The browser is "really a rectangle that we spend eight hours a day in." So "why would we not want to live in a good rectangle?"

Josh & team created Arc and Dia, two browsers full of life, creativity, and care. He sat down with me to reflect on The Browser Company’s journey about a year after it was acquired by Atlassian.

We talked about everything from the original decision to "optimize for feelings" to hiring unlikely stars to where Dia and the browser stand in the AI era.

Above all else, Josh believes in people. I’ve felt that, as have so many others who’ve collaborated with him or simply been around him.

I hope you’re inspired to believe in people too, and to leave your fingerprints on the things you make.

Available on Spotify, Apple, YouTube, X, podcast platforms, and here on Substack. Transcript and links here.

Dialectic 61: Josh Miller - A Good Rectangle

Description

Josh Miller (X, LinkedIn) is co-founder and CEO of The Browser Company, makers of Dia and Arc. The Browser Company was acquired by Atlassian last year.

Before The Browser Company, Josh was an investor at Thrive Capital, Director of Product in the Obama White House’s Office of Digital Strategy, and co-founder of Branch, which was acquired by Facebook.

He studied sociology and has always been thoughtful about environments: institutions, companies, and digital and physical spaces. We talk about his effort to improve the space many of us spend our days in: the browser. We discuss the tension between Josh’s creative and commercial instincts, optimizing for feelings, and hiring unlikely stars. Josh reflects on much of the journey with Arc and Dia and why he’s still betting on the browser in the AI era, now as part of Atlassian.

I hope you are inspired to believe in people and leave your fingerprints on what you create.

Dialectic is presented by Notion. Notion is a collaborative workspace for your life’s work and a hub for all the context you and your team use to work with each other and with AI. New models are available in Notion the day they launch, and you can work with agents you build in Notion or any other agents and tools you already use. As tools change, Notion is the Switzerland in the middle that keeps your context consistent across all of them. Learn more at notion.com/dialectic.

Timestamps

• (0:00) Intro: Josh Miller

• (1:55) Start: Not Commercial Enough & Optimizing for Feelings

• (9:14) Sociology, the Obama White House, Thrive, and the 5% Favicon

• (15:38) Bowling Alone, James Turrell, and Roden Crater

• (22:12) Betting on People, Leaving Thrive, and Where Computing Goes

• (34:54) “Assume You Don’t Know” and What Was Sacred at The Browser Company

• (41:58) Intuition, Road Trips, and Leaving Fingerprints on Things

• (53:57) Building in Public, Pulling Back, and the Road to Atlassian

• (1:03:23) The Internet Computer in the AI Era: Codex, Cloud Browsers, and Why Everything Is Converging

• (1:13:30) How Dia Wins

• (1:17:07) Agents, Muse, and the Red Giraffe

• (1:22:43) Software Is Becoming Art

• (1:32:13) Believing in People, Leaving Facebook for the White House, and What’s Next

• (1:47:17) Closing Questions

Patrick got expelled from college at 13, returned at 15, later worked on early CRISPR breakthroughs, and teamed up with Silvana Konermann and Patrick Collison to co-found Arc.

He works 3 jobs: core investigator at Arc, professor at Stanford, and venture partner at Thrive Capital. For all his intensity and ambition, he carries a lightness and boldness that is contagious.

We discuss:

• why research is 99% failure and even your best ideas kind of suck

• infinite games and speedrunning school

• the reach of GLP-1s and power laws in biotech

• what makes a good biologist

• Arc’s bet on people over projects

• lab robots that finally work

• AI-designed organisms and new forms of life

• why heart disease could go the way of infectious disease

• bro science, peptides, and biofuturism

• research taste in the age of AI

Please enjoy. Available on Spotify, Apple, YouTube, X, Transcript, and here on substack.

Dialectic 60: Patrick Hsu - Speedrunning the Infinte Game

Description

Patrick Hsu (X, Website, Arc lab) is co-founder and core investigator of Arc Institute, assistant professor of pathology at Stanford, and venture partner at Thrive Capital.

Patrick has always been precocious: he began college as a young teenager and contributed to early CRISPR-Cas9 gene-editing breakthroughs as part of Feng Zhang’s lab at the Broad Institute of MIT and Harvard. Today, the Hsu Lab at Arc works where genome engineering meets AI, from bridge recombinases that can rearrange up to a million bases of DNA at once to Arc’s Evo biological foundation models.

