In Depth

From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson


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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 @zebriez


You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

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