewing with a young founder or a young company, you should ask the executive who their mentors are. I thought that was a really good question.

Then I was thinking, who will the CEOs of this generation be mentored by? I wonder if there are new rules and it actually might not be that productive to be mentored by the previous generation.

Jackson: [00:34:37] Some things change a lot and some things don’t.

Brie: [00:34:42] True. But another friend is thinking about a leadership role, and she reasonably wants to know who the other leaders she’ll be surrounded with are. At this new company, the young people leading it say it doesn’t matter. And she says, “I know that it matters.”

Jackson: [00:35:04] And they’re just like, “Respectfully, you’re…”

Brie: [00:35:20] To me, it’s very refreshing and exciting that they still have that optimism. If they didn’t believe it was true, it surely wouldn’t be. They would be tolerant of the politics and weird dynamics. If they believed that companies had to get political, they would probably just accept it. I was thinking that maybe there’s some path dependence to believing you can run an apolitical org.

Jackson: [00:35:36] In a tweet fairly recently, you referenced the Billie Eilish Vanity Fair video.

Brie: [00:35:43] Oh my God, I love that video.

Jackson: [00:36:00] Specifically regarding the speed of company building in the AI era. You’re the first person to make that connection, which is amazing. I think they are on the eighth one of those. It starts when she’s 15. What’s so telling about that video is that she goes from 15 to 16, and you’re staring up the slope of…

Brie: [00:36:04] Compounding.

Jackson: [00:36:04] She goes from 200,000 followers to six million. I guess there’s a broad point here, and then more specifically on the infrastructure part: you helped spin up Stripe’s planning function. Is planning a thing in this world? Your point about Billie is that everything feels like one year is an infinite amount of time. Nothing is the same. It’s pure “Oh my gosh, I was so…”

Brie: [00:36:32] Naive. I’m not sure. I think it would be nice if companies could be more iterative. If you can move faster, you can trust that approach more, rather than needing to take big bets that require three months of work and coordination. If you have less coordination and can do things faster, maybe planning—at least on long time horizons—becomes a little more obsolete. But one function I think it does play is for these bigger swings that you really want to invest in. How do you make sure that the company is carving out time to do that?

Jackson: [00:37:11] Not urgent, but important.

Brie: [00:37:30] Important. Or even just exploratory. It would be really easy to get lost in little feature wars, so I think it takes some intention. That’s one thing I think planning can do that companies won’t outgrow. The other thing is maybe holding a mirror to shift inertia in some ways. For example, Cursor is thinking about this a lot right now. They are certainly their own best user as a startup developer, but they are not their own best user as an enterprise developer. Could planning help us understand how enterprises are different from us? What might we want to do to support that kind of work that doesn’t come naturally?

Jackson: [00:37:57] It’s almost like a reference point—a plot of land when you’re out on a boat. If there’s no land anywhere…

Brie: [00:38:04] Whoa. But it was not an accepted concept to work on planning at Stripe. That was a risky project because it felt off-culture at the time.

Jackson: [00:38:17] Well, this goes back to what I was saying: I think that some things don’t…

Brie: [00:38:22] Change.

Jackson: [00:38:22] Stripe and now Cursor are doing this—this is why I was laughing at you saying it’s the “old way.” Stripe is still one of the most innovative companies in the world. Maybe it turns out that on a long enough time horizon, people realize some long-term planning is really important.

Brie: [00:38:36] I still remember Patrick’s email to the company when we rolled out planning. It was something like, “We’re evolving beyond the Rube Goldberg machine of spreadsheets.” That is how it felt at that time. Cursor does not feel like a Rube Goldberg machine. It feels like a multi-armed Hydra. That’s what I mean by the “old way.” It was going slower. You’re watching the marble slide down the thing. Cursor doesn’t feel like that.

Jackson: [00:39:09] 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 do you scale how it feels to build it?

Brie: [00:39:19] I’m not sure, but maybe these more nuclear little collaborative pods. I think a really cool thing could be that your “team”—and maybe this is more like the Supercell way—is actually a very diverse set of people. My team is not a bunch of other marketers.

Jackson: [00:39:37] Yeah, it’s the Avengers.

Brie: [00:39:38] Yeah, that feels really fun.

44:25: The Soft Stuff: Great Company Values and Great Culture

Jackson: [00:39:40] I like that. To me, on the soft stuff, the culture stuff, I think one of your big ideas is that you have to get out ahead of things before the osmosis stops working. Patrick Collison said a lot of companies end up articulating their values too late. Maybe first, what do good company values look like, and how are they different from individual values?

Brie: [00:40:05] Values seem like something you would actually say or some way you would actually behave. I keep a doc of all values I’ve ever encountered from any company. I was just taking a spin through it the other day and I thought, “Wow, a lot of these suck.”

Jackson: [00:40:27] Why do they suck?

Brie: [00:40:29] They’re just boring. They’re so “ick.”

Jackson: [00:40:33] “Ick” because they don’t mean anything? Because they’re not honest? Because they’re generic?

Brie: [00:40:52] Any one of those things. One of the most commonly cited values at Stripe was “We haven’t won yet.” That was the humility one, but we were winning. It was this cheeky, funny thing. You would say, “We haven’t won yet, but I closed this massive asset.”

Jackson: [00:40:55] We’ve won eight championships in a row.

Brie: [00:40:57] It was the way to say we’re still humble, but now I will brag to you about this thing. Then I realized that actually kind of did make us more humble because nobody bragged about anything without saying first, “Okay, I know I’m bragging.”

Jackson: [00:41:11] It was a filtration system or something?

Brie: [00:41:13] It sort of makes you think, “Am I bragging?” Because if I am going to brag, I have to say this other thing first to be on the vibe. I wonder what the culture might have been like if you didn’t have to say that thing first and instead you just got to brag and thump your chest.

Brie: [00:41:31] Anyway, I think that was a good value, even though we made fun of it a lot.

Jackson: [00:41:35] You talk all about the stuff that companies do for the audience of themselves. What a beautiful definition of culture. There are obviously so many machinations inside of what that means, but how does that incrementally actually produce the desired output of culture?

Brie: [00:41:54] The “audience of itself.” I think this is a little bit what we were talking about: companies that want to be great companies themselves.

Brie: [00:42:03] One mechanism where this becomes clear is all hands or internal comms. How does the leader address the company? To me, it’s a privilege to see your colleagues work. It could be easy to dismiss all hands as meta-work, or just a box to check if we’re going to ship. A really good all hands is amazing because there is stuff you can say to your colleagues that you can’t say to the outside world yet. It’s a privilege to have the inside scoop or to understand something more about someone’s sense of humor or how they might design their slides.

Jackson: [00:42:46] Why does the sports team have to do the pre-game meeting? We treat some of that stuff as rote in a way that, if the context were different, might be perceived as more foundational.

Brie: [00:42:58] My friend who is a really talented lawyer and played soccer with me in college always says, “I like the bus and I like the locker room.” That’s her thing. She was extremely talented.

Jackson: [00:43:10] That’s what we all remember. You probably don’t remember that many of the goals you scored.

Brie: [00:43:32] I think I’m also a Locker Room Girly. I do think that impacts how the work gets out into the world. In general, people underestimate brand and marketing. It’s what your employees say to their spouse, when they’re out for dinner with their friends, or when they’re talking to their random uncle. Brand and marketing moves a lot through those channels and they are under-invested in.

Jackson: [00:43:42] Especially in a place like San Francisco.

Brie: [00:43:44] For sure.

Jackson: [00:43:46] That’s the true pulse of the company.

Brie: [00:43:49] Totally. At Cursor last week, a newer leader on the team had the company in stitches laughing about something silly. I know people were talking about that when they went home. It was totally off-brand; Cursor is a little more serious. It was a really silly moment, but it was memorable and it made people have a really good 15 minutes.

Jackson: [00:44:12] What is the line between lore or mythology and nostalgia?

Brie: [00:44:18] Stripe is kind of anti-nostalgia.

Jackson: [00:44:22] Are you anti-nostalgia?

Brie: [00:44:23] No. My friends say I’m the Ghost of Christmas Past. It’s actually fun. Another friend was texting me this morning about getting their new office set up. He said it’s chaos and all the furniture is in pieces. I told him, “Remember this part.” In five years, they’re going to talk about this on a podcast. I know it. These are core memory type things. Often they aren’t even fully true, but they…

Jackson: [00:44:50] They’re never true.

Brie: [00:44:51] Those stories are never fully true. They cement a feeling. They help you make a feeling legible or explain how you got this way. So I think the mythology is important. Now that we’re adding so many people so quickly and these companies are growing so fast, you want to bring people along with the story of the company.

Jackson: [00:45:12] To me, that’s lore or mythology. Maybe I’m driving a false dichotomy, but I think you’re right. Nostalgia feels good when you’re the person who was there. It doesn’t feel as good for others. Maybe the better question is: what is the role for nostalgia?

Brie: [00:45:29] In particular, I don’t feel that connected to people who wish they were at a different time or place. You can always tell when someone is telling a story and they wish it was still like that.

Jackson: [00:45:43] The good old days.

Brie: [00:45:45] Maybe that’s a little bit what nostalgia is like. I don’t think this guy wishes he was still at the phase where the furniture was in chaos.

Jackson: [00:45:55] But those moments were great.

Brie: [00:45:56] Yeah. You can always tell when you’re talking to someone and they say, “It used to be another way, and I want to be in that way.” You just want to say, “Catch up. Join us in the future, please.”

Jackson: [00:46:06] We talked a little bit about this Tolstoy thing. Is your instinct that all great cultures are truly original in the Snowflake sense? Or are they permutations, remixes, or something like an Enneagram or Myers-Briggs where there’s a dozen or so flavors?

Brie: [00:46:30] I think I’m evolving out of this theory, but one I used to consider is that great companies are extensions of their leaders. I might be evolving out of this idea with this collection of ICs thing that’s happening. Surely every page on the Stripe website is an extension of Patrick and John. But based on what I told you about how the Cursor website got out, it’s not so much an extension of the leadership.

Jackson: [00:47:07] One could say that’s less “finger feel.” But one could also say it’s actually an enlightened view from Michael.

Brie: [00:47:12] I think so. Or maybe you can say it’s just a little more indirect because he’s so prescriptive about who gets hired. He trusts them so much that it is an extension of him because he picks who does the work and who gets on the landing page. I think they’re probably all singular. Any great company… I try not to say good or bad, they’re just their own way.