We discuss Patrick’s pace and ambition, infinite games, and why he was drawn to biology. Then, we traverse power laws in biotech and the reach of GLP-1s, research taste and success, Arc’s multidisciplinary model, data limits in AI-enabled bio, and cell and bio foundation models. We also discuss how AI and new science will help us solve diseases, design life, and push the boundaries of sci-fi when it comes to human health. I hope you are inspired to raise your bar, commit to reinvention, and hold a lightness that makes the long and challenging journey fun.

Corrections:

1. Periodic Labs (41:13): Patrick said “room-temperature semiconductors.” He meant superconductors.

2. Yamanaka’s Nobel (1:03:44): Patrick said 2009. Yamanaka won the Nobel in 2012, for reprogramming factors discovered in 2006.

Dialectic is presented by Notion. Notion is a collaborative workspace for your life’s work, and it works with whatever AI you use. New models are typically available in Notion the day they launch, you can tag agents from inside Notion, and you can tag Notion from your other AI tools. As the tools around you change, Notion stays the one place that holds your context. Notion is also hiring across product, engineering, design, storytelling, and more. Learn more at notion.com/dialectic.

This episode is supported by Google. Gemini 4 Argon recently launched and is built for long-horizon work. I used it inside Antigravity and gave it all 60 Dialectic transcripts: more than a million words. Instead of summarizing episodes one by one, Argon synthesized across them, tracing how ideas from early conversations connect to later ones. Together we made The Dialectic Compendium, an interactive book of the themes that run across the show, with a dossier on every episode and a 3D version you can page through on the web. Gemini 4 Argon is available in the Gemini app, Antigravity, Google AI Studio, and the Gemini API.

Compendium: https://jacksondahl.com/dialectic/compendium

Timestamps

• (0:00) Opening Highlights

• (1:39) Intro: Patrick Hsu

• (4:29) Start: Boldness, Infinite Games, & Ambition

• (12:54) GLP-1s and Power Laws in Biotechnology

• (20:17) Expelled at 13 and Falling for Biology

• (25:51) What Makes a Good Biologist, Research Taste, and Biology’s Data Challenges

• (37:58) The Arc Model: Full-Stack Science

• (52:01) Betting on People, Style, & Learning to Simplify

• (57:22) Perturbation, World Models, and Evo

• (1:03:27) Virtual Cell Models

• (1:09:56) Designing Life: From Stem Cells to Genome Writing

• (1:18:39) Testing, Bro Science, and Human Data

• (1:24:26) Can It Exist vs. Will It Exist: Science Meets Markets

• (1:29:59) Biofuturism: Interoception, Peptides, Muscle Modulation, Sleep, and New Forms of Life

• (1:43:47) Fun, Obsolescence, Going Slow, and the Future

• America.gov: one front door to 29,000 government websites

• CritBuns, Joe’s RISD project that taught him design is half product and half story

• How design can create trust, from Airbnb to government

• Why design is about respect

• Moving quickly without sacrificing craft

• Building for people who don’t trust AI or government

• Going beyond the “mom test” to the “grandma test”

• How AI is changing product development

• A countdown clock to 2028 and enduring beyond one administration

Available on YouTube, Spotify, Apple, X/Twitter.

Dialectic 59: Joe Gebbia - Design We Deserve

Description

Joe Gebbia (Website, X, LinkedIn, Wikipedia) is the first U.S. Chief Design Officer, leading the National Design Studio. He is also the co-founder of Airbnb and Samara.

The NDS and this role were created by executive order of President Trump in August 2025. I met Joe Washington, D.C, to reflect on the past year and talk about bringing the care and ambition of great product design to the digital services that every American uses. Joe & NDS just launched America.gov, their flagship project of the last year: the central entry point for how Americans get what they need from the government.

Joe believes that design is how you respect and value the people who use a product or service. At Airbnb, that meant helping strangers feel comfortable in each other’s homes. In government, it means refusing to accept a low bar for the websites and processes that Americans use to interact with the government.

We begin with CritBuns, Joe’s RISD project that taught him that design is as much about storytelling as it is about product. Then, we discuss what he learned about designing for trust at Airbnb and his initial work at DOGE, streamlining and digitizing the federal retirement process. Joe walks me through America.gov, a single, AI-powered front door to government services. We discuss the challenges of scale and designing for people who are skeptical of both government and AI, including what it means to pass the “grandma test.” We wrap up with why ambitious technologists should aspire to work in government and his collaboration with Airbnb co-founders Brian Chesky and Nathan Blecharczyk.

I hope this conversation raises your expectations for the things we’ve learned to tolerate, and inspires you to think about how you might serve your community or your country.

Dialectic is presented by Notion. As new models and agents arrive constantly, Notion acts as a context and consolidation layer for all the ways you and your team work with AI: a command center or simply a resilience layer, so your context comes with you even if you switch models or agents. You can also work with agents right inside Notion and share skills with your team through the Skills API. Learn more at notion.com/dialectic.

