35: Brie Wolfson - Loving Attention & Ease in Craft

Summary

Dialectic Episode 35: Brie Wolfson – Loving Attention & Ease in Craft

Host: Jackson Dahl
Guest: Brie Wolfson
Date: January 6, 2026

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Episode Overview

Jackson Dahl hosts Brie Wolfson, a creative leader and writer known for her work at Stripe, Stripe Press, Figma, her own agency, Positive Sum, and Cursor. The conversation is a deep dive into the nature of craft, taste, organizational culture, career trajectories, creativity, and leadership. Brie shares insights from her wide-ranging experience, offering both practical and philosophical reflections on building great products, organizations, and a meaningful work life. The episode orbits around two central themes: the pursuit and experience of excellence ("craft") and the cultivation and expression of "taste"—all while maintaining organizational energy, ambition, and fun.

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Key Topics & Insights

1. The Nature of Craft & Ground-Level Mastery

• Craft as Time-on-Task: Brie argues that there’s no shortcut to true craft—what she calls a "finger feel for excellence." You earn it through repetition and exposure to details, not just surface overviews.
  • Quote: “The most reliable input if you want to get that finger feel thing is just time on the thing. It’s so unsatisfying in some ways. You cannot shortcut this thing.” (06:38)
• Leadership & ‘Fork Shaped’ Talent: She admires leaders who can go both broad and deep—“fork-shaped” people—as opposed to the classic T-shaped model.
  • Quote: “The leaders I like the most can go deep on lots of things… nothing can get by them.” (08:36)
• Staying Close to the Work: Great leaders and teams should avoid delegating understanding and stay close to the details—even as they rise in seniority.
  • Example: Leaders at Stripe and Cursor join in on sourcing and recruiting rather than just reading summaries. (09:29)

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2. Automation, Taste, and the Limits of Shortcuts

• Can Craft Be Automated?: Brie and Jackson debate if heuristic-driven automation can ever substitute for deeply internalized craft. Consensus: shortcuts can refine the process, but the core can’t be handed off to machines or detached systems.
  • Quote: “You kind of don’t know until you know. Similarly, a management philosophy that I have is, like, to do it before you manage it.” (12:55)
• Taste as Unconscious Competence: Taste is described as “unconscious competence”—but it starts with long periods of deliberate practice.
  • Quote: “Taste is unconscious competence. But you have to kind of go through that process.” (11:56)

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3. Process vs. Output; The Value of Exploratory Work

• Satisfaction in the Process: Brie prefers the slow, messy creative process (“the grunt work”) over simply producing outputs quickly—something she refers to as being high “P” in Myers-Briggs terms.
  • Quote: “I like the process of doing things more than I like the end state.” (14:08)
• Tension: Perfectionism vs. Volume: Creatively, she struggles with balancing a high bar for quality against the need for volume/iteration. She dislikes publishing work she doesn’t like.
  • Quote: “I know the difference between when I like something that I’ve produced and when I don’t. And if I don’t like it, I’m happy to put it under the bed.” (19:41)

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4. Marketing Rooted in Substance & Collaboration

• Marketing as Truth-Telling: The best marketing emerges from authentic, substance-driven work. Craft-focused companies are easier to market because their stories are real.
  • Quote: “People read bullshit pretty fast. So if you’re gonna bullshit, people will think you’re bullshit. And a good way not to bullshit is to just, like, tell the truth about what you’re doing.” (22:22)
• Collaboration Over Solo Work: Brie values working hand-in-hand with designers and others, not baton-passing, which leads to more innovative and integrated results.
  • Quote: “I want to work with design… Both hands on the baton the whole way through.” (33:10)

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5. Organizational Culture, the New Era of ICs, and Company Shape

• Wanting to Be Great: The true commonality between excellent organizations is their self-awareness and aspiration to be great—focused not only on products but also the people and organism of the company.
  • Quote: “I think the only thing these companies have in common is that they want to be great.” (26:31)
• Rise of the Individual Contributor: Work is shifting back towards valuing powerful, self-leveraging ICs, but collaboration and overlap between crafts remain critical to making magic happen.
  • Quote: “I think individuals have way more power in organizations now because they can do more wide.” (28:29)
• Remote Work and Creativity: Distance requires intentionality; serendipitous collaboration is harder, and some “creative overlap” is lost.
  • Quote: “Lack of proximity requires everything to be intentional… it doesn’t allow for the…” (33:55)

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6. The ‘Audience of Itself’ – Building for Internal Cohesion

• Great Culture Is for Employees: Internal marketing, lore, all-hands, and crafting company mythology benefit morale and make the company more cohesive.
  • Quote: “To me, I think it’s like a privilege to see our colleagues' work… a really good all hands is amazing…” (46:43)

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7. Taste: Cultivating, Appreciating, and Creating

• Taste as Deep Appreciation: Taste honors both appreciation and creation. She argues for a more generous, noticing form of taste—less about judgment, more about enjoyment and attention.
  • Quote: “To pursue [taste] 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.” (103:29)
• Generosity in Consumption & Curation: True curators uplift creators by giving "loving attention" and helping things be their best. Taste becomes a service to others.
  • Example: Close critique and thoughtful consuming in friend groups (e.g., discussing Rosalia's album). (107:32)
• Taste and Craft Intertwined: The most exceptional work is a blend of “skill and soul.” Great “taste” (the soul) improves the actual craft, and vice versa.
  • Quote: “Anything that’s good… we recognize soullessness so fast.” (113:12)

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8. Leadership, Morale, and Loving Attention

• Morale as Having Fun & Destiny: Citing Napoleon via Nabeel Qureshi ("morale is 75% of winning"), Brie emphasizes fun and a sense of destiny as central to great leadership and culture.
  • Quote: “You can compete with somebody having fun in all caps. And I think that’s true.” (61:08)
• Loving Attention: True progress and satisfaction come from being pushed and cared for—by a coach, peer, or editor—through careful attention and critique.
  • Quote: “Being in groups of people who will give each other that kind of loving attention is, like, amazing.” (70:50)

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9. Career Paths, Floundering, and Generalists

• Picking up Work in the Crannies: Brie’s "flounder mode" career approach collected messy, unclaimed responsibilities, which allowed her to develop unique expertise.
  • Quote: “There’s just all this work that lives in the crannies that doesn’t seem like it should be owned by anyone in particular, so why not me?” (71:57)
• Generalists in the New IC Era: Future generalists must still be able to produce output and not merely glue or coordinate.
  • Quote: “Generalists now have to be able to produce output…” (77:20)
• Publishing & Public Output: You don’t have to be Twitter famous, but artifacts (blog posts, projects) help crystallize your thinking and reputation.
  • Quote: “No, you don’t need to be Twitter famous, period… I think it’s really useful to publish your work.” (78:19)

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10. Taste, Editing, and Critique

• Editing as Closing the Gap Between Writer and Reader: Good editing respects the author’s voice and helps them fully realize it, rather than imposing the editor’s persona.
  • Quote: “Jeremy certainly has a distinctive voice… which he does not impose on me when he’s editing my work, which I think of as an incredible skill.” (120:09)
• Critique as Practice: Early experience in sports or music builds comfort with critique, which is then transferable to collaborative creative fields.

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11. Soft and Hard; Yin and Yang

• Ruthless and Creative: Brie self-describes as holding both ambition and vibes, intuitive and systems-thinking, hard and soft—attributes she sees as essential to creative collaboration.
  • Quote: “It does resonate. I don’t think about holding both because that’s just how I am.” (92:50)

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12. Miscellaneous Wisdom & Memorable Moments

• Magnet On/Off: "Magnet on" moments come from confidence and momentum, often noticed in both dating and creative life.
• High/Low: Brie admires the high/low synthesis in creative work (e.g., Tina Brown’s Vanity Fair). The best things combine intellectual rigor and mass appeal.
• Brag Document: Her “scrapbook of pride” consists mostly of compliments from people she admires—a reminder that meaningful affirmation is relational.
• On Usefulness: Quoting the poem “To Be of Use,” Brie underscores the satisfaction of real, tangible, and practical work.
  • Quote: “A joyful life is more around these things than the other things… that is the stuff.” (148:38)
• On Parental Influence: She aspires to give her daughter both the joy and warmth from her mother and the work ethic from her father—“being able to have them both at once.”

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Notable Quotes & Timestamps

| Speaker | Quote | Timestamp | |---------|-------|-----------| | Brie Wolfson | "You cannot shortcut this thing [craft]." | 06:38 | | Brie Wolfson | "Taste is unconscious competence." | 11:56 | | Brie Wolfson | "I like the process of doing things more than I like the end state." | 14:08 | | Brie Wolfson | "People read bullshit pretty fast." | 22:22 | | Brie Wolfson | "I think the only thing these companies have in common is that they want to be great." | 26:31 | | Brie Wolfson | "Once you've had [the finger feel] somewhere... you can spin up faster on more stuff." | 13:14 | | Brie Wolfson | "Being in groups of people who will give each other that kind of loving attention is, like, amazing." | 70:50 | | Brie Wolfson | "Taste honors... appreciation and creation. Those who create tasteful things are almost always deep appreciators." | 103:29 | | Brie Wolfson | “I think my natural view is the ‘skinny mirror’—amplifying others in their best light.” | 65:53 | | Brie Wolfson | "The real damning thing is just indifference to everything. That’s, like, the worst way to live." | 117:04 | | Brie Wolfson | “I think I am a hype girl. I’m really proud of that. And I’m discerning. I won’t hype anything. And I, like, won’t lie to you either.” | 96:14 & 12 | | Jackson Dahl | "What is the line between lore or mythology and nostalgia?" | 48:53 | | Brie Wolfson | “A team is actually a very diverse set of people. The Avengers. That feels really fun.” | 44:19 | | Brie Wolfson | “The deeper you go, the better it gets.” | 145:52 |

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Timestamps for Key Segments

• [05:26] Most roles should be craft roles—implications
• [06:38] The finger feel for excellence and ground-level work
• [14:08] Process vs. output in creative work
• [19:41] The challenge of producing high-quality, high-quantity creative work
• [22:22] Marketing rooted in substance versus hype
• [26:31] Common traits of excellent organizations
• [28:29][31:01] The shift to empowered, wide-reaching ICs and the need for collaboration
• [33:55] Remote work, intentionality, and collaboration creativity
• [44:19] Team diversity and building great teams (‘The Avengers’ metaphor)
• [53:25] Learning new technical skills and the challenge of moving from thinking to doing
• [61:08] Morale, fun, and manufacturing organizational energy
• [65:53] The refractive “skinny mirror” approach to amplifying others
• [70:50] The deeply motivating effect of “loving attention”
• [92:50] The creative/ruthless yin-yang
• [103:29] Taste as appreciation and creation
• [120:09] Editing that respects and enhances the writer’s voice
• [145:52] “The deeper you go, the better it gets.” Wisdom on relationships and people

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Memorable Moments

• Brie’s Honest Self-Assessment: Admits to both her ruthlessness and creative energy, crediting her ability to hold both to her effectiveness across creative and operational fields.
• On Accepting Critique: Easily accepts criticism due to lifelong immersion in “objective” feedback (sports, music), and views critique as a vital component of growth.
• On Internal Product-Market Fit: Describes a fast-moving culture where the internal adoption and excitement for a feature is now critical ("internal PMF").
• High-Low Examples: Discussion of Tina Brown’s “high-low” editorial sensibility and how it remains a north star for modern creators.

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Takeaways for Listeners

• Craft is painstaking and non-transferable— shortcutting leads to superficiality.
• Taste is cultivated through immersion, appreciation, and active creation, not just through consumption or judgment.
• Modern organizations thrive when individuals are empowered to act widely and deeply—yet the best results come from collaboration between distinct crafts.
• The best cultures and the best marketing are rooted in substance; hype must be backed by reality.
• Career paths need not be linear—curiosity and a knack for seizing neglected opportunities can build remarkable, idiosyncratic strengths.
• Loving attention, fun, and a sense of destiny are the lifeblood of organizations that want to be great.
• Editing—done lovingly—is generative, not punitive, and relies on both craft and taste.
• The ultimate enemy is indifference; the highest good is to care, deeply and specifically, about what you do and whom you do it with.

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This summary captures the episode’s lively, honest, and thoughtful spirit—full of both quotable wisdom and practical insight for original thinkers, craft-obsessed builders, and anyone charting their own path across the creative and organizational landscape.

Transcript

[Bri Wolfson]

A lot of the leaders that I work for, I think they're like fork shaped, like, you hear, like T shaped or something like. Or just like broad or just deep on one thing. I think the leaders I like the most can go deep on lots of.

[Jackson]

It's almost like vertical slices.

[Bri Wolfson]

Yeah, exactly. And it's just like they're kind of scouring the land. Scouring the land. And then it's just like, shoot, like deep on one really particular thing. And I like that quality in a person. I think it's like fun and interesting and I like that quality in a leader because it means that kind of nothing can get by them. I think I am a hype girl. I'm really proud of that. And I'm discerning. I won't hype anything.

[Jackson]

Yes.

[Bri Wolfson]

And I, like, won't lie to you either. I, like, I cannot fake it. We're talking a lot about loving attention and taste and the real. I think the real damning thing is just indifference to everything. And I think I was a little bit that kind of teenager of like, I don't care. I don't care. I don't care. That's like the worst way to live to me.

[Jackson]

Welcome to Dialectic, episode 35 with Bree Wolfson. Where to start on Bri. She wrote a piece recently, sort of about Kevin Kelly and sort of about herself, called Flounder Mode. And it's a fun play on Paul Graham's essay Founder Mode, if you haven't read it. And I think it describes Bri well in that she has spent her career, to some extent floundering and to other extents, doing all kinds of unexpected, brilliant, and compelling things. And I know I relate a bit to her and to Kevin in the way she describes it in that piece, as someone who has done a bunch of different things. And that's not necessarily a bad thing. Bri. She spent a bunch of time at Stripe, where she worked on organizational culture and systems and planning, as well as effectively being the internal founder of Stripe Press, which I, and I'm sure many of you know and love. She went on to Figma, where she worked on education, among other things. She started her own agency and helped companies and startups with everything from organizational culture to marketing and storytelling. And now she has two roles. She is the Chief Marketing Officer at. At Positive Sum, which is known probably most well for both the podcast Invest like the Best, hosted by Patrick o', Shaughnessy, as well as Colossus, their new publication, which Bri helped launch in the last year and has a number of just incredible features on people like Josh Kushner, Neil Mehta, Matt Huang, Graham Duncan, and more. And then Bri's other job more recently is head of employee experience at Cursor. She's doing both. I'm not sure how she does it all. And this is a conversation where we talk both about all those things I just mentioned, as well as things that I think are just distinctly Bri. We start with Craft. Bree talks about a. What she calls a finger feel for excellence, this ability to get to the ground level of things, to really feel the quality of things. Obviously that's something that resonates deeply with this podcast. We also talk about Taste, which Bri wrote an amazing piece on. And I think both Craft and Taste are, as former guest Tammy Winter would say, tacit things that Silicon Valley and technologists tend to talk about and aspire to, but don't always necessarily know how to get to. And Bri is just so eloquent in thinking about and talking about those. We also talk extensively about organizational culture, about her wide ranging career path. She's writing a book for Stripe Press for people early in their career. We talk plenty about marketing and storytelling and words and writing. Breeze also worked with some just truly incredible leaders. People like Patrick Collison, Daniel Dylan Field, Michael Truell, now at Cursor, and of course Patrick o', Shaughnessy, who someone I really look up to. And yeah, I just, I. I hope more than anything else that you find this conversation energizing, because I think that is something that Bri does perhaps better than anything else. Um, she is so energizing in so many different dimensions, whether it be on the ambition, company building, organizational side or on some of the more intangible things, talking about how we can actually get to the quality without a name that makes certain things so craftful, so tasteful, so special. Before we get into the conversation, I want to thank Dialectic's presenting partner, Notion. If you missed it last week, I'm now full time on Dialectic, thanks to Notion support, and I'm so proud to have them as a partner and a tool that I can speak about. Notion is a tool for your life's work. It's an AI powered workspace that allows you to take any of your ideas and expand on them, tinker with them, iterate on them, and collaborate around them. I think that last piece is probably the most important if you work with a team or really just any kind of collaborator. Even with Dialectic, where I'm mostly working solo, being able to whether it be in the research process as I'm prepping for interviews or afterwards trying to pull out the lessons and ideas that stand out most. Being able to have an AI tool to help me synthesize, separate signal from noise and make sense of it all is so powerful. Obviously that is even more significant when you're working with a team or a collaborator. And Notion makes it super easy to do that all in the same workspace. You can visit notion.com dialectic to learn more and I hope you build something with Notion. Nothing would make me happier. Thank you to Notion for their continued support and thank you to you for listening. With that, here's my conversation with Bri Bri Wolfson. We made it.

[Bri Wolfson]

Thanks for having me. Jackson.

[Jackson]

Thank you for having me. We're going to start. I actually couldn't find I was going back so I hope you actually did say this, but I believe you somewhere said recently I think you could argue most roles should be craft roles. Why? And would you have said that 10 years ago?

[Bri Wolfson]

first I'm thinking about. Did I say that? I was like it sounds like something that I would say. I think this is probably a few months ago now and I think I've refined my thinking on this thing and we're in the era of the IC that is totally different than a few years ago, which I think means that we're in the era of craft. Like you 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, I think so many other follow up questions I have might fall apart. Well, let's start with this. You have a quote. You say turpentine is what is really going on at the 1 inch altitude. It's. It's not the generic cliched shape of it observed from 10,000ft. Even the smartest, most thoughtful, best intentioned people won't get it right without the ground level perspective and visceral sense of what is. You talk about this like finger feel for excellence all the time. I guess to maybe take that metaphor literally. What are the biggest inputs towards the developing that when most of us live lives, at least people in our world live lives that are so digitally intermediated.

[Bri Wolfson]

Yeah, I think the probably the most reliable input if you want to get that finger feel thing is just time on the thing. It's like so unsatisfying in some ways. Cause we want to like shortcut and. But I think that's the whole point of it. You cannot shortcut this thing. It's funny hearing those words. I think that was. That must have been from like 2018.

[Jackson]

Yeah. A while ago.

[Bri Wolfson]

Before we've started really talking about this as a society. And it still rings really true and it's still really hard to get. And I think you kind of just know it when you've encountered a person that's got this quality, especially about a particular thing. But yeah, I think it's just time

[Jackson]

reps on the thing, ground level. Like, I think when we think of people who are spend a lot of time in something and especially approach mastery or leadership or whatever it might be. I don't know if everyone's mind goes to like being on the ground level.

[Bri Wolfson]

Yeah.

[Jackson]

If anything, it's like the more time, the more you rise.

[Bri Wolfson]

Yeah.

