Brie Wolfson
Writer and editor, helped found Stripe Press
Where to hear and read about Brie Wolfson1 episode or test
Brie Wolfson is a writer and editor who worked behind the scenes at Figma and Stripe and basically founded Stripe Press. The thing most worth learning from her is her editing method: write for one real person, cut hard with taste, and fund the last 20% of polish.
You have to find a place to fund the last 20% or else you're never going to get it.
The Art of “Taste” — Brie Wolfson
Brie Wolfson: the story and the lessons
1How Brie Wolfson started Stripe Press
Stripe Press began as the job of getting one book to every customer. Stripe's president, John, loved a manuscript that became Elad Gil's High Growth Handbook and wanted every user to have it. Wolfson had to source paper, find a printer, create a design language and sell physical products for the first time.
That infrastructure put them about 80% of the way to a second book, so they ran a four-book experiment.
Wolfson thought the press was her idea, but it was already Stripe's strategy. Tyler Cowen was one of the first four authors. He and Patrick had discussed a press for a long time.
Wolfson paid for physical details most readers only feel. Lay-flat binding uses give-y threads instead of glue on the spine, because glue pulls the pages back at the edges, and it costs more. The cover stock is colored all the way through, so corners can bend in a backpack and still look good.
She uses these as proof that reality holds a surprising amount of detail worth noticing.
2Why Wolfson treats writing as a way to think
Wolfson says clear writing is how you get clear thinking. She writes a lot she never intends to publish, just to understand herself, and occasionally a thread worth pulling comes out of it.
"You can get clear in your thinking by getting clear in your writing."
At Stripe, writing let ideas travel without meetings. Internal pieces such as a quarterly business review, a friction log on one flow, or a take on a topic were published to the whole org. Every email was copied into a group anyone could read, though she notes that policy may have changed since.
She traces Stripe's writing culture to its reading culture. The cost was that Stripe sometimes felt over-rotated on contemplation while looking fast from outside.
Wolfson believes some arguments are settled by building, not writing. She compares writing to a survey of what people would do and doing to watching them do it. When two values conflict, such as speed and quality, she suggests starting to build and seeing where you land.
She links this to a Facebook value along the lines of code settles arguments.
Wolfson says an editor's main job is remembering what the reader knows. Helping people write Stripe shipped emails, she asked what the story was and what interested them. People deep in a project forget what is interesting about it.
She borrows from fiction, where the author knows the whole plot and the reader knows none of it. "The thing people need most help with is just remembering what somebody else knows."
Writing keeps an idea steady where speech drifts. Her answer to Emergent Ventures' question about a consensus view she agrees with was that not even a simple message can survive a game of telephone.
She tested it with her much younger sister, and even a simple phrase broke down.
3Brie Wolfson's editing stack
Wolfson records herself reading drafts aloud and plays them back. Hearing the draft exposes sentences that do not sound like her. If she stumbles saying a line, she takes it as a sign something is wrong with the text.
She says it works better than reading silently and translating in her head.
Wolfson keeps a Darlings doc for lines she loves but cuts. A paragraph that no longer fits goes into the doc instead of the trash, and she rereads it now and then as a pump-up.
"I like having a place for cut stuff to go." A home for cut material makes cutting easier.
Wolfson compares her draft to paragraphs she loves. She keeps a note in Evernote of favorite paragraphs, and some live in her head from rereading. When a draft feels off, she asks what she likes about their vibe that hers lacks.
She reads a lot while writing a lot so good words keep flowing in.
Wolfson runs a positive-negative meter on her drafts and asks why. She borrows George Saunders' idea of marking everything yes or no, then works out why a line works or fails and how to move it somewhere better.
Putting words to why you like or dislike something is the hard part and takes time. It is the same process as cultivating taste.
Wolfson gets edited in person and bounces drafts off many people. She will not publish anything without feedback and prefers talking drafts through over comments in a doc. Her first-draft-to-final-draft overlap is now about 0%.
She once wanted her first draft to survive. A high school teacher's line that great writers edit eight times more than they write sounded inefficient to her then.
Wolfson wants editors who are critics and appreciators, not curmudgeons. She wants editors who look for the spark and pull it out. Curmudgeons treat everything as trash, which she finds exhausting.
She points to Harold Ross and Steve Jobs, who said no often but celebrated when something was right.
Wolfson writes huge volume and wades through the sludge. She sides with Seinfeld's view that it is a matter of tonnage: produce a lot, say no to most of it. Mid-draft she feels she is doing badly and only sees the progress when she explains it to someone.
Her tip is to reward yourself after the hard work.
Wolfson says polish only happens if you fund the last 20%. Stripe spent a whole extra week on a launch blog post, which was time not spent building. For an early writer she suggests a boss who allows it or a full Sunday.
She notes many people want polished outcomes but will not fund the hard work.
4How Wolfson makes writing memorable
Wolfson writes for one specific person with a face. She often pictures Stewart Brand and asks whether he would get a twinkle in his eye or go to sleep. Writing for a faceless audience gives a view from nowhere and a timid teacher voice.