Timestamps

• 0:00 Opening Highlights

• 1:26 Intro: Joe Gebbia

• 4:12 CritBuns & Why Design is Half Story

• 15:24 Airbnb, The Feeling of Belonging, & Designing for Trust

• 28:29 Public Service & Fixing Federal Retirement

• 42:16 Speed, Craft, and Respect

• 48:43 ND Studio Projects: TrumpRx, Trump Accounts, and Realfood.gov

• 56:18 America.gov: A New Front Door to Government

• 1:05:35 Trust, Privacy, and Government AI

• 1:15:30 America.gov’s Roadmap

• 1:19:54 Recruiting for ND Studio and Public Service

• 1:23:41 Reflecting on Year One & Passing the Grandma Test

• 1:31:05 A Ticking Clock Toward 2028 & Building Beyond One Administration

• 1:35:44 AI & Product Development

• 1:38:36 Closing Questions: Charles & Ray Eames, Airbnb Co-Founders, & Trust in People

Experimental History

1) Find what's true and make it useful. 2) Publish every other Tuesday. 3) Photo cred: my dad.

By Adam Mastroianni

Adam’s writing is usually about science, culture, and what to do with your life. Reading his writing makes obscure ideas feel intuitive. If you’ve ever read an amazing essay on substack with a black & white photo at the top, it was probably Adam’s. A few favorites:

• Good conversations have lots of doorknobs

• Face it: you’re a crazy person (aka, the coffee bean test)

• The Decline of Deviance

• Incentives are for losers

• I like ‘em thick (on “thick art”)

AND—Adam just announced his upcoming book, The Strangest Idea in the World! You can pre-order it now.

Available on twitter/x, Spotify, Apple, YouTube. Transcript here (created with a new tool I made myself thanks to Google Antigravity & Gemin 3.5 transcribe). Enjoy!

22 of my favorite lessons from the conversation below, too.

Dialectic 58: Adam Mastroianni - Let Me Be Useful

Description

Adam Mastroianni (Website, X) is an experimental psychologist and the writer of Experimental History. He earned his PhD in psychology at Harvard before leaving academia to pursue research and writing independently.

I first came across Adam through “Good conversations have lots of doorknobs,” which remains one of my favorite essays on Substack.

We talk about why psychology is stuck, why science needs people willing to look stupid, and how prestige can lead you toward a life you don’t want. From there, unpack Adam’s coffee bean test for figuring out what to do, getting “de-bogged,” and what improv teaches us about better conversations (or: create doorknobs). We also discuss writing that surprises its author, his upcoming book, The Strangest Idea in the World, and the prayer he says before publishing: “Let me be useful.”

I hope you leave a little more willing to question what seems obvious, risk looking stupid, and spend your time in ways you actually enjoy.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion AI works across your documents and context, while custom workers can automate recurring tasks and connect with your other tools. You can also explore Notion’s Knowledge Board, which evaluates how AI models perform on real knowledge-work tasks. Learn more at notion.com/dialectic.

This episode is supported by Google. Google Antigravity is Google’s agentic development platform. Describe what you want to build, and its agents can plan the work, write and run code, and test the result, with plans and changes you can review along the way.

Gemini 3.5 Transcribe turns audio into text with a choice of verbatim and Smart modes. Verbatim mode keeps fillers and false starts, and supports speaker labels and word-level timestamps to help you check the transcript against the recording. Smart mode removes filler words and repetitions and formats speech into readable text. I used Antigravity and Gemini 3.5 Transcribe to build a Mac app for producing and reviewing Dialectic transcripts.

Timestamps

• 04:33 Start: Why Psychology is Stuck & The Focus of Adam’s Blog

• 14:43 The Scientific Virtues of Stupidity and Rebellion & Escaping the Prestige Trap

• 25:08 Patronage for Weirdos

• 33:53 Progress in Psychology

• 52:15 Figuring Out What to Do, The Coffee Bean Test, and Unpacking Adam’s Day-to-Day

• 01:03:22 Getting De-bogged and Making Ideas Land

• 01:14:11 Conversational Doorknobs: Giving and Taking

• 01:22:23 Blogging, Community, and Rules we Invent

• 01:28:35 Writing Advice, Thick Art, Giving The Reader an Egg to Crack

• 01:44:03 Adam’s First Book: The Strangest Idea in the World

• 01:53:23 Closing Questions

Let Me Be Useful: 22 Lessons from Adam on Weird Science, Writing A Blog, and the Freedom of Being Brave

1. Be yourself now. Later never comes. Adam heard the same advice at every stage, from an Oxford scholarship through a PhD and two postdocs: “Just don’t be yourself now. You can wait until later.” Eventually he left academia to write full-time because “if the princess is always going to be in another castle, I have to stop going into the castles.”

