Picking Up the Crannies: A Nonlinear Career

Full transcript and all links: ⁠https://dialectic.fm/brie-wolfson⁠

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

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

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

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

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Timestamps:

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

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