[Jackson]

And we'll talk more about like company leadership later. But like, I'm curious. It seems like you've been around a lot of people who have the like finger feel and the mastery and the like. They're not in the ground level in a lot of ways and they kind of find themselves returning to the ground.

[Bri Wolfson]

Yeah, I'm attracted to those people. Like my friends joke that competence is my kink. I just like people that know how to do shit. And it's like you can just tell. Like I'm watching you guys tinkering with all of this equipment. Like I can tell you know what's going on with this stuff. And you're saying all these words I don't understand and you're like touching all these dials. I can't tell what they do. But to me that tells me that you're like in the details, you're on the ground level. And a lot of the leaders that I work for, I like. I think they're like fork shaped. Like you hear like T shaped or something. Like I. Or. Yeah. Or just like broad or just deep on one thing. I think the leaders I like the most, like, can go deep on lots of.

[Jackson]

There's almost like vertical slices.

[Bri Wolfson]

Yeah, exactly. And it's just like they're kind of scouring the land. Scouring the land. And then it's just like shoo. Like deep on one really particular thing. And I like that quality in a person. I think it's like fun and interesting. And I like that quality in a leader because it means that kind of nothing can get by them.

[Jackson]

Nothing can get by.

[Bri Wolfson]

They're like willing to go deep on just about anything.

[Jackson]

There's a former guest of mine, Stefan Ongo, who runs Obsidian. He has a post called don't delegate understanding. And he's sort of talking about the ways that, like, so much of modern society is like, removing friction and like, tempting you to just be like somebody else has it kind of figured out. You're. You're talking about almost the. Yeah.

[Bri Wolfson]

That if you're a company leader, you can structure your company such that like, you are briefed on anything or, like, whatever. You're an organizational leader, you're the President of the United States. Like, you can live on a brief.

[Jackson]

Yeah.

[Bri Wolfson]

And I think it's more fun to go into the weeds on stuff. So Patrick Collison, Dylan Fields, like, Michael Tr. Like, something goes by them. They want to know more. They're like, deep. They're like, they're like in the copy, pulling them forward. Yeah, yeah. They're like, my friend Jordan just joined to do recruiting at Cursor, and they're like, she's having the time of her life because she's like, this whole leadership team is like, on LinkedIn sourcing with me. Like, they don't want to look at the spreadsheet with like, the summarized thing. They, like, want to be on LinkedIn. They want to see the whole back history. They want to see how they frame the descriptions. Like, I understand that kind of learning that, like, speaks to me versus, like, okay, I've, like, got the summary. I can, like, I got the snapshot.

[Jackson]

Yep, yep.

[Bri Wolfson]

I think you just know something different when you've seen the details.

[Jackson]

Yeah, yeah. I mean, you started the answer with time earlier and it's like, there's no shortcuts to that level of, like, being in it, feeling it.

[Bri Wolfson]

It's so hard to describe to somebody, like, what's different if you just read the summary and the spreadsheet versus you read the whole LinkedIn profile.

[Jackson]

It's one dimensional or not multidimensional.

[Bri Wolfson]

But until you've like, I don't know, until you've done that thing, until you've gone deep yourself, until you've like, felt the pattern match that happens when you do the LinkedIn scouring yourself versus you read the spreadsheet. I think it's really hard to make the case for that kind of thing.

[Jackson]

On that note, then let's say you do it enough times to know what that feels like. Can CRAFT be automated at some point?

[Bri Wolfson]

Oh, I don't even know what that means. What would it look like for CRAFT to be automated?

[Jackson]

Maybe my best. The first thing that comes to mind would be, from what I've read about Elon, Elon will make sure. He understands the process. Kind of what you're saying. Like, he'll make sure he understands the process first and then he'll automate it.

[Bri Wolfson]

Yeah, sure, sure.

[Jackson]

That's maybe an easy plug and play with the sort of, like, robotic manufacturing idea. But, like, in theory, if whatever. Michael and the Cursor leadership team have, like, been in the LinkedIn weeds enough, they have started to develop heuristics. Maybe like, Autumn. Like, again, can craft be automated? Is very, like, on the nose and sort of has a strong connotation. But to the extent there are, dare I say, shortcuts, like, maybe a better way of asking this question would be like, how do these people have time for anything if they are in the weeds? On, like, what. What is. What does that sequencing look like? To go from, like, I really lived on the ground and now I need leverage or scale.

[Bri Wolfson]

I. Yeah, I'm picturing, like, Elon walking the factory floor or something. I've, of course, never seen it myself, but that is, like, very vivid imagery to me. Like, looking at all the parts, like, touching on the things, seeing all the people. I do think that gets faster over time. Like, I like Tammy's definition that I heard. I think it was from Cedric Chin that she talked about in your podcast, which is like, taste is unconscious competence. So I think it, like, takes a while doing conscious competence before you reach what we started off by describing as the finger feel. And, um. But you have to kind of go through that process. Funny, I'm working with a company leader now, and she's like, I just feel like I don't quite get the product yet. And she's spending a lot of time, like, shadowing SDR calls. And my sense is it's kind of just gonna click and then she will be able to, like, move off that. Um, but I think you kind of don't know until you know. Yeah. Like, similarly, a management philosophy that I have is, like, to do it before you manage it.

[Jackson]

That's kind of what I was saying with Dylan.

[Bri Wolfson]

So I don't know if you can automate it necessarily. I think you can, like, shrink the time it takes to get to that unconscious competence state. I also have, I think, observed a pattern where this kind of get it ness or finger feel is sort of contagious. Like, once you've had it somewhere, you sort of.

[Jackson]

You realize that the world is.

[Bri Wolfson]

Yeah. And you. You kind of. Okay, you know that there's, like, pathways to it. You kind of know what it feels when you have it, so you can kind of like, spin up faster on more stuff.

[Jackson]

I like that. It's funny. Like, so many of the things that used to be craft in the world are like, I want to talk more in the weeds about it, but like, at a super high level. Like the last two, three years has been like, for people who do kind of things that we do. Like all of the things that used to be craft. Like, you can now press a button.

[Bri Wolfson]

Yeah.

[Jackson]

Maybe it's just the ground level thing, but I'm curious, like, what is rattling around in your head as you think about, like having all of this leverage and all of this, like, so many things that you can. Is it about prioritization? Is it about, like, disregard efficiency, disregard ambition and just like choose to do the have craft and the things that you enjoy. But like, I'm curious how you're feeling about it.

[Bri Wolfson]

I think I'm lucky because I'm on Myers Briggs, like, super high P. I like the process of doing things more than I like the end state. So in some ways I'm lucky I'm not satisfied to hit the button and make the website go poof. That's not exciting.

[Jackson]

Yeah, yeah, yeah.

[Bri Wolfson]

To me. So I'm lucky in this era in some ways because I don't find it very satisfying to just get to the end really fast. Like, I want to do the grunt work. Yeah, yeah. Um, so I. I think I'm sort of like, well, maybe lucky is me. Maybe it's the opposite. Maybe I'm unlucky that I like that work because I'm inefficient or something. But I, like, quite literally just like don't and can't work the other way.

[Jackson]

Okay, different question. Um, you've talked a lot about how, like, you're not really like a high volume output person. At least consistency wise, like, substack didn't really work for you. You also have referenced like the Seinfeld. Like, it just requires a lot of tonnage. Producing a lot helps you get to the best stuff. Patrick o' Shaughnessy says, like, what if it works, it works fast. And so there's like this tension between like, you're really high bar, but also the fact that you like to be in the process. Maybe, maybe that's actually compatible. And this notion that like, it's like the classic ceramicist story about like the 30 bowls versus the one bowl. Like, how. How do you square all that?

[Bri Wolfson]

Yeah, I think this is like, this probably like the struggle of my life creatively is that I'm just a person that has to Throw a lot out. And it's funny. I wrote two novels once upon a time, and one of them I wrote between the hours of 5am and 7am in the striped kitchen. These were not the conditions for me to write a great novel. And my mind, maybe they were. Well, my mind.

[Jackson]

You wrote the novel?

[Bri Wolfson]

I wrote the novel. I finished it. Like, it got published. I'm not that proud of it. And my mindset during that time was like, I need to be very efficient and I need to maximize the number of words in the draft that makes it to the final page. I like, I hate what I came out with.

[Jackson]

This is Rosie or the other book?

[Bri Wolfson]

The other one.

[Jackson]

Okay.

[Bri Wolfson]

And that was first or second.

[Jackson]

Okay.

[Bri Wolfson]

And I hated that book. I hated writing it. I hated public, Like, I just hated everything about it.

[Jackson]

And it's like the scheduled, disciplined version of creativity.

[Bri Wolfson]

I think the schedule I didn't mind so much. It was just the concept that I couldn't do the carving. I just, I was like, high ratio of words in draft, in first draft,

[Jackson]

two words on final draft, like measure once, cut once.

[Bri Wolfson]

That was the metric in my head. I was like, no wasted words. Like, I need to shrink this into a short amount of time possible. And I couldn't do this like exploring and like cutting and culling and that I like to do with my work. And this is in between me and being prolific for sure. For sure. But I've just. I think I will bump into some challenges like, quote, operating in this like, age of sort of like the IC and being prolific and shipping stuff and it's easy to iterate. This is a. This is a personal challenge right now.

[Jackson]

What do you think would cause you to have more tonnage time?

[Bri Wolfson]

More time? You mean output,

[Jackson]

I guess. No. Yeah. I'm more asking, like, what would cause you to put out more within this existing allotted time and have it. Is there a version of that that would not net out? If you did that a bunch of times, would it just keep feeling like the book.

[Bri Wolfson]

I'm not sure. It's funny because I'm working on this book now for a straight press and I've sort of been like in and out of working on it and I'm realizing how much of a full body experience it is for me to work on something this big. Like, I need to be able to hold all the information in my head at once and like write parts of it and reference other parts of it. And if I'm doing too many other things at once, I cannot do that.

[Jackson]

Yes. Work.

[Bri Wolfson]

I like Lose my own thread. And I'm struggling with this because I want to be able to pick it up in chunks. Like, I want to be able to just, like, whip up this chapter and whip up that chapter and, like, have everything be discreet enough that it's. Yeah, it's easy to just sort of, like, whip out more pieces, but I literally can't. It just, like, doesn't work. It breaks.

[Jackson]

I've really benefited from forcing functions and constraints.

[Bri Wolfson]

Yeah.

[Jackson]

And there are some people who are like, whatever the. The person who's like, the midterm, the finals do at the end of the semester, I'm gonna do it halfway through. Ben Thompson talked about this with David Perel, where he's like, I don't know if I could write a book. Like, I have to publish every day.

[Bri Wolfson]

Yeah.

[Jackson]

And so I guess as someone who's, again, more of the, like, I'll do it the night before or whatever. Like, building. One of the reasons the podcast is good for me is, like, I can show up today prepared or unprepared.

[Bri Wolfson]

Yeah.

[Jackson]

Whereas writing is a little more like. And so I guess maybe one not to push you, but, like, what if you had to, like, a draft? Do I like is the way you get out of the first books, sort of like, measure ones cut once. Is like, I have this highly rigorously scheduled set of deadlines, but that aren't final. Like, they're draft deadlines.

[Bri Wolfson]

It was so it's funny that you're mentioning this. So a couple weeks ago, the Stripe Press team was like, oh, hey, like, by the way, we forgot to tell you, but this, like, amazing editor is gonna help you work on your book. I was like, oh. And that was, like, my most prolific two weeks. Because I just, like, let stuff out that I wouldn't have otherwise. Cause I was like, okay. I'm gonna guess you do a lot

[Jackson]

of self editing too. So I'm sure that there's.

[Bri Wolfson]

I do my filter between, like, my own head and, like, what makes the pages, like, very strong. Like, I'm doing a lot of work when it gets translated from my brain into my fingertips, like, onto the screen.

[Jackson]

And is that a good thing?

[Bri Wolfson]

I don't know. I think I'm still learning about my creative process. But I. Something I do know is I know the difference between when I like something that I've produced and when I don't. And if I don't like it, I'm happy to put it under the bed. Like, I really don't like publishing stuff

[Jackson]

I don't like, which is uncommon in the modern era for sure. Most people default to just like rip. Rip the tweet.

[Bri Wolfson]

Yeah. I think I've been lucky in my career because I've been doing this a long time and I've been rewarded enough times for sitting on my hands.

[Jackson]

Do you think that a really amazing editor makes you more likely to sort of just blob everything out of the page or are you filtering more?

[Bri Wolfson]

I was telling Jeremy that he's made me a much lazier writer cuz he's such a good editor.

[Jackson]

That's cool.

[Bri Wolfson]

It is cool. It is cool. And to the I. I think the ver.

[Jackson]

Sorry to interrupt you, but I think the best version of creativity instinctively to me is probably actually like your max. It's sort of like the right drunk at it sober, but between two people it's like you are maximally like unfiltered and then it gets shaped over time.

[Bri Wolfson]

I think so. I mean, I love being edited by Jeremy. He's an incredible editor. He sort of like understands the person on the other side and he's just got away with words. So you're like, wow, that would have taken me a while to come up with this turn of phrase, like, thank you so much. And like, I do like that process. Like, Michael and I at cursor were jamming on something recently and he was looking over my shoulder and he was like, oh, you use like the actual thesaurus. Like you go to thesaurus.com like, what is up with you, girl? And I was like, I do go to thesaurus. I like, I like that process of like, I just like it. I like doing that work.

[Jackson]

It's inside of all that. Everything you just said is like, is actually making writing a little more collaborative or multiplayer, which is. It's very, usually very single player, I think.

[Bri Wolfson]

Yeah, Yeah. I mean, all of my writing has seen like many hands and eyes before it's gone out. But I'm very careful with when I send my drafts out and I kind of know what I want to get at each phase.

[Jackson]

I think obviously we've been talking about craft and like so much of what you do is craft, but you're also maybe whether I don't know how much you like the term, but like, you are a marketer and I think you're known as a marketer and you're known as an excellent marketer and maybe a world also that like, isn't always the most thoughtful about marketing. When does marketing like emerge naturally or at least in. In this sort of compelling way out of Craft versus something else. And, like, why is. Maybe. Maybe the more important question is, like, why is marketing? It's rooted in craft and substance. So important.

[Bri Wolfson]

My general philosophy on marketing is people read bullshit pretty fast. So if you're gonna bullshit, people will think you're bullshit. And, like, a good way not to bullshit is to just, like, tell the truth about what you're doing. And if there's nothing interesting there, there's like, nothing interesting there. So I think one of the reasons I like working for, like, craft focused companies is just like, there is a story there. There's like something to say. It's not like lipstick on pins, like hand wavy stuff. There's just more substance. Like, we were talking about this a little bit last night, like, sort of closing the gap between what is true and what is perceived about a company. Like, I Like when there's like a rich or like a wide space.

[Jackson]

Yes.

[Bri Wolfson]

There's like, a lot for me to do.

[Jackson]

So much potential.

[Bri Wolfson]

Yeah. Like, I don't. I would never work for, like, an overhyped brand. That's like my nightmare. I always want to work for something underrated. And, like, clearly I've worked for very, like, highly rated brands like Stripe and

[Jackson]

Figment and Cursor and also they're highly rated.

[Bri Wolfson]

They're highly rated. And yet I believe they are still underrated. Like, I think Patrick and Michael and Dylan are known as like, incredible leaders. I think there's even more incredible stuff there. And to me, that's like a very exciting space. And to take it back to craft. Like, if there was no story, if there was no great leader, if there was no great craft, there's no story to tell. Like, there's no work for me to do. That's, like, boring.

[Jackson]

I just thought that's not intuitive. Because when people think about great marketing companies, think of Red Bull or Coca Cola and like, they don't even make the product.

[Bri Wolfson]

Yeah. Fair.

[Jackson]

Maybe put another way, you were talking about Harold Ross and you're like, he actually got the form right before he got the, like.

[Bri Wolfson]

Yeah, the.

[Jackson]

The content. Right. And he was so obsessed about this. Like, it feels like Silicon Val, maybe to your point, is actually like, all substance, no style. Typically. Like, is there a right balance in that? Like, maybe. Maybe. Maybe a more important question is how can there be craft in both style and substance?

[Bri Wolfson]

Yeah. I mean, I think now marketing is thought of as more of a discipline on its own. Like, I seem. I think we've seen enough examples of it working that we, like, want to hone that as its own craft. Like, it's not just telling the product story. Like, there's something else to do in the marketing.

[Jackson]

The marketing team the night before or whatever.

[Bri Wolfson]

Yeah. So anyway, I think we've, like, started to honor marketing as a craft more. I also think there's just noisier, so it's a little harder to cut across.

[Jackson]

Sure. There's something like. Another thing you said is, like, all substacks look the same and like, there's something about tech that, like. Because again, there's so much substance.

[Bri Wolfson]

Yeah.

[Jackson]

It's like.

[Bri Wolfson]

Yeah.

[Jackson]

Like the style, like. Or even like the MySpace to Facebook thing. It's like, just. Yeah. Make it look fine.

[Bri Wolfson]

Did you have a Tumblr?

[Jackson]

Are you like, I did, but not like, I wasn't super deep.

[Bri Wolfson]

The, like, first thing, the first way I ever coded was to update my, like, AOL profile. Yeah. I think I've always had an intuition that. Okay. Another thing I like about marketing is you have to simultaneously, like, be understood and known and also cut across at the same time. You're like doing two opposite things at once. You want someone to understand, to see truth, but you also want to be noticed.

[Jackson]

And those really are pulling at each other.

[Bri Wolfson]

Yes. I think they are intention and Red Bull is crazy. It's really eye catching. But there's something known about feels.

[Jackson]

For me, it's tethered to something.

[Bri Wolfson]

Yes. And I think I just enjoy that. I enjoy that space.

[Jackson]

I like that you brought up ICs earlier. And I think, like, much of this craft thing to me is sort of revolving around or at least a huge implication of it is what's going to happen to companies and organizations. And I think you're as much as you're known for the craft marketing stuff, you're known for working with organizations and helping them grow and figure out what culture means and all these types of things. I think, um, so many places. Stripe, figma, cursor, et cetera. Before we get too in the weeds, though, our friend Tammy asks, what do all of these incredible organizations have in common?

[Bri Wolfson]

This is actually a harder question than you would think it'd be to answer. When I started all this consulting work, I had that Tolstoy quote in my head. Happy families are all alike and unhappy families are different. I was like, every company should, like, work the stripe way. And then I met Figma and I was like, nope, this company does not work the stripe way. And they are certainly excellent. So I think I'll have, like, a cheating answer. I think the only thing these companies have in common is that they want to be great. Like, they aspire to be great companies themselves. They are, like, turned inward on, like, understanding that they want the organization to be great. And I think that's almost not that intuitive. Like, you know, you want to build a great product. You know, you want, like, customers to enjoy your work. I think it like, takes sort of, like an enlightened leader to understand, like, I want a great company. So I think wanting to be great, like, wanting your people to be great.