52:17: Thinking vs. Doing Cultures, 996 and Difficulty Sitting Still

Jackson: [00:47:36] On the note of varieties, this ties to what we were talking about earlier. You’ve said Stripe is very much a thinking culture. As we’ve clearly exemplified, Cursor seems more like a doing culture. Have you slid one way?

Brie: [00:48:11] Oh, yeah. I’m a chronic overthinker. This is why I was a good fit for Stripe. I love a doc. I love thinking through all the different outcomes. 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 a little easier. This week, I’m working on Cursor’s first company Pulse survey. We decided, “Let’s build it in Cursor.” I asked, “Okay, who’s going to help me build it in Cursor?” and the response was, “Well, can’t you build it in Cursor?” I’m still working on that. I wrote the doc that said, “These are the questions and this is the vibe,” and then realized, “Wait, I could just put this in Cursor.” So I’m still working on updating my own thinking. I have a feeling I will find this satisfying once I get over the hump, but I’m still writing briefs.

Jackson: [00:48:46] We all have different kinds of humps. It’s not a perfect example, but I’m sure there are people who, if they have to write something, are addicted to ChatGPT or try to get somebody’s help. You have the finger feel for that. This is new. You don’t have the finger feel yet. It’s like doing video podcasts: “How do I do anything? I can’t do it.” And then you wade in.

Brie: [00:49:07] I think the way “doing” helps is that you still have to start at the end. You have to know where you’re going. This is why I think Ryo is so good at what he does: he has a loose conception of what the thing at the end is, and he can poke and prod the clay the right way to get close to it.

If you go into the project without any idea of where it’s going to end up, you just get lost in an infinite ChatGPT chat forever. The work becomes the act of talking to ChatGPT, and you’re not really moving towards an end. For me, the brief helps with that process of getting to the end of the thing.

Jackson: [00:49:48] There’s a comment from Kari from Linear that reminded me of something I spoke about with Ryo, and I was curious to get your opinion. Kari says that before product-market fit, hiring a lot of people or working super hard might not actually work that well. To get to PMF, you need reflection and clarity. He observes that companies try 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 when what you really need is to get the product right. He’s pointing at the “996” work culture. Do you think startups are overweighting mimicking the aesthetics of the grindset? One of the things Ryo spoke to me about is that he has two modes: shaping the clay in Cursor, and going for a walk. There is that yin and yang. I’m curious for your reflections on the whole workaholic aesthetic.

Brie: [00:51:04] I’m not sure. Something I’m noticing in myself and in other people is that it’s really hard to sit still right now. It’s really hard not to be reading, thinking, consuming, or tweeting. It’s way harder not to.

Jackson: [00:51:20] You feel like you’re losing ground, maybe?

Brie: [00:51:22] Or there are just infinite things. Whatever amount of time you have, there’s something that can fill it. If you have one puzzle piece of time in your day, there’s a TikTok reel or a tweet or a blog post.

Jackson: [00:51:36] Get the AirPods in on the walk.

Brie: [00:51:37] Yeah. That is the part of hustle culture I feel the most—like I’m always behind on reading or didn’t see the latest news. To me, that’s the hustle culture feeling: I’m not up on it. I definitely notice a lot of people saying stuff in Slack just to produce “receipts” that they are at their desk. So many Slack messages are edited; people send them and then tweak them later. That is where I notice this constant doing, doing, doing.

Jackson: [00:52:15] And it’s an aesthetic, a little bit.

Brie: [00:52:17] Yes, I definitely notice a lot of versions of that. It’s hard to sit still. In many ways, I feel like I benefit from timing. I lived and worked in a world where this didn’t exist. My first jobs didn’t have Slack; we used HipChat or GChat. I lived and worked before this, so I had the chance to build habits around stillness that I still rely on. But because I know that they work for me, I think it would be harder to train yourself now that stillness or going for walks works.

Jackson: [00:52:55] I know it works, but I still forget. It’s just easier to be…

Brie: [00:53:00] Fidgety.

Jackson: [00:53:02] One of the things that stood out to me is when you talk about funding culture. 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…

Brie: [00:53:18] 20%.

Jackson: [00:53:18] Maybe it’s a false question, but 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?

Brie: [00:53:28]

It’s the “audience of yourself” thing. It’s whether you value that audience or not.

I do think this concept of internal product-market fit for your work is becoming more of a thing. I’m excited about that. I think it means that the internal work starts to look important.

Jackson: [00:53:54] Can you say a little bit more about that?

Brie: [00:53:56] One feature at Cursor, and for a lot of other friends who are at more AI-native startups now, is that the first thing you do is ship to the internal version and see if your colleagues are into it.

Jackson: [00:54:10] It’s like a test flight for the whole company.

Brie: [00:54:14] Yes. Old world versions of this are talking about your intentions and planning, writing the doc, or giving the all-hands presentation about what you’re going to do. But this is a little bit faster and more iterative, and there’s more responsiveness. I think people legitimately judge the validity of their ideas by how many Slack reactions they get.

Jackson: [00:54:31] That might be really good at a place like Cursor and really bad elsewhere, which is important. I would guess that Slack was using an internal version of…

Brie: [00:54:41] Slack. Yeah, sure.

Jackson: [00:54:42] Sure. I wonder how that will evolve. I wonder how much of it is just a product of building a specific type of tool that you yourself use versus something more meta.

Brie: [00:54:51] But now think about it not just for product stuff. Maybe a new enterprise engineering team is emerging in Cursor. A huge part of this team’s job is to get people pumped about enterprise, and they have to explain why it’s cool.

Jackson: [00:55:12] Probably try to find a way to live it a little bit too.

Brie: [00:55:16]

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 work on the enterprise product. That’s all internal marketing work.

One way you can think about that is negatively: people have to do these internal press tours to get their work done. One way you can think about it is positively because you’re building more cohesion.

Jackson: [00:55:42] Yes. Selling…

Brie: [00:55:45] Vision. Yeah. 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. Taking care of the internal audience.

1:00:37: Morale, Fun, Amplifying Leaders, and Loving Attention

Jackson: [00:55:55] I think it might be a little related. I want to talk a little bit about leadership, great organizations as a whole, and cultures. You retweeted Nabil Qureshi, a former guest of the pod. He tweeted Napoleon’s observation on war that morale is 75% of winning as one of the most important lessons for startup CEOs. Morale should be understood broadly here. It’s something like a sense of…

Brie: [00:56:20] Destiny.

Jackson: [00:56:21] Yeah. Maybe. Speaking of even just selling things internally with your team, what is morale and where does it come from?

Brie: [00:56:28] The word I would use instead is having fun. Devin sent me this tweet recently that said, “You can’t compete with somebody having fun” in all caps. I think that is true. When I think of morale, I think of creating excitement where you wouldn’t otherwise be excited. I’m creating morale that is above the baseline—genuine enthusiasm. I think you can manufacture it. Maybe this comes from my background doing sports, but it is just getting people pumped to do the thing. I’m thinking of this enterprise guy again. He has to get someone pumped to make a change that is going to be a huge deal for Nvidia. He has to tell that story and convince somebody else that it is sick, fun, awesome, and rocks. If he can successfully do that, the work will go better than if it came down from a top-down planning process.

Jackson: [00:57:35] The other part of that tweet I have to observe is a sense of…

Brie: [00:57:41] Destiny.

Jackson: [00:57:42] Yes. Interestingly, it seems you are drawn to both of those things. We might talk about greatness later, but you are clearly having fun and interested in having fun. However, fun isn’t the only point; it’s not “only vibes.” When I think of morale, it’s actually both of those things smashed together, which don’t necessarily always go together.

Brie: [00:58:14]

One of my earliest childhood memories is playing soccer. I was probably in kindergarten on the orange team. The coach asked, “Okay, girls, do we love to win or hate to lose?” Every single person said, “Love to win.” I said, “Hate to lose.”

That is one of my earliest memories. I realized I was so different from everybody else. I’m inherently very competitive. I hate to lose, but I also love to win. That environment is fun to me. Maybe I’m just lucky because I’m wired this way.

Jackson: [00:58:52] By the way, I should note that most “hate to lose” people don’t have that much fun.

Brie: [00:58:57] Yeah, but I’m just wired this way. Again, it’s locker room stuff.

Jackson: [00:59:04] We talked about them a bit earlier, but you’ve worked with a bunch of amazing leaders: the Collisons, Claire Hughes Johnson at Stripe, Dylan Field, Patrick Michael, folks at Cursor, and Patrick O’Shaughnessy. What about people like this makes someone like you want to magnify them and the cultures they build?

Brie: [00:59:35] I’ve gotten so much more out of those relationships than they got out of their relationship with me. Ultimately, the reason I wanted to do great work for these people is that they funded me doing great work. My story at Stripe was that I was just a person on the account management team. Then someone—I forget if it was Claire or Patrick—plucked me up and said, “You’re going to work on this weird project to integrate this team that we acquired.” That set me up to do my first leadership-facing work and my first weird, off-the-org-chart project.

Jackson: [01:00:10] You broke off the dependency?

Brie: [01:00:12] Yeah. I feel indebted to them forever for seeing me in a sea of people. It wasn’t that many people at the time, but I felt seen in that work. I thought, “Wow, I have a new chance to do something awesome.”

Jackson: [01:00:30] Let’s take away the Stripe people then. I’m sure you’ve gotten an amazing amount from all these people you’ve worked with since, but they’re hiring you for a…

Brie: [01:00:40] Why are they hiring me? I think they probably feel that I see something in them too. I respect and admire them. Kind of what we were saying before about how I think of my job as a marketer to close the gap between what is true and what the world knows about someone: I believe there’s more in them.

Jackson: [01:01:01] That was my real question. I have a sense of why they’re choosing to work with you, but I’m curious why you’re choosing them. I think it’s that you’re seeing this magnification desire. There’s something here that can be…

Brie: [01:01:14] Amplified. Yes. I want all those people that you just described—I think they are incredible human beings. I think more of their stuff out in the world is better for the world, and I want to help them do that. That’s genuine in me. Patrick O’Shaughnessy calls it the “skinny mirror,” which I love. He says you hold a mirror up to someone, but it’s always the one that makes them look really good when they’re doing their fit check. When I admire someone—and I will only work for people that I admire—my natural lens on them is the skinny mirror. With everything they say, I think, “How do we make that sound awesome? Let other people know. You should write about that. Let’s talk about that more. Say that a different way so more people get it.” That is an instinct within me. I want to refract these great people out, and I want more people to benefit. What I benefit from them is just being inspired, excited, or moved to act or think or whatever.

