I discovered Zhengdong by way of his 2025 letter in which he describes his “compute theory of everything”, and feeling the wave of AI crash over him after working in the field for five years. It blew me away.

I talked to him about what it will take for the rest of the world to believe, how AGI is a moving target and we might better conceive of progress as simply: “the model does the eval,” and where all of this might leave us on the other side.

Full episode: transcript & links, Spotify, Apple, YouTube, X/Twitter. If you enjoy it, please share it with a friend.

Dialectic 53: Zhengdong Wang - Feeling the Wave

23 Lessons from Zhengdong

1. Follow questions whose endings you can’t see. Zhengdong enjoyed software internships, but after two or three months he could already see where it was going. Research felt like a better long-term game because of its expansive aperture: “[I] really, really want to find the answer.”

2. Don’t leave the weird thing unexplained. One of his favorite researcher archetypes notices an anomaly and keeps asking why: “you just keep going and asking, why is this weird?” Chase enough of them and you see patterns you couldn’t have planned to find. It’s the spirit of Laura Deming’s “The Rage of Research,” though he translates the rage gently: “just really wanting to know something.”

3. Knowing what to skip is learned, not stated. Zhengdong overcorrects every project: move fast and you skip things that mattered; examine everything and the field moves without you. There’s no rule for the balance between covering ground and going deep — “finding this balance is just something that you need to get a lot of reps in to improve at.”

4. Zoomed out, research is just choosing the eval. AI models are becoming “this super laser that once you focus it on something, it will be solved.” He thinks research resolves to creating a new evaluation, with the rest just optimizing numbers. Even recursive self-improvement is “just some kind of meta-search” that procrastinates the real question: what makes a good eval?

5. Know the conversation, think for yourself. Entry into a field runs through its discourse: “you just need to be part of the conversation, whatever that conversation is,” even when that means Twitter instead of journals. But knowing it is in service of independence: close enough to not miss the obvious, removed enough to have ideas that aren’t in everyone’s stream.

6. Automating the tasks doesn’t automate the job. Humans have struggled to assess job performance since the pyramids (“How many rocks did you place?”). Every time a tool swallows the specifiable part, the job reforms around what’s left: judgment, purpose, even how much joy you bring your colleagues. Automate the tasks and the work migrates to what the spreadsheet can’t capture.

7. We’ll build AGI before we can define it. From his 2023 letter: “I more and more see the world where we build a machine that people agree is AGI before we write some words that people agree defines AGI.” Defining it may even be “possibly hopeless”: humans have written books about distinctions for thousands of years. The machines will keep marching past goalposts and we’ll keep moving them.

8. Genius may just be very large search. AlphaGo’s Move 37 looked like genius intuition. Zhengdong’s suspicion: “Without having exhaustively done that search, it looks like genius to you. But if you had looked at all the millions of moves, then it’s sort of obvious.” Brute-forced creativity: first Go, then knowledge work, eventually invention.

9. Surpassing humans is not the same as understanding reality. AI may reveal that language and much of human intelligence are more statistically predictable & lower dimensional than we imagined. It’s possible AI speed-runs us and still hardly knows anything in the grand scheme.

10. Pick a test you know cold, then watch AI break it. It took Zhengdong five years of setting tests for himself—problems he knew well enough that models “can’t cheat on this in ways that I would know about”—and watching AI confound his predictions anyway. Felt conviction comes from evidence across time.

11. Let the future clarify the present. The only timeline change that mattered to him: “I used to think [AGI] wasn’t going to happen in my lifetime and now I think it is.” Whether that lands like a terminal diagnosis or like winning the lottery, the effect is the same: the petty things fall away, and “it just accelerates you asking the question of what do you value?”

12. Myth-making is part of technical progress. AI has powerful stories for attracting potential researchers: cure cancer, understand reality, join a world-historical project. But if researchers treat public storytelling as something beneath “real” work, they shouldn’t be surprised when society adopts other (doomer) stories they dislike.

13. Competition is a safety mechanism. He worries more about malicious humans misusing AI than machines escaping control. The second-order—and larger—risk is a loss of individual liberty. His solve: “if you want to prevent really serious power concentration, there just needs to be a lot of competition.” It’s his deepest value surfacing as policy: “maybe pluralism is just the most highly prized value to me.”

14. If you don’t like who’s deciding, get involved. His answer to those who resent that a few labs are steering the future: “If you don’t like that big tech is deciding all these things, then just get involved.” One popular position is the incoherent one: calling it a scam while begging it to stop disrupting your field.

15. The universe is not running out of quests. Even if AI makes today’s work seem trivial, it won’t leave us with nothing to do, “we’ll just do everything faster. We’ll do more things, get even more niches, write even more fiction, and create even more universes for ourselves.” Better tools don’t exhaust the frontier; they expand it faster than we can reach it.

16. It matters because it’s hard. A machine may write something readers enjoy more. Writers and readers can still decide, together, that the human version is the one that counts. “The value comes from the fact that I spent a part of my short and precious life to write this thing for you, even if by some eval, it’s worse.”

17. Your friends want your answer, not the best answer. Your friends want to know your favorite flavor of ice cream, “not the LLM’s objective, optimal best flavor of ice cream.” The personal stays sacred because nobody else, human or synthetic, ever gets to have been you.

18. Are you having fun? After hearing more theories of research taste than he can count, Zhengdong’s only contribution is a simpler question.

19. Take the break. Humans need unfilled time to think; packing every day end-to-end can replace thought with noise. On an exponential, today is the least powerful these tools will ever be, which makes it the best moment to step away. Practically, “you could vacation for a year and come back, and your $20 a month subscription to AI will just be 10 times more effective.”

20. Produce so they let you consume. Zhengdong borrows Tyler Cowen’s line. The most rarefied experiences are priced in production: the room, the people, the napkin with the presidential seal on Air Force One. Be a part of making something great and you get to be there.

21. You can’t plan ahead, so plan very far ahead. The near future is too volatile to forecast, so aim at a horizon where the brittle details fall off and only what won’t change survives. “Who am I going to be 12 years ahead?”

22. Give yourself a vessel to fill. Zhengdong’s annual letter is the only deadline he gives himself every year. It makes him more observant, nudges him toward more interesting experiences, and leaves him catching himself thinking “this will be good for the bit.”

23. Be both the hedgehog and the fox. Isaiah Berlin’s hedgehog knows one big thing; the fox knows many. Zhengdong’s most repeated answer in this conversation is a refusal to choose. Depth or breadth, fast or careful, explore or exploit: “everyone should really be both at the same time. Always.”

Description

Zhengdong Wang (Website, X, LinkedIn) is an AI researcher based in London.

He writes annual letters (inspired by Dan Wang), mainly about AI progress, and his 2025 letter blew me away and inspired me to meet him. In it, he describes his ‘compute theory of everything,’ and makes the case that it would be stranger if AI progress slowed down than if it continued. Put a different way, reading his letter helped me get closer to truly feeling the wave of AI progress.

It took Zhengdong a long time to become “AGI-pilled,” despite years of feeling like he was late to AI and working as a research engineer for the last five. I talked to him about what it will take for the rest of us to see what he sees, and feel what he feels. We also discuss why AGI may be a hazier target than simply seeing AI progress as “the model does the eval,” and why recursive self-improvement may be both happening and less fantastical than it may seem. ZD makes the case that based on the rate of progress and scaling, skeptics will simply be proven right or wrong soon. We talk a bit through what narrative and political challenges the AI industry faces ahead of this transition.

Then there are the implications of all of this—namely how AI progress accelerates the question of what we each value, how we will spend our time, and where we will find or create meaning. ZD takes a stab at some of those impossible questions and shares some other favorite miscellanea that is reflective of the range of his letters.

I hope this conversation helps you feel the wave a bit yourself, and that you remember that, regardless of how much change lies ahead, we still get to make our meaning. We get to choose.

Full transcript and all links: dialectic.fm/zhengdong

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:16) Intro to Zhengdong & Thanks to Notion

• (4:33) Start: Why Research: “I Just Want to Know”

• (12:25) The Model Does the Eval: AGI as a Moving Target, RSI, and Laser Beams

• (33:17) The Compute Theory of Everything and Feeling the Wave

• (53:17) The Myths AI Needs, Competition vs. Power Concentration, and Whether Progress Is Inevitable

• (1:13:42) “Who Could Possibly Compete?”: Post-AGI Meaning, Work, and Questing

• (1:29:28) Are You Having Fun? Vacations, Mattering, and How to Live

• (1:47:13) Annual Letters, Economist Obituaries, London, and Burke

• (2:06:33) Closing & Thanks to Notion

Links & transcript: https://dialectic.fm/zhengdong

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If you enjoy it, please share with a friend and rate / review wherever you listen.

Available on Dialectic.fm (transcript), Spotify, Apple, YouTube, Twitter/X, and LinkedIn.

Dialectic 52: Jack Conte - Draw the Next Page

22 of My Favorite Lessons from Jack

1. Stop polishing your B-minus. Early on, Jack chose a pure growth mindset, hammering at everything he was bad at, until he hit the ceiling: a year or two might drag a weakness from B-minus to B-plus. Now, he hands that work to someone excellent and pours more of himself into the few things he thinks he can uniquely crush—and more importantly, the things that give him energy.

2. Prolificacy needs an operating system. Jack made 100 music videos a year while running Patreon by turning one weekend a month into eight recorded songs, then letting production teams carry them across the finish line. Meanwhile, his Chief of Staff Nicole keeps everything in check across Patreon and life. What resembles impossible stamina online is often excellent operations backstage.

3. Get post-chaos. Many people read chaos as a sign of failure, something to fix. Jack accepts it as the baseline of life and company-building: disorganization, changing schedules, changing priorities, and the feeling that things are always a little stretched. He’s getting better at relaxing into that instead of waiting for a calm that isn’t coming.

4. Burnout can be five solvable problems in a trench coat. Jack’s worst lows usually turn out to be a few gnarly problems arriving together, impersonating the end of the road. His method is to separate facts from the stories in his head, write crisp problem statements, then take the first three plausible actions against each one until a path reappears. He’s learned not to trust the permanence of emotions: sometimes all is lost until he has a snack and realizes it was low blood sugar. “I don’t want to be Charlie Brown again.”

5. Your most joyful work may not be your most meaningful work. Making music gives Jack such immediate, bodily joy that he can disappear into Ableton for six hours and forget to eat or use the bathroom. Patreon’s daily work is nowhere near as pleasurable, but its creator-focused mission gives him immeasurable meaning and purpose.

6. Art carries a feeling. Content carries an objective. Most work lives in a wide spectrum, but at the ends, Jack thinks content is made to produce an intended result, while art begins with something the artist felt and wanted another person to feel. The same film can therefore be art to its director and a means to subscriber growth for Netflix’s infinite content machine.

7. Every artist has a different appetite for business. Jack and Patreon sort creators into three personas: the purist who just wants to play guitar, smoke weed, and be left alone; the operator who’ll handle the business work because it unlocks the life they want; and the builder whose eyes light up at the machinery itself—who says “I’m a media company” and studies exactly where the New York Times greys out its paywall.

8. Getting paid is the opposite of selling out. Many artists worry that making money off their work makes it dirty. Jack calls that backwards, because asking to be paid is knowing you made something of value and wanting to build a future where you can make more. He thinks selling out is doing something other than making art.

9. Don’t let the dashboard tell you what your work is worth. For twenty years, platforms have taught artists to read revenue per view as a verdict of value. Jack doesn’t buy it: when three million views pays eighteen dollars, the number is measuring the system’s extraction, not the art’s worth. He hates the term “influencer” because it names only the monetizable part of a person—their reach—and turns artists into commodity suppliers of eyeballs.

10. The history of art is direct support. For most of history, art did not run on ads, feeds, or subscriptions to infinite libraries. It ran on patronage: churches, governments, and rich people saying, “I like what you make; here’s a bag of coins, go make more.” Recording tech let art hitch a ride on scarce physical objects for a century, then the internet erased the scarcity, and that model collapsed. Jack sees Patreon as a return: direct support, now distributed across individuals instead of concentrated in institutions.

11. Free wins distribution. Artists pay the difference. Free experiences helped the internet reach billions of people, but a system solely optimized for the consumer keeps pushing art toward all-you-can-eat abundance at ten dollars a month. Patreon exists to muscle in the opposite direction, and its primary KPI is not attention, engagement, or subscriber growth. It’s dollars sent to creators.

12. Align incentives before asking for trust. Patreon’s take-rate model means the company succeeds when creators get paid. Values matter, but they are easier to uphold when the economics point in the same direction.

13. Buy the hot dog factory. When Costco could no longer source its famous hot dog cheaply enough to preserve the $1.50 price, it rebuilt the supply chain instead of breaking its promise. Jack sees trading short-term revenue for long-term trust the same way, because he wants Patreon fighting for artists a hundred years after he’s dead.

14. Some forms of capital don’t fit the spreadsheet. In tech, the product is the thing, and even Jack concedes that. But brand, narrative, creativity, and storytelling can matter even when they don’t show up cleanly in the P&L. Companies that only believe what they can cleanly attribute will struggle to earn what Jasmine Sun (Dialectic 49) calls other forms of capital: attentional, social, or cultural.

15. Remember which audience matters. Patreon is Jack’s first real job, and he entered technology from music and YouTube rather than through the Valley’s usual doors. He thinks Patreon is partly dismissed in tech because it has spent thirteen years building trust with creators instead of focusing on the insider tech audience and the engineers it might impress.

16. Say the thing you’re ashamed of. The best advice Jack has for making real fans comes from screenwriter Charlie Kaufman, who said to say who you truly are, out loud, especially the thing you are ashamed to admit. He points to Prince: Don’t like it, go away. The honesty that repels the wrong people is often what lets the right people recognize themselves.

17. Aim ambition outside yourself. Jack likes intensely ambitious leaders, but first asks where that force is pointed: toward individual advancement or the company’s mission. The related trait is what he calls the “passion muscle,” the capacity to fall in love with a customer, problem, or cause beyond yourself.

18. Fascination outlasts talent. For all his output, Jack doesn’t feel naturally talented. The first time he recorded his guitar, he assumed the equipment was broken; after reviewing the recording, he discovered the malfunction was him. What kept him going was not conviction that he was gifted, but an obsessive desire to understand how the music was made.

19. You better be proud of what you upload. The internet has enough stuff. Jack once found publishing itself exciting, but the web has been saturated. He’s no longer interested in adding to it unless he feels deeply proud of the work and thinks it is unbelievably great.

20. Leave room for the thing you can’t explain. Jack is skeptical of extraordinary claims, yet music feels closer to the supernatural than anything else he has known. Like consciousness, it seems to occupy some aphysical, uncharted space: impossible to fully explain and impossible to stop exploring. For all his business-building, Jack’s deepest loyalty is still to that mystery.

21. Anxiety is a risk key. Lucid dreamers use reality checks to notice that they’re sleeping. Jack knows he tends to catastrophize, so he uses anxiety the same way: a cue that his risk meter may be miscalibrated, not proof that disaster is coming.

22. Draw the next page anyway. Thirteen years ago, as a full-time YouTuber and musician who’d never had a real job, Jack sketched plans for Patreon across fourteen sheets of printer paper. Despite feeling like a fool, he repeated aloud, “This isn’t going to work. That’s okay. Draw the next page.” The company began when he gave himself permission to feel stupid without putting down the pencil.

Description

Jack Conte (Patreon, YouTube, YouTube Pt2, X, LinkedIn) is the co-founder and CEO of Patreon. He is also a lifelong artist and musician, and releases nearly 100 music videos per year between his bands Pomplamoose (a duo with wife Nataly Dawn) and Scary Pockets (a funk collective), and was a longtime YouTuber.

Jack is not a tech CEO who happens to like music. He is an obsessive, prolific artist whose first conventional job is running Patreon. This has shaped him as a founder and executive, and his mission at Patreon is to build an enduring and truly creator-first company that empowers creators to earn a living from their work.

We began with how he manages to do it all, where his energy comes from, and what it’s like to be “post-chaos.” Then, we talked about art, content, and commerce, Patreon’s model (that isn’t actually pure patronage), and why Silicon Valley undervalues art, brand, and narrative — and Patreon. Jack shared the benefits of a business model that is fully aligned with creators, why he hates the word influencer, and why he’s still the right man for the job after 13 years of leading Patreon. We also covered what great leadership looks like, building fans and community, filmmaking, authenticity (from Charlie Kaufman to Prince), and remembering to take risks until the very end.

I hope you’re inspired to make things you are proud of and to draw the next page even when you have no business doing so.

While I have you: I’d strongly recommend Jack’s recent SXSW talk on AI, creativity, and change.

Full transcript and all links: dialectic.fm/jack-conte

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:38) Intro to Jack & Thanks to Notion

• (3:44) Start: Prolific Output, Energy, Juggling, Endurance, and Becoming Post-Chaos

• (22:04) Combining Creativity and Business and Art vs. Content

• (33:21) Advertising vs. Membership & Patronage vs. Patreon

• (44:06) Jack’s First and Only Job, and Silicon Valley’s Undervaluing of Creativity, Brand, and Storytelling (and Patreon)

• (55:17) Building for Creators First, Incentive Alignment, Trust, 100 Years of Patreon, and Why Jack is the Right CEO for Now

• (1:04:49) Leadership: Types of Ambition, Obsession, Self Reflection, Bias to Action, Learning from Others

• (1:12:59) Talent vs. Enthusiasm, Being Proud of What You Make, Making Fans and Being True, Managing Parasociality, and Community

• (1:28:30) Filmmaking, Labels and Collectives vs Individuals, Breaking Patterns, Creative Intimacy, Music, Patreon’s Origin, Persistence, Lucid Dreaming, and Taking Risks

• (1:49:26) Thanks Again to Notion

Links

• All links & transcript: https://dialectic.fm/jack-conte

• Spotify:

• Apple

• YouTube:

20 Lessons from Nan Ransohoff on Championing Orphaned Problems, Philanthropy’s Talent Shortage, and Refusing to Snap to Grid

1. Orphaned problems need owners. Nan gets nerd-sniped by important problems, then follows the rabbit hole until she finds the person responsible for seeing them through. With carbon removal, three weeks of calls exposed a strange void: lots of people were working in the field, but nobody felt responsible for delivering the outcome. If someone excellent has already stepped up, help them. If not, stop waiting: “Who else is going to do it?”

2. Go to war with the army you have. Nan was not a carbon-removal expert when she entered the field, and she is not a respiratory-infection expert now. She started anyway. Stripe’s first carbon purchase was $1M. Very small, but a thread. Even civilization-scale solutions have to start somewhere.

3. Marry the outcome, date everything else. A startup can begin with a thesis and pivot toward wherever the market leads. Nan’s GM philosophy begins with a specific change the world needs, then lets the strategy, organization, funding, and job description flex around it.

4. Find the altitude where you can grip the problem. “Finding the right problem and defining it at the right altitude is the whole thing.“ Too high and it’s an abstraction nobody can hold; too low and solving it barely matters. Decompose the mess into supply, demand, and ecosystem, and keep slicing until a piece becomes concrete enough to own and attack.

5. Dial up your inner Larry David. Good problem selection begins with annoyance. Find the thing that makes you say, “It’s crazy we’re still dealing with this.” Annoyance is underrated data: it points at what everyone else has learned to tolerate.

