35: Brie Wolfson - Loving Attention & Ease in Craft

Brie introduces the concept of 'finger feel' - a visceral, ground-level understanding of quality that comes from time and reps. She discusses how great leaders like Patrick Collison and Dylan Field are 'fork-shaped,' going deep on many things rather than just broad or T-shaped, and why nothing can get by them because they're willing to engage with details directly.

• •Developing finger feel requires time on the ground level - there are no shortcuts to this kind of mastery
• •Great leaders are 'fork-shaped': they can go deep on many different vertical slices rather than being broadly shallow
• •Pattern matching happens differently when you engage with raw details versus summaries - reading full LinkedIn profiles vs spreadsheets reveals different insights
• •The shift from briefings to direct engagement: leaders who source on LinkedIn themselves vs reviewing candidate summaries
• •Competence and the ability to 'know how to do shit' is deeply attractive in collaborators and leaders

Discussion of how craft evolves when AI can automate many tasks. Brie explores the tension between efficiency and the creative process, sharing how she's naturally high on Myers-Briggs P (process-oriented) and finds satisfaction in the grind work rather than just hitting a button for results. The conversation touches on whether craft can be automated and what that means for organizational leverage.

• •Elon's approach: understand the process deeply first, then automate - don't automate what you don't understand
• •Taste develops as 'unconscious competence' (Tammy Winter/Cedric Chin definition) - requires going through conscious competence first
• •Management philosophy: 'do it before you manage it' - direct experience is essential before delegation
• •Once you develop finger feel in one domain, it becomes easier to spin up faster in new areas - the skill of developing craft is transferable
• •Being naturally process-oriented (high P on Myers-Briggs) means finding satisfaction in the work itself, not just outcomes

Brie's philosophy on marketing centers on closing the gap between what is true about a company and what the world perceives. She explains why she only works for underrated companies with substance, viewing her role as helping great craft and leadership become more visible rather than creating hype around mediocrity.

• •Core marketing philosophy: 'people read bullshit pretty fast' - authenticity is essential
• •The best marketing work happens when there's a wide gap between reality and perception for genuinely great companies
• •Would never work for an overhyped brand - always seeks underrated companies with real substance
• •Even highly-rated companies like Stripe, Figma, and Cursor are still underrated in important ways
• •Marketing requires simultaneously being understood AND cutting through noise - these are in tension
• •Silicon Valley has evolved to honor marketing as its own craft discipline, not just product storytelling

Exploration of how companies are fundamentally restructuring around empowered individual contributors rather than management hierarchies. Brie shares her experience at Cursor learning to ship without approvals, the challenge of breaking learned helplessness around dependencies, and concerns about losing collaborative overlap moments when everyone works independently.

• •'Dependencies kill productivity' - learned helplessness around approvals and sign-offs is a major barrier
• •At Cursor, the careers page project revealed deep anxiety about shipping without multiple approvals - had to unlearn corporate habits
• •Risk of pure IC culture: missing the Venn diagram overlap moments where high-craft people collaborate to create novelty
• •Example of effective collaboration: working with designers with 'both hands on the baton the whole way through' rather than baton-passing
• •Remote work makes everything intentional, losing serendipitous creative moments - in-person proximity enables better collaboration
• •The new expectation: ICs must be able to produce output independently, not just coordinate others' work

Deep dive into what makes great company cultures, including the importance of doing work 'for the audience of yourself' and how values should reflect actual behavior. Brie discusses Stripe's 'we haven't won yet' value as a filtration system for humility, the privilege of seeing colleagues' work at all-hands, and the emerging concept of internal product-market fit.

• •The only commonality across great companies: they want to be great companies themselves, not just great products
• •Good values are things you would actually say or ways you would actually behave - most company values are boring and meaningless
• •Stripe's 'we haven't won yet' worked as a filtration system - had to acknowledge humility before bragging
• •All-hands and internal comms are privileges to see colleagues' work, not just 'meta-work' - underinvested channel for brand
• •Internal product-market fit: shipping to internal version first, judging validity by Slack reactions from colleagues
• •In bottoms-up cultures, internal marketing becomes crucial - convincing engineers to work on enterprise features requires selling the vision internally

Discussion of whether traditional planning functions still matter when companies can move so fast. Brie reflects on building Stripe's planning function when it was 'risky' and counter-cultural, and how planning can help with non-urgent but important work and shifting company inertia toward new customer segments.

