Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path

This week, I talk with Brie Wolfson, someone whose reputation precedes her. She’s the kind of person people rave about getting to work with. Brie was instrumental in bringing Stripe Press to life, partnering with John Collison and the Stripe team to build something truly special. After her time at Stripe, she moved to Figma before eventually facing burnout and needing a break. Brie has been open about her journey through depression, which we dive into during our conversation. Brie recently joined Colossus (founded by Patrick O’Shaughnessy) as Chief Marketing Officer. She also runs a consultancy called The Kool-Aid Factory (a truly brilliant name, I think), helping startups shape their company culture. Brie is empathetic, thoughtful, and relatable—traits that shine throughout this conversation. Let's get to it!

In this episode:

(00:00) - Intro
(03:52) - Writing to one person: techniques and inspirations
(06:57) - The role of writing in personal identity
(09:59) - Navigating the AI landscape
(12:21) - Turning down the noise: digital detox
(17:03) - Paul Graham’s ‘Founder Mode’ essay
(26:48) - The importance of taste and curation
(35:06) - Brie’s creative explosion in 2022
(37:12) - The writing process & self-editing
(40:19) - Is the nature of writing online changing?
(44:34) - Career docs and personal achievements
(54:26) - Brie’s essay on depression
(56:51) - Navigating depression and loneliness
(01:01:19) - The power of self-soothing
(01:07:59) - The importance of setting boundaries
(01:09:13) - On trusting others
(01:12:03) - The impact of athletics
(01:18:51) - Identity loss after sports
(01:22:17) - On leaving Stripe
(01:24:33) - Optimizing for good vibes
(01:26:55) - Communicating your value
(01:30:46) - What’s next for Brie?
(01:34:51) - Brie’s beautiful future
(01:39:38) - Who Brie is becoming

Key Takeaways

Writing Clarifies Your Thinking: Brie emphasizes the value of writing not only for others but primarily to clarify your own thoughts. She recommends setting high expectations by imagining you’re writing for someone you admire, which pushes you to articulate your ideas more clearly.
Embrace Defiant Joy: Brie talks about the importance of becoming “defiantly and joyfully” oneself, especially in creative work. It’s about embracing authenticity, pushing back against norms when necessary, and doing so with optimism and excitement rather than angst.
Use “The Tuning Fork of Resonance”: Writing and thinking through ideas by discussing them with others acts like a “tuning fork” to see what resonates. Brie values feedback from people she respects, which helps refine her ideas and improve her work.
Form Your Own Conclusions About the AI Landscape: The rapid advancement of AI has been unsettling for Brie. She shares that it’s a time of absorbing information, reflecting, and processing before forming solid conclusions, illustrating the importance of allowing yourself space to think in uncertain times.
Taste is a Virtue: Both Brie and Barrett discuss how refining your taste in things—whether it’s design, writing, or even coffee—can lead to a deeper sense of satisfaction and connection with your work. There’s a joy in learning from experts or “connoisseurs” in any field, appreciating their mastery and process.

Quotes

“The kind of writing I've found that I do is mostly to clarify my own thinking on something. So I think [writing to] a high-expectation stranger works for that. Our friends love us because they're tolerant of our weirdnesses and all the things that make us meander or not make that much sense. But I think speaking to this high-expectation stranger helps me meet that bar of, ‘have I clarified this sufficiently for the right person’.” ~ Brie Wolfson

“I'm feeling defiantly and joyfully myself. And I know that's happening when I can push back on stuff, but it doesn't make me angsty. The non joyfully and defiantly Brie is sort of angsty and wants to grumble about everything. And I think that's when I notice I'm not in the right space.” ~ Brie Wolfson

“Twitter is tapping a tuning fork and seeing what resonates. I very much like thinking through, talking through, and writing through feedback. I want that bi-directional thing going.” ~ Brie Wolfson

“The AI landscape is really throwing me for a loop. It’s just super fast. I’m not sure I totally understand the underpinnings of it all. I’m still marinating.” ~ Brie Wolfson

“If you refine what you like and then you find a way to get it, you are just at harmony in the world. When it’s right, it’s like bliss.” ~ Brie Wolfson

“There’s a real joy in beholding a connoisseur. I think curation is such an important new part of creation now.” ~ Brie Wolfson

Links