[Jackson]

Yeah. There's a subtle but very important shift from, like, we are building the product to building, like, we are building the organism that can produce the product or many products on the ic stuff. Like, the shapes inside of companies seem to be changing. Maybe back to the Tolstoy quote. And I want to talk about culture, but, like, I almost think of culture as sort of, like, the soft part

[Bri Wolfson]

of companies and called, like, the primordial ooze.

[Jackson]

But there's another part which is, like, the hard, the skeleton or the hardware or whatever. And, like, it seems very clear independently of cursor, but maybe especially with the example of cursor, that, like, the shape, the atomic nature of work inside of companies is changing in a world where, like, most roles at a company are craft roles. To go back to that first thing, and there's all this leverage and speed for the individual. Are we going back to. I think you have some quote where you say, like, a company going from the individual is the building block of the company to the. Or the team being the building block of the company. Like, are we going back to the individual being the building block again?

[Bri Wolfson]

I think so. I think so. I think individuals have way more power in organizations now because they can do more wide.

[Jackson]

Yeah.

[Bri Wolfson]

So what do I mean by this? Like, a recent project I took on at cursor was to update the Careers page. It's super simple. There's, like. It's just like, a few lines of copy on, like, a pretty blank text that, like, integrates with Ashby. But it's, like, a simple setup. My job was, like, the words. And I learned through this project that I had such a learned helplessness around, like, approvals and, like, having other people see stuff and, like, do stuff for me and, like, how many other people I think needed to be involved when, like, really only I needed to be involved?

[Jackson]

And you could just ship it.

[Bri Wolfson]

Yeah. But I had so much, like, anxiety.

[Jackson]

Yes.

[Bri Wolfson]

About that. That I literally could not do it. Like, I can't tell you how many pings I sent. Like, is this Copy approved. And it was, everyone was just like, ignore. And I'm like, but like is it approved? Like it's gonna go out? Like like many, many people see this page every day. I like looked at the analytics. Does anybody else wanna look? And everyone's just like, could you just like, did you, were you thoughtful about what you did? And I was like, yeah, trust you? Yeah. But I like that was hard to deal with. Honestly, like after being brought up in this other kind of.

[Jackson]

Yes. You say dependencies kill productivity.

[Bri Wolfson]

Yes. Yeah. And I just, I could not get out of my own way. I was just like left and right. Like I could have walked up to anybody sitting at their desk and be like, will you approve this copy please? But like I could have and I should have just gotten it out. But I like, I think this is a new way of thinking at work.

[Jackson]

On the note of like different shapes of companies. I don't, can't remember if you actually worked with them, but you were, you referenced supercell somewhere and supercell is pretty unique. Maybe like Valve would be kind of similar but they're known for having this. Like, maybe Amazon would be a closer tech comp of like not as like super top down, way more like there are these cells and like those cells do whatever they want and they produce cool stuff, they produce games, whatever. Maybe it's a. Something kind of unique to game reading or thinking about that. I was thinking of cursor and I was thinking about my conversation with Rio and like the way he works like back to the IC is the atomic thing. Like are we actually going to live in this world where like you have like Rio is a cell on his. All on his own and he just like decides to do stuff and then like reports back.

[Bri Wolfson]

Yeah. So here's my hang up with this setup. Like I actually, if we are going to be all about craft and like I'm like, okay, my thing is like the words.

[Jackson]

Yeah.

[Bri Wolfson]

And I actually, I don't try that hard on design. I really like partnering with designers, but it's just like not my thing.

[Jackson]

Yeah.

[Bri Wolfson]

My hang up about this world where all the ICs do all the craft work is that we're never gonna have the like overlap moment where I'm like, okay. And I had this a lot on straight press. It was like, okay, these are the words on the page. But like how should the page look and how should the book render? And like that collaboration is actually.

[Jackson]

We have the Avengers for making an awesome book.

[Bri Wolfson]

Yes. So I think in this world where everyone does things alone. You sort of like miss out on the. I think the novelty comes from like Venn diagram overlaps of like people, two high crafts people or like a few coming up with something truly innovative together. So I, I worry in this world of like I see only we sort of miss out on these moments of collaboration.

[Jackson]

I talked with Rio about this because on the other I think he's. And a lot of people are coming at the standpoint of like he's like a designer and he's like Google has visual designers and interaction designers and like everyone's like locked in their lane and like we should never publish some code. And so like you have that on one end obviously, which is I think a lot of. And now you have every designer being like, whoa, curse is pretty sick. What do you think the balance or how do you maybe. Maybe a more specific question like how are you trying to bring some more of that? Are you. What do you think the balance is to still get the amazing. Like you have maybe generalists with specialist spikes or the fork spikes. And then there's still the overlap.

[Bri Wolfson]

I want to, I want to. I'm working on a really fun project right now and the prompt was like sort of as you do. It was like you write the, you write the script and the prose and then like baton pass it to design and like they'll do their thing with it. And I was like, no, I don't want to. I want to work with design because I don't like copy on the page. Can look a particular supply chain either. Yeah, yeah. And a very design oriented and vibey company. They got that right away and they were like sick happy to play this way. Both hands on the baton the whole way through. It's so good. I'm like, I'm so proud of what's going to come out on this. And to me that was like true words visuals, collaboration. And I think it would have been hard to pull off without that true holding hands the whole time mindset.

[Jackson]

This is like, I mean the first place my mind goes. And I know you at least at the time had written extensively about the way that Covid and remote work was shaping things. Like it's sort of like you're making an album and it's like the guitar

[Bri Wolfson]

guys, the guitar sends you Remember Postal Service? Remember that band? And they, they literally did that.

[Jackson]

But I'm sure there are so many examples. Yeah, it's really easy to be like, let's all get around the table.

[Bri Wolfson]

Yeah.

[Jackson]

And look and mix things around like,

[Bri Wolfson]

oh, I Went down there for our design work, I was gonna say, because I. 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. I lament that I'm not.

[Jackson]

Lack of proximity requires everything to be intentional.

[Bri Wolfson]

Yeah.

[Jackson]

And intentionality is great, but it doesn't allow for the.

[Bri Wolfson]

Yeah, totally. It's so funny. I was just with a friend who's starting a new job. This is her first, like, AI native company, too. And she was saying if I ask someone if they'll schedule a meeting, they ignore me, and if I walk over to their desk and interrupt them, we'll have the meeting. And she's like, I don't get it. Yeah, but this is just the new way. This is the new way. Like, it's just fluid.

[Jackson]

Can fully remote companies actually be that creative?

[Bri Wolfson]

I'm sure. I'm sure.

[Jackson]

I mean, are you sure?

[Bri Wolfson]

I don't know. I.

[Jackson]

Have you ever been truly, deeply creative in this way? We're talking about this collaborative way, and maybe it's a spectrum, but, like, it's

[Bri Wolfson]

too hard to say if, like, the output would be better. I don't have the counterfactual. I just know how I feel doing the creative work, not through a screen. And for me, that's different. I don't. But, like, I'm extroverted and I like people and I have a big family and I grew up playing sports teams. Like, I don't know, maybe I'm just a particular way because I was shaped by a particular set of experiences, but that's just my feeling.

[Jackson]

Yeah, the cap cut kids.

[Bri Wolfson]

Yeah, exactly. Exactly. They have a different way of being. I don't know. You know, it's funny, I was thinking about, as you were saying all this, one of my pet peeve phrases at work is someone's like, I'm not a marketer, but I'm not a designer. But that's like the thing you say when you're trying to intrude on somebody's work. Like, I'm not a designer, but I'm going to tell you my design opinion. And I just. I hate that phrase. I hate that tee up. I hate that whole thing. And I think, like, Rio has really shaped my thinking on this. Like, just don't do that.

[Jackson]

I was going to say, what would you suggest instead?

[Bri Wolfson]

Just to be like, I have a design idea. This is how the design is hitting me, or something. Like a phrase I use a lot when I'm editing is like, this hits my ear funny. That is what I mean.

[Jackson]

I suspect these type of companies that you tend to work at, one of the things that built. Taking. Building the organism in the culture really seriously empowers and obviously the talent bar and all these things is like a baseline level of trust that's like, not like this dude from marketing is giving me product feedback, but instead, like, everyone here is awesome.

[Bri Wolfson]

Yes. Yeah. Trust is one word. Like, I'm not going to walk into a room with Wilson Minor and like, give him my design thoughts. I'm gonna, like, stay in my lane and kind of see what he does and then we can, like, play together.

[Jackson]

Yeah.

[Bri Wolfson]

So trust is like one more. But I'm more like, in awe of others. Like, I want their work to flourish. Like, same thing on this Vercel project. These designers are like, spectacular. They, like, produce beautiful stuff. I want them to come to the table with their part. Yeah. And I don't want to do. I'm not a designer, but. But I want to do like, ooh, what if.

[Jackson]

Yeah, yeah. Ooh, what if Is. Is. Is awesome energy on this. Still on this note, a little bit like, as far as I understand, Cursor has like no meetings. And I. I assume that's like, it's probably a pointing at something. Generally shifting of this sort of IC type thing. Like, how do you think? Like the. The back to this hard part. Like the skeleton scaffolding part. Like, how do you think infrastructure around stuff like management planning, established systems meetings. Like, clearly it's in flux. Or at least like, are we at risk of Chesterton fencing it where we're just like, actually, Cursor probably should have. Cursor's gonna need to have some meetings.

[Bri Wolfson]

Like how Cursor having no meetings is like extreme exaggeration. There are certainly.

[Jackson]

Rio told me he has one meeting a week, which maybe is a Rio thing, but

[Bri Wolfson]

Yeah, I guess another company truism that everybody's having their own experience of the company. That's probably true for Rio and he should have a lot of time for deep.

[Jackson]

Yeah, yeah, yeah, yeah, yeah. It depends on the person work.

[Bri Wolfson]

I don't know. I don't know. I think what almost certainly will be true is fewer people in the meetings.

[Jackson]

Yeah.

[Bri Wolfson]

Which helps. Yeah. Especially on zoom and like some of the drudgery of corporate life. Like these round the horn updates and like all that stuff. I think that's a little bit easier to go away.

[Jackson]

Yeah.

[Bri Wolfson]

There's more automation around that stuff. Like the rote stuff. Although I say that and then like a friend just joined a company in what I think people would call, like a quote, meta role. There was like, a lot of skepticism about, like, project management. Why do we need a whole role for that? And she's adding a ton of value.

[Jackson]

Yeah.

[Bri Wolfson]

Just by, like, organizing the chaos. So I don't know. I'm like, I genuinely am excited to see, like, what the new shape of company will be. I do think it's changing and I, like, I want to be a part of that.

[Jackson]

It's probably why you have two jobs.

[Bri Wolfson]

Yeah. But I do feel like an anthropologist in this way. Like, I. I feel I have studied company culture in the. In like the old way, and now I'm gonna.

[Jackson]

Old and. Yeah, yeah, old. Old. Phil's a little silly, but old on a relative basis. Yes.

[Bri Wolfson]

Yeah. I've been like a friend turned me onto this idea. Like, if you are interviewing with a young founder or a young company, you should ask the executive, like, who their mentors are. I thought that was a really good question. And then I was thinking, like, who would. Who will the CEOs of this generation be mentored by? I wonder if there's new rules. And it actually might not be that productive to be mentored by the previous generation.

[Jackson]

Some things change a lot and some things don't change.

[Bri Wolfson]

True, true. But I wonder if that, like a friend is. Another friend is thinking about a role, a leadership role, and she, I think reasonably wants to know who the other leaders she'll be surrounded with are. And this new company, young people leading it are like, it doesn't matter. And she's like, I know that it matters.

[Jackson]

Yeah. And they're just like, respectfully, you're wrong.

[Bri Wolfson]

Yeah. But I, like, I. To me, it's very refreshing and exciting that they still have that optimism about that. If they didn't believe that that was true, it would surely be not true. They would surely be tolerant of the politics and these weird dynamics. If they didn't believe that it had to. If they believe that it had to be the case that companies get political. They probably just are like, okay, so anyway, I was thinking that maybe there's some path dependence to believing you can run a apolitical org or whatever

[Jackson]

you. A tweet. Fairly recently you referenced the Billie Eilish Vanity Fair video.

[Bri Wolfson]

Oh my God, I love that video.

[Jackson]

Specifically, you said about how the speed of company building in the AI era. You're the first person to make that connection, lol. Which is amazing. I think they're on the eighth One of those for if people want to go watch. It's like, starts when she's 15. And maybe what's so telling about that video is she's gone from 15 to 16 and you're like, you're staring up the slope of compounding. It's like she has goes from 200,000 followers to 600 or 6 million. I guess there's a broad point here. And then also maybe more specifically like on the infrastructure part. Like, you helped spin up Stripe's planning function. Like, is planning a thing in this world? Like, your point about Billy is like, everything feels like it's like this one year is infinite amount of time. Nothing is the same. Like, it's pure. Oh, my gosh, I was so naive.

[Bri Wolfson]

Like, I'm not sure. I think it would be nice if companies could be more iterative. And I think if you can move faster, you can trust that approach more versus, like, we need to like, take these big bets and it's a big chunk and it's going to take three months of work and all this coordination, Like, I think if you have less coordination, faster to do things like maybe planning or like, at least on long time horizons becomes like a little more obsolete. But one function I think it does play is like, for these bigger swings that you really want to invest in. Yeah. How do you. Yeah. How do you make sure that the company's carving out time to do that? I think, right.

[Jackson]

Urgent, but not. Not urgent, but important.

[Bri Wolfson]

Yeah. Or even if, like, even just exploratory, I think it'd be really easy to get lost in like, little feature wars. And. Yeah. So I think it takes some intention. So that's one thing I think planning can do that will, like, companies won't outgrow. And the other thing is maybe like holding a mirror so that it's like you're kind of shifting inertia in some ways. So, like, one thing that Cursor is thinking about a lot right now is they're certainly their own best user as a startup developer. They're not their own best user as a enterprise developer. So could planning help us? Okay, how are enterprises different than us? What might we want to do to support that kind of work that doesn't come naturally, doesn't spring.

[Jackson]

Almost like a reference point when you're like. It's like, I don't know, a plot of land when you're out on a boat or something. It's like if there's no land anywhere, it's like, whoa.

[Bri Wolfson]

Yeah. But like, I mean, it was not like an accepted concept to work on planning at Stripe, like that was, it was like a risky project because it felt kind of off the culture at the time.

[Jackson]

Well, this kind of goes back to what I was saying, which is like, I think that some things don't change.

[Bri Wolfson]

Yeah.

[Jackson]

And like Stripe and now Cursor, like these companies, they're doing this is why I was laughing at you saying it's like the old way. Like Stripe's still one of the most like innovative companies in the world. And so like maybe it turns out like on a long enough time horizon, people realize like some long term planning is really good.

[Bri Wolfson]

It's funny, I think I still remember Patrick's email to the company when we rolled out planning and it was something like, we're evolving beyond the Rube Goldberg machine of spreadsheets. And that is how it felt at that time. Like a Rube Goldberg machine. Cursor does not feel like a Rube Goldberg machine. It feels like a multi armed something else Hydra or something. So I think that's what I mean by old way. Like it was going slower. Like you're like watching the marble slide down the thing. Cursor doesn't feel like that.

[Jackson]

You have a line where you say if you believe, like I do that what we build is a function of how it feels to build it. How does scaling, how do you scale how it feels to build it?

[Bri Wolfson]

I'm not sure, but maybe these more like nuclear little collaborative pods. Like I think a really cool thing could be that your quote team, and maybe this is more like the supercell way. Your quote team is actually like a very diverse set of people. My team is not a bunch of other marketers.

[Jackson]

Yeah, it's the Avengers.

[Bri Wolfson]

Yeah, that feels really fun.

[Jackson]

I like that. To me on the soft stuff, on the culture stuff, I think one of your big ideas is that you have to get 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, like what do good companies values look like and how are they different from individual values?

[Bri Wolfson]

Yeah, I think values seem like something you would actually say or some way you would actually behave. It's my. I keep a doc of all values I've ever encountered from any company. And I was just taking a spin through it the other day and I was like, wow, a lot of these suck.

[Jackson]

Why did they suck?

[Bri Wolfson]

They're just boring. They're so ick like, but ick because

[Jackson]

they don't mean anything. Ick. Because they're not honest. Ick. Because they're generic.

[Bri Wolfson]

Yeah, any. Any one of those things. Like, one of the most commonly cited values at stripe was we haven't won yet. And that was like, the humility.

[Jackson]

Yeah.

[Bri Wolfson]

One, but we were winning. So it was like this, like, cheeky, funny thing. You would say be like, I, we haven't won yet, but I closed this massive asset.

[Jackson]

We've won like eight championships in a row.

[Bri Wolfson]

And it was like the way to say, we're still humble, but now I will brag to you about this thing. And then I was like, wait, that actually kind of did make us more humble because nobody bragged about anything without saying first. Okay, I know I'm bragging, but it

[Jackson]

was a filtration system or something.

[Bri Wolfson]

Yeah. And it sort of makes you think, like, am I bragging? Because if I am going to brag, I got to say this other thing first to, like, be on the vibe. And I just. I wonder what the culture might have been like if you didn't have to say that thing first and instead you just got to, like, brag and thump your chest or something.

[Jackson]

Yeah.

[Bri Wolfson]

So anyway, I think that was like, a good value, even though we made fun of it a lot.

[Jackson]

You have. You. You talk all about, like, the stuff that companies do for the audience of themselves and like, what a beautiful kind of definition of culture. How does that. And there's obviously so many machinations inside of, like, what that means, but, like, how does that incrementally actually produce the desired output of culture?

[Bri Wolfson]

Yeah, I think, like the audience of it self. This is. I think this is a little bit what we were talking about, like, companies that want to be great companies themselves.

[Jackson]

Yeah.

[Bri Wolfson]

And I think one mechanism where this kind of thing becomes clear is like, all hands or like, internal comms. Like, how does the leader, like, address the company? To me, I think it's like a privilege to see our colleagues work. And I think it could be really easy to dismiss all hands. Like, it's like meta work. Like, if we're going to ship, it should be for box to check. Yeah. And I think a really good all hands is amazing because there's. There is some stuff that you can say to your colleagues that you can't say to the outside world yet, maybe. And so, like, it's a privilege to have the inside scoop or to, like, understand something more about, like, someone's sense of humor or, like, how might they design their slides?

[Jackson]

Or it sort of be like, why does the sports team have to do the pre game meeting or something like. Yeah, yeah. We treat some of that stuff as rote in a way that I think if the context were different might be perceived as more foundational.

[Bri Wolfson]

My friend who's like a really talented lawyer and we played soccer together in college, she always is like, I like the bus and I like the locker room. Like, that's her thing. And she was extremely talented.