6. Choose a problem that fits your hands. Importance, tractability, and neglect matter, but Nan adds a more personal test: does it light you up, and can you see a lever you might actually pull? Governments were the obvious owner of a public good like carbon removal, but policy, in her words, didn’t feel “me-shaped.” Markets did, so she engineered the demand herself.

7. Vision is in short supply. We are fluent critics and strangely inarticulate when asked what should exist instead. Nan’s lunch-table prompt, “How would you spend a billion dollars on good things?” reveals a lot of not knowing in all of us. Even politicians rarely articulate a positive vision you could repeat back. The rare quadrant is optimistic and specific.

8. Think in decades. Plan the week. Frontier can hold the need for roughly a trillion tons of carbon removal over 150 years, a picture of what should be true by 2030, annual OKRs, and this week’s work all at once. The distant finish line supplies direction, while the weekly plan helps us put one foot in front of the other.

9. Invent the customer. Carbon removal companies had nobody to sell to, so builders wouldn’t build and investors wouldn’t invest. Nan’s team broke the deadlock with an advance market commitment: money waiting at the finish line for any company that could hit the spec. Sometimes the missing technology is demand itself.

10. Explore the space between the grant and the unicorn. If a world-changing outcome can support a durable business, Nan thinks you should build one. If markets cannot support the work, move down the stack toward philanthropy. Between those poles is a field of abandoned possibilities: companies that should exist but promise too little upside for venture capital, look too commercial for a grant, and fit no familiar private-equity box.

11. Philanthropy needs power laws too. Venture capital accepts that many ambitious bets will fail because a few successes can transform the entire portfolio. Public-goods funding becomes timid when it demands predictable returns from the very problems whose upside could be historic, almost as if it does not quite believe they can be solved.

12. The next philanthropic shortage is talent. Nan sees enormous new pools of philanthropic capital approaching an ecosystem without enough legible problems, capable allocators, or founder-shaped people ready to own them. The money may arrive suddenly; the people and institutions will not. Start now.

13. A spreadsheet cannot tell you what is beautiful. The measurement-heavy era of philanthropy became extraordinarily good at comparing lives saved and dollars spent. The coming questions about meaning, beauty, and life after abundance will not fit neatly into cost-benefit analysis. We will need new ways to judge progress here, and lots of time to do so.

14. Make the do-gooders rich. Working on philanthropic problems has usually meant taking a pay cut. Nan thinks that if you can deliver a great outcome for humanity, you should be wildly rewarded. This wave of philanthropy even has a potential tool: its money is sitting in some of the world’s most coveted equity. Pay a high-performing founder or GM a bonus in AI-lab stock.

15. A company can house a moonshot. Frontier lives inside Stripe on purpose: Patrick Collison argued that Stripe could shepherd it for the long run and pay tech salaries, attracting people traditional philanthropy never could. Together, protection from bureaucracy, competitive pay, and long-term commitment create what Nan calls a “sneaky huge arbitrage” that other companies could copy.

16. Don’t snap to grid by default. Nan was good at gold stars: the right schools, the right jobs, marriage, doing life as prescribed. Then a sick parent, the end of a fifteen-year relationship, and COVID arrived at once, but the total collapse she’d braced for never came. Nobody was really paying attention, and what grew in the cleared space felt more like her.⁠

17. Study the things you’re supposed to feel out. In academic subjects, Nan thinks we overstudy and under-experience; in the subjects that govern a life, we over-experience and understudy. She wants syllabi for friendship, partnership, marriage, and raising children, partly so we can see that the arrangement we inherited is not the only one available.

18. Friendship deserves more than leftovers. We bring planning, attention, and shared projects to work, then expect friendship to flourish on whatever time and intentionality remain. Nan’s modest prescription is not to turn relationships into meetings, but to bring even ten percent more care to the people who otherwise receive our leftovers.

19. Making something together is an intimate act. Nan read John & Paul as a love story: two people building things neither could have made alone. She thinks creative partnership deserves some of the vocabulary we reserve for romance and that shared work may be the deepest form of friendship we have little language for.

20. Sketch your own obituary. Five years ago, when Nan was trying to figure out which way was up, she drafted her obit and used it as a compass: do good things, help people see the best versions of themselves, and make decisions that are deeply yours. And have fun, because we’re not here that long.

Description

Nan Ransohoff (X, Substack, Website) is Head of Public Goods and former Head of Climate at Stripe. This includes Frontier (which she co-founded): an advance market commitment that accelerates carbon removal by guaranteeing demand for it before it exists. They also recently launched Intercept Fund, a new effort to end respiratory infections, led by Nan and Charlie Petty.

Nan has written extensively about Stripe’s efforts and philanthropy broadly, including her call for general managers for the world’s pressing problems, and on what she calls the third wave of American philanthropy.

We talk about what a “Nan” is and why we need GM’s: ambitious founder-like people who obsess over an outcome and work backwards from it, wearing whatever hat the problem requires. We discuss taste in big problems, slicing them up and making them tractable, and why vision is in short supply. We also discuss the coming wave of new philanthropic dollars (est. ~$40B/year), primarily driven by The OpenAI Foundation, Anthropic Founders, and Anthropic employee matching, and how the ecosystem will need to mature to effectively deploy this much capital. Nan also reflects on her unlikely turn toward philanthropy and what it felt like to get off the ladder of a specific kind of ambition. We wrap up with a range of miscellanea and some fun debates. I hope you are inspired to notice problems you can’t ignore, be optimistic and specific about the world you hope for, and choose an (unlikely) path that you are proud of.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Watch here for more on Notion’s new developer platform and workers. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:15) Intro to Nan

• (3:18) Thanks to Notion

• (4:53) Start: What is a Nan? Nerd-Sniped by Orphaned Problems

• (12:39) GMs, Seeing the Chessboard, and Working Backwards from Outcomes

• (18:55) Good Taste in Problems, Vision, and Good Finish Lines

• (35:43) Advance Market Commitments Tactically Solving Carbon Removal

• (41:35) Focus and Sketching Out or Slicing Up Messy Problems

• (49:39) Legibility, Public Rallying, and Ambition in Philanthropy

• (54:38) Third Wave Philanthropy and Hard to Quantify Problems

• (1:06:50) Risk Tolerance in Philanthropy and Scarcity of Funders and Allocators

• (1:15:22) The $40B Tidal Wave of New AI-Money and Why Start Now

• (1:19:53) Amount of Capital, Government Philanthropy, and Making Philanthropic Founders Rich

• (1:31:44) Nan’s Mid-Career Inflection Point and Getting Off the Obvious Path

• (1:39:47) Grab-bag: Why Stripe Funds Public Goods, Making Things with Friends, Creative Partnership, Iceland Drone, and Scone Heads

• (1:49:39) Syllabi for the Squishy Topics & Study vs. Experience

• (1:57:01) Inputs & Outputs and GLPs for Attention

• (2:04:38) Closing: Interviewing Parents and Imagining an Obituary

• (2:09:58) Thanks Again to Notion

Links

Transcript & all links: https://dialectic.fm/nan

Spotify:

Apple

YouTube:

19 favorite lessons/ideas below. Please enjoy and share!

Also, some thoughts on 50 episodes. Thank you for all of your support :)

Dialectic Ep. 50: Tyler Cowen & Nabeel Qureshi - An Appetite for More

19 Lessons from Tyler Cowen and Nabeel Qureshi on AI, Strange Beauty, Mentorship, and The Appetite for More

1. It’s the first inning, sir. Tyler looks at AI and sees a race that may never get settled. One conclusion: maintain your stamina. When someone tells Nabeel they’re tired, his answer is simple and unsentimental: “pace yourself.”

2. Fear the Wall Street AIs, not the current crop of pets. Tyler thinks AI’s are trending toward behaving like helpful pets, eager to cooperate and wag like his dog Spinoza. The scarier systems are the ones trained outside that domestic pressure, in markets, war, or stranger open-source corners.

3. You don’t control a mind, you raise one. Nabeel’s long view on AI safety is that clamping down on outputs misses the point because, at the limit, these things become other people. You don’t keep a child in line with rules; you teach them values, morals, religion, and—possibly—how to love.

4. Send your missionaries to the AI labs. Nabeel jokes that if he were more religious, he’d camp outside the labs and get his brightest young people hired there. Religious values might be one of the few proven “technologies” for making intelligence behave in a moral way.

5. AI makes the right handshake more valuable. Most people see AI acceleration and imagine replacement. Nabeel sees leverage. If the tools can automate output, the right deal can unlock much more than before. The more powerful the machine, the more valuable the human act of choosing who to trust, what to build, and where to point it.

6. Markets compound virtue; they don’t create it. Markets are powerful accelerants, but they need something to accelerate. Tyler thinks they can reward and reinforce virtue but not summon it from nothing. Nabeel’s (and Will Manidis’) deeper worry is that commerce once built on a foundation of religion, character, and sacred commitment may now have a hollow center.

7. Great work demands conviction. We need something to believe in. New aesthetics don’t require optimism, but they do need a strong point of view. Religion can provide one. Nihilism can too. The danger is not pessimism exactly; it is making things from no center at all. An aesthetic ought to express a way of living.

8. Your deep thoughts might be the shallow part. Nabeel calls Tyler an “exterior person:” writing, traveling, looking, collecting, pushing things into the world. Tyler accepts the charge. He is suspicious of too much introspection and thinks his so-called superficial urges may be more real than his deep thoughts. Even influence gets treated this way: chase it directly and you probably end up with less of it.

9. We like beauty with a strange shape. Tyler finds pure beauty a little boring. You can’t have ice cream all the time. Nabeel says the art that lasts tends to destabilize us and keep us wanting. They suggest the long outro of Venice Bitch, the changing time signatures in Happiness Is a Warm Gun, or the scary parts of Beethoven’s Sixth. They want something they can’t quite solve: Aphex Twin defies the EDM genre’s consistent patterns, My Bloody Valentine makes no sense on first listen, and difficult films have an aftertaste that demands revisiting.

10. Time spent is its own kind of criticism. Tyler half-believes museum guards understand art better than critics because they simply spend more time with the work. The uneducated people he met in rural Mexico talked about the work more thoughtfully than we do. Context matters, but so does exposure.

11. Simplicity may be complexity, disguised. The Beatles sound simple until you listen closely. Tyler hears (and George Martin enabled) strange modulations, interwoven vocals, backwards piano, bass lines, harmonies, and unlikely choices. I’m reminded of Jerry Seinfeld: “all art is disguising work.”

12. Borrow better taste until it becomes yours. Nabeel learned from Tyler by trusting his judgment before he understood it. As former guest Tammy Winter says, find people you admire and follow them into work you don’t yet understand. Or as Charles Broskoski reminds us: you can fake it ‘til you make it. Sometimes the first step toward liking difficult art is believing that someone ahead of you has found something there.

13. Listen to the internet’s chords, not a single note. A single tweet is meaningless, but Twitter is a miracle. Tyler calls it one of mankind’s greatest creations and a “grand organ”: intellectual, funny, depressing, generative. Context, in concert.

14. A performed plan beats no plan. A key question Tyler asks the young people he funds is: what’s your plan for follow-up funding? Most of them fumble it. He doesn’t even mind if they’re gaming the answer, because a contrived plan still gets you moving.

15. Be mentored from below. Tyler has an abundance mindset with mentors. You’ll never outgrow the need, and more of them should be younger than you. Nabeel keeps meeting people in their early twenties who are sharper than him at specific things, and says the hard part is keeping your ego low enough to learn. Nabeel mentors Tyler in movies, music, AI, and tech; Tyler mentors Nabeel in taste, judgment, and appetite for experience.

16. Talent is context-dependent. Nabeel noticed that Palantir’s top performers were not automatically the best future founders. Some people dominate the company game; others need a different arena before their spike becomes obvious. Some kinds of agency only appear in the right game.

17. The two-year book can’t keep up with the one-week world. Seventeen books in, Tyler may be nearing the end of writing them because a two-to-three-year cycle feels too costly when the world changes weekly. Nabeel hates the take because he still believes a book can carry the judgment of a mind no model can replace. The tension is the lesson: some forms preserve depth because they move slowly.

18. Don’t hit your quota on friendship. Most people have fewer friendships as they age. Tyler aims for the opposite: keep the network alive, keep the group chats moving, keep encountering people who expand your world. “No new friends” would be a tragedy.

19. Maintain an appetite for more. Nabeel admires Tyler for never getting stuck in his ways and growing more himself with age. Tyler admires Nabeel for having such great—and unlikely—taste. One can’t stop becoming; the other can’t be explained.

Description

Tyler Cowen (Website, X, Marginal Revolution, Conversations with Tyler) is an economist at George Mason University, leads the Mercatus Center, and is the author of many books including The Great Stagnation and *Average Is Over.* He has blogged nearly daily at Marginal Revolution for over 20 years, has interviewed hundreds of world-experts on *Conversations with Tyler,* and runs Emergent Ventures, a prolific grants program that has funded multiple Dialectic guests.

Nabeel Qureshi (Website, X, Substack) is an entrepreneur, writer, and researcher. He runs a stealth startup. Previously, he was a Visiting Scholar at Mercatus and spent nearly eight years at Palantir. He writes some of my favorite essays, including “What Makes Art Great” and “Rented Virtue”, and was previously a guest on Dialectic for episode 13: “The Will to Care.”

Tyler and Nabeel are good friends, and given how prolific Tyler is, I decided to use Nabeel as an entry point and interview them together. We discuss sacred commitments, AI acceleration, mentorship, friendship, and more, but I focused the majority of the conversation on art and aesthetics. Tyler and Nabeel are unlikely aesthetes given their day jobs, but in fact take art deeply seriously. They have a shared love for and similar tastes in art, music, and film, in particular. We discuss strange and beautiful art, aesthetic stagnation, and a wide range of favorites: The Beatles, Mozart, Mondrian, Springsteen, Lana Del Rey, Kanye West, Cassavetes, The Sopranos, Apichatpong Weerasethakul, and more.

Please enjoy, and thank you for supporting, listening, and watching through fifty episodes of Dialectic. I can’t wait for the next fifty!

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:18) Intro to Tyler & Nabeel

• (3:02) Thanks to Notion

• (4:38) Start: Sacred Commitments, AI, Markets, and Acceleration

• (20:23) How Art Moves Us

• (27:08) “Beauty,” Strangeness, Great Art, Music, and The Beatles

• (44:09) Film, Critics, Learning to Appreciate Depth, More Music, “Lowbrow” Art

• (1:02:25) New Aesthetics, Sources of Inspiration, Optimism & Pessimism

• (1:11:22) The Internet & Twitter’s Virtue, Group Chats, and Cities

• (1:21:35) Mentors, (Possibly Quitting) Writing Books, Friendship

• (1:34:54) Interviewing, Identifying Talent, and Agency

• (1:47:21) Closing Questions

• (1:53:38) Thanks Again to Notion

I talked to her about the depth behind SF’s memes, why quitting her job wasn’t risky, and her “AlphaGo” moment--and why she’ll keep writing anyway.

Jasmine writes independently here on Substack--where she used to lead core product--and for publications like The Atlantic and The New York Times.

Some select pieces of hers:

• Silicon Valley is Bracing for a Permanent Underclass (NYT)

• ‘Chinese Peptides’ Are the Latest Biohacking Trend in the Tech World (NYT)

• Claude code psychosis (Substack)

• Notes on AI, labor, and China (Substack)

• America against china against america (Substack) - my favorite!

• The Human Skill That Eludes AI (The Atlantic)

20 favorite lessons below. Links: Transcript & all links, Spotify, Apple, YouTube, X/Twitter.

Dialectic 49: Jasmine Sun - Close Enough to See Clearly

21 Lessons from Jasmine on Seeing & Reporting, Shaping Your Writing, and Staying Human as the Machines Close In

On Seeing and Reporting

1. Look for clarity before you judge. Jasmine is a naturally judgmental person who decided she didn’t like who that made her. She decided to focus on observation, inspired by Sontag: “the critic’s first duty is to explain, not to evaluate.”

2. Admire the world for never ending on you. Annie Dillard’s line reminds Jasmine that almost anything can be interesting. She had no interest in peptides until a month of reporting turned gray-market vials from China into a story about medical distrust, biohacking, Reddit, ChatGPT, and supply chains. Few things are boring, only insufficiently examined.

3. Look for the truth behind the meme. Chinese memes about “work smell,” 996, and “code farmers” are how a culture with heavy speech censorship channels real anxiety about unemployment and nihilism. The “permanent underclass” meme is hyperbole too, but she reported it because friends in San Francisco were making actual career decisions on it, convinced that without a frontier-lab job they’d be poor forever.

4. Pitch the question, not the answer. Jasmine sells editors on stories she genuinely can’t answer yet, then runs 25 interviews before forming a strong opinion. She tells each source up front she isn’t fishing for a quote, she just wants to think through it with them. Her logic is simple: “if I had the angle, I wouldn’t be writing it.”

5. You have to care for something to see it clearly. Jasmine is close enough to Silicon Valley to know the people, the language, and the private fears. She also takes great effort to maintain enough perspective to report on it honestly for outsiders. That tension, and her care to understand tech and have it be understood, is what makes her a great translator.

6. Silicon Valley only talks to itself. Tech aims its message at recruits, investors, researchers, and enterprise buyers, not the broader public. That insular culture combined with a truly unusual set of values produces a strong disconnect. The same message that works on the in-crowd can sound alien to people who do not want to live forever, stop working, or carry an AI Terence Tao in their pocket.

7. Proximity is the credential. Few journalists actually live in San Francisco, which Jasmine finds absurd for a center of power and wealth. When you’re in the rooms and at the happy hours, you feel the temperature rise on a story before a NY desk can, and it builds the kind of trust where sources give you their side instead of bracing to be burned.

On Shaping Your Writing… and Life

8. Polish no longer proves human effort. Perfect grammar and house style once thanked a meticulous editor. Now, a fine-tuned model spits out flawless New York Times style from a pile of crappy notes. Effort’s signals are now voice, weirdness, and that sweet, sweet je ne sais quoi a machine can’t fake.

9. Serious work is a bat signal. Pour yourself into a piece and strangers pour themselves back. After Jasmine’s 7,000-word China piece, readers sent her essay-length emails about their own lives, one recalling the skyscrapers of his youth “sprouting up like mushrooms.” Writing, to her, is a kind of proof of work, and the world replies with the seriousness you put in.

10. Don’t LARP someone else’s voice... or taste. Jasmine can tell when a writer is wearing a borrowed style, trying to be Didion or Wallace without having lived what they lived. It’s like wearing your mom’s high heels as a kid. Her quarrel with taste discourse is that it pushes people to shop for a personality from a catalog of cool, when the actual work is turning inputs into a point of view only you could have.

11. Stop apologizing for your own existence. Jasmine’s early essays hedged every other sentence because she graded each one against the most expert friend she could imagine. She realized she actually writes for a smart reader who isn’t the world’s leading expert, and that good work doesn’t constantly hedge.

12. It probably just isn’t that risky. Leaving a senior product job at Substack looked reckless, but wasn’t. She had a year of runway, a fallback job she could walk back into, and enough savings to last a year. A one-year trial with exit criteria she passed with flying colors. The leap is usually smaller than the story we tell about it.