Jackson: [01:02:07] I was listening to Dax Shepard, who has this podcast, and he was interviewing Adam Grant, the psychologist. Adam’s observation of Dax was that he has “inverse charisma.” That’s why you’re such a good podcast host: you make other people…

Brie: [01:02:25] Charismatic.

Jackson: [01:02:26] That’s funny. What an amazing trait. Not exactly the same thing, but it’s…

Brie: [01:02:29] Similar. I think all these people are doing great on their own. They’re perfectly charming, wise, and thoughtful. My infinite energy is to help people say more awesome stuff. If any of them say something to me in a private room, I think, “Let’s write a blog post about it. That’s really interesting. We should let more people in on this thing that I got private access to.” Anyway, that’s always my lens on stuff: refract great people.

Jackson: [01:02:57] One last thing on this. You were writing in the COVID era about the lack of momentum that can show up in work. You say, “But I do think work can be a source of real meaning in life. But we’ll only ever get out what we put in. And in the case of work life, it’s kind of a collective decision. Once your neighbor starts signing off of Slack at 3:30 consistently, it’s hard not to do the same. If your closest collaborators don’t turn stuff around quickly, why would you?“ In a separate place, you said a few months ago someone complained to you that the new, very hot startup they were at had an LGTM, or “looks good to me,” culture. He looked down at his coffee for a moment. Quote, “I’m afraid I’m never going to see my best work again.” And then this is you in a different place again: **“**Call me masochistic, but I have to admit that it felt good to care about anything that much and to be around people who I know cared that much too. Of course, I believe you can love something without it having to hurt. But I’ve never truly loved anything that didn’t move me to my core.” You’ve talked about this feeling of being a part of something in so many places, going back to the All-American soccer days or startups. At a basic or foundational level, what is it about these groups that moves you so much?

Brie: [01:04:21] Do you feel like you’ve ever been excellent at anything? A taste of it?

Jackson: [01:04:29] I think I bounced off it.

Brie: [01:04:31] It’s quite elusive to me, but even being close to that sun is electrifying. I’m not good at generating that on my own. It takes the gaze of someone else. I always played better when I knew my coach had daggers on me. I wouldn’t want to go for the ball—I was too lazy to make the run. If I felt her presence, I’d think, “Okay, I better get my ass in gear.” I’m motivated by that kind of loving attention, someone who wants me to succeed. In these environments where people have a loving gaze on your work and say, “I think this could be better,” it creates a push I couldn’t generate on my own. This surprises a lot of people, but when I write, I still imagine Patrick Collison reading my stuff. I wonder what he’s going to think of it. I have not been in a room with him in almost a decade, yet here I am still craving his loving attention on my work. That is a core motivator: the gaze of people I admire, imagining how they’ll tune it better. Being in groups of people who give each other that kind of loving attention is amazing. All the people I sent the draft of the Careers page to who said, “The wording’s not quite it”—that was so motivating to me. I wanted to work it until it was perfect for them. It just means a lot.

Jackson: [01:06:10] You used that phrase “loving attention” several times, but the first time you used it, I thought I heard “loving [space] attention.” What a profound inverse. Of course, it’s loving attention. There are people who love attention, but what you are seeking is this very specific kind.

Brie: [01:06:34] I want someone who feels invested in making my stuff better. To me, that’s what’s so damning about LGTM. It was skimmed. It seems fine. Reliably, when I post something on the internet, Stripes will DM me a typo. I think, “I fucking love these people.” They actually read it. That’s how I know. Those typos are Easter eggs for them.

Jackson: [01:06:58] When a lot of people see the typo, they think, “I’m not going to bug them.”

Brie: [01:07:01] Yes.

Jackson: [01:07:01] Looks good to me.

Brie: [01:07:02] I think this is related to the funding thing. I’m going to take time to tell this person it has a typo, or I didn’t love this turn of phrase. I love that.

1:11:58: Career Path Advice for Young People

Jackson: [01:07:17] I want to talk about your career path. You say there’s all this work that lives in the crannies that doesn’t seem like it should be owned by anyone in particular, so why not me? You’re writing a book for people early in their career, and you’ve had quite this winding path. That’s probably not the most obvious template. How much weight do you put into picking up the things in the crannies?

Brie: [01:07:50] 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. I know a lot of people who just did the ladder, and it was great.

Jackson: [01:08:04] But you also pick things up in the crannies and make people care about the crannies.

Brie: [01:08:07] That’s true. 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.

Jackson: [01:08:16] You have a nose—going back to something we talked about earlier—for things that are not currently important but will someday be important.

Brie: [01:08:22] Yeah.

Jackson: [01:08:24] Or could be made to be important.

Brie: [01:08:25] I think I have a particular temperament for that because I like zero to one. To me, that’s the most fun phase. Often, if there are too many cooks in the kitchen, it can’t really flourish. I’m also totally fine giving away my Legos. Not everybody is. I’m happy to pass my work on. So I think I have a particular temperament for that flavor of work. Many more people want structure and validation. Show me a goal, I’ll hit it. And many people have great career paths that way too.

Jackson: [01:08:58] I think you were talking to Packy. You said it’s hard to have a finger 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.

Brie: [01:09:10] It’s true.

Jackson: [01:09:11] Given that conversation we had about craft, for the people who relate to you and see Brie, they think, “What an amazing opportunity it would be to have that path.” With the benefit of hindsight, how do you square the finger feel being so important? You capture this so well in Flounder Mode, and yet it’s still easy to sit there thinking, “If Kevin Kelly can do it, that’s cool, but how am I going to develop skills?”

Brie: [01:09:38] I’m smirking about this a little bit because there’s this thing happening in the world right now where there’s a real enthusiasm for people who can tell stories. That’s the word people are using: story. People want the story. Maybe six or seven years ago, when I was applying for Figma, I wrote this document to a company saying, “I want to be your head of storytelling.”

Jackson: [01:10:03] You were early.

Brie: [01:10:05] Yeah. And they basically said, “That’s cute.” I felt very ashamed after that. I thought, “Oh yeah, that’s a fake word.”

Jackson: [01:10:17] That’s like I went to the adult table and they told me to go sit back down.

Brie: [01:10:22] Yeah. And then I was like, why did I do that? I don’t think I could have gotten enough reps on this thing to have it be a full-time job otherwise. Now, I actually feel like I have the opportunity to do it. I basically had to do ops on the side so that I could do storytelling.

If I wasn’t a fantastic “get shit done” person, Stripe Press would have never landed on my plate. I had to be the person that could get us to print a frickin’ book and get it on Amazon to earn the right to tell stories about the authors. I had to do 90% of the other work. Now I think I can —today—I think there is permission for Brie to spend full-time just on the story stuff. But I generally had the self-awareness that I had to pay my dues with the ops stuff. There just wasn’t enough company work in story.

Jackson: [01:11:31] Maybe a generalized lesson here is that you’re allowed to dabble if you find enough ways to move bricks.

Brie: [01:11:43] I’m preparing a section on this in the book. I think operators underestimate this. The first question all managers talk about when it’s time to pick up another job is how they are doing at the core role. The reason I got to do that project at Stripe where I helped the acquired teams is because my account management book was doing great. I signed my renewal, so they were willing to spring me onto this other thing. You have to know why you’re at the company.

Jackson: [01:12:09] If you’re 22, that advice isn’t helpful because you have to get in the door first. Do you have any broad thoughts on the person who feels like a generalist? If their craft isn’t necessarily obvious, they might have a craft-full approach to things.

Brie: [01:12:27] I’m curious about how these careers will pan out soon. Really common hiring advice used to be to hire someone who’s done a couple of years at McKinsey. I wonder if that meme is still around or if we value these generalists. My sense is generalists now have to be able to produce output. They should be able to “cursorify” the company Pulse survey on their own. They shouldn’t need someone else’s time to do something like that.

Jackson: [01:12:57] That would be the version where the generalist is more valuable than ever.

Brie: [01:13:00] Yes. I think there is more expectation for people to be able to produce their own output. I spent the early part of my career being glue for people who had great ideas but couldn’t really get them done.

Jackson: [01:13:17] On the output front, how important is it before having the job? You’ve been relatively public in the last period of time, though I don’t know if you always were. If you’re 23, the obvious thing is you need to get a Twitter following, share your projects, and go viral. What’s your advice on that part?

Brie: [01:13:42] I put out a call for questions people hope the book will answer. The question I get the most is: Do I need to be Twitter famous? No, you don’t need to be.

Brie: [01:13:57] It doesn’t hurt. But you do not need to be Twitter famous, period. I think people are anti-pattern matching. They only pattern match on the people who are Twitter famous.

Jackson: [01:14:08] Yes. It’s otherwise illegible. Your career broadly is illegible, but it’s especially illegible if you don’t even see the specs of it.

Brie: [01:14:16] Twitter famous is the wrong way to describe it. I think it’s really useful to publish your work. It’s good to get it to completion. It’s good to put it on the Internet where other people can see it. I think you have to have something to point to. Were we talking about this the other day? The reason you go on a book tour is because the thinking has been codified. It’s a little bit about that. You have the book, but it’s also like, “Okay, my ideas are…”

Jackson: [01:14:46] Baked.

Brie: [01:14:47] Yes, on this. I think it’s pretty good to share a record of what you have, like an…

Jackson: [01:14:52] Artifact.

Brie: [01:14:54] Right. I don’t think that means you have to be famous, but if someone goes clicking around about you, it’s probably useful to…

Jackson: [01:14:59] Well, it’s also not necessarily an endless stream of noise.

Brie: [01:15:03] I think you have gotten a lot out of being online. I meet a lot of people I like. I like my Twitter feed. I think a lot of people don’t like theirs, but I like mine. So anyway, I get a lot out of being online, but I talk to a lot of founders who are like, “Ugh, I have to tweet every day.” I’m like, just don’t bother if you don’t want to. Don’t do it. I think it is some people’s medium of expression.

1:19:56: Kevin Kelly, Chasing Greatness, Illegibility, and Ease in One's Craft

Jackson: [01:15:31] On the Flounder Mode note, a quote: “I think somewhere along the way, the message about what it feels like to be great has become a bit perverted.” Kevin says in that piece that greatness is overrated. You seem to be chasing greatness still. Can flounders be great?

Brie: [01:15:56] I am. I don’t think I’m chasing greatness in the way that Kevin describes it.

Jackson: [01:16:02] I agree.