[Jackson]

But by the way, that's what we all remember.

[Bri Wolfson]

Yes.

[Jackson]

You know, probably don't remember that many of the goals you scored.

[Bri Wolfson]

Yes. So I like, I think I'm also like a locker room girly and I do think that impacts like how the work gets out into the world. And I think in general also, people sort of underestimate brand and marketing. Just like what your employees say when they're like, to their spouse or when they're out for dinner with their friends or like when they're talking to their random uncle. Like, I actually think brand and marketing, like moves a lot through those channels and they are under invested in.

[Jackson]

Oh, man. Especially in a place like San Francisco.

[Bri Wolfson]

For sure. Like, for sure.

[Jackson]

That's the true pulse of the company.

[Bri Wolfson]

Totally just at cursor last week, like one of the, A newer leader on the team, he like had the company in stitches, like, laughing about whatever, something silly. I know people were talking about that when they went home and like, it was totally off brand. Like, cursor's a little bit more serious and it was like a really silly moment and I think it was really memorable and I think it made people have like a really good 15 minutes.

[Jackson]

What is the line between lore or mythology and nostalgia?

[Bri Wolfson]

Oh, man. Strain was kind of like anti nostalgia.

[Jackson]

Are you anti nostalgia?

[Bri Wolfson]

No.

[Jackson]

Okay.

[Bri Wolfson]

I'm like, my friend say I'm like, ghost of Christmas pass. It's actually fun. Another friend was texting me this morning, like they're getting their new office set up and he's like, it's chaos. Like, all the furniture is in pieces. And I'm just like, remember this part. Yeah. In five years they're going to talk about this on the podcast. I. I know it, but I think these are like maybe core memory type things like these. And often I think they're like, not even fully true, but they just like, they're never true.

[Jackson]

Yeah, they know stories are fully true.

[Bri Wolfson]

They like cement a feeling or like they help you make a feeling legible or like how you got this way. So I think the mythology is important. I also think now that we're adding so many people so quickly to these Companies, they're growing so fast, you want to, like, bring people along with the story of the company.

[Jackson]

But to me, that's lore.

[Bri Wolfson]

Yes.

[Jackson]

Or mythology, which is maybe I'm driving, like, a false dichotomy. But nostalgia is like. I think you're right. And a lot of people are like, nostalgia feels good when you're the person who's there. It doesn't feel as good. Maybe the better question is, like, what is the role for nostalgia?

[Bri Wolfson]

In particular, I don't feel that connected to people who wish they were at a different time or place. Like, you can always tell you when someone's telling a story and they're like, I wish it was still like that.

[Jackson]

The good old days.

[Bri Wolfson]

Yeah. Yeah. And maybe that's a little bit what nostalgia is. Like. I don't think this guy will be like, wish he was still at the phase where they were like. Like furniture was in.

[Jackson]

But those moments were great.

[Bri Wolfson]

Yeah. And I feel like you can always tell when you're talking to someone and they're just like, it used to be another way. And I want to be in that way. And you're just like, catch up. Join us in the future, please.

[Jackson]

We talked a little bit about, like, this Tolstoy thing. And like, great companies are no way to know. But, like, is your instinct that all great cultures are, like, truly original in the, like, Snowflake, Snowflake sense? Or are they like, permutations or remixes or even something more like an Enneagram or a Myers Briggs where there's like. Yeah, a dozen or so flavors?

[Bri Wolfson]

You know, I'm. I think I'm evolving out of this theory, but one that I used to consider is that, like, great companies are extensions of their leaders.

[Jackson]

Yeah.

[Bri Wolfson]

I think I might be evolving out of this idea with this, like, collection of ICs thing that's happening. Like, surely every page on the web Stripes website is an extension of Patrick and John. Like, based on what I told you about how the Cursor website got out, like, not so much an extension of the leaders,

[Jackson]

but, like, one could say that's like, less finger feel.

[Bri Wolfson]

Yeah.

[Jackson]

But one could also say it's actually like an enlightened view from Michael.

[Bri Wolfson]

Yeah, I think so. Or like, maybe you can say it's just a little more indirect because he's so prescriptive about who gets hired and he trusts them so much that it is an extension of him because he picks. He's hired, who does the work, who gets on the landing page. I don't know, but I. I think They're. I think they're probably all singular. Any company greater? I don't know. I try not to say, like, good or bad. They're just, like, their own way, I guess.

[Jackson]

On the note of varieties, you. This ties to some of what we were talking about earlier, which is you've said stripe is very much a thinking culture.

[Bri Wolfson]

Yeah.

[Jackson]

As we've clearly exemplified by some of these examples, Cursor seems more like a doing culture. Have you slid one way?

[Bri Wolfson]

Oh, yeah. I'm like a chronic overthinker. This is why I was a good fit first. Right. Like, I love a doc. I love thinking through all the different outcomes. That feels. That's very natural to me. I do that in my personal life. I'm working on becoming more doing oriented, especially now that it's, like, a little bit easier with stuff like.

[Jackson]

Yeah.

[Bri Wolfson]

This week I'm working on Cursor's first, like, company Pulse survey, and we're like, let's build it in cursor. And I'm like, okay, who's going to help me build it in cursor? Just like, well, can't you build it in cursor? And I'm still working on that. Like, you know, I wrote the doc that was like, these are the questions, and this is the vibe. And, like, this is the. And it was like, wait, I could just put this in cursor. So anyway, I'm still working on updating my own thinking on that. I have a feeling I will find this satisfying, like, once I get over the hump. But I'm, like, still writing briefs over here.

[Jackson]

We all have different kinds of humps. Like, it's not a perfect example, but I'm sure there are people who, if they have to write something, are, like, I'm addicted into ChatGPT, or, like, I'm gonna try to get somebody's help. And, like, you have a. You have the finger feel for that, right? Like, this is new. You have. You don't have the finger feel. It's like, I don't know. I'm doing video podcasts. Like, how do I do anything? I don't. I can't do it. I can't do it. And then you weighed in.

[Bri Wolfson]

I think that, like, the finger feel thing or, like, the way doing will help is you still have to start at the end, though. You kind of have to know. This is why I think Rio is so good at what he does. He, like, he has a loose conception of what the thing at the end is, and he can, like, poke and prod the clay the right way to like get close to that thing. I think if you go into the project not like having any idea of where it's going to end up, you just like get lost in a ChatGPT chat infinite forever. And you. I can't like, the work becomes the act shave of talking to ChatGPT. You're like, not really moving towards an end. So anyway, for me, like, the brief sort of helps with that process of like getting to the end of the thing.

[Jackson]

There's a little bit from Kari, from Linear that reminded me of something that I spoke about with Cursor and I was with Rio and I was curious to get your opinion. Kari says, before pmf, hiring a lot of people or working, working super hard might not actually work that well. To get to pmf, I think you need reflection and clarity. What I see is that companies are trying to imitate success. Successful companies are busy, therefore I should be busy. Successful companies hire fast, therefore I should hire fast. They get the causation and correlation wrong. But what you really need is to get the product right. And he's kind of pointing at the996 type stuff. Do you think startups are. And granted, I think you've spent less time at super early stage startups, but you may have worked with some. Like, are startups overweighted to sort of mimicking the aesthetics of the grindset thing rather than. One of the things Rio spoke to me about is like he has two sort of modes. He's like shaping the clay in cursor and like, I'm gonna go for a walk.

[Bri Wolfson]

Yeah.

[Jackson]

Like there's not like that yin yang and obviously it's different at a company level. But I'm. I'm curious or maybe just any reflections probably on the whole workaholic kind of aesthetic thing?

[Bri Wolfson]

I'm not sure. I'm not sure. I. Something I'm noticing in myself and in other people is it's really hard to sit still right now. It's really hard to sit still. It's really hard not to be reading or thinking or consuming or tweeting or whatever. It's way harder to not because you

[Jackson]

feel like you're losing ground, maybe, or

[Bri Wolfson]

there's just infinite things or whatever amount of time you have, there's something in that unit of time that can fill that. Like if you've got like one puzzle piece of a whole of time in your day, there's like a TikTok reel or a tweet or a blog post

[Jackson]

or like whatever the airpods in on the walk. Yeah.

[Bri Wolfson]

That is a part of, like, hustle culture. I feel the most, like, I'm always like, behind on reading or I, like, didn't see the latest or to me, like, that's the hustle culture feeling to me is I'm not up on it.

[Jackson]

Yeah.

[Bri Wolfson]

Or something. Or. Yeah. Like, I definitely notice a lot of people who are just, like, kind of saying stuff in Slack. I don't really know why, but I think it's kind of like receipts, like at my desk kind of behavior and like, same thing. I like, so many Slack messages are edited. Like, people send them and then they tweak them after, like, that kind of. This is where I notice this, like, constant doing, doing, doing, doing.

[Jackson]

And it's aesthetic a little bit.

[Bri Wolfson]

Yeah. So I definitely am noticing a lot of versions of that. And then it's hard to sit still. And again, like, in many ways, I just feel like I'm benefit of timing. Like. Yeah. I lived and worked in a world where this didn't exist. Like, my first jobs didn't have Slack. Like, I think we use like, hipchat or gchat. So I've lived and worked before this. So I had the chance to build some habits around stillness that I still rely on. But because I know that they work for me, I think it'd be harder to train yourself up that, like, stillness or going for walks works.

[Jackson]

But I know it works, and it's still. I still forget. All right. It's just like, easier to be at fidgety.

[Bri Wolfson]

Yeah. For sure.

[Jackson]

One of the things that stood out to me, you talk about funding culture specifically. You have to literally and actively fund a great culture. Steve Jobs funded the last 1%. It can never be the best version unless you fund it. Find a boss or a place that will fund the last 20%.

[Bri Wolfson]

Yeah.

[Jackson]

Maybe it's a false question, but, like, do you think companies don't fund culture because they don't know how or because they don't want to sacrifice the capital and time for it?

[Bri Wolfson]

Yeah. Yeah. It's the audience of yourself thing. It's like whether you value that audience or not.

[Jackson]

Yeah.

[Bri Wolfson]

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

[Jackson]

Can you say a little bit more about that?

[Bri Wolfson]

Yeah. So one feature at Cursor and a lot of other friends who are at more AI native startups now, the first thing you do is shipped to the internal version and see if your colleagues are into it. And

[Jackson]

it's like a test flight for the whole company.

[Bri Wolfson]

Yes. And like old world versions of this are like you sort of like talk about your intentions and planning or you write the doc or you give the all hands presentation about what you're gonna 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 react GS they get.

[Jackson]

That might be really good at a place like Cursor and really bad elsewhere, which is important. Maybe I would guess that Slack was using an internal version of Slack.

[Bri Wolfson]

Yeah, sure, sure.

[Jackson]

I wonder how that will evolve. Yeah, I wonder how much of it is just a product of building like a specific type of tool that you yourself use versus something more meta.

[Bri Wolfson]

But now think about it, not for just product stuff. So maybe, okay, like a new enterprise engineering team is like emerging in cursor. It's like a little bit as we talked about before that's like different than the. So a huge part of this team's job is to get people pumped about enterprise and they have to like explain why it's cool.

[Jackson]

That's probably try to find a way to live it a little bit too.

[Bri Wolfson]

And like in a bottoms up culture where people mostly decide what they work on without some tops down planning process, they're gonna have to convince the average engineer to like work on the enterprise product to unblock the da da, da. And that's like all internal marketing work. And I, I think one way you can think about that is like negatively. Like people have to do these like internal press tours to get their work done. And one way you can think about it is positively because you're like building more cohesion.

[Jackson]

Yes. Like selling vision.

[Bri Wolfson]

Yeah. And you're like, you're excited about each other's work that you yourself can't do alone. So anyway, that's the version I'm excited for that's like, yeah, taking care of the internal audience.

[Jackson]

I think it might be a little related. I want to talk a little bit about leadership and great organization of a whole and cultures. You retweeted Nabil, former friend of the Pod, former guest Nabil Qureshi had tweeted Napoleon's observation on war that morale is 75% of winning is one of the most important lessons for startup CEOs. Morale should be understood broadly here. It's something like a sense of destiny.

[Bri Wolfson]

Yeah.

[Jackson]

Maybe speaking of even just selling things Internally with. With. With your team. What is morale and where does it come from?

[Bri Wolfson]

I. Yeah, the word I would use maybe instead is just having fun. I think Devin, like sent me this tweet recently that was like, you can compete with somebody having fun in all caps. And I think that that's true. For some reason, when I think of morale, I think of a little bit. Like, you wouldn't otherwise be excited, but I'm like, giving it. I'm creating some morale where.

[Jackson]

Above the baseline.

[Bri Wolfson]

Yeah. And just genuine enthusiasm is. Yeah. And I think you can manufacture it. I think you can manufacture it. Maybe this comes from my background doing sports, but. So anyway, that's the thing I think is just like getting people pumped to do the thing. Like, I'm just thinking of this enterprise guy again and he's just like gonna have to get someone pumped to like make a change. That's gonna like be a huge deal for Nvidia and he's gonna have to like, tell that story and convince somebody else that that is sick and fun and awesome and rocks and like, if he can successfully do that, like, that work will go better. Then like, it came down from this top down planning process and you're gonna like, check off your whatever.

[Jackson]

The other part of that tweet I have to observe is a sense of destiny.

[Bri Wolfson]

Yes.

[Jackson]

Interestingly though, it actually seems that, like, you think about and are. Are sort of drawn to both of those things. Maybe we might talk about like greatness a little bit later, but like, you are both very clearly having fun and very interested in having fun. And also not just like, fun is the only point. Only vibes, like, actually we're trying to like. And when I think of morale, it's actually both of those things smash together, which don't necessarily always go together.

[Bri Wolfson]

One of my earliest memories in childhood is playing soccer. I remember our team was the orange team. And for some, I think I was probably in kindergarten. And for some reason the coach was like, okay, girls, do we love to win or hate to lose? And every single person said, love to win. And I said hate to lose. That was. That's one of my earliest memories. And I was like, I'm so different than everybody else. So I'm like, I'm inherently like very competitive. I hate to lose. I also love to win. So, like, that environment is fun.

[Jackson]

Yeah.

[Bri Wolfson]

To me, again, maybe I'm just lucky because I'm wired this, but by the

[Jackson]

way, I should know, like, most hate to lose. People don't have that much fun.

[Bri Wolfson]

Yeah. Yeah. But I'M just wired. I'm just wired this way. Like, again, locker room stuff.

[Jackson]

We talked a bit about them a bit earlier, but, like, you've worked with a bunch of amazing leaders. The Collisons, Claire Hughes Johnson at Stripe as well, Dylan Field, Patrick Michael now, and other folks at Cursor, Patrick o'. Shaughnessy. What about people like this makes someone like, you want to magnify them and the cultures they build?

[Bri Wolfson]

Oh, man, I've gotten so much more out of those relationships than you described and they got out of their relationship with me. I think, like, ultimately the reason I wanted to do great work for these people is, like, they funded me doing great work. Like, my story at Stripe was I was just like a person on the account management team. And then someone I think it was, I forget if it was Claire or Patrick, had sort of like, plucked me up and was like, you're gonna work on this weird project to, like, integrate this team that we acquired and that sort of like, set me up to, like, do my first leadership facing work and do my first, like, weird off the org chart project.

[Jackson]

You broke off the dependency tree or whatever.

[Bri Wolfson]

Yeah. And I feel indebted to them forever for just, like, I don't know, seeing me in a sea of. It wasn't that many people at the time, but anyway, I just, like, felt seen in that work and I was like, wow, I have, like, a new chance to, like, do something awesome. I, like, really want to, but okay,

[Jackson]

let's take away the Stripe people.

[Bri Wolfson]

Yeah.

[Jackson]

You've also, like. Yeah. I'm sure you've gotten an amazing amount from all these people you've worked with since, but you're all like, they're hiring you for a reason.

[Bri Wolfson]

Yeah. Why are they hiring me? I think they probably feel that I see something in them too. And, like, I respect and admire them. Like, kind of what we were saying before about how I think of my job as a marketer to sort of close the gap between, like, what is and what's true and, like, what the world knows about someone is like, I believe there's more in them.

[Jackson]

Like, that's actually. That was my real question, which is I have a sense of why they're choosing to work with you. I'm curious why you're choosing them. And I think it's that you're seeing this. That's what my original question was. Like, this magnification desire is like, there's something here that can be amplified.

[Bri Wolfson]

Yes, I want to. I want. I. All those people that you just described, I think are incredible human beings. I, like, think more of their stuff out in the world is better for the world, and I want to help them do that. That's genuine in me. Patrick o' Shaughnessy calls it the skinny mirror, which I love, where he's like, you hold a mirror up to someone, but it's, like, always the one that makes them, like, look really good when they're doing their fit check. I think my natural view of. And I admire someone. And I will only work for people that I admire my natural lens on as skinny mirror. So everything they say, I'm like, like, how do we make that sound awesome? And, like, let other people know. And, like, you should write about that. And, like, let's talk about that more and, like, say that a different way so more people get it. Like, that is an instinct within me. I want to, like, refract these great.

[Jackson]

Yes.

[Bri Wolfson]

People out, and I want more people to benefit. What I benefit from them is just like, being inspired or being excited or being moved to act or think or whatever.

[Jackson]

Yeah, there's. I was listening to the only time I've ever listened to him, Dax Shepard, who has this podcast, and he was interviewing Adam Grant, the psychologist. And Adam's observation of Dak was that he's like, you have inverse charisma. That's why you're such a good podcast host, is you make other people charismatic.

[Bri Wolfson]

That's funny.

[Jackson]

I'm like, what an amazing trait. And it's like, not exactly the same thing, but it's a similar.

[Bri Wolfson]

Yeah, I think all these people, again, they're doing great on their own. They're perfectly charming and wise and thoughtful. And I just like. My infinite energy is to, like how people, like, say more awesome stuff. So, like, yeah, if any of them say something to me in, like, a private room, I'm like, let's write a blog post about it. Like, I think that's really interesting. Like, I think we should, like, let more people in on this thing that, like, I got private access to. So anyway, I think that's, like, always my lens on stuff. Refract great people out.

[Jackson]

One last thing on this. You were writing in the COVID era about the sort of lack of momentum that can show up in work. You say, but I do think work can be a source of real meaning in life. But we'll only ever get out what we put in. And in the case of work life, it's kind of a collective decision. Once your neighbor starts signing off of Slack at 3:30 consistently, it's hard not to do the same. If your closest collaborators don't turn stuff around quickly, why would you? A separate place, you said a few months ago, someone complained to me that the new very hot stuff startup they were at had an LGTM culture or a looks good to me culture. He looked down at his coffee for a moment. Quote, I'm afraid I'm never 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 or whatever it might be. Yeah. What is it? Like, a very kind of basic or foundational. What is it about these groups that moves you so much?