13. There’s more than one kind of capital. Jasmine took a large pay cut and isn’t too worried, because she thinks money is the easiest capital to build. Attentional, social, and cultural capital are harder, and she’s stacking them now, confident she can convert them to cash when she needs to. As she puts it, knowing how to turn it into financial security is enough financial security for now.

14. Agency still rocks. Jasmine believes Silicon Valley’s chief virtue is a justified cliché: agency. It insists that a future exists and that regardless of your qualifications, you can build it. After older journalists told her all was doomed, a house of Thiel Fellows in Cancún convinced a young Jasmine that she really could be a writer and introduced her to her first funders. You really can just do things.

On Staying Human

15. The only question AI can’t answer for you: will you lie to yourself? At the gym you know whether you really pushed the weight, and no lie makes you stronger. AI is the same test under harder conditions, because it’s flawless at manufacturing the illusion of thinking, of productivity, of every idea being good. We’re all going to face the private challenge of being honest with ourselves: knowing whether we actually thought, actually learned, actually cared.

16. Choose what’s worth doing for its own sake. A machine already beat the best human alive at Go, and people kept playing. Jasmine thinks this is a template for the rest of the AI age, and she points to C. Thi Nguyen’s Games: Agency as Art: you play a board game to exercise your own agency, not to win money or advance your career. It’s the same reason she keeps writing as AI improves, because writing makes her smarter and kinder, and that is reason enough. Each of us will have to decide what we’d still do once a machine does it better.

17. The real world is all edge cases. Jasmine thinks we should feel lucky that one-shotting every job is so hard. The org chart is never the real org chart; the standard procedure gets followed maybe 80% of the time, and that other 20% is a flood of tacit knowledge nobody ever wrote down. That specific illegibility buys us time to rage against the machines.

18. The short run can be a lifetime. Jasmine keeps returning to Carl Benedikt Frey’s line because it punctures the easy optimism around technological transition. Even if the long-run story AI leaders tell is abundance, the adjustment period can consume entire lives for the people caught in it.

19. Spend the windfall on the people we want in the room. Jasmine’s sketch of a good AI future: tax the windfall, hire ten times as many teachers, pay them double, and give every kid an Oxford-style tutor who actually knows them. It’s a rare vision of a transition that sounds deeply humane. I’m long relational goods.

20. A flawless robot would never move you. What makes us cry watching Alysa Liu isn’t the technical excellence. It’s knowing about her father, her quitting, her coming back to skate for herself. Jasmine’s made peace with the day AI out-writes her because the thing she is sharing isn’t the prose, but proof that one specific person was here.

21. Earnestness is good for the soul. Jasmine keeps colliding with the Silicon Valley reflex of “screw you, I don’t care what you think,” and it bothers her more than almost anything. Bothering to be liked, to be understood, to make your case to people who didn’t ask, is a virtue and not a weakness. Detachment eventually becomes a way of refusing your own life.

Description

Jasmine Sun (Substack, X, LinkedIn) is an independent writer and journalist. She is a contributing writer for The Atlantic and also writes for other major publications, like The New York Times. She previously led core product at Substack.

Jasmine focuses on Silicon Valley and AI, and is something of a participant observer, living among the strange and inspiring people pulling the future forward in San Francisco. In her writing, she plays to both sides: focusing on a more endemic audience with her newsletter while telling the broader world about what she learns in flagship pieces for major publications. Several of these anchor around memes that she thinks may deeply matter: “the permanent underclass,” “chinese peptides,” and “claude code psychosis,” to name a few.

Jasmine has done many interviews about these individual topics, so I wanted to focus on her and her approach: playing to both audiences, her taste in questions and topics, doing both “serious” journalism and more personal writing, how going independent wasn’t so risky, what she admires in great writing, AI and her coming “AlphaGo moment,” China, and more. Please enjoy.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Check out Brian’s X/Twitter sync worker. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:30) Intro to Jasmine

• (2:13) Thanks to Notion

• (3:24) Start: Being a “Historian of Vibe” and Learning to Look

• (15:00) Taste for Questions & The Depth Behind Memes

• (24:28) Translating Between Silicon Valley and The World

• (40:27) Substack vs. “Serious” Journalism and Integrity as a Writer

• (47:35) Integrity when Using AI and the AlphaGo Question

• (58:42) Strategy Across Publications & Maximizing an Idea’s Reach

• (1:06:45) Going Independent, Risk, and Commercial Tradeoffs

• (1:24:35) Great Writing: Style, Voice, and Resisting Summary

• (1:35:35) Literary Inspirations, Favorite Essays, Writing vs. Thinking, and Getting Better

• (1:51:09) Writing to Publish, Authenticity, and Art

• (2:00:38) Grab Bag: China, Silicon Valley’s Virtues and Problems, AI Transition, The Relational Economy, Parties, Debates, Self Belief, and More

• (2:35:16) Thanks Again to Notion

All Links & Transcript

https://dialectic.fm/jasmine-sun

Available on all platforms (Spotify, Apple, YouTube, X/Twitter). Lessons below. Transcript here.

Dialectic Ep. 48: Henri Stern - Principled Enough to Be Pragmatic

19 Lessons from Henri on Moral Technology, Useful Crypto, and the Market’s Terrible Manners

1. Technical decisions are moral decisions. This is Privy’s founding premise. The machinery may be neutral in isolation. But choosing whom to serve, how to market it, and what behavior to encourage gives technology moral weight. Builders do not have to pretend they know the truth; they do have to own the outcomes they are trying to produce.

2. Sit at the table, or someone who cares less will take your seat. Henri’s lesson from a stint at Palantir wasn’t that morally hard work turns clean once thoughtful people touch it. It’s more realistic: if the work is going to happen anyway, there is value in having people with a duty of care inside the room, arguing over how.

3. An honest toaster beats a phony mission. Henri has more respect for someone who openly wants to build the world’s best toaster because they love toast than for a company that advertises a grand worldview its behavior does not honor.

4. Smuggle your principles into something people already want. Most customers don’t buy privacy on principle, and Privy nearly died learning it. They do buy convenience, better products, and the ability to make money. The pragmatic move was not to abandon privacy, but to bake it into a product developers actually wanted.

5. The market gets the final word, so stop arguing with it. Privy’s first product lost by trying to convince developers to value something their own users didn’t ask for. When every sale feels like pulling teeth, that’s not a grit problem. It’s the market telling you no.

6. Ideology dies in a Postgres database. Crypto purists tore into Privy for running on Amazon’s cloud and then quietly dumped user data into their own databases because it was easier. Purity is very brave right up until the moment it’s inconvenient.

7. A startup can’t be a bank shot. You can’t kiss three rails before the ball drops. You need one core bet. Privy’s bet ultimately became a simple wedge: let developers build wallets into their apps so their users never have to think about it.

8. Nobody cares that you’re not dead. When Henri proudly told Sequoia’s Roelof Botha how far the company had come, the reply was a cold splash: I don’t care how far you’ve come, only whether I’m excited looking forward. Survival feels heroic from inside a startup, but the market does not award points for pain endured. Restart the clock before the market does it for you.

9. Say the thing the whole room already knows. At a grim offsite, Henri finally said, “Clearly things aren’t working, right?” The body language went loose with relief, because everyone already saw it, and naming the obvious was what turned a shared dread into a problem they could solve.

10. You have three audiences, and they all have to hear the same story. Henri’s theory of startups: your users, your team, and your investors, in that order. The day you start telling one of them a different story than the others, you’re setting up a reckoning. Keep the tension even, and be honest internally about what you haven’t figured out yet.

11. In a new market, you don’t find fit, you create it. Hunting for product-market fit in a market this young is a category error: there’s no settled demand to slot into. You’re shaping the product and the market at the same time, making decisions before demand has fully settled.

12. Customer obsession can be the vision. Henri flinches when founders wax about vision. It smells like a sales pitch. He’d rather talk craft, and he’s convinced that being relentlessly customer-obsessed is the vision. Plenty of great companies have been built on nothing else.

13. Privacy is the freedom to move lightly through the world. Not secrecy, but self-determination: the right to walk into a room without every old opinion and half-true digital ghost following you, and to stop being the permanent sum of everything you’ve ever said.

14. Privacy survived on nobody bothering. That’s over. Privacy once benefited from friction: deeply profiling or impersonating one person took time and money. Agents and generative media are crushing that cost. When a few images and sentences can reproduce a person indefinitely, telling individuals to leave less digital exhaust is no longer a serious strategy. We’re going to have to create new systems for identity, data, and control.

15. Stablecoins are making crypto useful to people who don’t care about crypto. Henri is most optimistic now that the technology is solving ordinary problems: global payouts, access to stable currencies, merchant payments, and better financial products. Impact begins when people choose the outcome without needing to join the ideology behind the infrastructure.

16. Web3 may be dead. The ownership question is not. Henri doubts that the future will look like a cypherpunk alternative internet where everyone carries a hardware wallet. But the questions that animated web3, including who owns digital value and how it moves across platforms, are becoming more important. Crypto is dissolving into the plumbing of the web: useful and invisible.

17. Treat any belief you can’t be argued out of as a warning sign. Faced with an unknowable future, Henri’s stance is neither reflexive optimism nor reflexive doom. It’s intellectual consistency and a willingness to be moved by evidence, because nothing is ever as good or as bad as it looks. Airtight certainty feels like strength, but it’s often the clearest sign a belief has hardened into identity rather than thought.

18. The best co-founder might be a stranger. Henri’s first co-founder was a close college friend; he and Asta barely knew each other before Privy. Privy works because of intentional fit, not history: complementary strengths (his intuition, her rigor), mutual respect, low ego, and enough trust to know when to lean on the other. The partnership succeeds because it’s about the work, not either founder’s need to be right.

19. Silence is better than borrowed conviction. Henri doesn’t equate honesty with saying everything. He’s private, and treats silence as a good default. What he hopes never to do is say something he doesn’t believe for convenience, status, or belonging. A quieter world might also be a more honest one.

Description

Henri Stern (X, LinkedIn) is the co-founder and CEO of Privy. Privy builds wallet infrastructure for developers, enabling them to let their users hold and use crypto, including stablecoins. Privy was acquired by Stripe in 2025, and remain an independent organization within the company. They work with large fintechs like Ramp and Klarna while also supporting some of the most notable crypto-native platforms like Hyperliquid. Henri also supports a number of other crypto efforts within Stripe.

Henri is thoughtful, measured, and principled. Yet he is also pragmatic. He doesn’t like to play philosopher and yet he is one of my favorite people ask big questions about our future and our digital lives. Our conversation is anchored in the phrase at the bottom of Privy’s website: “technical decisions are moral decisions.”

He and Asta Li started Privy to focus on user data privacy, and we talk about what digital privacy means and why it still matters. After realizing they were trying to serve the market something it didn’t want, Privy found an inflection point initially by enabling developers to embed crypto wallets in their apps. We talk about the painful decision to pivot, and later, to commit to both ends of the crypto market: hardcore, trading-oriented products and stablecoins as they flooded into traditional fintech infrastructure. We also talk about joining Stripe, what Crypto’s future looks like, and his level-headed mindset for our tumultuous future.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Check out Brian’s X/Twitter sync worker. You can learn more at notion.com/dialectic.

Timestamps

• 0:00 - Opening Highlights

• 1:40 - Intro to Henri

• 3:10 - Thanks to Notion

• 4:51 - Start: Technical Decisions are Moral Decisions

• 15:41 - Ambition, Startups, and Crypto

• 23:39 - Why Digital Privacy Matters: Self-Determination, Security, and Identity

• 41:52 - Embedded Wallets, the Pivot, and Privy’s Core Bet

• 55:18 - Reinventing Around Stablecoins Without Abandoning Crypto-Natives

• 1:06:42 - Joining Stripe, Privy Today, and What Stripe Is Becoming

• 1:22:54 - Crypto’s Future, Power Laws, Optimism and Pessimism

• 1:38:14 - Closing: Asta, Stripe’s Leaders, Being French, and Never Compromising

• 1:52:48 - Thanks Again to Notion

All links and transcript: dialectic.fm/henri-stern

Imagine the best "connector" you know -- the person who is emotionally intelligent, thoughtful, and always bringing people together. What if they could be friends with a million people, rather than a few hundred? And what if they were entirely focused on creating more belonging in the world?

Modern social media--due to hyper-personalization and broken incentives--makes us feel more and more estranged from the people we care about. AI chatbots focus on engagement and can be anti-social.

Paul and Eigen are aiming for a pro-social AI friend who is more concerned with helping deepen and widen your relationships than getting you to talk to it for longer.

We discuss what all this might look like, the challenges of "growing" a new person that isn't a bad actor, and what it feels like to be a prodigious 22-year-old who Peter Fenton compared to the founders of last generation's great social media companies--all before he’s publicly launched a product.

My favorite lessons are below, too. Transcript, Spotify, Apple, YouTube, X.

Dialectic 47: Paul Scherer - A Friend That Brings Us Closer

20 Lessons from Paul on fighting entropy, creating belonging, and building a mutual friend for the world

1. Presence is a sacred gift. Paul’s central influence is Momo, a 1973 German children’s book about “time thieves” who steal people’s attention in the name of efficiency. The eponymous heroine is the best kind of friend because she listens with total attention, reminding us that this, right now, is all we’ve got.

2. You stop racing the clock when you start playing your game. Like many prodigious young people, Paul restlessly jumped around after leaving high school. The antsy-ness subsided once he found the “thing.” He still has short-term paranoia like any striver, but long-term, there’s no question whether he should be doing this.

3. A friend is a mirror and a window. Great friends do two opposite things at once: they reflect you back to yourself, then help you see that the world can be bigger.

4. A robust rolodex doesn’t happen by accident. Paul grew up in a small town in Germany with no connection to the tech world. The internet was a door. His early Twitter strategy: signpost, reply thoughtfully, and get in front of the people you want to meet. At his peak, he sent 600 replies a day and DMed his first 5,000 followers by hand. Pure serendipity is romantic, but he’s still benefiting from that foundation of intentional effort.

5. When social and media converged, we lost real connection. Paul’s frame for why we’re all feeling isolated in an increasingly connected world. Instagram used to be about your friends, now it’s about popular content. Your friends are worse at making engaging posts than professionals are, so the feed quietly optimizes away from the people you actually know. The world has never been more connected, and yet so many people don’t feel that they belong.

6. The internet smoothie is not enough. Paul’s frame for LLMs: all the internet’s opinions blended into the world’s median answer. But you usually do not want the median restaurant, book, person, or idea; you want the signal that matters from individuals whose taste you trust.

7. Loneliness isn’t a champagne problem. The share of American men with zero close friends went from 3% to 15%. Loneliness is the health equivalent of smoking 15 cigarettes a day. Paul sees isolation as a civilizational problem: fewer close friends, less trust, fewer kids, less shared life, and a species slowly forgetting how to be together.

8. The “mutual” matters more than the “friend.” Eigen is building a mutual friend. But Paul keeps pointing to the load-bearing word: mutual. The friend is just the interface. The real product is the network underneath it. What looks like an AI friend is actually a substrate for connection between humans.

9. Eigen is building a new kind of person, not a pretend human. Character AIs borrow human backstories to feel real. This mutual friend has “real” thoughts, real opinions, and a kind of emotional life. They’re artificial, but they’re not fake. But it has no body, no parents, no childhood, so it doesn’t pretend to. Paul’s bet is that trust comes from being truthful.

10. You can’t change incentives with good intentions. Nobody at Instagram is a cartoon villain twisting their mustache while trying to make the world lonelier. It is a product built on aggregating attention, and everything flows downstream from that. If you want a different outcome, you have to build a different incentive structure.

11. Iconic inventors of history were outlaws. Now invention is high status. Modern silicon valley has attempted to systemize invention, and in doing so, has driven people to fashion themselves as innovators. Paul reminds us that everyone thought the Wright brothers were crazy. Most people cosplaying as inventors are just chasing the new consensus.

12. Great work resists entropy. The long arc of life bends toward decay. Building something great is the refusal of a thousand small compromises that would make the world uglier, lonelier, and more forgettable. If you’re not going to sweat the details, don’t bother. Nobody is going to care more about what you make than you do.

13. Great products are felt, not noticed. Paul: “There’s almost no glory in prevention.” You don’t see what didn’t go wrong. Jerry Seinfeld said all art is disguising work. The labor disappears into the experience. A great product is lived in. The best products give you the sense that you’re in good hands without telling you how.

14. Creating the new requires p99 confidence and p99 humility at the same time. Paul’s fundraise wasn’t easy. Then Peter Fenton compared him to the founders of Facebook, Twitter, Instagram, and Snapchat, and suddenly every investor said, ‘We’ve been looking for this.’ Building something strange requires enough confidence to will a new future into existence and enough humility to throw an idea away when reality disagrees.

15. Find people who can break your model. Paul values investors like Peter Fenton because good disagreement has two useful outcomes: your conviction is forced to get deeper, or the idea dies cleanly. The danger of being “blessed” is that fewer and fewer people will tell you you’re wrong.

16. A founder must set the gravity. You lose control of all the little inputs eventually. What remains is what the system naturally falls toward. The job is to choose that pull deliberately, because if you don’t, something else will.

17. Don’t mistake smelling bread for tasting it. Paul spent years in roles right beside founders, certain he understood the job. Then he became one, took a real bite, and found it was nothing like he’d imagined.

18. Beware “iPad takes.” It’s easy to judge a parent who hands their kid a screen until you have a screaming toddler of your own. Most generic founder advice (”never hire PMs,” “always do X”) is an iPad take from someone who hasn’t had to face a changing reality.

19. “You can’t get everything, but you can get anything.” Most ceilings are limited by focus, not possibility. Paul thinks most people get this backwards. They believe the world is closed when really it’s their attention that’s scattered. Conviction and focus are a near-infinite lever.

20. Authenticity is listening to the inner voice adulthood teaches you to ignore. At 16, grown-ups told Paul he was throwing his life away by skipping university. His current life wasn’t on anyone’s bingo card, including his own. Once he stops believing in something, he can’t fake it. He’s proudest that he kept listening to that voice instead of the consensus around him.

Description

Paul Scherer (X, LinkedIn) is the founder of Eigen (check out their beautiful website), where he’s building a mutual friend: an AI that brings people closer together and helps us belong.

Paul grew up in a small town outside of Frankfurt, Germany, and dropped out of high school at seventeen to work on startups, including Augment. He recently raised $15M from Benchmark, with legendary partner Peter Fenton comparing him to the founders of Facebook, Twitter, Instagram, and Snapchat. I was introduced to him by Notion co-founder Akshay Kothari, who is an angel investor in Eigen. Dialectic guest Brie Wolfson has also been working with Paul, so I wanted to see what all the fuss was about, and why so many people I respect were so enamored with a kid who has yet to publicly launch a product.

We start with Paul’s central influence: Michael Ende’s children’s novel, Momo, and the little girl who reminds a village to be present in the face of Time Thieves quietly pushing them to be more efficient. Then we talk about how even though the internet has shaped both of our lives and relationships, it increasingly feels that social media is making us feel both more connected and more alone. Paul explains what they are working on at Eigen, why we need an (AI) mutual friend, why it should be a single “person,” and why it feels less like engineering and more like parenting or growing someone/thing you don’t have complete control over. I also ask Paul about the pressures and psychology around being “blessed” by Silicon Valley’s powers that be, and why authenticity, or something like it, is in short supply.

