Brie Wolfson

Brie Wolfson, CMO of Positive Sum and Colossus and co-founder of Stripe Press, shares her journey through 'Flounder Mode,' a playful term for career paths driven by curiosity. She discusses her mentorship experience with Kevin Kelly, exploring his profound influence on her creative journey. Brie reflects on the challenges of navigating a non-linear career while comparing it to her peers' more structured paths. The conversation highlights the importance of storytelling, innovative workplace dynamics, and the value of genuine connections in personal growth.

Our guest today is Brie Wolfson. Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams.In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list. Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work. We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales. Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact.You can follow Brie on Twitter @zebriezYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson