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

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.