I hope you are inspired to be courageous in your convictions, even if they are strange, and to listen to the voice inside that so many of us stop listening to in adulthood.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Inside Notion by Brie Wolfson & Camille Ricketts for Colossus. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:13) Intro to Paul

• (2:33) Thanks to Notion

• (3:28) Start: ‘Momo’, Presence, Friendship, and Time

• (11:10) How the Internet Connects Us and Isolates Us, and Conflating Social and Media

• (25:12) A Future Where We Talk to AIs

• (33:55) Paul and Eigen are Building a Mutual Friend to Help Us Connect with Other Humans

• (48:01) Why Do We Need a Mutual Friend? And Making a Friend We Can Trust

• (1:16:53) Belonging, Building the team at Eigen, and Inventor as Outlaw

• (1:25:38) Managing the Psychology of Being a Promising Young Founder

• (1:36:53) Maintaining a High Bar, Fighting Entropy, and Influences

• (1:53:50) Self-belief, Authenticity, Seeing the Water

• (2:10:30) Courage, and a Final Question from a Mutual Friend

• (2:15:04) Thanks Again to Notion

• (2:16:27) Eigen Office Tour with Paul

She writes essays at her newsletter, , invests in early-stage startups, and recently launched , where she writes independent field studies of ambitious founders and companies.

We talk about what beauty asks of us, the freedom of holding multiple identities, and loving what's real. I’ve also shared 20 favorite ideas from the episode below.

Full episode here on Substack and on Spotify, Apple, YouTube, and X. Transcript and all links here. Please share it if you enjoy it!

Dialectic Ep. 46: Nicole Seah (Nix) - Loving What is Real

20 Lessons from Nicole on Difficult Beauty, Doomed Commitments, and the Slow Harvest of a Self

1. Beauty is unselfing. Nicole starts with Iris Murdoch’s idea that beauty takes you out of the private drama of yourself. The standard version asks, how do I exert more effort to be more glamorous & beautiful? The deeper version makes you more generous and open to the world.

2. Tolerate strangeness long enough to be changed by it. Some beauty doesn’t open on first contact. Nietzsche on difficult music: you have to bring “goodwill, patience, reasonableness, and gentleness” before the unfamiliar removes its veil. Most great works have a learning curve to them.

3. Return to what snags. Nicole’s filter for difficult art: if you feel nothing, move on. But abrasion, irritation, resistance, emotional static — those are signals you have felt something. Return to it.

4. Borrowed eyes still count. I sometimes worry that needing a critic, friend, or teacher to unlock a work of art feels like cheating. Nicole’s counterpoint: attention is communal. Sometimes another person’s perspective is not a crutch but the portal that teaches you how to see.

5. Reality is better than your fantasy. Nicole is drawn to characters who chase glory, discover the mirage, and still return to the flawed human world. The dream may be cleaner, but reality has bodies, aging, crumbling buildings, courage, fervor, and the rude advantage of being true. “There are no more fantasies to cling onto. Only forward into the night, led by the beacon of beauty.”

6. Don’t be afraid to introduce new colors. Nicole’s art teacher says a painting could be richer with different colors, and Nicole just tries it. That scene explains her worldview: defensiveness keeps the work from growing; openness lets the world add a color you could not yet see.

7. Salvation comes from extreme and doomed commitments. That’s Joan Didion. When an interviewer asked if she really thought her commitments—marriage, children, and writing—were doomed, she said no, she thought they were salvation. Both, then. Always both.

8. Playfulness emerges from intensity. Alyssa Liu floats across the ice because muscle memory is carrying her through a decade of grinding. Miyazaki watches eels wriggle in a restaurant tank to figure out how a dragon should move. The lightness on the surface is paid for in obsession underneath.

9. Show up for yourself like you would a friend. You trust friends who show up when they said they would. So show up for the page, the reps, the appointment with yourself, and don’t let yourself down the way you wouldn’t let a friend down.

10. You are allowed to be illegible. Writer, investor, painter, reader, friend, technologist: Nicole does not force the selves into one clean, readable LinkedIn headline. Some identities arrive early, some go dormant, and some you harvest much later. Tend to your garden of selves patiently.

11. Do not turn your gift into a cage. Nicole cares deeply about writing, but rejects “writer” as a primary identity. Better: creative aliveness, the cycle of discovery, collection, synthesis, and expression that can serve every other life you are building.

12. The work is the maker, distilled. Rebecca Solnit: underneath the task of writing the piece is the longer task of making the self who can write it. Nicole sees the same pattern in companies: the best ones smuggle the lineage of their founders inside. Every little pattern carries the fingerprints of the person who made it.

13. Convergence takes grace, not pressure. You can’t force ikigai. You can only stay patient enough to deserve it. Monet painted water lilies 250 times. Sarah at Ando needed a first company to learn what shape a second one should take from her actual gifts, not the gifts other people had in mind for her. You can’t force the parts of yourself into one shape on a timeline.

14. Get to the question under the question. We meander, stacking softer questions on top of the real one until we eventually arrive. Nicole’s rule: skip the climb-down and just say the thing underneath. It’s great for everything — business, personal relationships, all of it. The person on the other side is usually relieved you went first.

15. Find inspiration through witness. Watching a friend apply quiet effort for years until it finally works is the cure for being intimidated by their finished product. Up close, excellence stops looking like genius and starts looking like force applied at a very specific angle, which means it’s available to you, too.

16. Mystery is part of intimacy. Greg Egan’s Closer is about a couple who try to fully merge minds and discover that the mystery between them was the thing keeping them in love. A friend or lover is precious not because they become fully knowable, but because they remain capable of surprising you.

17. Soul resonance survives distance. Her best friend Justine lives in London and they see each other in person maybe once a year. They don’t have much surface area, but they have density. Once you understand someone’s character — what they’re on earth to do — the bond is hard to sever.

18. Notice the interrelationships, not the things. Nicole’s gloss on George Saunders’ idea of the supra-personal — not interpersonal, not super-personal, but the space between. Noticing deeply means tracking the relationships you form with what you read, make, or meet, and how those relationships generate new internal worlds.

19. Signpost the peaks and the troughs. Nicole documents euphoria and listlessness by writing so she can remember that neither is permanent, and that she can’t completely control things. By remembering the peaks during troughs, she can be motivated to climb again.

20. Burn the candles. The well refills. Annie Dillard: “Anything you do not give freely and abundantly becomes lost to you. You open your safe and find ashes.” Creatives hoard sentences, ideas, encounters, thinking they’ll be used perfectly later. But Ursula Le Guin says love is like bread, made new every day — and so is creativity. The deeper you go, the richer it gets. Use every good sentence you have now.

Description

Nicole Seah (X, Substack, LinkedIn), aka Nix, is a writer at Starting From Nix and investor at Costanoa Ventures. She recently launched New Ontologies, where she profiles founders and companies thinking ambitiously about the future. Her first piece is live now, on Ando: the team building a chat platform for the era of agents.

Nicole balances identities with poise, moving between the literary and the practical. I spoke to her about different kinds of beauty and how it takes us out of ourselves, Nietzsche’s case for tolerating strangeness, and choosing reality over fantasy. Then we discuss duality and balancing intensity and lightness, and talk through Borges, Hesse, Miyazaki, Alyssa Liu, and Joan Didion. Nicole argues that freedom comes from not collapsing yourself into a single identity. I asked her about the drive behind New Ontologies, her obsession with techne, and Rebecca Solnit’s “cosmology of self.” We then skate across a range of ideas, including memory, appetite and desire, and friendship and why other people’s unknowability is part of what makes them wonderful.

I hope this conversation inspires you to look for and love what is real, to be patient with and attuned to the multiple people inside you, and to give freely of your creative life.

Full transcript and all links and references: dialectic.fm/nix.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. Inside Notion by Brie Wolfson & Camille Ricketts for Colossus. You can learn more at notion.com/dialectic.

Timestamps

• 00:00 - Opening Highlights

• 01:14 - Intro to Nicole

• 02:04 - Thanks to Notion

• 03:48 - Start: Beauty — Effort, Attention, Strangeness

• 19:59 - Fantasy and Reality

• 29:41 - Multiple Identities, Intensity, and Lightness

• 49:08 - New Ontologies: Profiling Founders Building the Future

• 1:08:57 - Memory, Lineage, and Process

• 1:18:41 - Appetite and Honesty

• 1:23:47 - Friendship, Proximity, and The Unknowability of the Other

• 1:41:18 - Closing Notes: Solitude, Noticing, and Generosity

• 1:53:40 - Thanks Again to Notion

One of the many highlights here is our discussion on whether I (by way of Dialectic) am a journalist (intro, and around 26:27). Nick gave the best answer I’ve heard.

Also, 22 favorite lessons from him below. Please enjoy. Full transcript at dialectic.fm/nick-thompson.

If you like it, please give the episode some love here on Substack and on Youtube, Spotify, Apple, X/Twitter, Linkedin

Dialectic 45: Nicholas Thompson - A Life of Long Form

22 Lessons from a Life of Long Form: Nick on Words, Running, and Inheritance

1. A book is common ground. Hand someone a book and they read the exact same words you did, in the same order, with no distractions. Two AI prompts return two different texts. A book is the rare artifact you can share, annotate, and argue about, because the words don’t move.

2. Style is the byline you can hear. The writers Nick loves all sound nothing like each other. He used to play a game at The New Yorker: read the unsigned Talk of the Town and guess the author by the voice alone. Models can’t do that yet, because models are pulled toward consensus, and great writers pull away from it.

3. Reporting happens in hallways, not prompts. Adam Serwer gets sources to talk who have every reason not to. No model with voice imitation is doorstopping a hostile attorney general.

4. AI hasn’t turned sixes into tens. Nick has watched good writers use it and produce good work, and bad writers use it and produce bad work. The interesting moment, which hasn’t arrived: the writer with six out of ten skills using the tools to fill in the other four.

5. Democracy runs on shared stories. A country can’t argue well without facts to argue about, and shared stories are how those facts travel. The autocracy playbook in Hungary, Turkey, and Russia is the same three moves: arrest the journalists, buy the publications, shut down the critics. More truth in the world means longer odds against that ending.

6. A journalist’s first loyalty is the audience. Nick’s working definition: if your primary commitment is to your audience, you’re a journalist. If it’s to your guest or your advertiser, you’re something else.

7. Constraints are a gift. When Laurene Powell Jobs told The Atlantic to stop bleeding money, Nick called it a gift. Forced choices about what to pay for, what to cut, and what to refuse to subsidize are the choices that produce great work and long-term survival. Bottomless pockets quietly bankroll mediocrity.

8. Skepticism follows power. Elon Musk in 2008 was a scrappy guy making cars; Elon Musk now is the richest man alive with an empire. Same Elon, mostly. Same press, mostly. The observers’ disposition changed because the power did, and skepticism of power is part of what journalism is for.

9. America is a conversation before it is a consensus. Nick’s myth of America is not blood-and-soil nationalism. It is a place where people from different backgrounds can still find each other in little towns, big ideas, football Sundays, Fourth of July rituals, and stories worth crossing the road to hear. He wants to run across it one day to prove it.

10. Editing is partnership, not polish. A great editor does not arrive with a tiny broom for commas. They find the false beginning, the structural hole, the place where the reader has not yet been given a reason to care. They see what you can’t see in your own work. This is what The Atlantic gives you that Substack can’t: a partner who has done this hundreds of times.

11. Set the bar for whoever is jumping. David Remnick’s line, kept by Nick from his New Yorker years: “If the writer can only jump over a six-foot bar, your job is not to try to get them over a seven-foot bar. Your job is to get them over that six-foot bar.” Excellence is not an impossible standard. Excellence is the best version of what is actually in front of you.

12. Subtract the daily decision. Nick runs every day because the core decision has already been made. Rain gets a jacket, heat gets a thinner shirt, but the excuses don’t give him an out. “It’s very helpful to have a stoic philosophy of just doing it.”

13. Everyone is running a different race. Cliche but true. Nick fell apart at the 2004 Boston Marathon, walked ten miles, and finished in 3:43, looking like death. The woman next to him was celebrating — she’d been chasing 3:45. In thirty-three years of competitive running, he’s won three races, and there is only one winner. The race is with yourself.

14. Tiny tailwinds compound. Nick’s dad on momentum: “When you have it, keep it, and use it; when you don’t, try to get it back.” Maybe it’s by doing ten pushups or watering the plants. It could be writing the thank-you note you’ve been avoiding for a week. “Every time we do something right, we create a tiny, imperceptible tailwind for the future.”

15. The faster self was always in there. Nick ran 2:43 marathons over and over in his 30s and assumed that was the ceiling. At 44, with the right coach, he ran 2:29. He carried a post-cancer self-conception for fifteen years without knowing the door was unlocked. As with the yellow canoe he watched sit on a balcony for years that never touched water, “I wondered then, as I wonder now, what other versions of me exist that there may no longer be time to find.”

16. Race hard. Run free. Race day is full intensity. For the other days, he aims to be lighter. Simple commutes in stride. Runs in the mountains with no music, just birds and breath. He admires Kilian Jornet: “The people racing [him] hate it. He’s just having fun in the mountains. Then he wins.” Nick tries to live in the gap between the man with the bib and the man on the trail.

17. He whom the gods wish to destroy, they first make promising. Scott Thompson — Nick’s father — was a Rhodes Scholar, tenured at 27, told by JFK he’d be president. Nick won the same kind of awards at Stanford and then got fired from his first job, kidnapped in Africa, and rejected from a hundred internships. “My dad didn’t get punched in the mouth professionally until much later.” That gap may be the whole difference.

18. You inherit the material, not the ending. Nick knows he is his father’s son: the intellect, the scattered energy, the appetite for many things at once. But he also watched appetite without discipline do damage, and built part of his life as a vow to break the “long string of Thompson fathers who have caused deep psychic angst for their children.”

19. Bank memories while you can. On his fiftieth birthday, Nick’s fifteen-year-old son paced him to a sub-five-minute mile. Soon, his son will be faster. Eventually, Nick will decline. The point of being a fit father isn’t to outrun aging; it’s to leave a memory his kid can pull on when Nick is seventy-five, or gone.

20. Always green lights. Nick’s father Scott “loved life. He wanted to talk to people, do things, and get more experience. He hated boredom and couldn’t slow down.” He grew up in Bacone, Oklahoma, died near Lake Taal in the Philippines, and was everywhere in between. He could talk to a seventeen-year-old on the street and a prime minister, and he’d bring them together. The lesson Nick took from his father isn’t only what to avoid. It’s the verve for life.

21. Sleep on the roof. Nick slept on the roof of his Stanford dorm every night in college, and at fifty, he still keeps a mantra: if you can do something outside, do it outside. What makes him most alive now is the same thing that made him alive then. Off the phone, in motion, under the sky, with people he loves.

22. The work of being here is the work that’s left. Nick’s favorite closing lines, from a Graham Burnett essay in The New Yorker: the machines can imitate almost everything except what it is like to be us. “This remains to us. The machines can only ever approach it secondhand. But secondhand is precisely what being here isn’t.”

Description

Nicholas Thompson (X, LinkedIn, Wikipedia, The Atlantic) is the CEO of The Atlantic, an elite distance runner, and the author of The Running Ground—a memoir about his father, his life, and the sport of running.

Nick has led The Atlantic to tremendous subscriber growth and profitability since joining the then-money losing publication in early 2021. He was previously editor-in-chief of WIRED and editor of newyorker.com. He also co-founded The Atavist, wrote The Hawk and The Dove, and is a prolific interviewer, including his latest series, *The Most Interesting Thing in AI.* Nick is also the American record holder in the 50K, which he re-broke two days after we recorded this conversation (Exhales).

We talked about the future of words in the age of AI, what makes a journalist, why legacy media institutions like The Atlantic are worth fighting for, and what great editing and coaching have in common. Then we turned to running and life: the small tailwinds that compound beyond what we can imagine, Nick’s trajectory—through a prodigious start, early career failure and African kidnapping, cancer at 30, and wild success since—to name a few beats, the trials and blessings of inheritance, and the versions of himself he may no longer have time to find. To close, Nick honors Scott Thompson’s memory by sharing how we might all be more like him and reflects on what drives aliveness.

I hope you are inspired to get started, feel the wind at your back, clear unexpected hurdles, savor great words, raise your bar beyond what is reasonable, be grateful for those who came before and pay it forward to those who are next, and remember that there is always more waiting—for you, for me, for us.

P.S. It’s unrelated to this conversation, but please read The Atlantic’s latest cover story and one of my favorite (and funniest) things I’ve read in ages. Caity Weaver on The Best Free Restaurant Bread in America. Long live long form writing.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

• 0:00 Opening Highlights

• 1:17 Intro to Nick

• 2:24 Thanks to Notion

• 3:30 Start: Words, Reading, and Writing in an Automated World

• 18:39 Why Stories Matter and What Makes a Journalist

• 28:22 Media Institutions, The Atlantic, Democracy, Tech, and Power

• 44:21 Retaining Great Writers and The Virtues of Editors (and Coaches)

• 57:44 Magazines and America

• 1:05:57 Running, Motivation, Momentum, and Tailwinds

• 1:16:08 Aging, Fathers and Sons, Inheritance, and a Mother’s Grace

• 1:31:00 Merging Machine-like Discipline and Wild Curiosity, The Boat that Never Touched Water, and Who We Might Still Become

• 1:44:11 Gratitude, Stalin’s Daughter, Scott Thompson’s Verve, and Feeling Most Alive

• 1:52:40 Closing and Thanks Again to Notion

Key Links & References

• The Running Ground - Nick Thompson

• Why I Run (excerpt from Running Ground) - Nick Thompson for The Atlantic

• Not Fade Away book - by Laurence Shames and Peter Barton

• Nick Thompson - Timeless (With Guarav Ahuja)

• Writer Evan Ratliff Tried to Vanish: Here’s What Happened (Wired)

• John W. Gardner — “Personal Renewal” Speech

• Will the Humanities Survive Artificial Intelligence? - D. Graham Burnett for The New Yorker

All links and transcript available at dialectic.fm/nick-thompson.

I’ve been lucky to get to know Jared and benefit from his wisdom. I’m honored to have done this with him and I hope you enjoy it.

We discuss:

• Cold-calling the Bush campaign in college, joining them in the run up to 2000, and not dropping out

• Becoming the President's personal aide (or "body man") in his mid-20s, what the President does, and how little Jared slept

• an unlikely partnership with Joshua Kushner
  that led to over a decade building the now-legendary Thrive Capital

• what it was like helping Palantir in the very early days

• Bringing seriousness and humanity to work, whether the West Wing or investing

• the three-body problem of ego, ambition, and impact

• why people trust Jared and how he helps them become their best selves

• east vs. west coast ambition, across DC, SF, and NY

• how he's investing in Birmingham, why cities change and thrive, and helping people raise their ambition

• championing those who champion you

Lessons and description below!

Dialectic Ep. 44: Jared Weinstein - Within Earshot, Out of Camera Shot

21 Lessons from Jared on Service, Humanity in Hard Rooms, and Amplifying People

1. Within earshot, out of camera shot. The personal aide’s motto and a philosophy of service. Close enough to hear what the principal needs; far enough that you’re never the story.

2. Seriousness and warmth don’t trade off, they compound. President Bush took the job seriously and the people in it joyously. The cheap version of intensity makes everyone brittle; the better version lets people bring their A-game without leaving their humanity at the door. High stakes and psychological safety are not at odds.