Brie: [01:16:02]

I don’t care to run a company. I don’t need history books to admire me. That is not the kind of greatness I’m looking for. I just want to feel at ease in my craft. I think that will be a lifelong pursuit.

Jackson: [01:16:19] I want to push you slightly because I think you are doing both. You were an All-American soccer player. You’ve been exceptional in many ways, consistently. Granted, maybe it’s not perfectly intrinsically motivated. You’ve done a bunch of different things rather than one thing. But is it really just that you want to be at ease in your craft?

Brie: [01:16:41] You’re not on the list of people I call when I’m having anxiety swirls about everything. Being illegible has plagued me throughout my career.

Jackson: [01:16:53] You did an amazing job of capturing that piece, by the way.

Brie: [01:16:56] Oh, thank you. But imagine me at 27, sending this email to the CEO of an actual company saying, “I want to be your Head of Storytelling,” and them laughing me out of the room. That did not happen in a confident place. I was like, “I’m going to shoot my shot on this thing and be bold and put myself on the page.”

Jackson: [01:17:16] But we also weren’t laughing you out of the room. I suspect it was a little bit about the illegibility. More so than you.

Brie: [01:17:21] It was respectful, but it was like, “Oh…”

Jackson: [01:17:24] They weren’t ready. It was actually too illegible. You were totally onto something, but it wasn’t…

Brie: [01:17:31]

It wasn’t. None of us were surrounded in confidence. I was supremely self-conscious about that whole event. I think if I was truly at ease in my craft, I’d be like, “Oh, they just don’t see it yet or something.”

Jackson: [01:17:44] But this is when the comments bounce off of Kevin. He just doesn’t.

Brie: [01:17:49] He said, “I don’t even understand what you mean by ‘Does an audience have to validate you?’ Does not compute.”

To me, being at ease in my craft means knowing my value. People say, “Just call it Brie magic.” I would never call my work Brie magic. I think they’re saying something kind, but to me, it’s dismissive. I don’t want it to be magic. I want it to be real. I’m still on a journey with this.

Jackson: [01:18:22] The thing that stands out most about Kevin, and the way you convey him in that piece, is this disposition of abundance**. It’s 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.**

That sounds a bit like what you were just describing. You’ve also talked about feeling that, at this stage in your life and career, some doors are closed.

Jackson: [01:19:03] When do you feel this? At the end of that piece, Kevin talks about the well being bottomless. What beautiful imagery.

Brie: [01:19:12] That was all him.

Jackson: [01:19:14] When do you feel that abundance, and how do you try to get back to it?

Brie: [01:19:19] It’s funny, you’re tying my whole life together. After I graduated college and soccer was over, I was in a pit of despair that I would never be so good at anything again.

I was obsessed with it. I would get to practice early and practice my touch. I would go home and do planks while I watched TV. I really put in the time to be great. I was great at a Division 3 school, and everyone else on my team went on to D1 schools. It was awesome to be an All-American, but there were many stages above me that I thought about.

I think I’ve done this enough times now where I have to pass the torch and start over. That feels fun and exciting. I know I will do it again. The main thing writing the novel taught me was that I could do a huge thing by myself.

Usually, I trick myself into thinking, “This is the magnum opus.” Constellate is what it all laddered into, a piece of software that helps companies do great work. I had truly zero product vision, but I thought, “This is its final form.” Then I joined Patrick O’Shaughnessy. I thought, “Helping founders plus media—this is its final form.” Then I ramp something up and give it away. On this book, I thought, “This is my magnum opus. All the things I’ve ever thought about how to do great work are going to be in this book.” When they’re done, it’s sad. But now I’ve done this enough times where I know I’m going to try to be the very best. I think it would be so lame to go into these projects and say, “It could be okay.” I don’t want to write an okay book.

Jackson: [01:21:09] The abundance is what Kevin is doing. Kevin doesn’t seem to have that feeling that this needs to be the opus, yet it’s all great.

Brie: [01:21:17] I know. He says, “This doesn’t have to be the best walk across China that anybody’s ever done.” But also, “I’m not going to phone it in.”

Brie: [01:21:23] When I say “at ease in my craft,” I think of Kevin as at ease in his craft. He trusts himself that his version will be beautiful. What is even the best book about great operators? It doesn’t matter. It’s just my best book. That’s what I have to do.

Jackson: [01:21:42] This is Kevin’s most famous line: “Don’t be the best, be the only.”

Brie: [01:21:44] Yes, but that’s very hard to channel as this “hate-to-lose” competitive person. I think I will be happier when I trust myself to produce excellent work, understand my own worth and value, and trust the process instead of white-knuckling so much on the way. I’m afraid of this book.

Jackson: [01:22:05] Willpower’s overrated.

Brie: [01:22:06]

Maybe. But I don’t want to be afraid of my work. I want it to come out more joyfully. I think I’m always fighting that a little bit to nudge it and make it perfect. I would like a little more ease in the process.

Jackson: [01:22:26] One more from Kevin or on Kevin. His range is wide, but all his work somehow rhymes. What are the dominant rhymes for you and your work?

Brie: [01:22:35] Definitely excellent people around me and for an audience of other excellent people. That matters to me a lot. Optimism, I hope. I always want to paint the picture that the future is going to be better than it is now, and maybe a touch of something unexpected. I hope these would be very generous terms to describe my work, but that’s what I aspire to.

1:27:29: Special Talent and Contagious Ambition

Jackson: [01:23:08] Something else Tammy mentioned to talk to you about: She said you’ve talked to lots of great talent spotters for the book.

Brie: [01:23:16] I have.

Jackson: [01:23:17] What do they say about their best employees and the best early talent?

Brie: [01:23:21] The main thing they say is, “They’re just so good. They’re just so good.” I ask, “But why?” And they say, “I don’t know. They’re just so good.” I tweeted yesterday that I’m looking for a word for a general sense of “get-it-ness.” Lots of people have words for it, but they’re not quite right. I think what they’re saying is they generally can just move through space and get things done.

Jackson: [01:23:58] It’s like a knife cutting butter.

Brie: [01:24:01] Yes. Are they persnickety or not persnickety? They’re all over the map. Are they really “thinky” or really “dewy”? They’re all over the map. Maybe they’re momentum sources or flamekeepers or something. They just do it.

Jackson: [01:24:18] Is that innate? Is that obvious when they’re 20?

Brie: [01:24:21] I think so. And I still think it can be cultivated.

Jackson: [01:24:29] Or grown or compounded or something.

Brie: [01:24:31] Yes, and this is why I got so obsessed with talent. I had a couple of jobs before Stripe, but I had my real intellectual and agentic awakening at Stripe. Everybody was really good, and I wanted to be really good in that context. The job I had before that was at a startup. The office was on Church Street in San Francisco, and we had a storefront as our office. Someone once caught me watching The Good Wife at work. A user came in and asked, “Were you just watching The Good Wife on your laptop?” I was in the window of that storefront, and I said, “Yeah, I was.” I was really not trying that hard.

Jackson: [01:25:14] Sometimes you gotta feel it. You gotta be next to it. It’s a finger feel.

Brie: [01:25:17] Things really changed for me at work where I started to want to be good there. I had a clearer picture of what it would look like. I think it can be cultivated. A lot of people I talk to who I would consider great talent had a couple of early jobs where they didn’t quite feel it.

Jackson: [01:25:41] They were bouncing around.

Brie: [01:25:42] Yeah, they knew they weren’t doing that good of a job.

Jackson: [01:25:46] This is the hope. The optimistic case is that you don’t have to be a boy genius when you’re 18 or 20 and have only ever won.

Brie: [01:25:53] What’s that Steve Jobs quote? Keep looking. Follow the romantic sense. I talked to a lot of people who were not in the right container at first, and they knew it. They were also watching The Good Wife at work.

Jackson: [01:26:08] The question is: do you let the container suppress you, or do you find a way?

Brie: [01:26:13] It’s funny. At that time, I wouldn’t have said I was super ambitious at work. I remember thinking, “What do people do all day from nine to five?” I had no idea. I thought surely everybody else is also watching The Good Wife.

Jackson: [01:26:29] No way people are working for eight hours.

Brie: [01:26:30] That’s what I thought was happening at work.

Jackson: [01:26:35] I think that’s broadly true. Most people do not work eight hours a day.

Brie: [01:26:40] And they’re watching The Good Wife.

Jackson: [01:26:42] I don’t know what they’re watching. They’re watching TikTok. Things don’t take that much time.

Brie: [01:26:47] I had never seen a hive mind—a really buzzy workplace. So I just thought, “That’s what I do at work: not that much.” It took getting to a place where other people were doing that, but it wasn’t obvious to me that I wanted that for myself.

Jackson: [01:27:07] I think one of the most beautiful metaphors for this is that the fastest hundred-meter dash after Usain Bolt is the guy who raced him. This is just so clear. This is how we work.

Brie: [01:27:23] Yes. Everyone might have a different Usain Bolt. Certain cultures might work for you or not. One of the great talents I was talking about—one of the first places she worked, where she was not effective and not a fit, was in a lawn company. Surely you would expect that kind of environment would juice any ambitious person up, but it wasn’t a fit for her. She thought, “I guess I just won’t be that good at work.” But her environment was the intensity of an Elon Musk company. It wasn’t until she found the next job that she said, “Okay, now I’m alive at work.” You might find it in unlikely places.

1:32:22: Brie’s Spike: Charisma, Hard and Soft, Making Things Fun, and Belief

Jackson: [01:28:02] You seem to move between hard and soft, or yin and yang. Tammy said, “Brie is creative, but she’s also kind of ruthless.” There’s this yin and yang: vibes, but a lot of ambition. Very intuitive, but also into tracking and systems. There’s a super high bar for intangible things. I was going to ask if it resonates—it sounds like it resonates a little bit. How do you hold both of those?

Brie: [01:28:31] It does resonate. The first time Tammy said that to me, I said, “Tammy, that’s my best kept secret.” She said, “It’s not a secret. Everybody knows.” We were even talking about this at dinner last night. Am I type A or type B? It’s kind of hard to know. It does resonate. I don’t think about holding both because that’s just how I am.

Jackson: [01:28:56] Maybe you allow yourself to be both, whether it’s consciously or unconsciously. I wonder if we sort ourselves: “I’m this way, so I…”

Brie: [01:29:11] I like being around creatives. It’s almost necessary.

Jackson: [01:29:18] That makes a lot of sense for the worlds you like to inhabit.

