35: Brie Wolfson - Loving Attention & Ease in Craft
Full transcript and all links: https://dialectic.fm/brie-wolfsonBrie Wolfson (X) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus, where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review, their new print publication known for superb long form profiles.Brie also recently joined AI-programming behemoth Cursor as Head of Employee Experience and wrote about the company’s culture. She has worked with craft-oriented software companies throughout her career, including Stripe—where she helped launch Stripe Press and the company’s planning function, among other things—and Figma, where she worked on Education. In her words, she is drawn to companies where the reality is even more impressive than the reputation, and she has publicly and privately worked with a number of the most impressive leaders in Silicon Valley on marketing, culture, and storytelling.We cover a broad range of Brie’s expertise, including craft, marketing, organizational culture, unlikely career paths, and taste, editing, and writing. This includes how AI is causing companies to become even more oriented around the empowered individual contributor and who the best of them, including company leaders, are focused on an attunement to details that she likens to “finger feel.” We also talk about why she believes marketing should be a kind of truth-telling, closing the gap between reality and perception.
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Speaker A: A lot of the leaders that I work for, I think they're like fork-shaped, like you hear like T-shaped or something like, or just like broad or just deep on one thing. I think the leaders I like the most can go deep on lots of things. Speaker B: It's almost like vertical slices. Speaker A: Yeah, exactly. And it's just like they're kind of scouring the land, scouring the land, and then it's just like, shoop, 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. Speaker B: Yes. Speaker A: 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. Speaker B: Welcome to Dialectic episode 35 with Brie Wolfson. Where to start on Bri? She wrote a piece recently, uh, sort of about Kevin Kelly and sort of about herself called Flounder Mode. And it's a fun play on Paul Graham's essay Founder Mode, if you haven't read it. And 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.
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