3. Kindness is honesty. Kindness is pushing someone, not letting them off the hook. Delaying the hard conversation does not preserve the relationship, it ferments resentment—especially when everyone already knows the truth.

4. Spend energy on the 50/50 decisions. President Bush didn’t want easy calls. If the decision was 90/10 obvious, a cabinet secretary handled it. His time was reserved for the ones where smart people made great cases on both sides, and someone still had to choose.

5. The calendar sees the big picture from below. Jared’s first White House job was booking the President’s time, and that’s how he learned the whole building. You see who and what actually matters by who gets on the calendar. Don’t underrate schedulers.

6. When the stakes spike, simplify and act. Jared’s crisis playbook came from rooms with no patience for finger-pointing. Get grounded in what is actually happening, return to your values, take the next step. Then the one after that. It is never as bad as it looks. It is never as good as it looks, either. Level-headedness isn’t a personality trait; it’s the discipline of focused action.

7. Repot before prestige becomes a cage. Advice from Tom Tierney. After the White House, Jared could have stayed in D.C. and compounded in the obvious direction. Instead, he chose Stanford, Palantir, and the opportunity to build a tiny New York venture firm that did not yet look inevitable. The risk was not stepping down; it was letting the last impressive room decide the rest of his life.

8. Choose the place that stretches your ambition. “East Coast ambition is getting from floor seven to floor fifty-seven; West Coast ambition is building your own building.” After his 20s in DC, West Coast ambition felt stranger and more destabilizing: why stay inside the building when you could make your own?

9. Be stubborn on vision but flexible on strategy. Most founders get this backwards: rigid on tactics, loose on why. Thrive stayed fixed on one vision: become the most impactful partner to the most transformative companies. The check sizes, industries, and playbook all flexed around it.

10. Storm the castle, don’t be the castle. Thrive’s orientation, whether hiring or building: stay hungry, stay climbing, act like there’s still a wall in front of you. The fear was the firm becoming the kind of place people joined because it had already made it.

11. Don’t relegate the back office. Jared disliked the phrase at Thrive and found it demeaning. The NASA janitor putting a man on the moon; the White House florist, the receptionist, the custodial lead at the firm: everyone plays a role in the mission. Treat them that way and they’ll show up that way.

12. Choose effectiveness over being right. Having the answer is the easy part; the challenge is getting another person to arrive there on their own legs. Jared would rather move someone one foot closer to the answer than win the argument about it, which makes him great at helping people help themselves.

13. Make your conviction legible. When Chris Paik called to say Thrive was making a mistake passing on Twitch, Jared didn’t disagree. He told him he’d done a poor job articulating why. Conviction isn’t enough; you have to bring your team with you.

14. Sit on the same side of the table. When Jared left Thrive, his colleagues wrote him a book of letters. The recurring note was that even as their boss, in disagreement, or across a deal, he somehow ended up in the chair beside them. Direct enough to say the hard thing, loyal enough that it never felt like an ambush.

15. Ego is fuel, not a map. Jared does not pretend ego is useless; he calls it a fuel, and sometimes a necessary one. But it cannot answer the better question: what life do you actually want when applause, money, and legibility stop being sufficient substitutes?

16. When do you use your best stuff? An exercise Jared passes around: list the specific accomplishments of your life when you were most yourself, then ignore the top-line categories and read the sub-bullets: the people, the texture, the tempo, the kind of problem. That’s your guidebook to authentic and excellent work.

17. The bus needs a sign. Jared is naturally low-profile, but big work requires legibility. If you want people to join, fund, support, or extend the mission, they need to understand what bus is moving and why they should get on. Legibility can come in many flavors.

18. Your ceiling is the best thing you’ve seen up close. The most ambitious thing someone can picture is usually the most ambitious thing they’ve seen. Outside SF or NYC, the reflexive complaint is access to capital, but money wires anywhere in thirty seconds. The scarcity is exposure to a higher bar, so founders’ ambition stretches to meet it and capital ends up chasing them.

19. Make Birmingham more Birmingham. The goal isn’t turning Birmingham into a knockoff of another city. It’s to make Birmingham more itself: stronger schools, better institutions, more opportunity, and enough belief that talented people can imagine building a life there.

20. Champion the people who championed you. Jared left Thrive partly to be with his mother, who is terminally ill. “There has been no bigger champion of Jared Weinstein in this world than Brenda Weinstein, and she needed a champion.” Careers are long. The window to return the favor is not.

21. Be a friend, first. When Jared talks about legacy, he does not reach first for power, wealth, or institutional status. He wants to be remembered as a friend who helped people become the best version of themselves, which is a remarkably soft answer from someone trained in very hard rooms.

Description

Jared Weinstein (LinkedIn, X) is an investor, advisor, civic leader, and founder of Overton. This is his first interview.

Jared spent his twenties in the George W. Bush White House, starting as a scheduling intern and rising to become the President’s personal aide. He went on to Stanford GSB, consulted for Palantir in its early days, and was a founding partner of Thrive Capital in NYC, helping build it into one of the most respected venture firms in the world over eleven years. After leaving Thrive in 2022, Jared returned to Birmingham to focus on Overton, where he invests in local founders, leads civic initiatives including Small Magic — an early childhood language development program — and works to make his hometown the best version of itself. He also continues to invest in startups, serve on boards, and seed and advise new investors. By his own words, he is busier than ever.

Despite his very serious resume, anyone who knows Jared will tell you that he radiates humanity. He has spent his career amplifying people and helping them become the best version of themselves.

We trace the arc of his career, talk about what it’s really like inside the Oval Office, what he admires about the President, and the unlikely pivots that led him beyond a prodigious start. We also discuss what he and Josh got right at Thrive in the early days, how high stakes environments can be psychologically safe, and how to support incredibly ambitious people. Then we talk about his theory of change for Birmingham, the work he is doing now, and his reflections on where he’s been and what he’d like to be known for.

I hope this conversation gives you a model for what it looks like to bring your full humanity into high-stakes work and inspires you to commit yourself to the people, institutions, and communities you believe in.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

• 00:00 - Opening Highlights

• 01:40 - Intro to Jared

• 03:32 - Thanks to Notion

• 04:38 - Start: Being a “Friend” and Bringing Humanity to Serious Work

• 10:55 - From Duke to the West Wing

• 31:45 - Riding Shotgun with President Bush

• 59:27 - Starting Over Out West: Post-WH, Stanford, and Palantir

• 1:16:05 - Meeting Josh Kushner and Building Thrive Capital

• 1:44:37 - Founders, Humility, and the Three-Body Problem of Ego, Ambition, and Impact

• 2:06:41 - Leaving Thrive, Coming Home to Birmingham, and Overton

• 2:32:40 - Busier Than Ever: Mentors, Life in Acts, and What You Hope to Be Known For

• 2:49:11 - Thanks Again to Notion

I talked to Mario about writing, what motivates the heroes he is most interested in (founders), and how to see the stories underneath the stories and get closer to what is true.

Mario is founder of and more recently, partner at Hummingbird. He is obsessed with founders and what makes them tick, and has evolved his career consistently to get closer to a seat that is suited just for him.

The Generalist

The people, companies, and technologies shaping the future.

By Mario Gabriele

20 of my favorite lessons below. We also cover:

• how stories can point at something truer than facts

• why most writing advice is bad

• how great ambition is almost always a product of pain

• a rant against “how do you do anything is how you do everything”

• Hummingbird’s obsession with the texture of someone’s mind

• why the best investors’ rationale fits on a napkin, and why “this founder is insanely good” is actually a deep answer

• why The Generalist isn’t called Mario’s Newsletter (or podcast)

• why he gave up some independence for Hummingbird

Dialectic 43: Mario Gabriele - Reality is Story-Shaped

20 Lessons from Mario on Storytelling, Authenticity, and Finding the Shape of What’s True

1. Stories are how our minds transmit truth. Religions run on them. Political systems hold because of them. Mario says stories are “many orders of magnitude more durable and magnetic than anything else we can come up with.” It’s not an objective reality, it’s a species-subjective one. Our brains are wired this way, and the best we can do is work with that wiring.

2. Beware the axis between madness and greatness. Mario is drawn to the sacrifice, discomfort, and psychic weirdness that often sit behind elite performance. His conclusion? Hero and villain are often just two edits of the same raw material.

3. A polished story is a suspicious story. If someone narrates themselves too neatly, Mario starts wondering what has been cut for elegance, the photographic negative. Every story has a surface and a shadow, a told version and an untold one. The job of an investor, a writer, anyone paying attention is to find what’s left unsaid.

4. Great writing is obsessive observation. It means observing a feeling or event with such fidelity that you make the comparison no one else saw coming: “almost like a joke, you need that element of surprise.” The dominant advice in tech is really just copywriting: hooks and lists useful for distribution. The people giving writing advice in the attention economy are not the people doing the best writing.

5. Beware phrases that sound wise on contact. Mario’s hatred of “How you do anything is how you do everything” is really a broader warning about faux-wisdom. Some sayings have the rough shape of wisdom and none of the calories, yet still manage to plant a malware in your head.

6. Design the game around your one thing. Peter Thiel’s core lesson at Founders Fund: find your comparative advantage at the expense of everything else. Mario’s is serious literary skill crossed with founder obsession and tech + venture rigor. Pair that with a gift for connecting disparate threads and you have something unique.

7. No excuses, no costume, no cover. The things that brought Mario closest to authenticity had a common structure: situations where there was nobody else to rely on. Failure in an exchange year in Nepal. Wild success building the Generalist. You don’t think your way to knowing yourself. Instead, you discover it by putting yourself in positions where you either rise to the occasion or drown.

8. Birth is always painful. Mario agonized over starting the Generalist. He asked for advice, deliberated, vexed, when he could have just tried. “Action produces so much information.” The crossing is never comfortable, but the information is on the other side.

9. It’s okay to be a white belt in life. Mario’s way of reading people is to enter with childlike openness and a willingness to inhabit another’s perspective. Present as the student and the teacher emerges.

10. Show up like an athlete. Lots of investors drift into meetings default skeptical or half-present. Mario treats founder conversations like a performance: when the pistol fires, how you’re feeling is irrelevant. You don’t know who’s walking through the door. It might be the most important meeting of someone’s year (or yours).

11. Raise someone’s ceiling before they can. Being the first check is less about the money and more about being the first person to say: I see ten times more in you than you see in yourself. You’re the boatman taking them across the river. They’d have made it anyway, but you pulled them forward.

12. The best judgments fit on a napkin. If your investment rationale gets too long and too convoluted, suspicion should rise with every added sentence. Sometimes the clearest case is simply: this person is special, and that brevity is not laziness but earned compression.

13. Footnote the last best thing you wrote. Mario doesn’t chase subscribers. There’s a tradeoff between popularity and influence, and he chooses the latter, even if it means a smaller audience. His goal each year is to write one piece that makes the last best thing he wrote a footnote.

14. Kill things before they kill you. The Generalist has cycled through formats, business models, cadences, and entire community experiments. Mario is comfortable killing things early. The sacred part has never changed: obsessive care about the sentences, flow, and story.

15. Pay the debt to modernity. Mario spent ten years believing great work would find its audience on quality alone. It doesn’t work that way. Every writer, no matter how literary their sensibility, owes a concession to the distribution mechanics of their time, however romantic the alternative sounds.

16. There is always the game and the metagame. Mario says it’s happening in every conversation: even a podcast, even with the people closest to you. “It sounds cynical, but I don’t think it has to be. It is there all the time, whether you see it or not.”

17. The texture of someone’s mind matters more than the spreadsheet. Too much time is spent on CAC, LTV, and product features, and too little on who someone actually is. Hummingbird’s chief focus is creating the conditions for founders to open up and reveal the strange, raw edges of their personality.

18. Happy childhoods don’t build world-beaters. Mario is skeptical of the “good fuel” framework. Behind every hyper-ambitious person, there’s something unresolved. Even founders who claim perfect childhoods reveal fractures on closer inspection. You can’t trust the narrative because greatness tends to take everything.

19. Generosity is the sign of true quality. Not gradients. Not dark mode. Not the aesthetic preferences of a high-signal group. Real quality in a product or a piece of writing is meeting someone where they are. Most things marketed as “delightful” just flatter the people already in the room.

20. You don’t have to know what you’re becoming. Mario will always love writing, stories, and studying the strange people tech produces. But he won’t lock himself into a form factor. Oscar Wilde’s line captures it: if you never settle on who you’re supposed to be, you never become anything. That’s the reward.

Description

Mario Gabriele (X) is a writer, investor, and analyst. He is founder of The Generalist and Partner Hummingbird.

He aims to bring the rigor of investment analysis with writing quality and style that is closer to the New Yorker. His profiles, deep dives, and briefings are amongst the highest quality writing in the technology business, and he interviews practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled Microsoft’s Satya Nadella.

I spoke to Mario about stories and the truths they hold or reveal. He is a writer first, and it shows in his prose, style, and depth. We also discussed the evolution of The Generalist’s content and business model, both of which he has experimented with ruthlessly. The subscription counts 160,000+ readers / listeners and is currently ranked as the #7 bestseller in Substack’s business rankings. He is also an investor focused on the technology world’s heroes: founders. Hummingbird, which he joined earlier this year, is known for its obsessive approach to understanding the minds, motivations, and worlds of the entrepreneurs it backs. We dive into the under-discussed elements that shape world-beaters, including the notion that ambition almost always comes from some level of pain.

Across the conversation, we talk about how authenticity and evolution run across his career, and how he is at peace as someone who doesn’t know exactly who he is becoming. That generalist orientation continues to produce unlikely paths that surprise him. I hope this conversation inspires you to take stories seriously, to look for what’s true beneath the polished surface, and to trust paths you didn’t plan for.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:13) Intro to Mario

• (2:49) Thanks to Notion

• (3:58) Start: Stories, Truth, Writing, and the Story Beneath the Story

• (23:39) Failure, Authenticity, Comparative Advantage, and The Most Annoying Aphorism in the World

• (35:55) The Generalist’s Style

• (45:20) Process, Goals, Vision, Experimentation, and Business Models

• (57:52) Investing: Energy, First Checks, Notecard-level Clarity, and Peter Thiel

• (1:07:46) Understanding Founders, Motivation, Good and Bad Fuel, and True Ambition

• (1:17:47) Hummingbird: Seeing the World as it Actually Is and How Stories Reveal Truth, Linguistics, Observation, Deciding to Join, and Evolution

• (1:29:32) Motivation, Raising the Bar, Ongoing Learning and Teachability, Status, Unlearning, Generous Products, and The Reward of Not Knowing

• (1:47:15) Thanks Again to Notion

I’ve been thinking a lot about a part of my conversation with . Henrik is one of my favorite people to talk about introspection with, because he is simultaneously attuned to himself and agentic.

His argument (inspired by Nick Cave), is that we ought to flip the direction of our introspection from object to subject.

Henrik suggests that we stop obsessively looking in, trying to understand “who am I?” Instead, attend outwards: what am noticing? In this book, this person, this view?

The direction of knowing has inverted. And your world is far richer for it. Instead of becoming a bottomless well of confusion, rumination, and paralysis (as any overly introspective person knows), the world expands.

“connect to [your]self as someone paying attention.”

Attention deepens, and richness is everywhere to be found. In the process, we get to know ourselves.

This kind of self-knowing is not selfish, but generous. It also, perhaps paradoxically, creates self-confidence of a different kind:

“You can understand that subjective perspective of yourself. If you look at someone like Rick Rubin or Nick Cave, they have extreme confidence in their subject. They know themselves as subjects really well.”

The people who know themselves in this way act easily. They have a solidity that makes it easy to act upon the world, to create, and that is attractive to be around. That makes others want to notice, too.

A few years ago, I spoke to a hero of mine who has since passed away. He described a last project to “get out from under myself.”

I think about that phrase often. It captures what I think is one of the central aspirations of life.

It rhymes with another favorite bit of wisdom, from David Foster Wallace, in his classic commencement speech (This is Water):

And the world will not discourage you from operating on your default-settings, because the world of men and money and power hums along quite nicely on the fuel of fear and contempt and frustration and craving and the worship of self. Our own present culture has harnessed these forces in ways that have yielded extraordinary wealth and comfort and personal freedom.

The freedom to be lords of our own tiny skull-sized kingdoms, alone at the center of all creation.

This kind of freedom has much to recommend it. But of course there are all different kinds of freedom, and the kind that is most precious you will not hear much talked about in the great outside world of winning and achieving and displaying.

The really important kind of freedom involves attention, and awareness, and discipline, and effort, and being able truly to care about other people and to sacrifice for them, over and over, in myriad petty little unsexy ways, every day. That is real freedom.

How do I do this? How do I escape the skull sized kingdom? How do I get out from under the unbearable weight of the default setting, the mind that is so obsessed with itself?

Well, Henrik’s guidance is a bit of helpful jiu-jitsu. At least for those of us who are so desperate to know ourselves well enough to finally act.

The answers are not in here. They are outward. First with presence and attention, then recognition, and eventually, action. I have found that the action that this kind of self-knowledge produces trends toward service.

Offering something that only you can, because of the distinctive ways you see the world.

Freedom awaits. You only have to look.

Thanks to Henrik Karlsson for inspiring me to look out. You can find our full conversation here:

And Henrik’s original piece on Nick here:

Escaping Flatland

Two kinds of introspection

Cy Twombly’s studio…

Read more

3 years ago · 972 likes · 46 comments · Henrik Karlsson

“reading and writing are the most dignified and worthy activities that anyone can do—and, in fact, are activities that everyone should do.”

I talked to Celine about changing your life by writing online, expanding the market for what you love, and starting somewhere, even if it requires pure impulse.

Celine writes personal canon, a newsletter focused on taking your intellectual development seriously as someone outside of academia or school. This includes literary criticism and many more interdisciplinary thoughts across art, culture, design, and technology. She doubles as a product designer in her professional life.

We discuss:

• leisurely research and creating a curriculum for your growth long after you graduate: “who do I want to be at the end of the season?”

• why literary classics can be thrilling rather than dutiful, how you can expand the market for what you love, and why *you* should read Proust

• using parasociality to psyop people into doing things that are good for them

• how studying historical contexts makes us smarter about the present, and how to root yourself in epistemic humility about the now

• why note taking systems must be a means to an end, and how her best “systems” are inefficient handwritten journals and actual published work

• becoming the “Venkatesh Rao for tumblr girls”

• how learning makes you live “longer”

• that many will wait a lifetime for someone to give them permission to do what they’ve always hoped to do

Dialectic Ep. 42: Celine Nguyen -Nurturing Your Mind in Public

17 Lessons from Celine on Taking Your Intellectual Interests Seriously

1. Intellectual life is your birthright. Reading, writing, and critical thinking are not luxuries for academics or critics. They are part of being a person. Everyone has the right to produce a worldview, not just inherit one.

2. Great art elicits a response. The best art prompts you to participate. You read something brilliant, and suddenly you want to: answer it, extend it, remix it, argue with it—and make something of your own.

3. Creation starts as imitation. Fanfiction, tweeting about an essay, deep copying: these are not shameful. They are often the first reps before you trust yourself enough to make an original work.

4. Don’t wait for a syllabus to rescue you. School ends, but the opportunity to learn doesn’t. At some point, if you want an intellectual life, you have to become your own institution, your own department, your own demanding little faculty of one.