Brie: [01:29:22] I don’t just mean creatives who do art. I mean any kind of people who make stuff, who bring new stuff into the world. You need to exude a certain quality to be welcome in those places. If I walked into a creative brainstorm saying, “Get that timeline,” even though that is low-grade what’s going on in my head, I know that’s not the right place. I can read a room.

Jackson: [01:29:52] I was thinking about your spike. We’ve talked about a lot of the things you’re good at and the patterns. My best sense of it comes from a few quotes. You said, “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.

There’s this ambiguity. You said, “People love to tell me things and I like hearing them.” You said, “I want to be an active metabolizer.” 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 special minds, and working with ambition and joy. You referred to Harold Ross of The New Yorker as “excitable.” My best point at it is this: It’s a charisma specifically around being excitable. Why is being excitable a virtue that resonates?

Brie: [01:31:02] That’s a really nice compliment. I hope that’s true. It’s a virtue because stuff could just be a drag. Or it could be fun and exciting and interesting. That’s morale, and it’s captivating. Seeing stuff through a new lens—asking, “What’s the fun version of it?”—actually shifts the work in the right direction. It’s not lipstick on it; it actually changes something about it. I was on a three-way call with two girlfriends recently. One was putting her newborn down for a nap and asked, “Do you think he’s gonna stay down?” The other girl said, “Honey, I don’t think so.” I said, “He’s totally gonna stay asleep. He’s gonna stay asleep forever.” They said, “Bri’s just a hype girl.” But then he stayed asleep, and I said, “I willed it into existence.”

Jackson: [01:31:56] If you believe in magic, magic happens. You believe in miracles.

Brie: [01:31:59] Miracles. I think I am a hype girl. I’m really proud of that. I’m discerning. I won’t hype anything. I won’t lie to you either. I cannot fake it.

Jackson: [01:32:12] You believe it.

Brie: [01:32:15] I do believe the hype. I do believe it.

Jackson: [01:32:16] I’m saying I believe you. People around you believe your hype.

Brie: [01:32:20] I believe it. That’s my only criteria for this stuff: do I believe it? 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 in video. I said, “I’m not going to pitch this until I believe it.” They said, “Okay, well, then you’re just going to lose.” I said, “I don’t care.” Then I started to believe it, and I became the third-best salesperson in North America.

Jackson: [01:32:54] You can sell anything you believe in. That’s true for anybody.

Brie: [01:32:56] I seek to believe. I think that’s really fun. I want to find the awesome things about people. Like you said, people tell me things, and I like to hear them. I want to get into it. I want the “skinny mirror.” I want you to look good in your clothes. I don’t want to talk shit behind your back; I want you to look good. I think people feel that in me and know that I’m not fake. Often, someone will try something on and I’ll say, “No, let’s try it again.”

Jackson: [01:33:31] Yes, yes, yes.

Brie: [01:33:31] That energy is contagious. Someone just sent me a really nice note saying that something they learned from working for me was to make it fun. Most people want it to be some version of fun. I try to bring that. I don’t always, but I try.

Jackson: [01:33:53] What does it mean to be an API to X?

Brie: [01:33:54] Maybe this is what we’re talking about. Being legible to two different things at the same time is like connecting two things that shouldn’t be connected. I’m very comfortable in that place. It’s like, “I want to put these two wires together, but you really have to stretch them.” I’m very willing to do that.

Jackson: [01:34:17] That’s a great mental image. You tweeted a napkin drawing of a “Good at Talking” matrix. It had “Good at Talking” on one axis and “Good at Doing” on the other. The one that’s good at talking but not good at doing is the “Yapper.” The top right is the good one. You’re definitely in the top right. How did you get there?

Brie: [01:34:47] I think people generally like having me around—in the right setups. I get to learn from a lot of really good people, and then I just copy what they do. I don’t think I’m great at “doing” yet. I think writing is kind of being a professional thinker.

Jackson: [01:35:13] There’s a lot of output, though.

Brie: [01:35:15] I guess I like getting stuff done. Sometimes I make checklists just to check things off.

Jackson: [01:35:22] This is also like the “picking up the crevices” thing.

Brie: [01:35:24] That’s fair. I do get stuff done. I think I just like to.

Jackson: [01:35:32] I think it was on a podcast, maybe with Packy or Perell, where you talked about Steve Jobs wanting to know how the parts of a thing work. You said, “I have that with people, and I have that with ideas.” What do you love about people and ideas?

Brie: [01:35:50] It’s an infinite puzzle, and everything is different. It’s an infinite game. You cannot fully understand people. You cannot wrangle ideas. I’m definitely not the smartest person in most rooms, but I am one of the most willing to ask questions. Maybe you relate to this. To me, that’s a very satisfying way to live. I have no shame about being dumber.

Jackson: [01:36:20] One last thing on the career advice bit. You were talking to Barrett Brooks and said, “I finally realized I just want cool people to think I’m cool.”

Brie: [01:36:32] Patrick honestly helped me get to that insight.

Jackson: [01:36:36] It’s beautiful. You followed that up by saying, “I had the clue. I just wasn’t listening.” You even talked about how some aspects of this feel fundamentally unrigorous, female-gendered, or like “vibe queen.” We all have this in so many aspects of our lives, not just our career paths. Do you have advice for people to get better at listening to the clues?

Brie: [01:37:10] That’s a really good question. I’m still working on getting better at this. I think it’s related to the quietness and stillness we talked about earlier. It’s about thinking when everything is quiet. When I make a career decision, I’ll often go on a tour of all my friends. Sometimes I think it would be better if I just went into an empty room. Part of listening better is trying to make everything else quiet so I can hear. It’s really hard to do. We’re surrounded by smart people, there’s a lot of writing on everything, and people have opinions. It seems silly not to hear from them. But I’m on a journey of learning to trust myself a little more. To make decisions in the direction of yourself, you also have to believe that you have what it takes on your own. No matter what was happening when I joined Stripe at 22 or 23, that was the right career decision. The thing competing with it at the time was to stay working at Dandelion Chocolates and be a soccer coach. That might have been more fun or felt like “listening to myself,” but Stripe was the right step for me to take. It’s hard to know when to listen and when not to. But you should at least document the signs so you have a record of what’s going on inside.

Jackson: [01:38:52] You have this image of putting the microphone close to yourself.

Brie: [01:38:57] Yes.

Jackson: [01:38:58] The other metaphor I try to lean on is letting the snow globe settle. I’m viscerally shaking this thing, looking for answers, but stillness is important.

1:43:23: Taste, Appreciation, Generosity, Skill and Soul

Jackson: We’ve made it well over an hour and a half without talking about taste, but we have to.

Brie: [01:39:14] I thought you were just using craft as a stand-in.

Jackson: [01:39:17] I think they’re very related, but a little different. Taste is such an input to craft. You’ve written a lot of great things, but if people are going to read one thing, I hope it is Notes on Taste. It is wonderful and very influential to me. I want to pull out a few things. 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. To pursue it is to appreciate ourselves, each other, and the stuff we are surrounded by a whole lot more. Appreciation is a form of taste. Creation is another. Those who create tasteful things are almost always deep appreciators. Though finally, taste cannot sublimate, it can only bloom.” It’s telling that you say appreciate things more, not judge things more.

Brie: [01:40:20] Yes.

Jackson: [01:40:21] Can you say a little more about…

Brie: [01:40:22] 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 drink it from the gas station and that was fine with me. But he is so into coffee. If you look over there, there is a whole setup with scales and temperature controls. He is like a scientist, and he dials in every factor. Every morning, we do this ritual together where we make coffee and talk about if we like it. It would be so much easier to get it from the gas station, but it is a lovely ritual. Now I always know where the beans are roasted because we like African blends. It makes me think a little bit more deeply about what is going on and where these beans come from. It reminds me of Steve Jobs taking things apart or John Collison saying the world is a museum of passion projects. It just makes me think more about how things came to be.

Jackson: [01:41:20] A deeper state of attention, I think you also call it.

Brie: [01:41:23]

It makes me feel like things are precious choices, and that I can make them too. I can exert more influence on my experience of the world. I think more about people.

Jackson: [01:41:43] There are a few themes in that essay that all point to this. There is the quote from Tina Brown about noticing things—you can’t teach somebody to notice things or listen to what is going on inside them. We were just talking about what I like and why, with an emphasis on the “why.” Another theme is that you say, “I think I’m a good consumer.” You also used the word connoisseur, specifically how being a good connoisseur actually makes the output better. Great connoisseurs who don’t hoard make great curators. The thing that came to me here is that it is actually a form of generosity in two ways. It is generous in consumption because a receptive audience makes the thing better. There is generosity on the other side, too: if you are not hoarding it, if you are curating, you are being generous. What do you see in your favorite—and particularly the most generous—consumers and curators?

Brie: [01:42:47] Honestly, just spending time talking about stuff. That connoisseurship idea comes from Fran Lebowitz. She says the reason art was so good in the 70s is because the audience was so good. People were really paying attention, critiquing, and pushing their creators. I hope that when someone makes a TV show, they imagine me and my friends at brunch talking about all the choices.

Jackson: [01:43:16] Yes, and loving attention.

Brie: [01:43:27] Yes, loving attention. Just recently, Rosalía released a new album. Have you listened to it yet? It is unbelievable. She is on another level. My friend and I discuss every track—the transitions, when the drums come in, her voice. It is loving attention on her work. I trust that she worked very hard to create something amazing, and I appreciate it. I am live-tweeting all day. I am canceling meetings because I got a text about this. I love her art, and it is so fun to pay attention to it, talk about it, learn from it, and get excited about it. I am not a musician, but I am enjoying beholding her art.

Jackson: [01:44:04] You aren’t a musician, yet this goes back to what we were saying earlier: “I’m not a designer, but you’re kind of doing it.” You aren’t a musician, but you are engaging with the work in a way that I think she would appreciate. It is loving.

Brie: [01:44:18] It requires attention—gabbing about it at brunch with the girlfriends.

Jackson: [01:44:20] There is something you talk about in the piece, which is that taste is an external and internal thing together. There is an external sensibility or recognition—maybe closer to correctness—and then there is listening to what is going on inside you. Does great taste require both?

Brie: [01:44:43] I think so. Anna Mitchell gave me this term of a “true original.” If you think about the person who has the best taste in fashion, she isn’t just porting over something else. She is coming up with her own stuff. Something is happening in there. I framed it in the piece as a kind of alchemy, and I believe that is the quality of it. I also quote the idea of being “in accordance with the good and the true.” Fashion needs to adhere to certain laws of physics to look good.