She says brilliant speaking friends send her fact-heavy writing with no humanity until they picture a person.
Wolfson cuts to the best bits instead of covering everything. She cites Harold Ross trading biographical completeness for humor and intrigue, and says a profile gets about three great anecdotes. A piece on hotels could follow only the walk from check-in to the key card.
"We don't need to know everything. We just need to know the best bits." Experts resist because they hate leaving out anything core.
Wolfson asks what question she is answering for the reader. Writing for yourself is a fine start. The next level is asking what you are helping the reader see.
She was inspired by a friend's warm pre-visit questionnaire about pillows and morning moods, and by Rilke's Letters to a Young Poet and Stegner's Angle of Repose.
Wolfson tells writers to lean into their weirdness. What cuts through often looks odd on the page and risks nobody liking it. Borrowed style, like a friend's borrowed joke, falls flat because it does not feel like you.
"Be your authentically weird self, that's why your friends love you, that's why your reader will love you."
Wolfson designs the packaging so readers arrive in the right mood. She notes Ross got the look of the New Yorker right before the content, and Tina Brown wanted it recognizable thrown on the floor and opened to a random page.
Wolfson learned this at Figma and spent a long time on the How I Write logo. She laments that Substacks all look alike.
Wolfson is clever only when it serves something true. A little clever is nice and too clever is annoying. Her bar is honest or true, and she keeps working a piece until it feels that way.
5How Brie Wolfson thinks about taste
A CEO's undefined hiring criterion sparked Wolfson's taste essay. A hire executed the spec perfectly on candidate-tracking software but chose the wrong implementation, and the CEO added taste to his criteria without defining it. Wolfson became obsessed.
She compares it to culture fit, which nobody could define before it was dropped.
Wolfson used numbered notes so a slippery word stayed unflattened. She borrowed the form of Susan Sontag's Notes on Camp, after a friend suggested it, and ended with 28 numbered beliefs. Her editor pushed her down from about 50.
The format made it easy to see which notes were not the core.
Wolfson tells people not to silence the sense that something is off. At work that Spidey sense gets switched off because it sounds ridiculous in a meeting. She says to listen and look for language for it.
Harold Ross had no style guide, only a writers' room where he said what he disliked, and the style emerged. Pinning taste to terms too early loses some of the magic.
Wolfson learns style from lowbrow and scientific sources too. She cites the word-and-image play of Captain Underpants, NASA's aspirational mission names, and the American Heart Association periodical called Circulation.
She says she is good at the long version of an idea and bad at naming it, so these show her how simple names can be.
Wolfson pairs high standards with the ability to say that's good. She says Jobs said "That's good" when he saw craft, and Ross got excited when he saw the right thing. Saying no a lot is fine if getting it right becomes a celebration.
Without the celebrating phase, she says, it's no fun.
The Art of “Taste” — Brie Wolfson
Brie Wolfson explains how writing forces clear thinking, and how to edit toward a voice that sounds human and notices things other people miss. The technique worth hearing is her editing stack: record yourself reading the draft aloud, keep a Darlings doc for cut lines, and write for one real person with a face.
Stripe Press began as the job of getting one book to every customer. Stripe's president, John, loved a manuscript that became Elad Gil's High Growth Handbook and wanted every user to have it. Wolfson had to source paper, find a printer, create a design language and sell physical products for the first time.
That infrastructure put them about 80% of the way to a second book, so they ran a four-book experiment.
Wolfson thought the press was her idea, but it was already Stripe's strategy. Tyler Cowen was one of the first four authors. He and Patrick had discussed a press for a long time.
Wolfson paid for physical details most readers only feel. Lay-flat binding uses give-y threads instead of glue on the spine, because glue pulls the pages back at the edges, and it costs more. The cover stock is colored all the way through, so corners can bend in a backpack and still look good.
She uses these as proof that reality holds a surprising amount of detail worth noticing.
Wolfson says clear writing is how you get clear thinking. She writes a lot she never intends to publish, just to understand herself, and occasionally a thread worth pulling comes out of it.
"You can get clear in your thinking by getting clear in your writing."
At Stripe, writing let ideas travel without meetings. Internal pieces such as a quarterly business review, a friction log on one flow, or a take on a topic were published to the whole org. Every email was copied into a group anyone could read, though she notes that policy may have changed since.
She traces Stripe's writing culture to its reading culture. The cost was that Stripe sometimes felt over-rotated on contemplation while looking fast from outside.
Wolfson believes some arguments are settled by building, not writing. She compares writing to a survey of what people would do and doing to watching them do it. When two values conflict, such as speed and quality, she suggests starting to build and seeing where you land.
She links this to a Facebook value along the lines of code settles arguments.
Wolfson says an editor's main job is remembering what the reader knows. Helping people write Stripe shipped emails, she asked what the story was and what interested them. People deep in a project forget what is interesting about it.
She borrows from fiction, where the author knows the whole plot and the reader knows none of it. "The thing people need most help with is just remembering what somebody else knows."
Writing keeps an idea steady where speech drifts. Her answer to Emergent Ventures' question about a consensus view she agrees with was that not even a simple message can survive a game of telephone.