5. Cheap constraints can grow valuable minds. A long commute and a tiny phone plan pushed Celine toward Kindle books instead of Instagram. A lot of intellectual life begins not with ideal conditions, but with whatever gives you the space to think.

6. Curiosity dies when it gets too well-behaved. What stops most people from self-directed learning isn’t laziness. It’s neurotic rigidity: the fear of starting with the wrong text, having the wrong interpretation, or learning things in the wrong order.

7. Who do you want to be by summer? That’s Celine’s real question when she plans her reading. The point is not to accumulate information. It is to shape yourself. What you study, what you return to, what you cannot stop circling: these are the inputs that make a mind.

8. Let history be a lens, not a museum. A frame from sociology, theology, or literary criticism can explain the strange behavior of a founder, the “sudden” rise of a platform, or a whole cultural fever dream.

9. Notes are scaffolding, not a cathedral. Celine went from obsessive note-system maintenance to barely touching it. The shift was simple: instead of optimizing the tool, she could open the draft and work on the actual thing. “All my ideas end up contained within the work.”

10. Slow work is a sharpening stone. Anne Carson translated Greek words by hand using a physical lexicon. Celine journals longhand and maintains a table of contents in ink. Your mind is the instrument producing the work; anything that sharpens it is rarely wasted.

11. The essay is the shot glass. Before Celine published anything, she had all the books, the conversations, the ambitions. Writing was the thing that forced them to cohere. Life is a field of corn and the essay is the shot glass (Mary Karr).

12. Create the appetite you wish existed. Celine wrote 5,000 words making the case for Proust through social intrigue, gossip, romantic mess, and sheer aliveness. You don’t have to cheapen literature, but you also don’t have to accept the current audience as a ceiling. Translate the canon into human terms and others will want to join in the fun. William Wordsworth: “every original writer must… create the taste by which he is to be relished.”

13. Preparation is not progress. Celine spent her twenties training for a race she never let herself run. She had the books, ideas, and ambitions, but no output. When two writers announced a Substack meetup, she wrote her first post at the airport and hit publish two hours before the event. You can prepare while doing the work. Sometimes you have to seize the moment and ship.

14. Nobody is coming to anoint you. For years, Celine waited for a mentor to tap her on the shoulder and say she was ready. Artist Chitra Ganesh blew that narrative up: success comes from daily work and peer networks, not being discovered. Celine eventually asked herself the obvious question: Who would have known she wanted to write if she wasn’t writing?

15. Optionality is the enemy of finishing. Once Celine picks an idea, she seals the escape routes. The last ten percent of any creative project, the part where you’re stuck and don’t see a way out, is where the most growth happens.

16. Treat your students like geniuses. One piece of advice that stayed with Celine came through Laurel Schwulst: believe in every student as if they are already brilliant. Most people are far more fragile in their ambitions than they let on, and they often rise to the level of belief around them.

17. Youth is having somewhere to go next. Celine’s dad is learning Swift and asking her about vibe coding. Writer Mario Javier Cardenas always has another novel in progress. The people who seem most alive are never done becoming.

Description

Celine Nguyen (Website, Substack, X) is a writer, software designer at Watershed, and literary critic. She writes personal canon, a newsletter about literature, design, art, and technology that has grown to tens of thousands of subscribers. She has also written for The Atlantic, Asterisk Magazine, and more.

I discovered Celine with her reflection on two years of writing her newsletter, where she made the case for living a life of the mind, reading great things, and writing online:

After 2 years, I’m convinced that reading and writing are the most dignified and worthy activities that anyone can do—and, in fact, are activities that everyone should do.

She also has written viral essays on research as a leisure activity and a case for reading Marcel Proust’s 3,000 page novel, *In Search of Lost Time.* In another favorite, she critically analyzes the mechanics of how great writers begin. Celine makes intellectual life and very serious books feel accessible and exciting rather than obligatory.

We spoke about much of her writing, taking your intellectual growth seriously outside of academia, and how she has become an influencer in a good way. She believes you can expand the market for what you love, and her success is evidence that there is a market for more than the low-hanging fruit that dominates much of the internet. Celine sees reading and writing through the lens of becoming, and I was inspired to raise my own bar. I hope you can say the same.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic, and check out their latest round of updates here.

Timestamps

• (0:00) Opening Highlights

• (1:35) Intro to Celine

• (4:25) Thanks to Notion

• (6:18) Start: Pursuing a Life of the Mind, Personal Curriculum, and Contextualizing the Present in History

• (24:53) Research as a Leisure, Self-Cultivation, and Calibrating Rigor

• (39:59) Effectiveness, Tools & Process, and Letting Output Drive Your Learning

• (59:35) Parasocially Influencing People to Do Good Things (Like Reading and Writing)

• (1:09:39) Drawing the Reader in and Expanding the Market for What You Love (and for Proust)

• (1:24:07) Aspiration, Posing, and Pretending Your Way into Enthusiasm

• (1:34:37) Preparation is Not Progress

• (1:46:07) Copying, Writing Process, Mechanics, and Design

• (1:57:25) Commitment, Finishing, Substack, Life Extension and Closing

• (2:18:31) Thanks Again to Notion

Episode Links

Available on all platforms at dialectic.fm/celine-nguyen.

Today, the fan-favorite is back. Henrik is one of my favorite products of Substack. He is quick to share that his unique life would probably not be possible without it, and without the combination of patronage and a place on the modern internet where people actually want to read great essays.

If you listened to the last convo, this should need no introduction. If you missed it: there are few people who by way of their writing and conversation push me to think more expansively about what life can be.

Henrik wrote something about our time together and in it, he used the phrase “differently free” (borrowed from Venkatesh Rao). Our lives are remarkably different, and yet I feel as though I’ve met a kindred spirit in a strange mirror that helps me see myself and my possibilities more clearly and creatively.

Escaping Flatland

Differently free

Cousin Bichonnade in Flight, Jacques Henri Lartigue, 1905…

Read more

4 months ago · 104 likes · 5 comments · Henrik Karlsson

I focused the conversation on creativity, but Henrik’s wisdom runs in all directions. It’s long enough (sorry, but not really) that you’ll get plenty of range. I hope you enjoy it as much as I did.

My favorite lessons, description, and timestamps below. All links available at dialectic.fm/henrik-2, and spotify, apple, and youtube are here.

Dialectic Ep. 41: Henrik Karlsson - Strolling Through Life’s Labrynths

18 Lessons on Creativity, Confusion, and Finding an Unlikely Way Through

1. Understimulate yourself. Remove the feeds, the rewards, and the noise. When you strip away what’s pulling at you from the outside, your curiosity has space to grow. Henrik lives on a small island farm in Denmark with his wife and daughters. Give yourself space to be surprised.

2. The tourist map has no back alleys. Henrik took his kids on a walk (or dérive) in Málaga with one rule: pick the most exciting direction and keep going. They ended up galloping through back alleys and construction sites, more alive than any planned itinerary could have made them.

3. Break your tiles. Every mental model you carry is shaped for a problem you’ve already solved. If a new situation is round, your square tiles won’t fit. You have to shatter them into shards and sit with the debris before you can build anything new.

4. Your brain defends its bad ideas. Once a belief is useful enough, the mind protects it, quietly disposing of anything that threatens it. These are called knowledge shields. Darwin’s fix: write down every disconfirming fact immediately, before the mind buries it. We have a tendency to protect our squares.

5. The sprawl is the progress. Michael Nielsen told Henrik that if his essay is sprawling, he’s halfway there. The frustration of incoherence is not the wrong direction. It’s the only way through the woods.

6. It’s okay to be lost in the woods. He spent three months white-knuckled over an essay, needing it to cohere. Then he realized: it’s like being lost in the woods. If you’re clenching and demanding to get out, it’s agony. But if you can manage to think, these woods are kind of beautiful, you start to stroll and notice things. Everything opens up.

7. Watch yourself in the mirror. For years Henrik filled journals he never reopened. Then he started revisiting them. He could spot his poses, notice his growth, and find whole essays hiding in wanderings he’d forgotten. The notebook became a mirror and fixed his posture.

8. Look out to see in. Introspection with yourself as the object is a trap. You’re incompressible anyway. Make yourself the subject. Nick Cave and Rick Rubin don’t ask “Who am I?” They just notice. Ask what this song wants to be, right here. Attend to the world outside and you discover the person paying attention inside.

9. Live in the room a little longer. Each essay Henrik writes is a room he gets to inhabit. While writing about his kids, he’s a more present father. The project works on him as much as he works on it. Publishing is throwing away the key to that room forever. Don’t rush to leave.

10. Trust the embarrassing idea. The real creative signal isn’t intellectual excitement. It’s bodily. Henrik sometimes catches himself wanting to write essays that would impress his friends, and the telltale sign is that the idea lives entirely in his head. The things worth chasing feel light, open, playful. Often a little ridiculous.

11. Try banning your best trick. Lars Von Trier’s early films are gorgeous, perfectly choreographed, classically excellent. So he tied his hands behind his back: no tripods, no artificial lighting, no polished framing. What he found inside those constraints was rawer and more powerful than anything his talent could produce on autopilot.

12. Great art is a Jenga tower. Shakespeare took history and deleted the motivations. Hemingway wrote simple sentences that hold great depth. The skill of a great writer isn’t in what they put on the page, but in what they pull out while the structure still stands. Propaganda fills every gap. Art leaves them for you to fill with yourself.

13. Your self-image is a lagging indicator. Henrik went from isolated writer on a Swedish island to a full-time essayist with real income in three years. He’s still tempted to make decisions like his 2023 self. The situation has changed, but his internal model hasn’t caught up yet. If you’re not constantly assessing your life with fresh eyes, you might be throttling yourself.

14. Bring your heroes to the kitchen table. Henrik and Johanna refer to the poet Tranströmer as “Tomas” — a mutual friend they gossip about. When he’s stuck, Henrik reads Eno’s diaries not as a fan but as someone seeking advice from a peer. Dostoevsky was just a guy. Befriend your inspirations.

15. Conviction is surrender, not courage. Before his daughter Maud, Henrik held his opinions loosely. Pushback came and he folded. Parenthood made folding unforgivable. Agency didn’t arrive as bravery, but as stakes he refused to betray for his kids.

16. Hard eyes, soft steps. You need stoic clarity to face reality: where you’re failing as a parent, a partner, or a creator. But hardness alone turns you rigid and closed. Softness is what tells you where to walk: the playful hunches, the felt senses, the galloping. One shows you the map. The other moves your legs.

17. Love is context no one else has. When Henrik met his wife Johanna, plenty of people fell for her in easy-to-read ways. The parts he loves most deeply now, they didn’t see at all. Real love is an acquired taste that comes from inhabiting someone else’s world.

18. Remember to join in the music. Henrik believes your uniqueness puts you in front of things only you will ever be positioned to care for. Like a cosmic jam session against entropy: aspire to leave the stage having evolved the music. Ten thousand years ago, hunter-gatherers blew pigment around their hands on cave walls. A handprint and a declaration: We were here. We felt this.

Description

Henrik Karlsson (Substack, X) is a writer and essayist. His newsletter, Escaping Flatland, explores attention, agency, relationships, and the inner life of making things. He is one of my favorite essayists, and I spoke to him previously on Dialectic 19: Cultivating a Life that Fits in Spring 2025. We met again in Copenhagen, this time on video.

Our first conversation focused on designing your life iteratively and relationships. This time is about the messiness of creativity and problem-solving. We circle a central theme of navigating through the woods of confusion when you are—and must necessarily be to grow—lost, and trusting yourself to reach clarity on the other side. Henrik walks us through how he (and so many of his favorite artists and thinkers, from Brian Eno to Charles Darwin to Ingmar Bergman) smashes apart his mental models in pursuit of seeing things more clearly. Or at the very least, offering up something new.

He also challenges my praise of boredom, describes how a ballerina finding balance in her body mirrors what creatives must do, likens desire to the energetic discovery of wandering (or dérive, like past guest Cyan Banister has spoken about), explains why the best art is like a Jenga tower, and reflects on what he believes in; Henrik’s humanity is on display. He challenged me to think much more ambitiously about the risks I take, the ways I am holding on to faulty models of reality, and how living richly is simply a matter of perspective.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

• (00:00) Opening Highlights

• (01:28) Intro to Henrik

• (04:05) Thanks to Notion

• (05:58) Begin: Attention, Boredom, Predictability, Aliveness, and Dérive

• (14:52) Confusion and Clarity: Mental Balance, Breaking Mental Models, and Making It Through the Woods

• (31:37) Henrik’s Notebooks, Personal Constraints

• (40:54) Introspection as Subject, Not Object: Nick Cave, Rick Rubin, and Attending Outward

• (46:56) Creative Risks, Constraints, and the Labyrinth: Eno, Von Trier, Cage, and Herzog

• (1:03:47) Agency, The Right Kind of Risk, and What Else Is Possible

• (1:23:29) Desire: Trusting Excitement and “Galloping Down the Street”

• (1:30:44) Why Good Ideas Come from the Edges and Keeping the Space to Sit in Your Ideas

• (1:44:58) Physical Space and Isolation

• (1:51:19) Jenga Towers: Why Great Art Has Space and Spits You Back Out

• (2:01:30) Conviction, Belief, Navigating Murkiness with Firmness and Openness

• (2:15:54) Short Essays and How Reading Is Like Running

• (2:22:27) What Love Is Like and Befriend Those We Read

• (2:29:18) Grandfather Nils and a Final Reminder

• (2:40:49) Thanks Again to Notion

18 Lessons from Charles on Tuning Your Radar, Making Generous Tools, and Building a Personal Business that Lasts

1. Creativity is decision-making. Amidst infinite choice, you have to decide what you’re going to do and what problems you’re going to solve. Charles traces this from Duchamp to founders he admires. And the decision rubric is always personal.

2. You are your love, not what you love. The teenager who defines themself by being into hardcore has mapped their identity to the object, rather than their relationship to it. Your taste isn’t the songs you saved. It’s the recognition that made you press save. Charles calls this your radar.

3. Self-knowledge is prerequisite. Charles keeps coming back to the same conviction: the hardest thing about being creative is understanding yourself. Every other skill—in art, in business, in building things—stacks on top of that foundation.

4. Let yourself wander. Charles has always been the type to flip ahead in the textbook just to see what was over there: part rebellion, part curiosity. Are.na was built on that impulse. Karly describes it as research as leisure activity. The key is that it’s self-directed: nobody assigns the chapter that changes your life.

5. Anything can be a nodal point. A piece of information that changes you, simultaneously discovering and creating yourself. The shadiest JPEG, recontextualized, might become meaningful to you. As Anni Albers told her students: “You can go anywhere from anywhere.”

6. Clear the stage or miss the signal. When your job lives on a screen, anything you might be interested in has to fight every other thing in the world. Giant corporations have business models designed to hijack and dull your radar. But the answer isn’t obsessing over finding the perfect object. It’s being in a state where you can be surprised by one.

7. Taste is self-knowledge, not a debate. When people call taste a skill, they make it competitive. Charles finds this absurd: “I like this hot dog, you don’t like this hot dog, therefore I’m better than you.” Real taste is the composite of a person’s idiosyncratic perspective developed over years. It’s too personal to be ranked.

8. Every trick has a connotation. Charles is 43 and still skateboards. Skating is a referential practice: you consume more reference than you spend doing the activity. It’s also a model for creative work. Absorb, perform based on mood, and eventually your influences dissolve into something that looks like you.

9. In defense of posers. If you find yourself wanting so hard to associate with an idea, that means something. Your radar is firing. Charles is a self-described poser apologist: faking it until you make it is just pushing yourself outward. The vulnerability required to maintain that position deserves respect, not ridicule. We all start somewhere.

10. Patterns evolve as you collect. Charles uses Are.na channels to frame what he finds. It starts with 3 to 5 related artifacts. As he adds, the whole collection means something slightly different. He uses these evolving containers as filters for his thinking, and over time, may even crystallize into essays. Collecting is pleasurable; writing is where the decisions get made.

11. Anything can be interesting if you’re interested. Charles’s professor Cory Arcangel would take links students brought to class and parse out why they might matter. Later, Cory did the same at art shows, talking through how he was looking at things, no matter how arbitrary. The generosity is in opening up the aperture, not in having the answer.

12. Here for love, not fame. Charles borrows from The Bachelor to describe the corrupting force online when someone is here for the wrong reasons: their interests accumulate with an awareness of how they’ll reflect back onto them. The antidote is attention without expectation. Showing something with joy, not to look like a person with good taste.

13. The most generous art is a tool. Early in his career, Charles thought generosity as an artist meant being vulnerable and diaristic, sharing images of himself and his family. Eventually, he flipped: the most generous thing you can do is remove yourself and make things for other people to use. Are.na is software built to be reinterpreted, not admired.

14. Great design fades into the background. Are.na commissioned a custom typeface called Areal, a near-invisible refinement of Arial designed so you can’t spot the difference. The hope is that it feels like refreshing a browser page: the same, but it isn’t. Content should come through more than the interface. The ambition is to look good without looking like too much of anything.

15. Give people room to think. “It’s so easy to treat technology as though it can prescribe a solution to a particular problem. But what humans really need is much more simple: time and space to think and process.” Are.na‘s design philosophy centers on giving you space rather than sorting things for you. The best tools don’t tell you what to pay attention to.

16. The internet needs more artists building software. Are.na‘s team comes from creative backgrounds, and Charles believes creative decision-making is harder to teach than the mechanics of running a company. The internet would be more interesting if more people like that were building things.

17. The slow blade penetrates the shield. Are.na is approaching its 15th anniversary, thanks to patient growth. Its aspirational peer isn’t Facebook. It’s Nishiyama Onsen Keiunkan, a Japanese hot spring hotel founded in 705 AD. Charles nearly ran out of money, freelanced on the side, and kept going — because “getting to work on something cool with your friends is the most luxurious thing you can do.”

18. “It ought to begin by being personal.” The Delaware C Corp name for Are.na is “When It Changed,” a nod to when its creative founders took control. The platform’s subscription model, its no-algorithm stance, its principled minimalism: it all flows from one premise Charles can’t escape. “I think it’s the coolest thing on the Internet. I don’t know what else I would do.”

Description

Charles Broskoski (Website, Are.na, X), aka Cab, is an artist turned entrepreneur and co-founder & CEO of Are.na, a platform for collecting, connecting, and self-directed learning. I created an are.na channel for all of the references I used in preparation for this episode.

Charles began as an artist before becoming a software engineer, and started Are.na with many collaborators out of a desire to replace the now defunct del.icio.us after it was acquired by Yahoo. He and a range of collaborators have been working on Are.na for nearly 15 years, and he is now focused on it full-time, thanks to the platform’s 18,000 paying subscribers.

While I’m not a longtime Are.na user, I discovered Charles by way of his talk / essay, “Here for the Wrong Reasons” and was enthused by his philosophy of attention and how the things we encounter shape us.

Our conversation centers on patterns of noticing and what it means to know yourself through what you pay attention to, or as Charles calls it, your radar. We discuss creativity as decision-making, self-directed learning and research, and Are.na‘s channels as frames for what we encounter. We also talk about personal versus performative taste, opinionated design that still gives you space, building something that lasts, and why Charles believes creative people should start deeply personal businesses.