Jackson: [01:45:18] Proportions, colors, and good materials.

Brie: [01:45:19] Exactly. There are ways to break those rules in a way that is tasteful, and ways that aren’t. It just takes loving attention to get there.

Jackson: [01:45:32] You may have already given me my answer, but I had another question about why curiosity alone doesn’t make for tastefulness. Maybe it’s that curiosity can be internally driven, but it doesn’t give the thing the time to percolate inside you.

Brie: [01:45:53] I use the word “metabolize” a lot. You want to do some work on it. If I listen to the Rosalía album, I could text a friend, “Love this album.” Or I could say, “Here are all the sounds I heard, the cool noises, and transitions.” Those are very different things.

Jackson: [01:46:16] Who has most shepherded your taste?

Brie: [01:46:18] A lot of people. Definitely Tammy, my friend Charlton Lamb, and my friend Matt Kallman.

Jackson: [01:46:30] What stands out when you think of those people? What about their taste is so wonderful?

Brie: [01:46:39] To me, these people are the ultimate polymaths. Tammy knows everything. She reads everything.

Jackson: [01:46:48] This runs against something you say in the piece, though. You imply that you can’t really have great taste in lots of things, which I am not sure I agree with.

Brie: [01:46:58] It is hard to be truly great at everything; otherwise it would be exhausting. But Tammy, Charlton, and Matt read and know everything, which means they know how to exert pressure on a thing in a particular way. They can draw from math, pop culture, literature, or history to push on an idea.

Jackson: [01:47:22] It is like the fork thing a little bit. You need the breadth.

Brie: [01:47:25] Yeah. Let’s go back to music. If you listen to Beyoncé’s album with an awareness of Black history, something unlocks for you. That polymathic approach helps you push and question in more informed ways. Those things improve my taste because they open new doors. I actually don’t have a great command of Black history, but I liked Beyoncé’s album. Getting into conversation with Charlton and Matt showed me there was deeper to go. That is a whole new door.

Jackson: [01:48:03] To try to compress taste and craft slightly, you talk 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.

Brie: [01:48:19] You’re picking out all my heroes in this conversation.

Jackson: [01:48:22] It’s all bangers. He’s talking about his students. Taste honors someone’s standards of quality, but also the distinctive way the world bounces off a person. I think that describes you. Finally, you briefly referenced this: When we recognize true taste, we are recognizing that alchemic combination of skill and soul.

Brie: [01:48:42] That taste piece had a great editor.

Jackson: [01:48:48] For what it’s worth, I was going to ask about that. What examples come to mind when you think about craft and taste, or skill and soul, coming together?

Brie: [01:48:59] Everything. Anything that’s good. We recognize soullessness so fast.

Jackson: [01:49:06] Are you sure? Is the world getting worse at that, or is that a false fear? People are very worried about slop.

Brie: [01:49:20] I’ll take that nudge. Do you think people are eating McDonald’s and think it’s good food?

Jackson: [01:49:30] I think digital is harder. There’s a materiality to the physical world that is fundamentally more scarce. I’ve eaten McDonald’s and thought it was good.

Brie: [01:49:42] I don’t mean does it taste good. I mean, is it skill and soul?

Jackson: [01:49:46] We were just talking last night about how we know some people who write very well, but they don’t totally “write” it. Does that mean it’s less soulful? I don’t think so, but maybe that illustrates your point. I do wonder about the soul piece. I feel soul with Rosalia in a way that, with another person, I might think, “This is craft. There’s a lot of craft here,” but I don’t feel it.

Brie: [01:50:16] It is in the eye of the beholder, but not all the time. I think there are a lot of universally recognized special combinations.

Jackson: [01:50:25] From Christopher Alexander down the list, history would indicate that people are pretty good at sniffing this out.

Brie: [01:50:34] I think so. Maybe we’ll get better at it. That would be nice, because there’s so much slop. The real risk is that slop is better at hijacking our brains. That’s the real problem here. I don’t think anything I see on TikTok is good, but I can spend a lot of time on it by accident.

Jackson: [01:50:56] I saw my first feature film directed by a TikToker, Baron Ryan, whom I watched in 2020 and 2021. He just made his first movie. One of the things that always stood out was that his work actually has a lot of soul for a one-minute video. I think you’re right. The fear is that you don’t even get the chance because you’re mind-numbed. Mark Zuckerberg’s got you.

Brie: [01:51:21] Or you don’t want to. It’s challenging to read Moby Dick. There is a lot in there. I had to have a friend walk me through it chapter by chapter.

Jackson: [01:51:36] What a gift.

Brie: [01:51:37] I don’t know why I wanted to read it, but I was struggling. It would have been much easier to watch Real Housewives or something, but I feel up to the challenge of soulful and craftful things. Can I say one more thing about George Saunders that is striking? Imagine being George Saunders, one of the most accomplished writers. A room of eighteen-year-olds shows up, and you believe that they are already perfect. What a generous belief.

Jackson: [01:52:16] I suspect he has this unbelievably refined ability to see people and see their magic or their light. By the way, I don’t think he’s being nice.

Brie: [01:52:31] No, me either. I don’t think he’s being nice. But this is why he’s one of my heroes. You can be at peak craft and believe someone unshaped has arrived already perfect.

Your job is to make them more themselves. What a beautiful way to approach someone who’s a student to you.

I hope to move through the world more like that. We’re talking a lot about loving attention and taste, and I think the real damning thing is just indifference to everything. I was a little bit that kind of teenager—“I don’t care, I don’t care, I don’t care.” That is the worst way to live to me.

Jackson: [01:53:10] It’s the optimism and so much of the stuff we were talking about earlier.

1:57:26: Great Editors, Saying No and Getting to Yes, and Being Receptive to Editing

Jackson: I want to talk a little bit about taste and editing. You say 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.

Brie: [01:53:30] It seduces. That’s a little extra.

Jackson: [01:53:33] Amazing. Speaking of Saunders, he’s got this P.N. thing. I think you’ve talked about that, both in the literal editing sense but also as this amazing template for what it feels like to actually taste more. How do you edit towards ineffability?

Brie: [01:53:51]

I’m glad you’re asking this, because I’m working with a leader right now. I think he’s got amazing taste, and the main way it comes out is he says no to stuff. A thing that we’re working on together is how do you get it to yes?

It’s actually less interesting that it’s no. You need to know what dials exist so that we can get it to yes. That’s the happy place.

Jackson: [01:54:14] Steve Jobs was really amazing at saying no and also had a few awesome yeses.

Brie: [01:54:18] Yes, and you have to know what dials you have. It’s no fun to be the person reviewing tweets and just saying, “It’s not good enough.” A true leader says, “Okay, this is how we make it good enough.” There is a lot in there: content, skill, language. There is just lots to work on there to help understand how to get it to yes. One of my most fashionable friends is now in her thirties. Throughout her twenties, she wore some ratchet stuff, but she was trying. She was playing. She got a lot of no’s, and now she is dialed to the yes place. I am picturing a cockpit. You need to have all these knobs and know what to turn and when to get it to yes. You can’t just be a no.

Jackson: [01:55:06] Pure correctness without taste is like the minimalism slop thing. To your point, you actually have to go wide. You have to be willing to take a risk.

Brie: [01:55:15] Yes.

Jackson: [01:55:15] To get to something really…

Brie: [01:55:17] Figma taught me a lot about design thinking. That was part of what was really fun about being there, with a lot of people who had been trained in that mindset. One thing early designers do is copy and paste something, then change one thing about it to make it more you. I think that’s mostly the journey.

Jackson: [01:55:32] Virgil Abloh talks about 3% better, 3% different.

Brie: [01:55:35] Remake this movie poster that you’ve seen the movie of. It’s a lot of copy paste.

Jackson: [01:55:42] Tweak. It’s a great slope into agency and creativity.

Brie: [01:55:44] Yes.

Jackson: [01:55:45] You mentioned both of them earlier: Jeremy Stern at Colossus and that editor for this piece. What made them great editors?

Brie: [01:55:57] 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. He’s peak at his craft and then he’s letting me do it.

Jackson: [01:56:18] He’s amplifying.

Brie: [01:56:19] I think of that as very generous. They often see work when it’s not perfect and have the enthusiasm to keep going. They never say anything is bad.

Jackson: [01:56:33] Part coach, part evaluator.

Brie: [01:56:37] Speaking of hands on the dials, they know exactly how to get it to “yes.” It’s really rare, but every now and then there’s something that I do want to hold onto, and 100% of the time they just say, “Okay.”

Jackson: [01:56:52] I like that. I think we talked about this, but maybe we’re hitting it again. You have this amazing desire to be edited and a comfort with being critiqued. Is that innate? Can you get better at that?

Brie: [01:57:12] I’ve had critics my whole life. This is one of the things I learned the most from being an athlete. My friends who played music growing up seriously have this too, where there is an objective rightness. It’s a little easier to be critiqued. If I make a bad pass, I know it’s bad.

Jackson: [01:57:33] Right.

Brie: [01:57:33] If you hit the wrong note, you know it’s bad.

Jackson: [01:57:36] It’s nobody’s opinion.

Brie: [01:57:38] It’s a little easier to stomach because it’s pretty clear what the rules are. Since I’ve had people critiquing me my whole life, now when these things are more nebulous—what’s the right word to use here, what’s the right color, how should this look—I think I already have a comfort with the language of critique. This is another thing I learned at Figma. Critique is a huge part of the design process. There’s no such design process without it. So having mechanisms that build this in—where we all look at this work together and talk about what we like and don’t like—feels very normal to me now.

Jackson: [01:58:16] I think a lot of people have not had that. It feels like a personal attack.

Brie: [01:58:17] Totally. Another version of this is watching tape in sports, where you just go back and watch yourself doing stuff and you ask, “Why?”

Jackson: [01:58:26] It’s a way of being, though. It’s assumed.

Brie: [01:58:28] Right.

Jackson: [01:58:29] It’s not special. We watch tape every time.

Brie: [01:58:32] Exactly. It’s not a punishment. It’s just part of the craft. I had this at Google when I was working in sales. They would film us doing our pitches. This is where I learned that if I have an earring in, I’ll play with it. So I don’t wear earrings anymore because I don’t want to fidget. But until you’ve seen yourself in a meeting…

Jackson: [01:58:49] So you’ve heard yourself on a podcast.

Brie: [01:58:51] I never listen to any. But anyway, I feel like it’s a comfort with being in the critique.