She tested it with her much younger sister, and even a simple phrase broke down.
Wolfson records herself reading drafts aloud and plays them back. Hearing the draft exposes sentences that do not sound like her. If she stumbles saying a line, she takes it as a sign something is wrong with the text.
She says it works better than reading silently and translating in her head.
Wolfson keeps a Darlings doc for lines she loves but cuts. A paragraph that no longer fits goes into the doc instead of the trash, and she rereads it now and then as a pump-up.
"I like having a place for cut stuff to go." A home for cut material makes cutting easier.
Wolfson compares her draft to paragraphs she loves. She keeps a note in Evernote of favorite paragraphs, and some live in her head from rereading. When a draft feels off, she asks what she likes about their vibe that hers lacks.
She reads a lot while writing a lot so good words keep flowing in.
Wolfson runs a positive-negative meter on her drafts and asks why. She borrows George Saunders' idea of marking everything yes or no, then works out why a line works or fails and how to move it somewhere better.
Putting words to why you like or dislike something is the hard part and takes time. It is the same process as cultivating taste.
Wolfson gets edited in person and bounces drafts off many people. She will not publish anything without feedback and prefers talking drafts through over comments in a doc. Her first-draft-to-final-draft overlap is now about 0%.
She once wanted her first draft to survive. A high school teacher's line that great writers edit eight times more than they write sounded inefficient to her then.
Wolfson wants editors who are critics and appreciators, not curmudgeons. She wants editors who look for the spark and pull it out. Curmudgeons treat everything as trash, which she finds exhausting.
She points to Harold Ross and Steve Jobs, who said no often but celebrated when something was right.
Wolfson writes huge volume and wades through the sludge. She sides with Seinfeld's view that it is a matter of tonnage: produce a lot, say no to most of it. Mid-draft she feels she is doing badly and only sees the progress when she explains it to someone.
Her tip is to reward yourself after the hard work.
Wolfson says polish only happens if you fund the last 20%. Stripe spent a whole extra week on a launch blog post, which was time not spent building. For an early writer she suggests a boss who allows it or a full Sunday.
She notes many people want polished outcomes but will not fund the hard work.
Wolfson writes for one specific person with a face. She often pictures Stewart Brand and asks whether he would get a twinkle in his eye or go to sleep. Writing for a faceless audience gives a view from nowhere and a timid teacher voice.
She says brilliant speaking friends send her fact-heavy writing with no humanity until they picture a person.
Wolfson cuts to the best bits instead of covering everything. She cites Harold Ross trading biographical completeness for humor and intrigue, and says a profile gets about three great anecdotes. A piece on hotels could follow only the walk from check-in to the key card.
"We don't need to know everything. We just need to know the best bits." Experts resist because they hate leaving out anything core.
Wolfson asks what question she is answering for the reader. Writing for yourself is a fine start. The next level is asking what you are helping the reader see.
She was inspired by a friend's warm pre-visit questionnaire about pillows and morning moods, and by Rilke's Letters to a Young Poet and Stegner's Angle of Repose.
Wolfson tells writers to lean into their weirdness. What cuts through often looks odd on the page and risks nobody liking it. Borrowed style, like a friend's borrowed joke, falls flat because it does not feel like you.
"Be your authentically weird self, that's why your friends love you, that's why your reader will love you."
Wolfson designs the packaging so readers arrive in the right mood. She notes Ross got the look of the New Yorker right before the content, and Tina Brown wanted it recognizable thrown on the floor and opened to a random page.
Wolfson learned this at Figma and spent a long time on the How I Write logo. She laments that Substacks all look alike.
Wolfson is clever only when it serves something true. A little clever is nice and too clever is annoying. Her bar is honest or true, and she keeps working a piece until it feels that way.
A CEO's undefined hiring criterion sparked Wolfson's taste essay. A hire executed the spec perfectly on candidate-tracking software but chose the wrong implementation, and the CEO added taste to his criteria without defining it. Wolfson became obsessed.
She compares it to culture fit, which nobody could define before it was dropped.
Wolfson used numbered notes so a slippery word stayed unflattened. She borrowed the form of Susan Sontag's Notes on Camp, after a friend suggested it, and ended with 28 numbered beliefs. Her editor pushed her down from about 50.
The format made it easy to see which notes were not the core.
Wolfson tells people not to silence the sense that something is off. At work that Spidey sense gets switched off because it sounds ridiculous in a meeting. She says to listen and look for language for it.
Harold Ross had no style guide, only a writers' room where he said what he disliked, and the style emerged. Pinning taste to terms too early loses some of the magic.
Wolfson learns style from lowbrow and scientific sources too. She cites the word-and-image play of Captain Underpants, NASA's aspirational mission names, and the American Heart Association periodical called Circulation.
She says she is good at the long version of an idea and bad at naming it, so these show her how simple names can be.
Wolfson pairs high standards with the ability to say that's good. She says Jobs said "That's good" when he saw craft, and Ross got excited when he saw the right thing. Saying no a lot is fine if getting it right becomes a celebration.
Without the celebrating phase, she says, it's no fun.