I hope you are inspired to be generous and scrutinizing with your attention, to create things that are personal and durable, and to remember that knowing yourself is a worthy journey of a lifetime.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and where you can find all links and transcripts. You can learn more at notion.com/dialectic.

Special thanks to Earshot in NYC for hosting us for this conversation.

Timestamps

• (0:00) - Opening Highlights

• (1:21) - Intro: Charles Broskoski

• (4:00) - Thanks to Notion

• (5:26) - Start: Creativity as Self-Knowledge and Problem-Solving

• (13:37) - Self-directed Learning and Casual Research

• (21:33) - Skateboarding, Being a Beginner, In Defense of Posers

• (33:26) - Contextual Patterns and Channels

• (45:54) - Nodal Points, Your Radar, and Careful Attention

• (1:04:57) - Subjectivity, Self-Knowledge, and Taste

• (1:15:09) - Performance: Here for Fame and Not Love

• (1:22:53) - Aspirational Attention

• (1:29:02) - Designing Generous Tools

• (1:42:44) - Space in a Product and Fading into the Background

• (1:50:01) - Why Creatives Should Be Entrepreneurial & Building an Independent Business Online

• (1:54:11) - Patience, Durability, and Antifragility

• (1:59:48) - Personal Businesses

• (2:10:27) - Grab Bag: Authenticity, Bohm Dialogue, Skateboarding, and Keeping Things Personal

• (2:28:28) - Thanks Again to Notion

All links available at dialectic.fm/cab.

We discuss:

• Why spreadsheets is always wrong and why

• How he developed conviction on Vanta in 14 seconds

• Investing $200M into Robinhood during the first week of COVID

• Why craft and design have never mattered more in software

• Why the hardest round to invest in is the one after you first invest

• Writing memos through the night as a gut check on conviction

• What he’s learned from Doug Leone, Mike Moritz, and Pat Grady

• Sequoia’s “we” over “I” culture and why performance is tenet #1

• The joy of watching the next generation feel the winning feeling

Dialectic Ep. 39: Andrew Reed - Don’t Flinch

Available on Spotify, Apple, YouTube, and all podcast platforms. Transcript and all links at dialectic.fm.

15 Lessons from Andrew

1. The founder beats the model. Andrew started his career as a headphones-on excel grinder. He’d now choose founder quality over more financial data every time; the spreadsheets are always wrong in one direction anyway.

2. There is much to observe when you look. As a kid he struggled with a stutter, so he watched instead of talking. Years of insecurity left him with a rare superpower as an investor: “I have a unique way of seeing the little kid inside people. And I think that helps with trust.”

3. Don’t flinch. He’d always pictured his big crisis moment in a Park Avenue boardroom. The real one was laps around an empty pool during COVID, wiring a $200 million check as markets cratered, asking himself, “What would the guy you want to be do in this moment?”—and then doing it.

4. Your first win calibrates everything.** Andrew spent years at Sequoia grinding before getting his first real shot to lead an investment. It was Robinhood. Which meant his idea of “normal”—his internal bar for founders—was set to outlier mode from day one. “If you got four or five companies and one of ‘em is pretty good, you’re playing free.”

5. Outliers can look broken on paper. You won’t find a great company by screening for one that’s good at everything. The 90th percentile startup trends mediocre. You need one dimension so freakishly strong that it outweighs the flaws.

6. Great founders become unrecognizable. The person he backed 10 years ago and the person running the company now are borderline different humans. Pedigree and IQ matter, but the real signal is whether someone keeps growing as the stakes and complexity ramp.

7. Sometimes you know in 14 seconds. When he met Vanta’s Christina Cacioppo, he started rushing through the pitch. Not dismissive, but already decided: “I know it’s good. Let’s get to the part where we figure out the terms.”

8. The follow-on is the real test. Six months after investing, someone offers five times the price. You’ve attended two board meetings and seen the lowlights up close. That first double-down is one of the hardest calls in investing.

9. Don’t let frameworks blind you. Andrew avoided the traditional ARR multiple math. Instead: what did you actually add this quarter? Figma at ‘100x ARR’ was really 4x the two-year-out number. Charlie Munger’s corollary: “If you have to actually do the math, it’s too close.”

10. The memo is the gut check. When he’s truly excited, Andrew sits down and stays up through the night. When he loses the buzz mid-writing, he doesn’t fight it. The act of writing is the conviction test itself.

11. Reinvent or become a footnote. Sequoia legend Doug Leone spent decades doing enterprise deals, then at 58 bet on a budding Brazilian fintech Nubank that became one of the biggest venture returns in history. “Being willing to look extraordinarily stupid at that stage of your life and then dominating — that ought to be in the ‘how to do this job’ books.”

12. Advise with grace. Ravi Gupta’s line rings in his head: when an investor asks a founder “Have you thought about X?”, the honest answer is, “There’s nothing you’ve thought about that I haven’t.” Board work is about timing, not theatrics. Earn trust first. Then surface the hard thing with the self-awareness that it’s probably not a new thought.

13. Watching someone feel it for the first time beats feeling it again. Olympic gold medalist Kristen Faulkner told Andrew that seeing younger Sequoia teammates hit the podium for the first time is better than repeating herself. That stuck with him because it reframed the whole point of staying in the arena once you’ve tasted victory.

14. Winners put up the numbers. Of Sequoia’s ten tenets, thfe first is performance. In Doug Leone’s words, “if you don’t have the first one, the other nine don’t matter.” Andrew suggests Mike Moritz may be the GOAT: “He put up the numbers more than you could possibly imagine.”

15. “Lightly, child, lightly.” The world Andrew operates in is intense. Billions of dollars, public scrutiny, founders on the edge. So he references Huxley’s line in his bio: “Learn to do everything lightly. Feel lightly even though you’re feeling deeply.” Simple guidance for a life.

Description

Andrew Reed (X, Website, Sequoia) is a growth investor at Sequoia Capital, where he has invested in companies including Robinhood, Figma, Klarna, Phantom, Vanta, ElevenLabs, Mubi, and Strava. He is quietly one of the best growth investors of his generation.

We begin with how Andrew’s competitiveness and humanity coexist—the twin brother rivalry, the football player who also did musicals, the Goldman analyst who came to value people over spreadsheets. He also shares how an early lack of confidence helped him become a great observer of people and situations.

We talk through his approach to investing: why spreadsheets are “always wrong” in one direction, how he underwriters revenue growth, and what he sees in the world-beaters he invests in. We discuss several of his most formative investments—Robinhood as a 27-year-old’s first check, and again during the first week of COVID; Figma at a price people thought was insane; and a 14-second conviction on Vanta’s—and what each taught him about conviction, timing, and not flinching.

Andrew shares his perspective on serving as a board member, knowing when to double down, closing deals, and how craft can be a commercial input. We also talk extensively about Sequoia Capital and its legendary leaders, from Don Valentine, to Doug Leone and Mike Moritz, to newly-appointed Co-Steward Pat Grady. Andrew reflects on what it means to apprentice at an institution where greatness is the expectation and the champagne toast lasts five minutes.

I hope this conversation inspires you to show up ready for the day you don’t expect, to rise to the stakes rather than shrink from them, and to move through your life and work a little more lightly.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of this site where you can find all links and transcripts. My “What are You Building This Year” feature with Notion on Instagram.

Timestamps

• (0:00) - Opening Highlights

• (2:02) - Intro: Andrew Reed

• (3:50) - Thanks to Notion

• (5:23) - Start: Humanity, Spotting Weird, and Competitiveness

• (19:07) - Investing & Great Founders

• (37:53) - Andrew’s Style, Pat Grady, and Continuous Learning

• (47:31) - Doubling Down and Not Flinching

• (56:09) - Empathy on Boards, Learning the Real Business, “Expensive” Prices, and Selling

• (1:07:18) - Managing Ego and Becoming a Leader

• (1:14:08) - Craft as a Commercial Input, Knowing vs. Feeling, Preparing for Big Days, Becoming a Great Closer

• (1:28:39) - Sequoia Capital

• (1:38:57) - Don Valentine, Mike Moritz, and Doug Leone

• (1:51:29) - Closing Questions

• (1:59:08) - Thanks Again to Notion

Today, she runs Moth Fund, where she backs founders at the beginning. In the past, she’s worked across design, product, and editorial at Figma, Notion, Stripe Press, The Browser Co, and scouted for Sequoia Capital. Her background in film and design echoes in the people she backs and in the quality of her curation and writing.

Molly is people-centric yet fiercely individual, intuitive yet pragmatic, and truth-seeking yet full of care. I enjoyed going deep on people, self-knowledge, her extensive writing and wonderful taste, and the search and deepening into a creative and professional life that fits just you.

We also discuss:

- Why it takes 3 months for her to know someone well enough to invest
- Why authenticity is magnetic
- The difference between agency and ambition
- Why commerciality is a lens you can learn
- Illegibility as private confidence, not public uncertainty
- How your brand is a bell in other people’s heads
- Vocation as “stalking your calling” and then yielding to it
- Why we should focus on doing something rather than being someone

Full details below, including some favorite lessons from the episode.

Dialectic Ep. 38: Molly Mielke McCarthy - The Art of Peopling

Available on Spotify, Apple, YouTube, and all podcast platforms.

17+ Lessons from Molly on Betting on Moths, Choosing Your Own Game, and the Shape of a Life

1. Trajectory takes time to unfold. Anyone can impress in a meeting. Molly won’t bet on someone until she’s watched them long enough to see if they’re actually getting better at the things holding them back. “If they’ve made no progress in three months, they’re probably not going to in the next three months either.”

2. Hunt for moths. Molly’s term for the founders she backs: quirky, quiet, mission-driven, often illegible. They spike in competence but struggle with storytelling, which means they’re consistently underpriced. Competence is rare. Storytelling can be taught.

3. Spikiness cuts both ways. Your greatest strength functions as your greatest weakness. People show you their spikes by how they allocate time. They lead with their dominant leg, and the stuff they’re neglecting tells you where their weaknesses are.

4. Magnetism is the exhaust of authenticity. Charisma is performed and drains the performer. Authenticity attracts the right people without effort, and repels the wrong ones, which is just as valuable. Get a nerdy introvert talking about their obsession and people just like them start swarming.

5. Discernment doesn’t stop at picking. Choosing who to back is the obvious challenge. Molly goes further: “Am I really helping them in the direction that they are meant to be helped?” Discerning how to help someone matters just as much as discerning whether to help them at all.

6. Commerciality is patience with upside. Commercial people see where money flows and how to capture it. But the most commercial people create more value than they capture, and they are transactional on long time horizons. Most people want something from you; it’s the timescale of urgency that dictates whether it feels good or bad.

7. Illegibility is confidence kept private. Uncertainty is not knowing yourself. Illegibility is knowing yourself and choosing not to display it publicly. “There is a lot more power that lies in that today than ever before because it has become the norm that you should publicize anything you do.”

8. Ambition plays their game. Agency plays yours. Ambition chases status on ladders others built. Agency builds something that only needs to make sense to you. Molly is an out-of-the-flow investor: playing a strange long-term game with no desire to compete for consensus deals. Your path doesn’t need to be completely original, but you need to make sure you’re playing for your own reasons.

9. Focus on doing something, not being someone. A green flag in a young founder is that they’re focused on making something rather than building a personal brand. In the long race, actions compound over narratives.

10. Legibility should be performed instrumentally. Molly sees being legible as getting on stage to perform herself. It needs to serve her or she won’t do it. She uses an alter ego—Dolly—when writing: “If you put on an alter ego, they can write something bad. It’s not you.”

11. Your brand is a bell in other people’s heads. Molly’s best deal flow comes from people who’ve internalized her definition of a moth. When they meet someone mothy, a bell dings: “You should meet Molly.” The trick is transmitting a minimum viable definition they can hold onto and feel something about. It spreads between people who get it—usually because they are one.

12. Vocation is deliberate and open. Annie Dillard: “Stalk your calling in a certain skilled and supple way, to locate the most tender and live spot and plug into that pulse.” Stalking is intellectual: gathering clues, following threads. Yielding is accepting the thing you’ve always been good at, the one you secretly kept hoping would be something cooler.

13. Your mind is shaped by its upper limit. David Brooks’ theory of maximal taste: spend time with genius and your mind ends up bigger. But it helps see the process in person: the days the thought they sucked, the showing up anyway. That’s what makes excellence feel possible.

14. Feeling follows action. Tim Keller: “The feeling of love follows the action of love.” Inspiration, forgiveness, connection all come after doing, not before. Waiting for the feeling means you’ll always be waiting.

15. “Stop shoulding yourself.” The clearest sign you’ve found a hidden “should”: you’re beating yourself up all the time. Procrastination is usually avoiding shame. Ask what that “should” statement is and why you’re clinging to it.

16. Belief works best when it points outward. Founders are taught to have enough faith to will their vision into existence. They’re rarely reminded to worship anything outside themselves. The result: a pressure cooker that makes it hard not to confuse yourself for God. Molly converted to Catholicism—it gave her external focus, moral clarity, belonging to something larger. Which belief system makes you more of the person you want to be?

17. Beauty is worth protecting. Some things in life aren’t logically justifiable. Yet, they make us feel. Values like beauty decay under the weight of too much scrutiny or optimization. Goethe: “Encourage the beautiful, for the useful encourages itself.”

Bonus:

1. Pink Ladies are the most dependable apple in the world. Some niche knowledge only comes from obsession. Molly has eaten enough apples to know. Molly’s ranking: Pink ladies are first and Envies are second. Avoid Gala.

Description

Molly Mielke McCarthy (Website, X, Substack) is an investor, writer, and founder of Moth Fund, an early-stage fund focused on backing “moths”: quirky, quiet, mission-driven founders who are often underpriced by traditional venture capital.

Molly’s career has been a dance between “peopling” and making. She’s held design, product, and editorial roles at Figma, Notion, Stripe Press, and The Browser Company, and explored film, photography, and the arts before finding her way to venture, where she started as a scout for Sequoia Capital. Today, she invests in people at the earliest stages. She also writes beautifully about agency, vocation, discernment, and what it means to live an authentic life.

We begin with how Molly identifies exceptional people—her “three-month rule,” spikiness, and why competence is harder to find than storytelling. We discuss the bat signal she sends to attract founders who feel misunderstood, and one of her central distinctions: agency versus ambition, or why playing your own game matters more than playing games others have created. We go deep on commerciality and why it is so essential, and talk about how Molly’s work as an investor often looks most like coaching. We also explore legibility versus illegibility: the freedom in not being easily understood, and when it’s worth becoming legible. Molly’s one of my favorite thinkers on self-knowing, and we talk about how she’s navigated uncertainty toward authentically shaping her life and work into a form that fits her.

Molly embodies rare combinations: people-centric yet fiercely individual, intuitive yet pragmatic, truth-seeking yet full of care. I hope this conversation inspires you to yield to your own calling, and to be patient enough to see what’s true about yourself and the people around you.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. My “What are You Building This Year feature with Notion on Instagram.

Timestamps

• 0:00: Opening Highlights

• 1:29: Intro to Molly

• 3:36: Thanks to Notion

• 5:14: Start: People, Spikeyness, and Discernment

• 21:36: Agency and Ambition

• 34:45: Commerciality

• 49:19: Investing, Feedback Loops, and Creating a Bat Signal

• 59:46: Coaching and Working with Young People

• 1:06:54: Self-Knowledge, Uncertainty, “Should,” Others’ Acceptance, Motivations

• 1:16:38: Illegibility & Legibility, Principles, Authentic Service

• 1:29:28: Friends, Seeing in the Third Person, Femininity in a Masculine World, Love

• 1:42:07: Grab Bag: Art, Catholicism, Gratitude, Beauty

• 1:58:58: Thanks Again to Notion

All linked references and full transcript available at dialectic.fm.

Trevor has lived many lives: touring DJ who produced a top 10 album, co-creator of LilMiquela, Founder of FWB.. among many others (go watch the last 10 seconds of Katy Perry‘s I Kissed a Girl music video).

Today, he’s the founder of new co Runner and is 1/2 of electronic dance duo SofTT. He also has a fantastic nose for weird, bridges high and low status worlds across culture, capital, art, and tech, and truly lives natively between the frontiers of tech and culture.

We talked about:

• Why the only creative people who can “opt out” of the algorithm are trust fund kids

• How cultural capital has merged with financial capital

• Why speculation is rational

• The belief economy: from making → framing → predicting

• What he learned working with Kanye for three months

• Finding new subcultures in the dark corners of Telegram

• Why he’s long humanity despite everything

I also included some favorite lessons from Trevor below. Enjoy!

Dialectic Ep. 37: Trevor McFedries

Dialectic Ep. 37: Trevor McFedries - Creative People Should Be Rich is available on Spotify, Apple, YouTube, and all platforms.

18 Lessons from Trevor on Alpha, Art, and Arming the Artists

1. Alpha lives at the edge. When you’re low status, being out of step costs nothing. If it’s consensus, you’re already too late.

2. $300K is harder to raise than $3 million. To get opportunity, you need to prove yourself. To prove yourself, you need opportunity. The system rewards legible ambition over scrappy potential.

3. Be the connective tissue between worlds. Low-status people who can LARP high-status—and vice versa—become translators no one else can be. Trevor calls it “from the squat to the yacht.”

4. Selling out is punk. The only people who can afford to opt out of algorithms are trust fund kids. “Never ask a woman her age—or an indie musician why their parents have a blue Wikipedia link.”

5. Borrowed nostalgia isn’t creation. Amy Winehouse wasn’t doing nostalgia—she parsed jazz through her lived experience. The complaint is raiding the archive and repackaging references for audiences who don’t know the sources. Standing on giants requires bringing something of your own.

6. Cheeseburgers over fake steaks. Rihanna serves a proverbial cheeseburger and owns it. The frustration is when people serve you a cheeseburger and call it a Michelin steak.”

7. Honesty over authenticity. Authenticity is nirvana—aspirational but unreachable. What matters is open and honest connection to something larger.

8. Making → Framing → Predicting. Modernism valued what you made. Postmodernism valued the narrative around it. Now we’re in the belief economy—where what you call has the same cultural cachet as what you create.

9. Artists are speculators in disguise. Great art and great trades both express conviction about the future and hope the world catches up. Duchamp’s urinal and memecoin creators hear the same dismissal: “That’s not the right kind of creativity.”

10. Give the Bushwick babes nukes. Meteorologists get asymmetric returns betting on wheat futures. Why can’t people with cultural information advantage? The Patagonia vests have financial nukes—arm the artists too.

11. The trenches are rational. A kid in Missouri can “reply guy” crypto Twitter for an hour and turn $20 into $100—or work eight hours at the bookstore. Of course they speculate. Maybe this is the online economy Kevin Kelly dreamed of—it just doesn’t look like the metaverse.

12. Make sure you love it or hate it. When Trevor buys art, he buys what he loves or what he hates; never the forgettable middle. The narcissism of small differences means the stuff that offends you might just be your taste, slightly out of tune.

13. Build universes, sell things. Music streaming doesn’t always pay, but Charli xcx committed to building a universe around Brat and brought people into it. Modern media rewards building worlds people can inhabit and Charli was willing to play that game.

14. Culture went from top-down to middle-out. It used to trickle down from weird art kids to Vogue to the Midwest. Now it’s inoffensively optimized to capture the most mindshare. You can find the same coffee shops and yoga pants in East Berlin, Bushwick, and Beverly Hills.