Jackson: [01:59:00] My last thing on this. Our mutual friend Molly Mielke tweeted this yesterday. It’s actually a little harsh, but I thought of you—in a good way, I promise. She says: “In Silicon Valley, ‘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.”

Brie: [01:59:29] That’s funny.

Jackson: [01:59:30] 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?

Brie: [01:59:43] Yeah, those are Tammy’s words. Why do you think it’s harsh?

Jackson: [01:59:48] Maybe harsh is the wrong phrase. It’s poignant and very opinionated. I’m not sure I fully agree with her or Tammy on the “deployed taste” thing. It gets a little subtle. There’s nuance. What is a curator? Is a curator deploying taste? Am I deploying my taste? All I do is talk and curate people.

Brie: [02:00:12] The way this is hitting me is actually more of the API thing. When people are doing a taste check with me, they ask, “Will this resonate with another community?” I think that’s valuable. That is deploying taste. I’m saying, “If we tune this knob, I think it will land better.”

Jackson: [02:00:32] Which I don’t think is what Molly is talking about when she talks about the tastemaker either.

Brie: [02:00:36] But I think the difference between an influencer, as Molly is describing it, and this tastemaker is that the tastemaker is in the wings. They’re never famous. The influencer is the famous one. They’re deploying taste for—

Jackson: [02:00:49] I think she’s saying that we call people tastemakers who aren’t actual—

Brie: [02:00:52] Really? I see. That makes sense to me. But I mostly don’t stand to gain anything.

Jackson: [02:00:58] I doubt many… maybe they do. But I would be 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.

Brie: [02:01:07] I don’t think a lot of people ask me for my take on something, like, “Do you think this is good?” I don’t think people refer to me as that.

2:05:25: Great Writing: What do You Have the Right to Do that Others Don't?

Jackson: [02:01:16] We are well in on multiple hours. I have two sections left: a quick one on writing, and 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 that you already brought up that it seems like we’re really in the storytelling era.

Brie: [02:01:36] Yeah.

Jackson: [02:01:37] Which is cool. It’s a time for Brie Wolfson’s “What Makes Writing Clever.”

Brie: [02:01:42] Clever. That’s a good word. There’s another George Saunders-ism: good writing is only that you want to read the next sentence. I think clever has an element of surprise in it. You can be lulled to sleep really easily with most stuff. If it’s good writing and it’s keeping your attention, there’s probably a degree of clever.

Jackson: [02:02:05] You’ve talked about how so much of modern writing lacks editing, especially on the internet and social media. What editing does is ask: Who is this for? And what will they get from this? You’ve also said self-editing is a real virtue. I think you used this language: how does editing close the distance between the writer and the reader?

Brie: [02:02:29] I think Morgan Housel would say that he doesn’t think of his audience at all. A lot of people say they’re writing for themselves. I think that’s another good way to produce good writing. I don’t think this is the only way—closing the…

Jackson: [02:02:44] He also one-shots it. He talks about how he edits as he goes, and when it’s done, it’s…

Brie: [02:02:51] Done. He is a very practiced writer, but he is self-editing.

Jackson: [02:02:58] The whole writing process.

Brie: [02:02:59] I think it was Fran Lebowitz, or maybe Tina Brown, who said good writing knows its place. I think that’s more of what this is like. You know that meme on Twitter that says “Nobody:” followed by a blank, and then “Me:” followed by something? A lot of writing is that. The taste piece struck a chord because people were talking about it already. It was an answer to what I was hearing. It wasn’t random. It knew its place in this sense.

Jackson: [02:03:32] It’s not like I’m rolling up to the function and lobbing a take in. I’ve been in the context, and I’m listening.

Brie: [02:03:38] This is what’s hitting so much about the Colossus stuff. I can see the meme: “Nobody,” and then “Here’s 20,000 words on Josh Kushner.” But I actually think we’re craving more depth. That felt true to me regarding what was going on in the culture. Everything was short-form and clippy. What does the longest, deepest, most intimate treatment look like? That was an answer to something that knew its place. I’m trying to respond to what I’m feeling in the world. It’s not just random.

Jackson: [02:04:11] Speaking of the Josh profile and the Colossus ones, you’ve talked about The New Yorker and how much you love their profiles. You mentioned this chain of obsession and how exclusives are interesting because they make you not compete, whether that’s by being obscure or timeless. Maybe it relates to “Last Thing” or profiles broadly, but should we aim for our writing to be less competitive as a general rule?

Brie: [02:04:39] Maybe this is more like Kevin’s idea: don’t be the best, be the only. With the Colossus stuff, we often ask ourselves, “What do we have the right to do that others don’t?” It’s not to make it better. It’s just: what do we know about this person, or how do we experience them? That is what makes us special and earns us the right to do this work. Generally, we haven’t run into this yet because we were mostly staying in the investor and founder pool. But we would really question ourselves if there was someone truly outside of our network who we did not understand or know, or felt we didn’t have the right to cover. That comes up a lot.

Jackson: [02:05:22] What makes Jeremy so good at writing? I asked about editing.

Brie: [02:05:26] Oh man, I don’t know. He’s another one of those people. He knows everything. He’s read everything.

Jackson: [02:05:30] Maybe a better question is: what goes into having such a strong voice?

Brie: [02:05:36] I wonder how he would respond to this, but he reads to me as very confident in his voice. I don’t know if you experience this, but I still definitely do. When I sit down to write, I assume this “teacher voice” persona. Even if I’m writing a diary entry, I suddenly assume words I wouldn’t normally use or describe things in weird ways that feel technically correct, but no human would ever say. Jeremy allows himself to say the human words. It should be easier, but it’s actually harder.

Jackson: [02:06:16] What do we love so much about numbered lists?

Brie: [02:06:20] Oh my God. I don’t know. It’s funny.

Jackson: [02:06:23] I think the best way to…

Brie: [02:06:24] On this last Cursor piece, Jeremy said, “I really don’t love listicles generally, but I think we can make it work with this one.” I think it’s just easy to scan.

Jackson: [02:06:38] It does some of the work, too. It’s so easy for your brain to just ratchet down the case numbers. What’s the best essay you’ve ever read?

Brie: [02:06:53] There are so many. There is probably a recency effect here, but the two that live rent-free in my head at the moment are Nadia’s “Basic as a Virtue” and “Reality Has a Surprising Amount of Detail.” I think about those things a lot.

Jackson: [02:07:12] Why?

Brie: [02:07:13] They taught me something I didn’t know before. Then it was like that Baader-Meinhof thing where I started seeing it everywhere. Like we were saying, I was so anti-Marina when I was living in the Mission at 22 years old. Now, every time I go to the Marina, I think, “Nadia was right the whole time.” It reached me before I was quite ready.

Jackson: [02:07:34] It was ahead of you.

Brie: [02:07:35] It was out ahead of me. So was “Reality Has a Surprising Amount of Detail.” That was before this insight about the world as a museum of passion projects. I thought, “Wait a second, is this true?” Because if it’s true…

Jackson: [02:07:48] John Salvatier. What an incredible essay.

Brie: [02:07:52] It’s so good. Also, “Geeks, MOPs, and Sociopaths.” Do you know that one?

Jackson: [02:07:58] Is this Kevin? I’m familiar with the name, but I don’t know if I’ve read it.

Brie: [02:08:03] It’s so good. It’s basically about how movements get started. First are the true believers, then the people who just glom on but don’t really have an impact. Then the sociopaths come and try to commercialize it and make it suck.

Jackson: [02:08:16] I think maybe I have read this.

Brie: [02:08:18] Because of the work that I do, which is often trying to find a little dim flame somewhere, I’m very conscious of it. I feel the conversation around taste is ruined.

Jackson: [02:08:28] 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 writing thinking and talking thinking?

Brie: [02:08:40] They’re looping for me.

Jackson: [02:08:43] Writing thinking gets a lot of praise. Talking thinking less so.

Brie: [02:08:47] I’ve actually been thinking a lot about this. Instead of just writing on my own personal blog, I’m now writing for a magazine that has a different standard. I don’t know if ethics is the right word, but in the taste piece, I would happily just copy and paste someone’s words and put them in there. In this professional magazine, I wonder if I should credit them. The lines are blurring. I think the issue with talking is: Is it your idea? That’s why people don’t like talking thinking. With writing thinking, everybody knows it’s all your stuff because it’s just you and the paper. Those are all your own original ideas.

Jackson: [02:09:30] What does talking do for you that you’re cycling through?

Brie: [02:09:34] I’m so attuned to the glint in the eye. I throw a lot of stuff out, and then I realize, “That’s the phrase.” Patrick O’Shaughnessy is actually great at that too. He’s waiting to hear what gets echoed back.

Jackson: [02:09:46] He’s so amazing at that. Unbelievable.

2:13:55: Grab Bag: Optimism and Pessimism, High and Low, and Closing Maxims

Jackson: Okay, my last string of things. Forgive me, you said her name last night—Eka from Stripe? On critique: Why is it so good to be a micro-pessimist and a macro-optimist?

Brie: [02:10:04] Generally, you think about the ways that it will go right, and you tune into the details to tweak them to get it there. If you do it in the context of pessimism, it’s no fun. It’s just all “No.”

Jackson: [02:10:25] Yes.

Brie: [02:10:26] You want more?

Jackson: [02:10:26] Something came up. I can’t remember who was in an interview, maybe it was with Henrik Carlson. We want less “not that” and more “maybe this.”

Brie: [02:10:38] Yes, I love that. Imagine you’re editing a blog post. It was supposed to ship two days ago, but we’re still revving the words. If someone asked, “This blog post is going nowhere. No one’s gonna read it. What’s the point of fixing all the details?”

Jackson: [02:10:57] It’s about momentum.

Brie: [02:10:59] Preservation. Exactly. You’re like, “This is so close to great. Just a few tweaks, and it’s gonna be great.” That’s the energy you want to bring to fixing stuff. “This word is not doing it for me. This whole paragraph, I’m not sure.” In the context of “this could be awesome,” it is really fun to fix. Otherwise, not so much.

Jackson: [02:11:17] You said you were starstruck by Kevin Kelly. Are you starstruck by anyone else?

Brie: [02:11:25] Definitely. I get weird in front of celebrities. If I pass one on the street in New York, I have no chill at all across the board. For some reason lately, I’ve really set my mind on meeting Tina Brown. I think I’d be freaked out in front of her for sure.

Jackson: [02:11:48] All right, we gotta make it happen.

Brie: [02:11:49] Yeah.