• •Billie Eilish Vanity Fair video as metaphor for AI-era company building: one year is infinite time, constant naivety about how much will change
• •Planning wasn't an accepted concept at Stripe initially - felt off-culture, like a 'Rube Goldberg machine of spreadsheets'
• •Planning's remaining value: carving out time for bigger swings and exploratory work, preventing 'little feature wars'
• •Holding a mirror to help companies shift inertia - example of Cursor needing to think differently about enterprise vs startup developers
• •If companies can move faster and be more iterative, long-horizon planning becomes less critical
• •Some fundamentals don't change - on long enough timelines, companies realize planning's value

Brie explores what creates morale in organizations, defining it as genuine enthusiasm and fun rather than manufactured motivation. She introduces the concept of 'loving attention' - the specific kind of invested feedback that pushes work to excellence, distinguishing it from generic praise or LGTM culture.

• •Morale is about having fun and genuine enthusiasm - 'you can't compete with somebody having fun'
• •Loving attention vs loving space: seeking invested feedback from people who want your work to be better, not just approval
• •The 'skinny mirror' concept (Patrick O'Shaughnessy): holding up a mirror that shows people's best version, helping them articulate greatness
• •LGTM culture is damning - 'looks good to me' signals disengagement rather than invested attention
• •Stripers DMing typos is a sign of loving attention - they actually read the work carefully
• •Motivated by imagining admired people's gaze on work - still imagines Patrick Collison reading her writing after nearly a decade

Brie discusses her unconventional career path of picking up work 'in the crannies' - problems that don't clearly belong to anyone. She shares the lesson that operators must excel at their core role before earning permission to explore, and how she had to do ops work to eventually earn the right to focus on storytelling full-time.

• •Working in the crannies works when you have a nose for problems that aren't currently important but will be
• •Must excel at core role first - got to do special projects at Stripe because account management book was performing well
• •Spent years doing ops work to earn the right to focus on storytelling - had to prove could 'get shit done' before creative work was trusted
• •Six years ago, 'head of storytelling' was dismissed as cute - now there's real enthusiasm and permission for story-focused roles
• •Zero-to-one temperament and willingness to give away LEGOs makes cranny-work sustainable
• •Operators underestimate this: first question in promotion discussions is always 'how are they doing at the core role?'

Reflection on the Flounder Mode essay and Kevin Kelly's perspective that greatness is overrated. Brie distinguishes between Kevin's complete indifference to external validation and her own journey toward 'ease in craft' - knowing her value without needing it to be called 'magic' or illegible.

• •Not chasing Kevin Kelly-style greatness (running companies, history books) - seeking ease in craft as lifelong pursuit
• •The illegibility of her career has been a source of anxiety, not confidence - the 'head of storytelling' rejection at 27 was painful
• •Kevin Kelly's ease comes from complete indifference to validation - 'does not compute' when asked if audience needs to validate
• •Wants work to be seen as real and legible, not dismissed as 'Brie magic' - magic feels dismissive rather than kind
• •Earliest memory: being the only kindergartner who said 'hate to lose' instead of 'love to win' - inherently competitive
• •The right mix: hate to lose AND love to win, combined with locker room energy - competition can be fun

Discussion of taste as discernment and curation, the challenge of maintaining stillness in an era of infinite content, and the aesthetic of hustle culture manifesting as constant Slack activity and edited messages. Brie reflects on being shaped by a pre-Slack era and how that gives her different habits around stillness.

• •It's really hard to sit still right now - infinite content fills every unit of time (TikTok, tweets, blog posts)
• •Hustle culture manifests as feeling behind on reading, not seeing the latest, constant AirPods-in-on-walks consumption
• •Slack behavior as aesthetic: constant messages, many edited after sending, 'receipts' of being at desk
• •Benefit of timing: worked before Slack existed (HipChat/G Chat era), built stillness habits that still work
• •Knowing that stillness and walks work, but still forgetting - easier to be fidgety
• •The challenge for younger workers: harder to train yourself that stillness works when you've never experienced work without constant connectivity