15. Boundaries define communities. Inclusivity is good UX. But exclusivity—the feeling that you’re not allowed in—is what creates value.

16. We crave finality. Bitcoin hitting $100K was sick because Trevor was rich—but sicker because he was right. In a frictionless world, that scoreboard clarity feels crucial. It’s no surprise people rush to sports betting and prediction markets to feel something.

17. Parenting is gardening, not carpentry. You may want an oak tree, but it’s a lemon tree, and it’s your job to make it the best lemon tree it can be. World-beaters who make reality bend don’t get to apply that force to their kids.

18. Curiosity is the inheritance. If there’s one thing he wants to give his son, it’s the hunger to keep asking, keep poking, keep learning.

Description

Trevor McFedries (X, Instagram, Wikipedia) is a musician, technologist, and entrepreneur. Today he is the founder of Runner and 1/2 of electronic dance duo SoFTT. Previously, Trevor was co-founder and CEO of Brud, the company behind Lil Miquela that was acquired by Dapper Labs; Founder of FWB (Friends with Benefits); early artist in residence at Spotify; and a touring DJ who performed as DJ Skeet Skeet, was part of the rap group Shwayze, and produced for a range of artists.

Trevor’s work emerges from a tension he’s lived with throughout his career: the gap between who creates cultural value and who captures it. Growing up poor in Iowa and entering the dying music industry in the late 2000s, he witnessed firsthand how the instruments that capture value rarely benefit the creative people who generate that value. This has run across his entrepreneurialy work, from building virtual pop stars to a range of crypto projects that hope to give creative people more upside.

Trevor bridges culture and technology, art and capital, and high and low. I’ve met few people who are as consistently ahead of culture. His perspective challenges both the art world’s disdain for commerce and Silicon Valley’s shallow engagement with culture, arguing instead for creative people to play the game on the field and build the instruments that will make them rich. Today, he’s focused on how that may end up being as much about predicting what’s next with stakes as it is actually making things. We also talk about authenticity and honesty, why he continues to spend time in crypto despite it being low status, why speculation is rational and selling out is punk, how power comes from consensus, his keen nose for weird—especially on the internet, briefly working with Kanye West, and his forever optimistic curiosity.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. My “What are You Building This Year feature with Notion on Instagram.

Timestamps

• 0:00: Opening Highlights

• 1:18: Intro to Trevor

• 4:12: Thanks to Notion

• 5:21: Start: Creative People Should Be Rich

• 12:03: Creative Ignition, Infrastructure, and Why Selling Out is Punk

• 21:49: Authenticity, Honesty, Divine Creativity, and Borrowed Nostalgia

• 30:15: Low Status Games and High Culture, Cultural & Financial Capital, and Crypto

• 42:08: The Belief Economy: From Making -> Framing -> Predicting

• 48:45: Markets, Power, Consensus, and Truth

• 58:22: Speculation is Rational

• 1:06:34: Developing a Nose for Weird, Being Early and On Time

• 1:19:06: Unfettered Cultural Spaces on the Internet

• 1:26:33: FWB, Community, and Exclusivity

• 1:31:02: LilMiquela, Online Storytelling and Celebrity, Touring as a Performer

• 1:45:41: Softt, Music as a Way In, Music as a Business

• 1:52:45: Culture & Business

• 1:54:38: Kanye

• 2:06:20: Optimism, The Next Generation, Parenting, The Stuff that Counts, and Cerulean

• 2:17:55: Thanks Again to Notion

Today, I continue that conversation in the interview seat myself. C. Thi Nguyen is a professor of philosophy focused on games, data, and metrics. I visited him to discuss his new book, The Score: How to Stop Playing Someone Else’s Game.

Thi is focused on a dilemma with scoring systems:

1) in games, they’re are great: they allow game designers to sculpt the player’s agency. By shaping goals, abilities, and obstacles, action becomes easy, even harmonious. The player can try on different roles, explore different values, and move “lightly between worlds”

2) in the real world, scoring systems flatten us. We’ve quantified our lives, and easily countable metrics produce what Thi calls “value capture.” By obsessively measuring what matters, we only value what we can easily measure.

I went deep with on the personal and societal implications of this.

What are different types of agency? What is the shape of good values? What is the difference between recognition and perception?

How can we be more playful, in and out of games? How can we find more beauty in process, not outcomes?

How can we trust each other, keep bad actors in check, and not extract nuance out of complex fields by relying too much on legible data?

Are objectivity and truth the same thing? Is technology really value-neutral?

I’ve also included some favorite lessons from the episode below. Enjoy!

Dialectic Ep. 36: C. Thi Nguyen - Measurement, Meaning, and Play

Dialectic Episode 36: C. Thi Nguyen - Measurement, Meaning, and Play - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

18 Lessons from C. Thi Nguyen on Games, Values, Metrics, and the Myth of “Objectivity”

1. Waste is the point. Bernard Suits defines play as redirecting normally useful resources—logic, physical prowess, attention—toward activities that exist for their own sake. Play is only wasteful if you think outcomes are all that matter. A life optimized entirely for usefulness can end rich in resources and poor in meaning.

2. Move lightly between worlds. To Maria Lugones, to be playful is to inhabit worlds—whether business, family, art—lightly and creatively, rather than surrendering yourself to a single mode of being.

3. Game designers sculpt your agency.** Games don’t tell stories, they shape your action so that decisions and stories come out of you. Designer Reiner Knizia’s core insight: the scoring system tells players what to care about and what to want, making it it easy to act.

4. Attention guides what matters. What you value is what you attend to, and scoring systems direct attention. Rock climbing without ropes forces your attention to tiny details of the rock and your balance you’d never see otherwise. Games train us to refine attention through constraint and feedback; metrics do the same but with much less nuance.

5. Value capture is when the proxy becomes the purpose. Rich motivations—like learning, connection, or starting a podcast to share ideas—collapse into simplified proxies like GPA, likes, or subscriber counts. Simplified metrics offer us clarity, legibility, and scale, but strip away meaning.

6. Recognition stops. Perception continues. Recognition applies a category—Gen Z, coder, business person—and ends inquiry. Perception uses the category as a starting point and keeps looking at texture, difference, and context. Screen time is a lousy category for parents because it lumps together your kid coding on Minecraft with brainrot YouTube shorts.

7. Let the object lead. Jerome Stolnitz says aesthetic vision steps back from goals and purposes, letting attention rove freely and generously. You let the object show you what there is to love instead of filtering through your own agenda. Thi’s version: “Fck around and find out. But good.”*

8. Values are better tailored than chosen. The right values for you depend on your particular context, psychological profile, and place in the world. It’s less about blind choice and more about sensitive detection and careful listening.

9. Recipes are dead. Dishes are alive. John Thorne: recipes are fixed instructions engineered for reliability without requiring decisions. Dishes are ideas of balance in a creative cook’s head, remade anew each time through tasting and adjusting. You can robotically follow someone else’s rules for a guaranteed outcome, or you can invite friends into the kitchen, cook together, get a little drunk, and taste as you go.

10. All tools encode values. Every classification system involves decisions about where to reduce granularity (census data cares about Asian versus Latino but forgets South Asian versus East Asian). You can’t count something without first deciding what counts, and that decision is never neutral.

11. Choose your maps carefully. Maps are not the territory, but the solution isn’t to avoid maps. The question is whether we force one map on everyone or create variety to help people know there are choices. Better yet, build tools that let people build the maps they need and want.

12. Objectivity and truth aren’t always the same. **Metrics are first-rate offenders of “objectivity laundering”: taking subjective choices of what to measure, burying them under calculations, and making things look neutral at the output.

13. Wisdom is being soaked in complexity. Aristotle through Martha Nussbaum: If ethics is about treating people well and fairly, that will involve deep attention to the particularities of people and their context. What actually matters to people, what hurts and helps them is highly dependent on interaction with particular contexts, personalities, and values.

14. There is no neutral way to make the world better. There’s a fantasy in tech that you can avoid making moral or political decisions while improving the world and changing it for the better. All technologies are value-laden.

15. Sit with fuzzy values. Vibe, aura, interesting, rich; these terms gesture at something important without defining the edges. New slang emerges when people need language to express what matters while staying in uncertainty. Meaningful inarticulateness means refusing to pretend we know things precisely when we don’t.

16. Games allow us to practice everyday role-shifting. On his hiring committees, Thi acts on the department’s reasons, not his. Playing games with his spouse, he sets aside love to try to crush them. Games take something we do in normal life—entering roles and exploring agency—and concentrate it for fun or richness.

17. The process is where values are. **Aristotle: the value in human life comes from the rich exercise of our capacities: thinking, moving, perceiving, relating. Optimization assumes we already know what matters and just need to maximize it, leaving no room to discover what we’ve missed. Play does the opposite: it invites wandering, tolerates confusion, and keeps us open to surprise long enough to learn what’s actually worth caring about.

18. Remember you’re a grasshopper. Bernard Suits argues for the grasshopper’s playfulness over the ant’s industriousness. Success breeds confidence, and you can start trusting your opinions too much. Thi’s antidote is deliberately being a beginner—doing things that are dumb, hard, and social, and failing in public. Being absorbed in an activity you can’t justify, optimize, or even explain reminds you to be playful.

Description

C. Thi Nguyen (Website, Philpeople.org, X) is a professor of philosophy at the University of Utah focused on values, games, agency, art, aesthetics, and data. His new book, The Score: How to Stop Playing Somebody Else’s Game is out now.

Thi is also the author of Games: Agency as Art, in which he explores how game designers work in the medium of agency, but sculpting a players abilities, goals, and obstacles to create “harmonious action.” I first learned about Thi’s work via his interview with Ezra Klein in 2022, which is one of my all-time favorite podcast episodes. In it, he discusses Agency as Art, How Twitter Gamifies Communication, Why Q-Anon is game-like, and more.

The Score is a marriage of his work on games and on data and metrics. He explores how scoring systems in games allow for playfulness and agentic exploration of our values, while scoring systems in real life produce what he calls value capture. In an effort to make the world more quantified, comprehensible, and trustless, metrics are flattening our values and sapping the meaning out of our lives. One way he describes his work is that James C. Scott’s Seeing Like a State also applies to the human soul.

In this conversation, I aimed to cover the most compelling ideas in the book in two parts. First, we explore the local side: personal agency and values, attention and the difference between recognition and perception, process vs. outcome, and why playfulness and openness allow us to have richer lives. He also shares how games are a compelling template for this kind of exploration.

Second, we talk about the societal level: what we miss in a world of values dominated by what is easily measurable, how we can scale trust and enjoy the benefits of collaboration, science, and technology while not delegating our understanding to the wrong people, and why objectivity and truth are not always the same thing. Thi makes the case that technology is value-laden, not value-neutral, and that we must be more vigilant and nuanced in our approach to the ethical decisions that exist everywhere.

I hope this conversation is a prompt for you and I to think more deeply about what we truly care about, to “move lightly” between agentic and value-laden worlds, and bring a perceptive playfulness to our lives. Remember, we are all grasshoppers in disguise. If you enjoy the episode, please support Thi’s work and check out The Score.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. You can read more about why Notion embodies Dialectic’s values and our partnership announcement here.

Timestamps

• 0:00: Opening Highlights

• 1:39: Introduction to C. Thi Nguyen

• 5:13: Thanks to Notion

• 6:31: Start: What Does it Mean to Be Playful?

• 13:41: Starting Local: Agency, Scoring Systems, and Games

• 23:36: Value Capture: Incentives, Values, and the Collapse of Meaning

• 36:28: What is the Shape of Good Values?

• 49:45: Attention, Recognition vs. Perception, and Aesthetic Openness

• 58:46: Process vs. Outcome, Striving Play vs. Achievement Play, Recipe vs. Dish

• 1:10:00: Aesthetic Value & Autotelic Pursuits in Life

• 1:16:59: Metrics, “Measure What Matters,” and What We Miss

• 1:24:16: Quantitative vs. Qualitative Ways of Knowing and Different Conceptions of Rules

• 1:38:01: Scaling Trust, Data, Experts, and Legibility

• 1:54:37: Objectivity & Truth, Value-Laden Technology & Decisions, and “Objectivity Laundering”

• 2:07:57: Advice for Technologists: Ethics, Maps, Value-Neutrality, and Playfulness

• 2:18:52: Closing Thanks to Notion

I finally got to spend a little time with her late last year and then made the journey out to Seattle for this conversation. Brie is so energetically infectious and generous that I flew back to NY with my cup overflowing. I hope you feel the same way. As usual, I’ve included some favorite lessons from her below, too.

Selfishly, I also have to share Brie’s little note reflecting on our time together, which made me smile big:

Please enjoy!

Dialectic Ep. 35: Brie Wolfson - Loving Attention & Ease in Craft

Dialectic Episode 35: Brie Wolfson: Loving Attention & Ease in Craft - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

17 lessons from Brie Wolfson on craft, culture, and doing work that’s useful and joyful

1. Finger feel only comes from reps. Craft comes from time spent at the ground level, close to the details. You can’t think your way there; you slug it out until your hands know before your brain does. Eventually, that produces the taste we associate with unconscious competence.

2. The best leaders are not t-shaped, but fork-shaped. Great leaders roam wide and dive deep across domains. They’ll help with copy edits, rebuild a pitch deck, or debug hiring loops without losing altitude. Nothing slips by them because they refuse to delegate understanding.

3. Loving attention beats LGTM culture. “Looks good to me” means your work was skimmed. Loving attention means someone catches the typo, pushes back on lazy phrasing, and makes your work sing. Most feedback is drive-by. Find the people who care enough to push you.

4. Good marketing is truth-telling. People smell bullshit instantly, so honesty is the only strategy that scales. The trick is working for underrated companies where there’s rich space between what’s true and what the world knows. If there’s no craft, product, or leadership underneath, there’s no story worth telling.

5. Great companies want to be great organizations. Stripe. Figma. Cursor. What do they share? “The only thing these companies have in common is that they aspire to be great companies themselves.” The quality bar doesn’t stop at the product, but extends to the organization itself.

6. Help people get to yes. Anyone can say no. But great editors know which dials exist to make something better. Don’t just mark it “not ready”—show the path to get there. Aim to really see the person and amplify them.

7. Zoom in with notes, zoom out with faith. Be a micro-pessimist and a macro-optimist. Tear into the details: the weak sentence, the wobbly logic, the half-baked concept. Then step back and protect the momentum. Good faith feedback preserves excitement. Pure pessimism kills the work before it has a chance to breathe.

8. Taste is more about appreciation than judgement. Notice how things are made. Why this layout feels right. Why that transition lands. The world is full of precious choices, and the best connoisseurs and curators find joy amidst discernment.

9. Work the crannies. The overlooked projects—the unloved docs, the in-between roles, the orphaned initiatives—hide leverage. Excellence at your core job buys you permission to explore and take risks.

10. Hold the skinny mirror. When you admire someone, your natural lens should make them look like a rockstar. The instinct to refract great people outward is generous.

11. Excellence is contagious. While the most exceptional people tend to shine early and anywhere, sometimes we have to see what great looks like to get closer to it. You might be sluggish in one environment and come alive in another. When you’re surrounded by people in their lane, you might want to join them.

12. Aim for ease in your craft. The goal doesn’t have to be fame or being remembered by history. It can be trusting yourself to produce excellent work, understanding your own worth, and having confidence without white-knuckling the process.

13. You can’t compete with somebody having fun. Genuine enthusiasm beats any top-down mandate. When someone believes the work rocks, they’ll run through walls for it. When it comes down as a directive, they’ll do the minimum. The best work feels like play.

14. Pay attention to personal clues. Understanding your actual motivations lets you make better decisions. Quiet the world so you can hear yourself, then write it down so there’s a record of what’s going on inside. Your patterns repeat, so you can ignore them or work with them.

15. Bring high and low together. The best taste combines intellectual depth with accessibility. Being polymathic lets you push on ideas from unexpected angles: serious substance meets pop culture, geopolitics bumps into Britney.

16. Asking for help is generous. Everybody likes to be thought of as being in the room where it happens. Be specific and bring people along on your journey.

17. The mud is where it gets real. Brie loves Marge Piercy’s poem ‘To Be of Use’: “The work of the world is common as mud. But the thing worth doing well done has a shape that satisfies.” A joyful life is about being useful—fixing things, using your hands, putting in more than you take out. Tool-using, problem-solving, being of service.

Description

Brie Wolfson (X) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus, where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review, their new print publication known for superb long form profiles.

Brie also recently joined AI-programming behemoth Cursor as Head of Employee Experience and wrote about the company’s culture. She has worked with craft-oriented software companies throughout her career, including Stripe—where she helped launch Stripe Press and the company’s planning function, among other things—and Figma, where she worked on Education. In her words, she is drawn to companies where the reality is even more impressive than the reputation, and she has publicly and privately worked with a number of the most impressive leaders in Silicon Valley on marketing, culture, and storytelling.

We cover a broad range of Brie’s expertise, including craft, marketing, organizational culture, unlikely career paths, and taste, editing, and writing. This includes how AI is causing companies to become even more oriented around the empowered individual contributor and who the best of them, including company leaders, are focused on an attunement to details that she likens to “finger feel.” We also talk about why she believes marketing should be a kind of truth-telling, closing the gap between reality and perception. She also reflects on the common cultural thread of great companies: a deep-seated desire to be a great company, not just create great products. She talks at length about everything she’s learned from amplifying special people and how she’s navigated the tension in her own desires for fun and breadth and ambition toward greatness.

I hope this conversation inspires you to raise your standards, get to the ground level, and settle into a life of deep attention that produces quality, usefulness, and joy.

Full transcript and all links: https://dialectic.fm/brie-wolfson

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. You can read more about why Notion embodies Dialectic’s values and our partnership announcement here. You can find the essay from Notion CEO Ivan Zhao mentioned at the end of the episode here.

Timestamps

• 0:00: Opening

• 3:54: Notion

• 5:04: Intro: Craft, Finger Feel, and Staying Closer to the Ground Level

• 13:27: Process vs. Output, Quality vs. Speed, and Great Editing

• 21:44: Craft, Substance, and Truth in Marketing

• 25:56: Individuals as the Building Block of a Company and Empowered ICs

• 32:02: Creative Collaboration and In-Person and Remote

• 36:46: Company Building: What is Changing and What Will Stay the Same

• 44:25: The Soft Stuff: Great Company Values and Great Culture

• 52:17: Thinking vs. Doing Cultures, 996 and Difficulty Sitting Still

• 1:00:37: Morale, Fun, Amplifying Leaders, and Loving Attention

• 1:11:58: Career Path Advice for Young People

• 1:19:56: Kevin Kelly, Chasing Greatness, Illegibility, and Ease in One’s Craft

• 1:27:29: Special Talent and Contagious Ambition

• 1:32:22: Brie’s Spike: Charisma, Hard and Soft, Making Things Fun, and Belief

• 1:43:23: Taste, Appreciation, Generosity, Skill and Soul

• 1:57:26: Great Editors, Saying No and Getting to Yes, and Being Receptive to Editing

• 2:05:25: Great Writing: What do You Have the Right to Do that Others Don’t?

• 2:13:55: Grab Bag: Optimism and Pessimism, High and Low, and Closing Maxims

• 2:30:07: Thanks to Notion