Jackson: [02:11:50] You’ve talked about “magnet on” times and “magnet off” times. Any further realizations on what causes the magnet to be on?

Brie: [02:11:58] The “magnet on” thing first came from friends and periods of dating where “magnet on” is just like, the hotties are knocking. I think it just comes from confidence. But confidence is not in a vacuum. You’re starting to get some momentum.

Jackson: [02:12:18] You said it takes a ridiculous person to fund something like Stripe Press. Back to funding culture, partially at least. And Colossus. Who else is doing this? What else could be done?

Brie: [02:12:31] I think this story movement is a vote to fund weird ideas. Hopefully we’ll get this story studio type thing spun up at Cursor. The pitch was six stunts a year. These are a few thought-through, big, weird ideas. That kind of thing is resonating. We can’t really write out what a stunt is, but I think this work is getting funded more now.

Jackson: [02:13:04] Taste is a good dinner party topic because everyone’s got a thought on it—something you said. What are other good dinner party topics?

Brie: [02:13:11]

I’m gonna take any weasel word or suitcase word. Anything that’s memey. Anything everyone has an opinion on.

Jackson: [02:13:25] Sontag said, “To snare a sensibility in words, especially one that is alive and powerful, one must be tentative and nimble.” She’s talking about camp and taste. We have other buzzy words like agency, which is a little clearer. I’m curious if other immediate words come to mind. If you were going to do Notes on X in 2028, what might it be on?

Brie: [02:13:52] Good question. I could do Notes on Marketing right now. Everyone’s got a really different definition for that.

Jackson: [02:14:02] Patrick O’Shaughnessy told me to ask you, how do your friends decide where to work?

Brie: [02:14:10] Where to work? That’s funny. Most of my friends are in Silicon Valley, so they’re likely ground level on what the hot stuff is. It’s talking to other friends. Again, in the dating era of life, we used to say, “Where are the hotties at?” This is like that for work.

Brie: [02:14:35] Where are the hotties at? Where are the smart people at?

Jackson: [02:14:39] You mentioned Tina Brown a bunch, or I did. We didn’t get to talk about it a lot, but one of my favorite ideas is high-low.

Brie: [02:14:46] It’s the best.

Jackson: [02:14:47] So many ways.

Brie: [02:14:48] Those people I mentioned—Tammy, Matt Charlton, my tastemakers—are all high-low.

Jackson: [02:14:54] You said, or I think she said, the uncanny valley between high and low brow is very wide. How do you know when you’ve made it to safety? How do you know you’ve made it out of the chasm on either side?

Brie: [02:15:06] I don’t know. Do you have an idea?

Jackson: [02:15:11] I don’t know either. One of the things that is important is to recognize that high and low can come together, which is maybe the core point. You talk about Vanity Fair and give the example of cultural affairs, geopolitics, and Britney. So many of the best things…

Brie: [02:15:33] Hold both.

Jackson: [02:15:33] Yeah. But I think it’s more of a taste thing. You have to know when you see it. You know when it’s in the uncanny valley.

Brie: [02:15:41] For sure. One of the mysteries of marketing and taste is that every now and then I know when something’s gonna hit, but I mostly don’t. I think most people mostly don’t. Maybe there are a few, like the MSCHF people. Maybe they have cracked it.

Jackson: [02:16:00] It’s more mechanical, though. To some extent for MSCHF, which is one of the reasons I think Gabe and those guys are done with it. Mr. Beast is extremely mechanical. He’s obsessive about YouTube like it’s basketball.

Brie: [02:16:11] Yes. Maybe there’s something there for those people, but I generally don’t know.

Jackson: [02:16:17] You have a scrapbook of pride in a brag document. Any highlights in there that come to mind?

Brie: [02:16:25] Honestly, this is why the insight about just wanting cool people to think I’m cool matters. It’s mostly compliments from people I think are cool, as it probably should be. I don’t think that’s the way to build your internal flame source, but that’s mostly what’s in there.

Jackson: [02:16:44] It’s good to live a relational life, I think.

Brie: [02:16:48] I think that’s a nice way to put that.

Jackson: [02:16:51] What types of things does writing as a medium miss?

Brie: [02:16:57] One description of my writing a long time ago was “cinematic,” and I thought, “Then shouldn’t it just be a movie?” It misses visuals, or I guess this could also be thought of as an asset. This was actually one of the founding ideas for Colossus—using photography to make that medium bigger in the magazine and give that visual peek. It obviously misses the visual stuff, but on the flip side, it allows you to paint a mental picture. My friends Nick and Devin are really into how stuff on the web doesn’t have any sounds right now.

Jackson: [02:17:38] Not Ryo OS.

Brie: [02:17:41] There you go. I’m interested in that, but I think it’s its own thing. I don’t think too much about what it misses.

Jackson: [02:17:50] What do you love about Matisse?

Brie: [02:17:51] It is just pleasing to my eye. I think it’s because of the sharp contrast.

Jackson: [02:18:00] That’s all you need to say. You said Graham Duncan’s concept of grip quite literally changed your life. Why?

Brie: [02:18:06] Now I see it everywhere. That would be another good candidate for an essay I think about a lot. It’s one of those things where, becoming self-aware about it, I ask: What is my grip on this?

Brie: [02:18:19] It’s seeing the water. You’re probably getting a sense of my temperament from this conversation. My grip is almost always too tight, and it gets in my way because I can’t bring the loose quality that makes me happy. More than any other person in the world, Patrick O’Shaughnessy has loosened my grip on things. It helps me get to joyful.

Jackson: [02:18:45] Faster.

Brie: [02:18:45] Wow. You know him, he’s intense and competitive, but he has a light grip on everything. It makes him so much more fluid and flexible without sacrificing any power or...

Jackson: [02:19:00] Effectiveness.

Brie: [02:19:01] Yeah, it’s empowering. To me, the happy place is the lighter grip place. All my problems are related to grip. Now that I can see the water on grip…

Jackson: [02:19:15] You have a few maxims or little lines on your website that are all great. “Have a real friend in the generation above and below you.”

Brie: [02:19:24] Oh, yeah.

Jackson: [02:19:25] What do you look for in intergenerational friends?

Brie: [02:19:28] That’s a good question. I’m thinking of one. My best friend in the generation above me is a woman named Leslie Berlin.

Jackson: [02:19:37] Most notably, at least recently, for the Steve Jobs Archive stuff. Amazing. “Make Something Wonderful.”

Brie: [02:19:45] She’s an amazing woman. The main criteria for her is that it’s fun to hear the problems facing someone my age, yet she still has wisdom that feels relevant to me. She’s not dismissive of my experience because I’m younger or because it wasn’t like that when she was coming up.

Jackson: [02:20:15] It’s one of the best traits in an older person.

Brie: [02:20:18] Yes, and the same is true from a younger person. My sister is much younger than me; she’s very squarely Gen Z. A younger generation can look at the generation above it and think it’s old news and doesn’t have anything to offer. It’s respect for what’s coming before or after.

Jackson: [02:20:36] Everyone wants to help. Ask for what you need.

Brie: [02:20:39] Oh, yeah.

Jackson: [02:20:40] How have you gotten better at asking?

Brie: [02:20:42] Just being more specific. Weren’t you saying this the other day? Don’t send an email asking, “Can I pick your brain?” or “Can we catch up?” Who wants to do that? Who’s got the time?

Jackson: [02:20:54] I want to help, and there’s an abundance in helping. That’s the thing I’m working through. You don’t necessarily get one shot.

Brie: [02:21:01] Doesn’t everybody like to be thought of as being in the room where it happens? It’s actually generous.

Jackson: [02:21:06] Yeah.

Brie: [02:21:07] For a brief moment in my life when I had a startup, many people later said they were sad I didn’t ask them. They were on a list, and I thought I would never ask these people for money. That broke my brain a little bit.

Jackson: [02:21:26] Everything will be different in six months.

Brie: [02:21:29] That is totally true in startup life. Especially now that I have an infant. She’s a new person every day. It’s amazing_. Having an infant and moving out of California, where there are seasons, has changed my conception of time for sure._

Jackson: [02:21:45] The deeper you go, the better it gets.

Brie: [02:21:50] This insight also preceded all the taste stuff. I wrote this after I thought there were a bunch of people I didn’t like, and then I was forced to hang out with them for a weekend. I realized, “Oh, I like them.”

Jackson: [02:22:05]

People are hard to hate close up.

Brie: [02:22:06] Yeah. Whenever someone feels like some flavor of enemy to me, the antidote 100% of the time is just to go hang out.

Jackson: [02:22:16]

It’s a life’s work to bridge the inside of you and the outside.

Brie: [02:22:23] A therapist friend told me that she has seen people survive anything but a cruel inner voice. I don’t have the kindest inner voice at all times, and it made me think, “What a waste.” I’m trying to quiet down that voice and 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.

Jackson: [02:22:58] 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 that comes to mind.

Brie: [02:23:11] My mom gave me all the joyful stuff. I think she had a complicated relationship with too much joy and too much excitement, but she gave me that, and I treasure it. I want my daughter to have fun with things. My dad gave me the hard-working side.

Jackson: [02:23:42] It’s that hard and soft a little bit.

Brie: [02:23:43] Being able to have them both at once—once I truly can integrate and enjoy them both—that will be it. I hope my daughter has those things, for sure.

Jackson: [02:23:54] One last thing. You tweeted this the other day—“To be of use.” It’s just a little excerpt: “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 amphoras for wine or oil, Hopi 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?

Brie: [02:24:33] This is basically why I married my husband. He teaches me this every single day. There is not a thing in this house he would not repair. Everything he wears is old and patched up. Every time we’re going to get anything, he asks, “Is it useful?” Especially now with an infant, there are all these single-use products and everything is being marketed to you. He reminds me every day that the main point of a life is to put in more than what you get out. Use your hands and recycle. He reminds me that this is our thing. We are tool users. We can fix and problem-solve and be useful. A joyful life is more around these things than the other things. I love that poem, and I tweet it probably once a year because I’m trying to remind myself. It’s very easy to get caught up in the stuff that’s not that. That’s why I like that line about the mud. When I see mud, the main thing I want to do is not go near it. But this reminds me that that is the stuff.

Jackson: [02:25:53] That’s the whole thing.

Brie: [02:25:54] That’s the whole thing. Mostly, that’s a note to self as well.

Jackson: [02:25:57] Thank you, Bri. This is all I got.

Brie: [02:26:00] Jackson. Have fun.

Jackson: [02:26:00] Oh, what a gift. Thank you.