[Bri Wolfson]

Do you feel like you've ever been excellent at anything? Like, a taste of it?

[Jackson]

I think I bounced off it.

[Bri Wolfson]

It's also, like, quite elusive.

[Jackson]

Yeah.

[Bri Wolfson]

To me, but even being close to that son is, like, very. It's like, electrifying. And I'm not good at generating that on my own. Like, it takes sort of like the gaze of someone else. Like, I always would play better when I knew my coach was like daggers on me. Like, I wouldn't want to go for the ball. I was, like, too lazy to make the run. And if I felt her presence, I'd be like, okay, I better get my ass in gear year. So I'm motivated by that kind of loving attention. I think like someone who wants me to succeed. So anyway, I think these environments where people are like, I have a loving gaze on your work. I think this could be better. It would be impossible for me to generate that push on my own. I think this surprised a lot of people when I say it. Still, when I write, I imagine Patrick reading my stuff, Carlson, and like, I wonder what he's gonna think of it still. Like, I have not been in a room with him in almost a decade. And, like, here I am still, like, I crave his, like, loving attention on my stuff. I wonder what he will think of my work. And I think this is like, to me, that is like a core motivator is, like, people. I admire their gaze on my stuff, like, imagining how they'll tune it better. And I think, like, being in groups of people who will give each other that kind of loving attention is, like, amazing. Like how, like, all these people I sent the draft of the careers page to who are, like, wording's not quite it. That, like, that was so motivating to me. Like, I wanted to work it until it was perfect for them. So it just means a lot.

[Jackson]

You use the. You use that phrase loving attention several times, but the first time you used it, I thought I first heard, like, loving space attention. And what a profound.

[Bri Wolfson]

Yes.

[Jackson]

Inverse. It's loving attention. It's both attention is, of course. But I think my recognition from you is there are people who love attention, but what you are seeking is this very specific kind of attention.

[Bri Wolfson]

Yeah. I want someone who feels invested in making my stuff better. And I think that's. To me, that's what's so damning about lgtm. It was, like, skimmed. It seems fine. Like, reliably. When I post something on the Internet, Stripes will DM me a typo, and I'm like, I love these people. Like, they actually read it. That's how I know I'm like, those type of their Easter eggs for you.

[Jackson]

But, like, when a lot of people see the typo, I'm not gonna bug them.

[Bri Wolfson]

Yes.

[Jackson]

Looks good to me.

[Bri Wolfson]

Yes. So anyway, I just like. I like that kind of. Yeah, this. I think this is related to the funding thing. It's like, I'm gonna take time to tell this person it has a typo or, like, I didn't love this turn of phrase. And, like, I love that. I love it.

[Jackson]

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

[Bri Wolfson]

I don't think that works for everyone, but it worked for me because I got to do stuff that where no one would say no because nobody. A lot of people just didn't care. But I know a lot of people who just, like, did the ladder, and it was great for.

[Jackson]

But you also pick things up in the crannies and mean people care about the crannies.

[Bri Wolfson]

That's true. That's true. Yeah. I do think I've had, like, a particular nose for the type of problems in the crannies, I think you don't want to be an obscurity.

[Jackson]

You have a nose going back to something we talked about earlier. You have a nose for things that are not currently important but will someday be important.

[Bri Wolfson]

Yeah, yeah.

[Jackson]

Or could be made to be.

[Bri Wolfson]

Yeah. I think I have a particular temperament for that because I, like, zero to one, to me, that's, like, the most fun phase. And often, if too many people are too many cooks in the kitchen, they're like, right, right. It can't really flourish. Um, and I also have, like, a. I'm also totally fine giving away my Legos. Not everybody is. I'm, like, happy to pass my work on. So I think I have, like, a particular temperament for this kind of. That flavor of work. I think many more people want more sort of, like, structure, validation. Show me a goal, I'll, like, I'll hit it. And many people have great career paths that way, too, I think.

[Jackson]

You were talking to Perel. You said, it's hard to have a finger feel for things if you. I mean, it was packy. 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. Hard to have a lot of reps if you do many things.

[Bri Wolfson]

It's true.

[Jackson]

Again, revolving around a similar thing here. But given that conversation we had about craft, like, for the people who do relate to you and see Bri, and they're like, man, what an amazing opportunity would be to have that path. Like, with the benefit of hindsight, how do you. How do you. How do you square the finger feel so important. And also, I. You capture this so well in flounder mode.

[Bri Wolfson]

And.

[Jackson]

And yet I think it's still easy to sit there being like, if Kevin Kelly can do it, that's cool, but how am I going to develop skills?

[Bri Wolfson]

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. And that's the word people are using. Story. People want the story. Maybe it was probably six or seven years ago, I think it was when I was applying for Figma, I wrote this document to a company that was like, I want to be your head of story telling.

[Jackson]

You were early.

[Bri Wolfson]

Yeah. And they basically were like, that's cute. I'm like, no. And I was. I, like, felt very ashamed after that. I was like, oh, yeah, that's a fake word.

[Jackson]

That's like, I went to the big boy table and like. Or the adult table and they told me to go sit back.

[Bri Wolfson]

Yeah. And then I was like, oh, like, why did I do that? I don't think I could have gotten reps, enough reps on this thing to have it be a full time job. And now I actually do feel like I have the opportunity to do it. Like, I've basically had to do ups on the side so that I could do storytelling stuff.

[Jackson]

Sometimes this is the crannies.

[Bri Wolfson]

It's like, yeah, I think if I wasn't like a fantastic get shit done person, Stripe Press would have never landed on my plate. Like, I had to do all.

[Jackson]

Darn it.

[Bri Wolfson]

Yes, I had to do all. I had to be the person that could like, yeah, get us to print a fricking book and get it on Amazon and like all this stuff to like earn the right to just like tell stories about the authors. But I had to do 90% of that. The other work. Now I think I can just. Today I think there's like permission for Bree to spend full time just on the story stuff. But I think I generally had that self awareness that like I had to pay my dues with the ops stuff. Like there just wasn't enough company work in story.

[Jackson]

Right.

[Bri Wolfson]

But now I think there might be.

[Jackson]

Maybe a generalized lesson here is like, you're allowed to dabble if you like find enough ways to move bricks or whatever.

[Bri Wolfson]

Yeah, I'm preparing like a section on this in the book. I think operators underestimate this. Like the first question all managers are talking about when it's time to like pick up another job is like, how are they doing at the core role? Yeah, like, the reason I got to do that project I described at Stripe where I helped the acquired teams is because like my account management book was doing great. I like signed all my renewal. So I was like, sure, spring her onto this other thing. But like, you have to know why you're, why you're at the company.

[Jackson]

If you're 22, like, that advice isn't that helpful because you got to get in the door first. Like, do you have any broad thoughts on like the person who sort of feels like a generalist or like, it doesn't. They're not, they're not. Their craft isn't necessarily that obvious. They might have a craft full approach to things.

[Bri Wolfson]

I'm curious about like how this will. Yeah. How these careers will pan out soon. Like really common hiring advice, like if you just wanted horsepower was like, hire someone who's done A couple of years at McKinsey. I actually wonder if that meme is like, still around. Like, if we value these generalists. My sense is generalists now have to be able to produce output. Like, they should be able to like cursorify the company Pulse survey on their own. They shouldn't like need someone else's time to do something like that. So. Yeah.

[Jackson]

And that would be the version where the generalist is like, more valuable than ever.

[Bri Wolfson]

Yes. So I don't. I like, I think there's more expectation for people to be able to produce their own output. Whereas I think I spent the early part of my career being like glue for people who had like great ideas but like, couldn't really get them done.

[Jackson]

Yeah. On the output front, how important is. Especially pre having the job, you've been pretty public. You've been relatively public in the last relative period of time.

[Bri Wolfson]

Yeah.

[Jackson]

I don't know if you always were.

[Bri Wolfson]

Yeah.

[Jackson]

Like, I think the, if you're 23, like, the obvious thing is you got to get a Twitter following or whatever or like share your projects and go viral. Like, what's your advice on that part?

[Bri Wolfson]

I. I put out a call for the book. Like, if you have questions that you hope the book will answer, what are they?

[Jackson]

Yeah.

[Bri Wolfson]

And the question I get the most is, do I need to be Twitter famous?

[Jackson]

Yeah.

[Bri Wolfson]

No, you don't need to be.

[Jackson]

It doesn't hurt.

[Bri Wolfson]

It doesn't hurt. But you do not need to be Twitter famous, period. I think what people are, they're like sort of anti pattern matching. They only pattern match on the people who like, are Twitter famous.

[Jackson]

Yes. Well, it's the otherwise illegible. Your, your career broadly is illegible, but it's especially illegible if you don't even see the.

[Bri Wolfson]

Yes. Twitter. This is like the wrong way to describe it. I think it's really useful to publish your work. I think it's good to get it to completion. I think it's good to like put it on the Internet where other people can see it. Like, I think that have something to point to. Yes. And also like, just have. Were we. Who was. Were we talking about this the other day? Like, the reason you go on the book tour is because like the, the thinking has been codified. It's like a little bit about that. You have the book, but it's also like, okay, my like, ideas are baked.

[Jackson]

Yes.

[Bri Wolfson]

On this. I think it's pretty good to like, like share record of like, what. Yeah. What have you.

[Jackson]

Like, it's an artifact that. Yeah, yeah, yeah, yeah.

[Bri Wolfson]

I don't think that means you have to be, like, famous, but I think if someone goes clicking around about you, it's probably useful to.

[Jackson]

When it's also not necessarily, like, an endless stream of. Yeah, noise.

[Bri Wolfson]

Yeah. I. I think, like, you have gotten a lot out of, like, 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. I like mine. So, anyway, I get a lot out of being online, but I talk to a lot of founders that are like, ugh. Like, I have to, like, tweet every day. I'm like, just don't really bother.

[Jackson]

Yeah.

[Bri Wolfson]

If you don't want to. Yeah, don't do it. So, anyway, I think it is some people's, like, medium of expression

[Jackson]

on the fodder mode. Note a quote. I think somewhere along the way, the message about what it feels like to be great has become a bit perverted. Kevin says in that piece and everywhere that greatness is overrated. You seem to be chasing greatness. Still, can flounders be great?

[Bri Wolfson]

I am. I think I'm not chasing greatness in the way that Kevin describes it.

[Jackson]

I agree.

[Bri Wolfson]

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

[Jackson]

Is that me? I want to push you slightly because I think you are both doing that and you. You. I mean, you were, like, an all American soccer player. You've, like, done. You've been exceptional in many ways, consistently. And granted, maybe it's not perfectly intrinsically motivated or whatever. You've done a bunch of different things rather than one thing. But, like, is it really just you want to be, like, at ease in your craft?

[Bri Wolfson]

You're, like, not on the list of people I call when I'm having, like, anxiety swirls about everything. Like, this. Being illegible has, like, plagued me throughout my career.

[Jackson]

Like, yes, you did an amazing job of capturing that piece, by the way.

[Bri Wolfson]

Thank you. But, like, imagine me at, like, 27, sending this, like, email to the CEO of, like, an actual company being like, I want to be your, like, head of storytelling. And then, like, laughing me out of the room. Like, that was, like, that did not happen in a confident place. Like, I was like, I'm gonna, like, shoot my shot on this thing, and I'm gonna, like, be bold and, like, put myself on the page.

[Jackson]

We also weren't laughing you out of the room. I suspect it was a little bit about the illegibility. More so than you fool.

[Bri Wolfson]

It was respectful, but it was like, oh, like, I.

[Jackson]

They weren't ready. They actually. It was too illegible.

[Bri Wolfson]

Yeah, it was.

[Jackson]

It was. You were actually totally onto something. But it wasn't.

[Bri Wolfson]

Yeah, but I'm like, I. It wasn't. None of us was surrounded in confidence. I was, like, supremely self conscious about that whole event. And I think if I was, like, truly at ease in my craft, I'd be like, oh, they just, like, don't see it yet or something.

[Jackson]

But, like, this is the Kevin. This is when the comments bounce off of Kevin because he just doesn't care.

[Bri Wolfson]

Yeah. He's like, I can't even.

[Jackson]

I'm good.

[Bri Wolfson]

Yeah. He's like, I don't even understand what you mean by like, does an audience have to validate you? He was like, does not compute. So I. To me, at ease in my craft is like, I know my value. People say this. People are always like, just call it Bri magic. I would never call my work Bri magic. I think they're saying something kind, but to me, it's like, dismissive. Because I don't want it to be magic. I want it to be real.

[Jackson]

Yeah. Yeah.

[Bri Wolfson]

So I'm like, still on a journey with this thing.

[Jackson]

There's a. The thing that most stands out about Kevin, the way you convey Kevin in that piece, is this demeanor or this disposition of abundance. It's kind of what we were saying about the bouncing off thing. Like, what I'm talking about is taking your interests seriously enough to have the courage to stay moving. You can give stuff away. You can abandon things. You can tolerate failure because you know that tomorrow there is more.

[Bri Wolfson]

Yes.

[Jackson]

That. I mean, honestly sounds a little bit like what you were just kind of describing. You also, though, have, like, what you were just saying. You've talked about, like, feeling at this stage in your life, in your career, like some doors are closed. When do you feel this? At the end of that piece, Kevin talks. Or maybe you talk about, like, the well being bottomless. Like, what a beautiful imagery.

[Bri Wolfson]

Like that was all him.

[Jackson]

When do you feel that abundance and how do you try to get back to it?

[Bri Wolfson]

Yeah, it's funny. You're like, tying my whole life together. After I graduated college and soccer was over, my. I was in a pit of despair that I would never be so good at anything again. Like, Truly, truly true.

[Jackson]

You were really, really great at that.

[Bri Wolfson]

And I was obsessed with it. Like, I would get to practice early and practice my touch. Like, I would go home and, like, do planks while I watch tv. Like, I was obsessed. Like, I really put in the time to be great. And I, like, was great at, like, a Division 3 school and everyone else on my team, like, went on to D1 schools. So, like, yeah, it was awesome to be an all American, but there was, like, many stages above me that I. That I thought about. And I think I've done this now enough times where I, like, have to pass the torch and start over. That it's like, that feels fun and exciting. I know I will do it again. Like, this is the main thing. Writing the novel taught me was like, I could do a huge thing by myself, but, like, I don't know, winding down constantly. I, like, usually I trick myself into thinking, like, this is the magnum opus.

[Jackson]

Time is different.

[Bri Wolfson]

Yeah. Like, constellate is like, what it all laddered into, like, a piece of software that, like, helps companies do great work. And I had truly zero product vision. But I was like, this is its final form. And then, like, I joined Patrick o' Shaughnessy and, like, yes, like, helping founders plus media. Like, this is its final form. And then I, like, ram something up and I give it away. And I'm just like, on this, this book, I'm like, this is my magnum opus. This will be, like, all the things I've ever thought about, like, how to do great work is, like, gonna be in this book. And then when they're done, it's, like, sad. But now I've done this enough times where I'm like, yes, I'm gonna try to, like, be the very best. Like, I think it'd be so lame to go into these projects and be like, it could be okay. I don't wanna write an okay book. Yeah, that would be so lame. That's.

[Jackson]

The abundance is like, what Kevin is doing. Kevin doesn't seem to have that. This needs to be the opus yet. It's all great.

[Bri Wolfson]

I know. Yeah. He's like, this doesn't have to be like, the best walk across China that anybody's ever done.

[Jackson]

And also, I'm not going to phone it in.

[Bri Wolfson]

Yes.

[Jackson]

Yeah.

[Bri Wolfson]

So I think I'm trying, like, when I say at ease in my craft, like, I think of Kevin as at ease in his craft. Like, he trusts himself. That, like, his version will be beautiful.

[Jackson]

Yeah.

[Bri Wolfson]

And like, what is even, like, the best book about great operators like, it doesn't matter. It's just, like, my best book. That's what I have to do.

[Jackson]

This is Kevin's most famous line. Don't be the best, be the only.

[Bri Wolfson]

Yes, but that's, like, very hard to channel as this, like, hate to lose competitive person. But, like, I think I will be happier when I trust myself to produce excellent work and to, like, understand my own, like, worth and value and all that stuff. And, like, trust the process instead of, like, white knuckle. So much on the way. Like, I'm afraid of this book.

[Jackson]

Willpower is overrated.

[Bri Wolfson]

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

[Jackson]

One more from Kevin or on Kevin. His range is wide, but all his work somehow rhymes. What are the dominant rhymes for you in your work?

[Bri Wolfson]

Definitely excellent people around me and, like, for an audience of other excellent people, that matters to me a lot. Optimism, I hope. Like, I always want to paint the picture of the future is going to be better than it is now and maybe, like, a touch of something unexpected. I hope these are. These would be, like, very generous terms to describe my work, but that's what I aspire to. Yeah.

[Jackson]

Tammy, something else Tammy mentioned to talk to you about. She said you've talked to lots of great talent spotters for the book.

[Bri Wolfson]

I have.

[Jackson]

What do they say about their best employees and the best early talent?

[Bri Wolfson]

Yeah, The main thing that they say is, like, they're just so good. They're just so good. I'm like, but why? And I don't know. They're just so good.

[Jackson]

I'm trying to, like, is that get it ness?

[Bri Wolfson]

Maybe that was actually. Yeah. Jackson's referring to, like, I tweeted yesterday, I'm, like, looking for a word for, like, a general sense of get itness. And lots of people have words for it, but they're not quite right. And, yeah, I think what they're saying is, like, they generally can just, like, move through space and, like, get things done.

[Jackson]

Like a knife cutting butter.

[Bri Wolfson]

Yes. Yes. And I'm like, are they, like, persnickety or not persnickety? They're all over the map. Like, are they, like, like, really thinky or really dewy? They're all over the map, but it's just like, it just. Maybe they're like momentum sources or, like, flame keepers or something. Like, they just. They just.

[Jackson]

Is that innate? Like, is that. Is that obvious when they're 20?

[Bri Wolfson]

I think so.

[Jackson]

Yeah.

[Bri Wolfson]

I think so. And I still think it. You can. It can be cultivated, like, or grown

[Jackson]

or compounded or something. Yeah.

[Bri Wolfson]

Yeah. And this is why I got so obsessed with town. Like, I had a couple jobs before Stripe, but I had my real, like, both intellectual awakening and like, agentic awakening at Stripe, where it was like, everybody's really good, and I wanted to be really good in that context. But, like, the job I had before that was at a startup that was. The office was on Church street in San Francisco, and we had, like, a storefront as our office. And, like, someone once caught me watching the Good Wife, like, at work, like, in this. Like. Like, a user came in and they're like, were you just, like, watching the Good Wife on your laptop? Like, and I was, like, in the window and I was like, yeah, I was. But, like, I was, like, really not trying.

[Jackson]

Sometimes you gotta feel it. You gotta be next to it. It's a finger feel again.

