Brie Wolfson is a writer and editor who helped found Stripe Press and has worked at companies like Figma and Stripe, where she developed a reputation for care, craftsmanship, and quality in writing. This episode explores how she thinks about writing, editing, taste, and how to put personality into work.
Writing as thinking and organizational tool
At Stripe, writing served two main purposes: clarifying one’s own thinking and creating artifacts that spread ideas across the organization without requiring meetings or one-on-ones.
Stripe had an open email policy where emails were CC’d into groups anyone could read, making thinking visible org-wide.
Brie distinguishes between routine work writing and what she calls a “curation layer” on top: things like quarterly business reviews, friction logs, or reflections published into the org for others to read.
The downside of a strong writing culture is that it can create an unhealthy relationship between thinking and doing, where people over-contemplating or pontificate instead of just building and learning from the result.
Stripe Press
Stripe Press started when Stripe’s president John Collison received a manuscript (Elad Gil’s High Growth Handbook) and wanted to send it to every Stripe customer. Brie was tasked with turning it into a physical book, which meant building sourcing, printing, and design infrastructure from scratch.
After completing one book, they realized they were 80% of the way to being able to publish more, so they ran an experiment with four books. It turned out to be an unexpectedly powerful talent brand: many people said they joined or got excited about Stripe because of the books.
The books were designed with obsessive attention to physical detail. They use lay-flat binding (threaded, not glued to the spine) so they stay open flat on a table. The covers use impregnated paper stock dyed all the way through, so wear and tear doesn’t reveal white edges. The saturated accent colors were chosen so the books would still feel vibrant after being carried in backpacks and taken to coffee shops.
Brie sees her superpower as strapping herself to thinkers and tinkerers and pulling out what’s interesting, functioning as an internal editor who helps people tell the story of their work.
The craft of editing and writing less
A recurring theme is that experts struggle to remember what their audience doesn’t know. Brie draws on fiction writing: authors must constantly calibrate what the reader knows at each point, avoiding both over-explaining and under-explaining.
Harold Ross, founder of The New Yorker, was known for being a maniacal editor who couldn’t articulate his values in words but was endlessly obsessive about tone and style. He revered his artists and creatives, gave them real space, and was willing to say no to almost everything until he found the right thing.
Ross was passionate about profiles but not interested in biographical completeness. He preferred humor and intrigue, sacrificing full scope for a more interesting piece. Brie notes this is a lesson for all writing: we don’t need to know everything, just the best bits.
The cardinal mistake Brie sees in students is trying to write about too much. Narrower scope makes it easier to go deep and be memorable. She gives the example of writing about hotels through the single prism of the check-in experience rather than trying to cover everything.
Brie’s editing process includes: recording herself reading her writing aloud and listening back (which catches things that feel weird spoken that don’t show up on the page), maintaining a “Darlings” doc where she saves cut paragraphs she’s attached to, and seeking in-person feedback rather than just doc comments.
She draws an analogy to athletes watching game film: there’s comfort in watching yourself at work, being critiqued, and iterating. The combination of self-review and coaching from someone who knows what great looks like is powerful.
She reads her favorite paragraphs over and over, keeping them in an Evernote, and returns to them when something feels off in her own writing to recalibrate her sense of vibe and rhythm.
Writing to one person
Brie strongly advocates writing to a specific, real person rather than an abstract audience. She often imagines Stewart Brand, someone she describes as smart, funky, and high-low, as her reader.
She contrasts this with what she calls the “view from nowhere” writing that has become common, especially on platforms like Substack and Twitter, where people write for an audience of one (themselves) without thinking about what the reader gets from it.
She points out that many of the greatest books in history are structured as letters from one person to another (Rilke’s Letters to a Young Poet, Stegner’s Angle of Repose), and that intimacy between writer and reader is something worth cultivating.
A story she loves: a friend’s wife in Alabama sent her a questionnaire about her preferences as a guest that was so warm, funny, and well-written that Brie felt like the woman was sitting right next to her laughing. It’s an example of caring deeply about your reader.
Taste
Brie’s piece on taste was sparked by a CEO who added “taste” to his hiring criteria after someone executed perfectly on a spec but still produced the wrong implementation. When Brie asked him to define taste, he couldn’t, which made her realize the term was being thrown around ubiquitously without anyone knowing what it meant.
She structured the piece as a numbered list of observations, directly inspired by Susan Sontag’s Notes on “Camp”, because taste was too slippery a concept to force into a single narrative. She started with around 50 observations and an editor helped her curate down to the best ones.
Fran Lebowitz’s concept of connoisseurship: the reason theater was so good in the 1970s was that audiences had high expectations, which forced artists to deliver. Being a good consumer, someone who really thinks about what they’re ingesting, is part of cultivating taste.
George Saunders’ idea of running a positive-negative meter on everything, noticing what you like and don’t like, and over time putting language to your emotional landscape. This is the same process as editing: evaluating what’s working and what isn’t, then understanding why.
Susan Sontag argued taste is domain-specific (vertical in lanes), but Brie thinks the practice of cultivating taste has knock-on effects: it makes you more observant, more appreciative, and helps you see that everything in the world is a choice someone made.
Harold Ross never created a style guide for The New Yorker. The standards emerged over time through the editing process. Brie thinks there’s a temptation to pin things down too early, which can kill the magic. Sometimes you just know something feels off before you can articulate why.
Cultivating inspiration from unexpected places
Brie looks for inspiration in lowbrow and unexpected sources: children’s books like Captain Underpants (which she calls genius for its playfulness and mix of words and images), NASA mission names (aspirational and well-chosen), and the American Heart Association’s journal Circulation (clever naming).
She’s drawn to things that are simple, human, and relatable, and thinks writers too often limit themselves to highbrow sources in their own domain.
Cultures of excellence
When Brie first found Stripe, she could immediately tell it was different. She believes cultures of excellence require actively funding the last 20% of the work: giving people extra time on a launch blog post, hiring additional people for a big project, or accepting that other priorities will slip.
Many people want polished outcomes but won’t fund the time to get there. Her advice to early writers: find a place where the last 20% is funded, whether that’s a boss who gives you space or giving yourself an entire Sunday to write something.
Fiction’s influence on her nonfiction
Brie has written fiction and says the most important thing it taught her was that she could do a big project entirely by herself. Every word in her novel was hers, and it gave her a sense of ownership that’s hard to achieve in collaborative work.
Fiction also taught her to be very intentional about how she moves a reader through a story, controlling pacing and awareness of what the reader knows at each point.
She’s trying to beat some of the lyrical verbosity out of her business writing, but she thinks fiction gave her a sense of world-building and character that brings life to her nonfiction.
Volume, patience, and the pain of writing
Brie references Seinfeld’s principle of “tonnage”: producing a huge volume, saying no to most of it, and trusting that what’s left is great. She resonates more with this than with the “if it flows, let it rip” approach.
She describes writing as physically uncomfortable when she’s stewing on an idea, feeling unsettled until it’s sorted. Her median feeling while writing is “I am doing such a bad job.”
She only feels she’s made real progress after stepping away and talking to someone else, when she realizes how much depth and dimensionality she’s discovered through the process.
She rewards herself after hard writing sessions, a tip she attributes to the Seinfeld interview.
She cannot publish anything without feedback from others. She distinguishes between curmudgeons (who hate everything and are exhausting) and critics (who are great appreciators trying to find and pull out the spark). She wants critics.
She describes herself as an explainer rather than an original thinker, more like Einstein (explaining the world as it is) than Walt Disney (bringing new ideas into the world). Her writing is about curating and articulating what she observes and experiences.