[Bri Wolfson]

Yeah. So I don't know, things really changed for me at work where I started to, like, want to be good there. And, like, I don't know, I had a clearer picture of, like, how you could or what it would look like or. So, yeah, I think it can be cultivated. I think a lot of actually, people that I talk to who are. I would, like, consider a great talent, they had a couple early jobs where they didn't quite feel it.

[Jackson]

They were bouncing around.

[Bri Wolfson]

Yeah. They, like. They knew they weren't doing that good of a job. They were, like, in kind of.

[Jackson]

This is the hope, this is the optimistic case, is, like, you don't have to be boy genius when you're 18 or 20. And, like.

[Bri Wolfson]

Yes.

[Jackson]

Have only ever won.

[Bri Wolfson]

Yes. I think. What's that Steve Jobs quote? Like, basically, keep looking.

[Jackson]

Yes. But, yeah, follow the romantic sense.

[Bri Wolfson]

Yes. I, like, did talk to a lot of people who, like. Yeah, they were not in the right container at first and they knew it. Like, they were also watching the Good Wife at work or whatever.

[Jackson]

Yeah. The question is, do you let the container sort of, like, suppress you or do you find a way?

[Bri Wolfson]

Yeah. It's funny, at that time, I wouldn't have said I was super ambitious, like, at work, because I was just sort of. Yeah. Doing what? I remember having a thought like, what do people do all day from 9 to 5 every day? I had no idea I was like, certainly everybody else is also watching the Good Wife.

[Jackson]

No way. People are working for eight hours.

[Bri Wolfson]

Yeah. I was like, they're also watching the Good Wife. Like, that's what I thought was happening at work. I just didn't really.

[Jackson]

I think that's broadly true.

[Bri Wolfson]

No, maybe.

[Jackson]

No, no. Definitely is. Most people do not work eight hours

[Bri Wolfson]

a day and they're watching the Good Wife.

[Jackson]

I don't know. What if they're watching. They're watching TikTok. Yeah. Things don't take that much time.

[Bri Wolfson]

Yeah. I had never seen, like, I had never seen, like, a hive, like, hive mind. Like, really buzzy, buzzy workplace. So I was like, yeah, I'll just, like, that's what I do at work.

[Jackson]

Yeah.

[Bri Wolfson]

Like, not that much. And it took me getting to the place where other people were doing that, but I don't think I, I. It was obvious to me that I wanted that to myself.

[Jackson]

I think, like, one of the most beautiful metaphors for this is just like the fastest hundred meter dash after Usain Bolt is the guy who raised him.

[Bri Wolfson]

Yes.

[Jackson]

Like, yes, this is. This is just so clear. We're like, this is how we work.

[Bri Wolfson]

Yes. Yes. So. And that, like, you're used. Everyone might have a different Usain Bolt. Like, certain cultures might work for you or not, like, one of these, like, great talents. I was talking about one of her first, like, one of the first places she was working where she was, like, not effective and not a fit was in a lawn company. And, like, surely you would expect that, like, that kind of environment would, like, juice any ambitious person up. But it, like, wasn't a fit for her. She was like, I guess I just, like, won't be that good at work. But, like, her environment was the intensity of an Elon Musk company. And it wasn't until she, like, found the next job that she was like, okay, now I'm, like, alive at work. So anyway, you couldn't. You might find it in unlikely places.

[Jackson]

You seem to move between, like, hard and soft or like, yin and yang. Tammy, one more time. She said, bri is creative, but she's also kind of ruthless. And so, like, there's this to the yin yang. There's, like, vibes, but a lot of ambition. There's, like, very intuitive, but also into, like, tracking and systems. There's this, like, super high bar for intangible things. I was gonna ask if it resonates. It sounds like it resonates a little bit. Like, how do you hold both of those things?

[Bri Wolfson]

It's funny. It does resonate I think the first time Tammy said that to me, I was like, tammy, that's my kept secret. And she was like, it's not a secret. Yeah, everybody knows. Which is funny. Yeah. We were even talking about this at dinner last night. Like, am I type A or type B? Like, it's kind of hard to know. It does. It does resonate. I don't think about holding both because that's just how I am. But they, like,

[Jackson]

maybe you allow yourself to be both, whether it's consciously or unconsciously. Whereas I think people, you. I almost wonder if we, like, sort ourselves. I'm. I'm this way. And so I gotta. Yeah.

[Bri Wolfson]

Yeah. And I like being around creatives.

[Jackson]

It's almost necessary.

[Bri Wolfson]

Yeah.

[Jackson]

That makes a lot of sense.

[Bri Wolfson]

Yeah.

[Jackson]

For the two. The worlds you like to inhabit.

[Bri Wolfson]

Yeah. And I don't just mean creative, like people who do art, like any kinds of people who make stuff, bring new stuff into the world. So I think you need to.

[Jackson]

To.

[Bri Wolfson]

Yeah. You need to exude a certain quality for, like, to be welcome in those places.

[Jackson]

Yeah.

[Bri Wolfson]

Like. Yeah. If I was like walking into a creative brainstorm, being like, get that timeline, even though that is, like, low grade, what's going on in my head, like, I know that's not the right. I know that's not the right place. I could read a room.

[Jackson]

I was thinking about, like, what is your spike? And we've talked about a lot of the things you're good at and a lot of the sort of patterns. My best sense of it, I think, comes from a few quotes where you say it had become hard to explain what I was good at, most importantly to myself. And then the people who become legendary in their interests never feel they have arrived. That's from the Kevin piece. It's like, what is the. There's this. There's this ambiguity. People love to tell me things and I like hearing them. That's one thing you said, I want to be an active metabolizer. And then finally I became the person you asked to have a coffee with when you wanted to quit your job and do something weird. You talked about helping people tell their stories, being this empowering force next to special minds. We talked about that. Working with ambition and joy. You referred to Harold Ross of New Yorker as excitable. And so my best point at it is this. It's a charisma. Specifically around being excitable.

[Bri Wolfson]

Yes.

[Jackson]

Why is being excitable a virtue that resonates?

[Bri Wolfson]

That's a really nice compliment. I hope that that's true. It's a virtue. Because, like, I don't know, stuff could just be a drag. Stuff could just be a drag. Or it could be fun and, like, exciting and, like, interesting and back to

[Jackson]

morale a little bit.

[Bri Wolfson]

Yeah. And captivating. And I think a lot of the stuff, like, seen through a new lens of, like. But that's like, the fun version of it is, like, it actually, like, shifts the work in the right. Yes. It actually shifts the work in the right direction. It's not like lipstick on it. Like, actually changes something about it. It's funny. I was like, on a three way call with two girlfriends recently and mom was putting her newborn down for a nap and she was like, do you think she's gonna stay down? And the other girl was like, honey, I don't think so. And I was like, he's totally gonna stay asleep. He's gonna stay asleep forever. And they're like, bri's just a hype girl. But then he stayed asleep and I was like, I willed it into.

[Jackson]

If you believe in magic, magic happens. You believe in miracles.

[Bri Wolfson]

I think I am a hype girl. I'm really proud of that. And I'm discerning. I won't hype anything.

[Jackson]

Yes.

[Bri Wolfson]

And I, like, won't lie to you either. I, like, I cannot fake it.

[Jackson]

You believe it. I do believe the hype.

[Bri Wolfson]

I do believe it. And, like, I'm sorry.

[Jackson]

I'm saying I believe you. People around you believe your hype, which is so critical.

[Bri Wolfson]

Well, I believe it. Yeah. And like, I think that's my only bar for this. Or at least like, my only criteria for this stuff. Like, do I believe it? And I won't work on it if I don't believe it. Which is why I picked these great people to work for. Like, I have to believe in it. I don't wanna fake it. In fact, I even. I got that in my very first performance review at Google. I was in sales and I, like, didn't believe this. Like, it's funny. It was video. I, like, didn't believe in video. And I was like, I'm not gonna pitch this until I believe it. And they're like, okay, well then you're just gonna, like, lose. And I was like, I don't care. And then I, like, started to believe it. And then I was like, the third best salesperson in North America after.

[Jackson]

But, like, I sell anything you believe in. That's true for anybody.

[Bri Wolfson]

Yeah. So I like. And I, like, I seek to believe. I'm not like, yes, I want to. I think that's like, really fun. I want to find the awesome things about people like you said. Like, what did I say? Well, I like, people tell me things, and I like to hear them. Like, yeah, I want to get into it. Like, I want the skinny mirror. I want you to look good in your clothes. Like, I don't want to talk shit behind your back about how you look fat. Like, I want you to look good. So I think people feel that in me and also that I'm not fake. Like, oftentimes someone will try something on and be like, no, let's try it again.

[Jackson]

Yes, yes, yes.

[Bri Wolfson]

So I think that energy is, like, contagious, too. Actually, someone just sent me a really nice note that, like, something they learned from working for me was, like, to make it fun. I think think most people want it to be some version of fun. So, anyway, I try to bring it. I don't always, but I try.

[Jackson]

What does it mean to be an API to X?

[Bri Wolfson]

Maybe this is a little bit. We're talking about being legible to two different things at the same time. It's like, connect two things that shouldn't be connected.

[Jackson]

And a lot of that.

[Bri Wolfson]

Yeah, I think I'm very comfortable in that place. Like, oh, I want to put these two wires, but you really got to stretch them. I'm very willing to do that.

[Jackson]

That's great. It's a great mental image. You tweeted, I think, a napkin drawn, good at talking matrix that it's sort of, like, good at talking on the. Whatever, the Y axis or something. And then competent or good at doing. It was good at doing on the other axis.

[Bri Wolfson]

Yeah.

[Jackson]

And one of the good at talking but not good at doing is the yapper.

[Bri Wolfson]

Yeah.

[Jackson]

And the top right is the good one. You're definitely in the top right. How did you get there?

[Bri Wolfson]

I think people just generally like having me around. Well, not everybody like the right setups, so I think I just get to learn from a lot of really good people, and then I get to just copy what they do. I actually. We talked about this before. I don't think I'm, like, great at doing yet. I think, like, writing is kind of being, like, a professional thinker.

[Jackson]

There's a lot of output, though.

[Bri Wolfson]

Yeah. And I guess I like getting stuff done. Sometimes I make checklists to just check things off.

[Jackson]

This is also, like the picking up the crevices thing.

[Bri Wolfson]

Yeah.

[Jackson]

Like, yeah.

[Bri Wolfson]

Yeah, okay. I do. Yeah, that's fair. I do get stuff. I do get stuff done. I think I just like to. I think I just like, to.

[Jackson]

There's this. I think it was on a podcast, maybe with Paki or Perel. You talked about Steve Jobs wanting to, like, know how the parts of the thing work, like this story. And you said, I have that with people and I have that with ideas.

[Bri Wolfson]

Yes.

[Jackson]

What do you love about people and ideas?

[Bri Wolfson]

It's like an infinite puzzle and everything is different. Like, you can. Yeah, it's an infinite game. There's no. You cannot understand people. You cannot, like, wrangle ideas. And I. I'm definitely not the smartest people in most rooms, but I think I am, like, one of the most willing to ask questions. Maybe you feel like you have some of this relate. Yeah. And to me, that's, like, a very satisfying way to live. And I have, like, no shame about being dumber than others.

[Jackson]

One last thing. On the kind of career advice bit, you were talking to Barrett Brooks and you said, I finally realized I just want cool people to think I'm cool.

[Bri Wolfson]

Patrick Ghosh honestly helped me get to that insight.

[Jackson]

It's beautiful. And what you followed that up by saying was, I had the clue. I just wasn't listening. Evergreen, I think you even talked too, about it. Like, sort of. Maybe some of the aspects of this feel, like, fundamentally unrigous or, like, female gendered or, like, five queen or whatever. I think we all have this in so many aspects of our life. Not just career path, but, like, two people who, like. Do you have advice for people to get better at listening to the clues, seeing clues?

[Bri Wolfson]

That's a really good question. I'm still. I'm still working on getting better at this. I think it's related to this quietness and, like, stillness thing we talked about earlier. I think it's like thinking when everything is quiet. Like, when I make a career decision, one thing I'll do is, like, go on, like, a. Like, a tour of, like, all my friends. And sometimes I'm like, maybe it'd be better if I just went into an empty room. I. I think that's, like, part of listening better is just, like, trying to make everything else quiet so I can hear. But it's really hard to do. Like, we're surrounded by smart people and there's a lot of writing on everything, and people have opinions on this or that, and they're smart and, like, it seems silly not to, like, hear from them. But I think I'm, like, still on journey of learning to trust myself a little more. And I think to, like, make decisions in the direction of yourself, you also have to believe that like you have what is it takes on your own. Like if no matter what was happening when I was 22 or whenever, 23, whenever I joined stripe, like that was the right career decision. I think the thing like competing with it at the time was like to stay working at Dandelion Chocolates and like being a soccer coach. And it was like, I think maybe that could have been like more fun or like quote listening to myself. But like that was the right step for me to take. So anyway, I'm like, it's hard to know when to listen and when to not. But I think at least like documenting or hearing what the signs are. So at least you have some record of what's going on inside.

[Jackson]

You have this image of like, I think in the context of writing, which obviously applies here, but like putting the microphone close to yourself.

[Bri Wolfson]

Yes.

[Jackson]

The other thing I think about metaphor I try to lean on is like, it's like you gotta let the snow globe settle. It's like I'm viscerally shaking this thing, looking for answers. It's like, yes, stillness is something. We've made it well over an hour and a half without talking about taste, but we have to.

[Bri Wolfson]

I thought you were just using craft as a stand in.

[Jackson]

I. I think they're very related, but I think they're a little different. And I think obviously like taste is such an input to craft. I think that you've written a lot of great things, but you have. If people are going to read one thing, I hope it is notes on taste, which is just so wonderful and very influential to me and certainly precedes a lot of the discourse and whatever else. I want to just pull out a few things because we could spend. And I think you kind of have spent lots of time talking about this with people. First you say taste is something we can and should try to cultivate. Not because taste itself is a virtue per se, but because I found a taste filled life to be a richer one. 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.

[Bri Wolfson]

Yes.

[Jackson]

Can you say a little more about that?

[Bri Wolfson]

Yeah. The best example I have is coffee. I like to say that my husband ruined my life by getting me into coffee because like I used to be able to just like drink it from the Gas station. Yeah, station. And that was fine with me. But he's, like, so into coffee. Like, if you look over there, there's, like, a whole setup. There's, like, scales and, like, temperature. Like, all this stuff. He's like a scientist, and he dials in every factor. And, like, every morning, we do this whole ritual together every day where we make coffee and we, like, talk about if we like it. It's such. We have so much going on. It's like, it'd be so much easier to just, like, get. Get it from the gas station. But it's just, like, a lovely. And anyway, I just, like, notice. And, like, now I know where. I always know where the beans are roasted because, like, we like African blends. So just, like. I don't know, it just makes me think a little bit more deeply about, like, what's going on. Where did these beans come from? That same, like, Steve Jobs taking things apart or like, John Collison's, like, world is a museum of passion projects. Like, it just makes me think more about, like, how things came to be.

[Jackson]

A deeper state of attention, I think you also call it.

[Bri Wolfson]

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

[Jackson]

Yeah. Yeah. There's a few. Few sort of themes in that thing in that essay that all point to this. Like, there's the quote from Tina Brown about noticing things. You can't teach somebody noticing things, listening to what's going on inside you, where you're talking about what I like and why. Emphasis on that. And why. Another theme is, well, you say, I think I'm a good consumer somewhere. Not in that piece. And then you've also used the word connoisseur and specifically how being a good connoisseur actually makes the output better. Great connoisseurs don't hoard, who don't hoard, I should say, make your great curators. And the thing that came to me here was, like, it's actually a form of generosity, both in two ways, which is generous in consumption in the way that maybe it makes the thing better. A receptive audience and generosity on the other side, which is if you're not hoarding it, if you're curating, you're generous. What do you see in your favorite and particularly the most generous consumers and curators?

[Bri Wolfson]

Just, like, honestly spending time talking about stuff like that connoisseurship thing comes from Fran Leibowitz, and she says, like, the reasons art was so good in the 70s is because the audience was so good. People were really paying attention, and they were critiquing and they were pushing their creators. Like, I hope that, like, when. I don't know, if someone makes a TV show, like, they, like, imagine, like, me and my friends at brunch, like, talking about all the choices.

[Jackson]

Yes. And, like, loving attention.

[Bri Wolfson]

Yes, loving attention. Just recently, like, this, Rosalia released a new album. Have you listened to it yet?

[Jackson]

Unbelievable.

[Bri Wolfson]

It's so good. She's on another level. But, like, my friends and I are, like, every track are, like, the transition like this. Like, did you hear when those drums came in? Like, her voice, like, yeah. Loving attention on her work. Like, I trust that she worked very hard to, like, create something amazing. And I'm, like, appreciating. I'm like, like, live tweeting all day. I'm like, sorry, meetings are canceled. Like, I gotta. I gotta text about this. And I, like. I love her art. I like. And it's so fun to, like, pay attention to it and talk about it and, like, learn from it and get excited about it. I'm not a musician. I just, like, I'm enjoying beholding her art.

[Jackson]

You're not a musician, and yet this goes back to what we were saying earlier. I'm not a designer. But, yeah, you're kind of doing it, which is, like, you're not a musician, but you are engaging with it in a way that I think she would appreciate, which is that it's loving attention.

[Bri Wolfson]

Yes. Gabbing about it at brunch with the girlfriends.

[Jackson]

There's something I think you talk about a bit in the piece, or at least point out, which is like, taste is kind of this external and internal thing together. There's an external sensibility or even recognition, maybe closer to, like, the correctness. And then there's, like, listening to what's going on inside you. Does great taste require both?

[Bri Wolfson]

I think so, because I think it's actually Anna Mitchell, who gave me this term of, like, a true original, where, if you think about the person who has, like, the best taste in fashion, it's not like she's just porting over something else. She's, like, coming up with their own.

[Jackson]

Something's happening in there.

[Bri Wolfson]

Yeah. Like, I think I framed it in the piece as some kind of alchemy, and I do believe that that's kind of the quality of it. It's like. Or I think there's another quote in there that's, like, in accordance with the good and the true. It's like, yes, there are some, like, laws of physics that, like, fashion needs to adhere to to, like, look good. And probably has to do with proportions and colors, materials. Yeah, yeah. And some things. And, like, there's ways to break that in a way that's, like, tasteful and not. But I think it just. Yeah, it takes loving attention to get there.

[Jackson]

I think maybe you already given me my answer, but I had another question about, like, why curiosity alone doesn't make for tastefulness. And maybe it's this. Maybe it's that curiosity can be. I don't know if it's only external, but it actually can be internally driven. But it doesn't give the thing the time to sort of percolate inside you or whatever.

[Bri Wolfson]

I think I use the word metabolize a lot. And this is why it's like, you want to do some work on it. Like, I think it's related. Like, if I just. To the Rosalia did lgtm, Like, I could text a friend, like, love this album. Or I could be like, you're all like, here's all the sounds I heard and all the cool noises and transitions and whatever. Like, those things are very different. Those things are different.

[Jackson]

Who has most shepherded your taste?

[Bri Wolfson]

Oh, man. A lot of people. Like, really a lot. Give us three, definitely Tammy, my friend Charlton Lamb and my friend Matt Kallman.

[Jackson]

What is there anything that stands out about when you think of those people and the way that's happened for you, or what. What. What about their taste is so wonderful?

[Bri Wolfson]

To me, these people are like the ultimate polymaths.

[Jackson]

Yeah.

[Bri Wolfson]

Like, Tammy knows everything. She reads everything.

[Jackson]

This runs against something you say in the piece, though, which is that you. You sort of imply that most people, you can't really have taste. Great taste in lots of things, which I almost. Not. I'm not sure I agree with.

[Bri Wolfson]

It's hard to. I mean, like, I think, like, truly great, otherwise it'd be so exhausting. But, like, I think what Tammy can do and Charlton and Matt, all these three people are this way. They read and know everything. And that means that they know how to, like, exert pressure on a thing in a particular way. Like, they can draw from math or pop culture or literature or history to, like. Like, push on an idea.

[Jackson]

It's like the fork thing a little bit. Yeah. It's like you need the broads.

[Bri Wolfson]

Yeah. It's like, if you. Let's go back to music. Like, if you listen to Beyonce's album with an awareness of black history. Like, something else, something unlocks for you.

[Jackson]

Yeah, yeah, yeah, yeah.

[Bri Wolfson]

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

[Jackson]

Yeah. Maybe to try to compress taste and craft on the nose slightly. You're talking about George Saunders in the piece a lot. At this level, good writing is assumed. The goal is to help them acquire the technical means to become defiantly and joyfully themselves.

[Bri Wolfson]

You're picking out all my heroes in this conversation.

[Jackson]

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 it's you. And finally, you briefly referenced this. When we recognize true taste, we are recognizing that alchemic combination of skill and soul.

[Bri Wolfson]

Yeah. That taste piece had a great editor.

[Jackson]

For what it's worth, I was gonna ask about that. Yeah, yeah. What? Maybe, like, what examples come to mind when you think about craft and taste coming together or skill and soul coming together? Like.

[Bri Wolfson]

Yeah. I mean, everything. Anything that's good. We recognize soullessness so fast.

[Jackson]

Are you sure? Do you. You do. Is the world getting. Is the world getting worse at that? Is that. Is that a false fear? People are very worried about slop.

[Bri Wolfson]

Yeah.

[Jackson]

Almost to the point where it's like.

[Bri Wolfson]

We're like, yeah, okay, I'll take that nudge. I don't know. Do you think people, like, are eating McDonald's and think it's, like, good food?

[Jackson]

I think digital, it's harder. Like, there's a materiality, physical world thing that's just, like, fundamentally more scarce.

[Bri Wolfson]

Yeah.

[Jackson]

I've eaten McDonald's and thought it was good.

[Bri Wolfson]

No, I don't mean like, that. Like, does it taste good?

[Jackson]

Yeah.

[Bri Wolfson]

I mean, like, is it skill and soul?

[Jackson]

Yeah. Yeah. But, like, I know we were just talking last night about how we know some people who write very well and, like, they don't totally write it. Like. And by the way, does that mean it's less soulful? I don't think so.

[Bri Wolfson]

No.

[Jackson]

But. So maybe that illustrates your point. But I do wonder. And even. Even the soul piece, like, do you and I feel soul With Rosalia in a way that other person might be. Like, this is craft. There's a lot of craft here. But like, I don't know.

[Bri Wolfson]

Yeah. Is in the eye of the beholder. Not all the time. I think there's like a lot of universally recognized. Yeah. This special combination.

[Jackson]

History would also, I mean like Christopher Alexander go down the list. Like the quality of the name. Like, like history would indicate, like, people are pretty good at sniffing this.

[Bri Wolfson]

I think. So maybe we'll get better at it.

[Jackson]

That would be nice.

[Bri Wolfson]

Because there's so much slop. Like, I think actually the real risk is that like, slop is it's like better at hijacking our brains. I think that's the real problem here. Like, I don't think anything I see on TikTok is like, good. But like, I can spend a lot of time on it by accident.

[Jackson]

I saw my first feature film directed by a tick tocker that I had like watched in 2020. 2021. He just made his first movie and one of the things that always stood out was like, this actually has a lot of soul for a one minute video. This guy Baron Ryan. I think you're right. I. I think the fear. I think I maybe talked about this a little bit with Nadia, but like, the fear is you just like, you didn't get the chance because you're just like, mind numbed.

[Bri Wolfson]

Yes.

[Jackson]

Mark Zuckerberg's got you and his.

[Bri Wolfson]

Yeah. Or you like, don't want to. Like, I think it's like. I think it's challenging to read Moby Dick.

[Jackson]

Yeah. Yeah.

[Bri Wolfson]

I mean, there's like a lot in there. Like, I had a. I had to have like a friend, like, walk me through a chapter by chapter to like, I don't know why.

[Jackson]

Great. What a gift, by the way.

[Bri Wolfson]

Yeah. And I don't know why I wanted to read it, but I just did. But I was struggling. So anyway, I like, it would have been much easier to watch like Real Housewives or something. But anyway, like, I feel up to the challenge of. Yeah. Like soulful and craftful things. Can I say one more thing about George Saunders that's like, just strike me as you say this when he says, like, his students arrive already. Wonderful. Imagine being George Saunders, like one of the most accomplished writers and this like room of like, I don't know, 18 year olds, like shows up and you believe that they are already perfect. Like, what a generous belief. How cool is that?

[Jackson]

I suspect he has this unbelievably refined ability to see people and see their Magic or whatever, their light.

[Bri Wolfson]

But I think this is not.

[Jackson]

By the way, I don't think he's being nice.

[Bri Wolfson]

No, me either. I don't think he's being nice, but this is why he's one of my heroes. You can be at peak craft and believe someone unshaped has arrived already. Perfect. That's like. And, yeah. Your job is to make them more themselves. What a beautiful way to, like, approach someone who's a student.

[Jackson]

Yes.

[Bri Wolfson]

To you.

[Jackson]

Yes.

[Bri Wolfson]

So, anyway, like, I. Yeah, I hope to move through the world more like that. Like, I. We were talking, like, we're talking a lot about loving attention and taste and the real. I think the real damning thing is just indifference to everything. And I think I was a little bit that kind of teenager of, like, I don't care. I don't care. I don't care. That's, like, the worst way to live.

[Jackson]

To me, it's the optimism and so much of the stuff we were talking about earlier. One connection I think on. I want to talk a little bit about taste and editing. You say, but taste gets you to the thing that's more than just correct. Taste hits different. It intrigues, it compels, it moves, it enchants, it fascinates, it seduces.

[Bri Wolfson]

That's a little extra amazing.

[Jackson]

And speaking of Saunders, like, he's. He's got this PN thing, and I think you. You've talked about that, both in the literal editing sense, but also as this amazing template or sort of, like, what it feels like to actually, like. Like, taste more. How do you edit towards ineffability.

[Bri Wolfson]

Yeah, it's. I'm glad you're asking this, because I'm actually. I'm working with a leader right now, and I think he's got amazing taste. And the main way it comes out is he says no to stuff. And a thing that we're working on together is like, how do you get it to yes? Like, it's actually less interesting. Like that. It's. No, like, you need to know what dials exist so that we can, like, get it to yes. Like, that's the happy place.

[Jackson]

Steve Jobs was really amazing at saying no and also had a few awesome yeses.

[Bri Wolfson]

Yes. And, like, you have to know what dials you have. Like, it's no fun to, like, be the person reviewing tweets and just being like, it's not good enough. It's not good enough. Like, a true leader is like, okay, this is how we make it good enough. And there's a lot in there. There's like, content, there's skill, there's language, there's like. Yeah. There's just lots to work on there to, like, help understand how to get a ts. And I think this, like, taste like one of my most fashionable friends throughout. Now in her 30s, throughout her 20s, she wore some like, ratchet stuff, but she was trying, like, she was playing. She got a lot of no. Yeah. She got a lot of no's. And now she's like dialed yes, yes, yes to the yes place. So anyway, I think you just need to, like. Yeah, you need. I'm like, picturing like a air like a cockpit. Like, you need to have all these knobs and you, like, know what to turn, when to, like, get it to yes. You can't just be like, like, no.

[Jackson]

Well, pure correctness without taste is like the minimalism slop thing. And to your point, like, you actually have to go kind of. Maybe why you have to be willing to take a risk.

[Bri Wolfson]

Yes.

[Jackson]

To get to something really special.

[Bri Wolfson]

Yeah. Figma taught me a lot about, like, design thinking. That was part of what was really fun about being there. Like, a lot of people who had been trained in that mindset and one thing that early designers do is you copy paste something and then you change one thing about it to make it more you. And I think that's mostly the journey of.

[Jackson]

Yeah. Virgil Alba talks about 3% better, 3% different.

[Bri Wolfson]

Yeah. And just like, it's like, oh, like, remake this movie poster that you've seen the movie of. Or it's like a lot of copy paste tweak.

[Jackson]

It's a great slope into agency and creativity.

[Bri Wolfson]

Yes. Yeah. Yeah.

[Jackson]

Well, you mentioned earlier both. You mentioned both of them. Jeremy Stern at Colossus and that editor for this piece. What was so special? What. What made them or makes them great editors.

[Bri Wolfson]

They like, they keep you in it. Like, Jeremy certainly has a distinctive voice when he's writing that he does not impose on me when he's editing my work, which I think of as an incredible skill. Like, he's peak at his craft and then he's like, letting me do it.

[Jackson]

He's amplifying. He's not. Yeah.

[Bri Wolfson]

Yes. So I think of that as, like, very generous. And like, they often see work when it's not perfect and, like, the enthusiasm to keep going. Like, they never say anything is bad.

[Jackson]

Part coach, part, like, yes. Evaluator.

[Bri Wolfson]

Speaking of hands on the dials, they know exactly how to get a ts. And it's really rare. But every now and then there's like, something that I do want to hold to. And 100% of the time they just say, okay,

[Jackson]

I like that. I think we talked about this, but maybe we're hitting a lot again. How do you. You. You have this amazing desire to be edited and a comfort with being critiqued and edited. Like, is that innate? Can you get better at that?

[Bri Wolfson]

Oh, yeah. I've, like, had critics my whole life. This is, like the. This is one of the things I learned the most from being an athlete. But. And my friends who played music growing up, like, seriously, they have this too, where there is an objective rightness. So it's, like, a little bit easier to be critiqued. Like, yeah, if I make a bad pass, I know it's bad.

[Jackson]

Right.

[Bri Wolfson]

If you, like, hit the wrong note, you know it's bad.

[Jackson]

Nobody's opinion.

[Bri Wolfson]

Yeah. So it's, like, a little easier to stomach. Like, it's pretty clear what the rules are. So anyway, I've just had people critiquing me my whole life, and now. So now when these things are more nebulous, what's the right word to use here? What's the right color? How should this look? I think I, like, already have a comfort with the language of critique. And this is another thing I learned at figma. Like, critique is a huge part of the design process. It's like, there's no such design process without it. So I think having mechanisms that build this in. We all look at this work together and talk about what we like and don't like, that feels very normal to me now. I think a lot of people have not had that.

[Jackson]

It's on a personal attack.

[Bri Wolfson]

Totally. Or like, another version of this is watching tape in sports where you just go back and you. You watch yourself doing stuff and you're like, why?

[Jackson]

It's a way of being, though. It's.

[Bri Wolfson]

It's.

[Jackson]

It's assumed.

[Bri Wolfson]

Yes.

[Jackson]

It's not a special. Yes, we watch tape every time and.

[Bri Wolfson]

Yeah, exactly. It's not like a punishment. It's just sort of part of the craft. And I had this at Google when I was working in sales. They would film us doing our pitches. And this is where I learned. Like, I. If I have an earring in, I'll play with it. So I don't wear earrings anymore because I don't want to, like, fidget. But, like, until you've seen yourself in

[Jackson]

a meeting, like, so you've heard yourself on a podcast?

[Bri Wolfson]

Yeah, I never listened to any because I. Yeah. But anyway, this I like. I feel like it's like a Comfort.

[Jackson]

Yeah.

[Bri Wolfson]

With, like, being in the critique space.

[Jackson]

My last thing on this. Our mutual friend Molly Milky McCarthy tweeted this yesterday. It's actually a little. Little harsh, but I thought of you in a good way, I promise. She says in Silicon Valley, quote, tastemaker is the consolation title given to people who somehow maintain proximity to power without ever building anything of their own. There's another word for that elsewhere, influencer. But no one seems to talk about that.

[Bri Wolfson]

That's funny.

[Jackson]

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?

[Bri Wolfson]

Yeah, that's Tammy's words. Yeah. Why? Do you think it's harsh?

[Jackson]

Maybe harsh is the wrong phrase, I guess. I mean, it's poignant and a very opinionated. I'm not sure I fully agree with her or Tammy on the deployed taste thing. I also think it gets a little bit subtle, which is, like, there's nuance, which is what is a curator? Is a curator deploying? Am I deploying my taste? All I do is talk and curate people.

[Bri Wolfson]

Like, the way this is hitting me is actually more of the API thing. I think when people are doing, like, a taste check with me, they're like, will this resonate with another community? Yeah, I think that's valuable. Yeah, I think that's like deploying taste. Because I'm like, yeah, if we tune in this knob, I think it will land better.

[Jackson]

Which I don't think is what Molly's talking about when she's about the tastemaker either.

[Bri Wolfson]

But I think the difference between an influencer, as Molly's describing it, and this, like, taste maker is the tastemakers and the wings, they're never famous. The influencer is a famous one. They're, like, deploying taste.

[Jackson]

I think she's saying that we call people tastemakers who aren't actual.

[Bri Wolfson]

Yeah, I see, I see, I see. That makes sense to me.

[Jackson]

Yeah.

[Bri Wolfson]

But, yeah, I mean, I mostly don't stand to gain anything.

[Jackson]

I doubt many. Maybe they do, but I would be kind of surprised if people refer to you as a tastemaker, even though you clearly are. They're referring you by the things you actually done, which is maybe the point.

[Bri Wolfson]

Yeah. I don't think a lot of people will, like, ask me for my take on something like, do you think this is good or something?

[Jackson]

Yeah, yeah, yeah.

[Bri Wolfson]

But I don't think. Yeah, I don't think people refer to me as that.

[Jackson]

We Are we are well in on multiple hours. I have two sections left. One is a quick one on writing and then a final one which is just a bunch of miscellaneous things we can run through. One of the first thoughts I had on the writing front is just you already brought up like, we. It seems like we're really in the storytelling era.

[Bri Wolfson]

Yeah.

[Jackson]

Which is cool. It's a time for. For Brie Wilson's what makes writing clever.

[Bri Wolfson]

Clever. That's a good word. Yeah. This is another George Saunders ism. Like good writing is only that you want to read the next sentence. And I think clever has an element of surprise in it. And I think you can be lulled to sleep really easily with most stuff. So, yeah, I think if it's good writing and it's keeping your attention, there's probably a degree of clever.

[Jackson]

You've talked about how so much of modern writing lacks editing, especially on the Internet and social media. And what editing sort of does is like. It's like, who is this for? And what will they get from this?

[Bri Wolfson]

Yes.

[Jackson]

You've also said self editing is a real virtue. As we. I think we talked about. How does editing like. I think you use this language like close the distance between the writer and the reader.

[Bri Wolfson]

Yeah, yeah. I think like Morgan Hounschel or something. He would say that he doesn't think of his audience at all. I think like a lot of people say like they're writing for themselves. I think that's another good way to produce good writing. So I don't think this is the only way, like closing the gap.

[Jackson]

He also, I think like one shots it. Like he. Yeah, he's talking about how he just like he'll edit it as he's going and he's just like, when it's done, it's done.

[Bri Wolfson]

Yeah, he. I mean he's also like a prac. A very practiced.

[Jackson]

Yeah.

[Bri Wolfson]

Writer.

[Jackson]

But he's self editing the whole writing process also.

[Bri Wolfson]

Yeah, Yeah. I think. I think this was also Franley Blitz or maybe it was Tina Brown. Yikes. Who says like good writing knows its place. I think that's more of what this is like. You know that meme on Twitter that's like nobody. And then it's like. Then it's blank and then it's like me. And then it's something. I think a lot of writing is that it's like. I think why the taste piece struck so much is because people were talking about it already. It was like sort of like an answer to what I was hearing. It wasn't like, random. So I think it, like, knew its place in this.

[Jackson]

It's not like I'm rolling up to the function and lobbing a take in. Like, it's like, I've been in. I've been in the context, and I'm listening.

[Bri Wolfson]

Yeah. And I think this is what's hitting so much about the Colossus stuff. Like, I. I can see the meme that's like, nobody. And then it's like, here's, like, 20,000 words on Josh Kushner. But I actually think we're, like, craving more depth on stuff like, that felt true to me. That was going on in the culture. It was like, everything short form, everything clippy. Like, what is actually, like, the longest, deepest, most intimate treatment look, like that was, like, an answer to something that knew its place. I think so anyway, I'm trying to, like, respond to, like, what I'm feeling in the world. It's not just random.

[Jackson]

Yeah. Yeah. You. Speaking of the Josh profile and the Colossus ones, you've talked about the New Yorker and how much you love their profiles and this chain of obsession and how exclusives are so interesting because they kind of make you, like. Like, not compete, whether that's being obscure or being timeless or whatever. Maybe it relates to last thing or profiles broadly. But, like, should we aim for our writing to be less competitive as a general rule?

[Bri Wolfson]

Maybe this is more, like Kevin stuff of, like, don't be the best, be the only.

[Jackson]

Yeah.

[Bri Wolfson]

Like, I think with the Colossus stuff, we often ask ourselves, what do we have the right to do that others don't? It's not, like, to make it better or anything. It's just, like, what do we know about this person? Or how do we experience them? That's what makes us special, what makes us earn the right to do this work. And generally, we haven't run into this yet because we were mostly staying in the investor and founder pool. But I think we would really question ourselves if there was someone truly outside of our network we did not understand or know. Like, that we didn't feel like we, like, had the right to cover. Like, that comes up a lot.

[Jackson]

Yeah. Yeah. What makes Jeremy so good at writing? I asked about editing.

[Bri Wolfson]

Oh, man. I don't know. He's another one of these people. He knows everything. He's read everything.

[Jackson]

He's very. Maybe a better question is, like, what goes into having such a strong voice?

[Bri Wolfson]

I think he has, like. I wonder how he would respond to this, but he reads to me as very confident in his voice. Like, he will. I don't know if you experience this. I still definitely do. Like, when I sat down to write, like, I assume this like, other, like, I call it teacher voice Persona. Like, even if I'm like writing a diary entry, I'm like, why am I like, all of a sudden assume like words I wouldn't normally use, like, or like, describe it in like weird ways that like, feel technically correct, but, like, no human would ever say. Jeremy, I think, allows himself to like, say the human words, which I don't. It should be easier, but it's actually harder.

[Jackson]

Yeah. What do we love so much about numbered lists?

[Bri Wolfson]

Oh, my God. I don't know.

[Jackson]

I think the best way to go

[Bri Wolfson]

viral on the Internet, on this last cursor piece, Jeremy was like, you know, I really don't love Listicle generally, but like, I think we can make it work with this one. But yeah, I think it's just easy to scan.

[Jackson]

It does some of the work too, of like. It's just like so easy for your brain to just like ratchet up the. Ratchet down the taste numbers.

[Bri Wolfson]

Yeah.

[Jackson]

What's the best essay you've ever read?

[Bri Wolfson]

Oh, man. I mean, really? So many. But I think probably there's a recency effect here. But maybe the one that lives the most, the two that probably live the most rent free in my head at the moment is Nadia is basic as a virtue and reality has a surprising amount of detail. I like, think about those things a lot.

[Jackson]

Why?

[Bri Wolfson]

I think they taught me something I actually did not know before. And then it was like that Bader Meinhof thing where I was like, now I see it everywhere. Everywhere. We were saying now I was so anti Marina when I was living in the mission and 22 years old. And now every time I go to the Marina, I'm like, Nadia was right the whole time. But it reached me before I was quite. I quite.

[Jackson]

It was ahead of you. It was out ahead of you.

[Bri Wolfson]

It was out ahead of me. And so is reality has a surprising amount of detail that was like before this insight about the world's museum of passion projects. It was. I was like, wait a second, is this true? Because if it's true.

[Jackson]

John Salvatiere. What an incredible essay.

[Bri Wolfson]

Yeah, it's so good. And also, you know what geeks, moths and sociopaths do?

[Jackson]

You know that one is this Kevin. I'm familiar with the name, but I don't know if I read it.

[Bri Wolfson]

It's so good. It's basically about how movements get started. And it's like first the true believers. And then it's like the people who just glom on, but they don't really have an impact on it. And then it's like the sociopaths come and try to commercialize it and make it suck.

[Jackson]

But I think maybe I have read this.

[Bri Wolfson]

I think because of the work that I do, which is often trying to find a little dim flame somewhere, I'm very conscious of, I feel taste is. The conversation is ruined.

[Jackson]

Yes, yes, yes, yes, yes. You love to talk through things, and you also love to write. I can relate, I think, by talking. What are the pros and cons between thinking writing thinking and talking thinking?

[Bri Wolfson]

They're looping for me.

[Jackson]

And I think writing thinking gets a lot of praise. Talking thinking, less so.

[Bri Wolfson]

Yeah. Yeah. Why is talking thinking? It's funny, I've actually been thinking a lot about this now that instead of just writing on my own personal blog, I'm writing for a magazine that has just a different standard of. 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 it in there. In this professional magazine, I'm like, should I credit them? Anyway, the lines are blurring. I think the talking is. Is it your idea? That's why people don't like the talking thinking, like, the writing thinking. Everybody knows it's all your stuff because it's just you and the paper, so that's all your own original ideas. If it's just writing thinking, what does

[Jackson]

talking do for you? That writing that you're cycling through?

[Bri Wolfson]

I'm, like, so attuned to the glint in the eye on a thing. So I throw a lot of stuff out, and then I'm like. That's the phrase. Patrick o' Shaughnessy's actually great at that, too. He's, like, waiting to hear what gets echoed back.

[Jackson]

Yeah. Yeah. He's so amazing at that.

[Bri Wolfson]

Yeah.

[Jackson]

Unbelievable. Okay, my. My last string of things. I. Forgive me, I. You said her name last night, and I don't. Eeka Eka from Stripe on critique. Why is it so good to be a micro pessimist and a macro optimist?

[Bri Wolfson]

I think because generally you think about the ways that it will go, right? And you're being tuned into the details to, like, tweak them to get it there. But if you do it the. I guess not the opposite. But if you do it in the context of pessimism, it's, like, no fun. It's the same thing. It's like, all. No no. Yes.

[Jackson]

Yeah.

[Bri Wolfson]

You want more? Yes.

[Jackson]

Yeah. Some. Something came up. I can't remember who was an interview. Maybe it was with Henrik Carlson, which is like, we have. We want less. Not that. And more. Maybe this.

[Bri Wolfson]

Yes. Yes, yes, yes. I love that. I love that. Like, you never, like, like, okay, imagine you're, like, editing a blog post, and it's like, it was supposed to ship two days ago, but we're, like, still revving the words. And if someone was like, this blog post is going nowhere. No one's gonna read it. What's the point of fixing all the details? Why would that.

[Jackson]

Yeah, it's about momentum preservation.

[Bri Wolfson]

Yes, exactly. You're like, this, like, is so close to great. Like, just a few tweets, and it's, like, gonna be great. That's the energy you want to, like, bring to fixing stuff. And, like, this word is not doing it for me. Like, this whole paragraph, I'm not sure, like, in the context of, like, this could be awesome is really fun to fix. Otherwise, not so much.

[Jackson]

You said you were starch. Starstruck by Kevin Kelly.

[Bri Wolfson]

Oh, man.

[Jackson]

Are you starstruck by anyone else? Or have you been?

[Bri Wolfson]

Definitely. I, like, totally. What's that thing you have when you, like, get weird in front of celebrities? If I, like, pass one on the street in New York, I'm like, no chill at all.

[Jackson]

Across the board.

[Bri Wolfson]

Yeah, here goes the dog. But. But who? For some reason lately, I've, like, really set my mind on, like, meeting Tina Brown. I think I'd be freaked out in front of her for sure.

[Jackson]

All right, we gotta make it happen.

[Bri Wolfson]

Yeah, yeah, yeah.

[Jackson]

You've talked about magnet on times.

[Bri Wolfson]

Oh, my God.

[Jackson]

Off times.

[Bri Wolfson]

Lol.

[Jackson]

Any further realizations on, like, what causes the magnet to be on?

[Bri Wolfson]

It's funny. The magnet on thing actually is first came from, like, friends and periods of dating where magnet on is just like, the hotties are knocking. But I think it just comes from confidence. But I think confidence is not in a vacuum. You're starting to get some momentum.

[Jackson]

You said it takes a ridiculous person to fund something like Stripe Press.

[Bri Wolfson]

Yes.

[Jackson]

Back to funding culture partially, at least.

[Bri Wolfson]

And Colossus.

[Jackson]

And Colossus. Who else is doing this? And maybe what else could be done?

[Bri Wolfson]

I think this, like, story movement is a vote to fund weird ideas, basically. Like, hopefully we'll get this kind of story studio type thing spun up at cursor. And the pitch on, it was six stunts a year. So this is, like, a few thought through. Like, big, weird ideas. Like, that's the pitch and that Kind of thing is resonating and it's just like, okay, can we, like, write out what a stunt is? And it's like, not really, but anyway, so I think this work is getting funded more now.

[Jackson]

Taste is a good dinner party topic because everyone's got a thought on it. Something you said.

[Bri Wolfson]

Yeah.

[Jackson]

What are other good dinner party topics?

[Bri Wolfson]

I'm gonna take any weasel word or suitcase word, whatever they're called, or, I mean, anything that's like Mimi, anything everyone's

[Jackson]

got something everyone has an opinion on. Yeah, yeah. Sontag said to snare a sensibility in words is on the same note, especially one that is alive and powerful. One must be tentative and nimble and. She's talking about camp. She's talking about taste. Maybe part of what you were just saying. But like, what? We have other buzzy words like agency that I don't think.

[Bri Wolfson]

Oh, my God.

[Jackson]

But agency, like, a little clearer at least. Maybe it's like, I'm curious if there are other immediate words that come to mind that maybe if you were going to do notes on X in 2028, what it might be on.

[Bri Wolfson]

Good question. I could do a notes on marketing right now, probably. I think everyone's got a really different definition for that.

[Jackson]

All right, we'll have to. We'll have to wait and see. Patrick o' Shaughnessy told me to ask you, how do your friends decide where to work?

[Bri Wolfson]

Where to work? That's funny. Most of my friends are in Silicon Valley, so I think they're ground. They're probably ground level on what the hot stuff is. And I think it's talking to other friends. I think it's. Again, in the dating era of life, we used to say, like, where are the hotties at? This is like, for work. Yeah. It's like, where are the hotties at? Like, where the. Where are the smart people at?

[Jackson]

You mentioned Tina Brown a bunch or. I did. One of my. We didn't get to talk about it a lot. One of my favorite ideas is high, low.

[Bri Wolfson]

It's the best. So many ways those people I mentioned, Tammy, Matt Charlton, my tastemaker, all high,

[Jackson]

low, 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? You made it out of the chasm on either side?

[Bri Wolfson]

I don't know. Do you have an idea?

[Jackson]

I don't know either. I mean, I think one of the things that's important maybe is just to think about it and recognize, like, high and low. Can Come together, which is maybe the core point. You're talking about Vanity Fair and you give the example of like, whatever or cultural affair or like political geopolitics and Britney or whatever. Just so many of the best things are hold. They hold both.

[Bri Wolfson]

Yeah.

[Jackson]

But, yeah, I don't know. I think it's more of a, you know, this is back to the taste thing. You have to know when you see it. Like, it's in the uncanny valley, you know, when it's in the uncanny valley.

[Bri Wolfson]

Yeah, for sure. I actually think, like one of the mysteries of, like, marketing and taste and all this stuff, like every now and then I know when something's going to hit. I mostly don't. I mostly don't. And I think most people mostly don't. Like, maybe there's a few, like the mischiefs or the mystery. Like maybe they have cracked more mechanical though.

[Jackson]

Yeah, to some extent for mischief. Which is one of the reasons I think Gabe and those guys are, like, done with it.

[Bri Wolfson]

Yeah.

[Jackson]

Mr. Beast is extremely mechanic. He's. He's like obsessive about YouTube. Like, it's basketball.

[Bri Wolfson]

Yes, yes. So, like, maybe there's something there for those people, but I generally don't. No.

[Jackson]

Yeah. You have a scrapbook of pride in a brag document.

[Bri Wolfson]

Yeah.

[Jackson]

Any highlights in there that come to mind?

[Bri Wolfson]

It's honestly, this is why the insight about, like, just wanting cool people to think I'm cool. It's like mostly compliments from people I

[Jackson]

think are cool, as it probably should be.

[Bri Wolfson]

Yeah. I don't think that's the way to, like, build your internal flame source, but that's mostly what in there.

[Jackson]

It's good to live a relational life, I think.

[Bri Wolfson]

Yeah, I think that's a nice way to put that. Yeah.

[Jackson]

What types of thing? Maybe we talked about this kind of with the talking thing, but what types of things does writing as a medium miss?

[Bri Wolfson]

Yeah, it's like one description of my writing, like, a long time ago was cinematic and I was like, then shouldn't it just be a movie? So I think it missed like. Or I guess this could also be thought of as an asset that it's like, there are no visuals. But this is actually one of the founding ideas for Colossus was photography to make that medium bigger in the magazine and give that visual peak. So, yeah, I think it does sometimes miss the. I mean, obviously it misses the visual stuff, but on the flip side, it allows you to paint a mental picture. My friends Nick and Devin, they're like, really into right now how stuff on the Web doesn't have any sounds.

[Jackson]

Not Rio. Os.

[Bri Wolfson]

Yeah, there you go. I'm interested in that. But I don't know, I like, I think it's its own thing. I don't think too much about what it misses.

[Jackson]

What do you love about Matisse?

[Bri Wolfson]

I don't know. It just is pleasing to my eye. I think it's because of sharp contrast. Yeah.

[Jackson]

That's all you need to say. You said Graham Duncan's concept of grip quite literally changed your life. Why?

[Bri Wolfson]

It's I now I see it everywhere. That would be another good candidate for an essay that I think about a lot because now I. It's one of those things that. Becoming self aware about it, like, what is my grip on this?

[Jackson]

Seeing the water.

[Bri Wolfson]

Yes, it's seeing the water. And almost always like you're, we're. You're probably getting a more sense of my temperament from this conversation. Almost always my grip is too tight and it's getting in my way because I can't bring the loose quality that like, makes me happy. And more than any other person in the world, Patrick o' Shaughnessy has like, like loosened my grip on things. So it like, helps me get to joyful faster.

[Jackson]

Wow.

[Bri Wolfson]

And he, you know him, he's like also intense and competitive, but he has a, he has a leg grip on everything and it just makes him. He's so much more fluid and flexible without sacrificing like any power or effectiveness. And anyway, it's just like, it's empowering. Yeah. To me the happy place is the lighter grip place. Like my. All my problems are using your craft. Right, Exactly. All my problems are related to grip. So anyway, now that I can see the water on grip, just the talk we.

[Jackson]

You have a few maxims or like little lines on your website that are all great. Have a real friend in the generation above and below you.

[Bri Wolfson]

Oh yeah.

[Jackson]

What do you look for in intergenerational friends?

[Bri Wolfson]

That's a good question. I'm thinking of one. My, like, my best friend in the generation above me is this woman named Leslie Berlin.

[Jackson]

And I like, most notably at least recently for the Steve Jobs archive stuff. Yeah.

[Bri Wolfson]

Amazing.

[Jackson]

Make something wonderful.

[Bri Wolfson]

And she's just, she's an amazing woman. And I think the main criteria for her is like, like, it's, I think it's like fun to hear like the problems facing someone like my age. And yet she like, still has wisdom that feels relevant to me. Like, she doesn't, she's not dismissive of like my experience because I'm like younger or like, it wasn't like that when she was coming up.

[Jackson]

It's the best, one of the best traits in an older person.

[Bri Wolfson]

Yes. And I think the same is true from a younger person. Like, my sister is much younger than me. She is like very squarely Gen Z. And like, I think a younger generation too can look at the generation above it and think it's like old news and doesn't have anything to offer. So anyway, I think it's that it's like respect for what's coming before or after.

[Jackson]

Everyone wants to help. Ask for what you need.

[Bri Wolfson]

Oh yeah.

[Jackson]

How have you gotten better at asking?

[Bri Wolfson]

Just being more specific. Weren't you saying this the other day? You were like, yeah, don't ask. Like, if you send an email, that's like, can I pick your brain? Or like, can you catch up? Who wants to do that? Who's got the time?

[Jackson]

I want to help. Yeah. And there's an abundance in helping. That's the thing I think I'm working through. It's like you don't get one shot necessarily.

[Bri Wolfson]

Doesn't everybody like to be thought of of like in the room where it happens? It's actually generous.

[Jackson]

Yeah. Yeah.

[Bri Wolfson]

When for this like very brief moment in my life where I had this startup, like many people later were like, I was like, sad you didn't ask me. And I, I. They were on a list and I was like, I would never ask these people for money. So anyway, that like broke my brain a little bit. Oh yeah.

[Jackson]

Everything will be different in six months.

[Bri Wolfson]

Totally true. In the startup life. Yeah. Especially now that I have an infant. She's like a new person every day. It's amazing she's been that like having an infant and moving out of California where there's seasons has like changed the conception of time for sure.

[Jackson]

The deeper you go, the better it gets.

[Bri Wolfson]

This insight also preceded all the taste stuff. And I wrote this after, actually. I like, thought there was a bunch of people I didn't like and then I was like forced to hang out with them for a weekend and I was like, oh, I like them.

[Jackson]

People are hard to hate close up.

[Bri Wolfson]

Yeah. And now whenever, like someone feels like some flavor of enemy to me, the antidote 100% of the time is just to go hang out.

[Jackson]

H. It's a life's work to bridge the inside you and the outside you.

[Bri Wolfson]

Yes. This came from. It's going okay, I would say, but a therapist friend told me that she has seen people survive anything but a cruel inner voice. And I don't have the kindest inner voice at all times. And it made me think, what, what a waste. So I'm just like trying to. Yeah. Like, quiet down that voice and like let more of the inside come out. It's always better. But I don't know why everyone has a lot of fear around that.

[Jackson]

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.

[Bri Wolfson]

I. Yeah, good question. My mom gave me all the joyful stuff and I think she had a complicated relationship with like too much joy and too much excitement, but she gave me that. That I like, I treasure. I want my daughter to.

[Jackson]

Yeah.

[Bri Wolfson]

Like, have fun with things. And my dad gave me the hard working side. Like he gave me the.

[Jackson]

Like it's that hard and soft a little bit.

[Bri Wolfson]

Yeah. And like I being able to have them both at once, like once I truly like can integrate and enjoy them both. Like that will be. And I hope my daughter has those things. For sure. For sure.

[Jackson]

One last thing. Your dog's gonna kill me. You tweeted this the other day to be of use.

[Bri Wolfson]

Oh yeah.

[Jackson]

Just a little excerpt from it. The work of the world is common as mud botched it smears the hands, crumbles to dust but the thing worth doing well done has a shape that satisfies clean and evident Greek for wine or oil Hoppy vases that held corn are put in museums but you know that they were made to be used the pitcher cries for water to carry and a person for work that is real. Why is work that is real worth it?

[Bri Wolfson]

This is basically like why I married my husband. He like teaches me this every single day. Like, there is not a thing in this house he would not repair. Everything he wears is like old and patched up. Like every time we're gonna get anything, he's like, is it useful? And like especially now with an infant, there's like all these like single use products and everything's being marketed to you and all this stuff. Like he just reminds me every day like the main like point of a life is to like, I don't know, put in more than what you get out and like use your hands and like recycle and like, he just, he's very good like that. He like reminds me that like, I don't know, humans are sort of. Yeah, this is our thing. Like we are tool users and we like can fix and problem solve and like, like be useful and like a joyful life is more around these things than the other things. But yeah, I love that poem and I think I tweet it probably like once a year because I'm just like trying to remind myself it's very easy to get caught up in the stuff. That's not that, but that's why I like that line about like, it's mud. Like it's kind of like down in there. Yeah. Yeah. And it's like, I don't. When I see mud, it's like the main thing I want to do is like, not go near it. Yeah. But this reminds me, like, oh, that is the stuff.

[Jackson]

That's the whole thing.

[Bri Wolfson]

Yeah, that's the whole thing. So, yeah, mostly that's a note to self as well.

[Jackson]

Thank you, Bri. This is all I got, Jackson.

[Bri Wolfson]

Have fun.

[Jackson]

Oh, what a gift.

[Bri Wolfson]

Oh, thank you.

[Jackson]

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