2. Don’t mistake the exception for the institution. Adam loved his PhD, his advisor, and his lab, which is what made leaving so hard: “I kept thinking, ‘Well, there’s a good version of this.’” It took time in other places to see how rare his advisor was, and that the good version “existed despite everything, not because of it.”

3. Effort isn’t evidence of desire. We learn what we like by watching what we do, so someone grinding out papers with Pomodoros and caffeine concludes, “I must really want to do it.” It’d be so “convenient if what I like is what I’m already doing, what is prestigious, and what other people would like me to do.” You can force yourself through the wrong work, “but not well.” Even the right work has suffering, but it’s “negative emotions in the service of something.”

4. Do you want the job, or the daydream? When academics tell Adam they want to open a coffee shop, he asks where they’d get the beans, which machine they’d buy, and how they’d upholster the chairs. If the details don’t interest you, you might be kidding yourself. “If you really wanted to do this, you would be googling this at night.” Unpack the thing you think you want.

5. Spend your resources on risk. A lot of money is sloshing around alternative science, and it keeps building “the same kind of institutions, just with a futuristic font.” What’s missing is “the appetite for reputational risk.” If you have a bunch of money, “shouldn’t you be able to buy yourself out of caring about looking like an idiot? That’s what the money’s for.”

6. Every frontier needs an apostle to the normies. Academics already think Adam is crazy, and his reaction is “There’s a whole level crazier than this.” For example: the pseudonymous bloggers Slime Mold Time Mold. He’s legible enough to talk to one side and close enough to the edge to see the other. That gives him a useful role: helping people with resources recognize unconventional thinkers they might otherwise dismiss.

7. Naming something isn’t understanding it. We call our propensity to make things “creativity.” Psychology rates creativity on scales and tests whether heat or sleepiness changes it, often without trying to understand the core drive. That’s like explaining a car by saying, “Well, the engine has propulsion. We know the engine makes going. It makes a go-force.”

8. Progress is a miracle, not a default. Humans have been around for 300,000 years, yet most of what surrounds us comes from the last 500. Adam’s book The Strangest Idea in the World argues that our minds weren’t built to discover things, which makes it “miraculous we can do it at all.”

9. You can leave a party lonely. Nobody leaves an all-you-can-eat buffet hungry. But loneliness doesn’t push so hard. Adam suspects our drive for company evolved when we were rarely alone, so it “didn’t have to be that strong,” and modern life has put us in “a situation that we don’t have the drives to get ourselves out of.”

10. Rule out hunger before your existential crisis. Hedgehogging is Adam’s word for ignoring the obvious insight of the people around you. Sometimes Adam’s sense that everything is wrong turns out to be simpler: “Oh, I wasn’t listening to my wife when she said, ‘You’re hungry.’”

11. Taking the spotlight can be generous. Adam’s ‘conversational doorknobs’ idea, rooted in improv: givers ask questions, and takers make statements. Taking isn’t selfish by default: “taking focus can be a supportive move and not just a selfish move.” Some of his favorite friends ask him zero meaningful questions, but “they give me something to respond to.”

12. Write to find out, not to declare. “The mark of a good piece is that I didn’t know the end of it when I started it.” Adam writes “from the inside out,” growing paragraphs around a single idea or line until they connect. “Often the thesis is what gives you the reason to leave home in the first place, and it’s not the thesis that you come back home with.”

13. Most of the work never shows up on the page. Adam will spend 90 minutes on a paragraph and throw it away, or 45 minutes tracking down an example that turns out to be wrong. None of it appears in the post, yet the published work “could not exist if I didn’t waste all this time.”

14. Go where the machines aren’t. Adam looks for ideas in “old stuff. Stuff other people aren’t reading,” and experiences that never get fully captured in writing or on film, like improv: “Being there, I’m getting fed data that the machines can’t get fed yet.”

15. Most writing is a battering ram. Good writing finds the right angle. Watching videos of ants and humans steering a T-shaped object through a maze, Adam thought, “That’s exactly what writing is.” The job is angling an idea through the folds of someone’s mind, starting with one question: “Why would someone be different at the end than they were at the beginning?”

16. True advice can be useless if you don’t feel it. “Don’t sweat the small stuff” is true but useless, because “if I thought it was small, I wouldn’t sweat it.” You can’t make tea by just dunking the bag, which is why Adam spends a lot of time laying tracks with his writing. Per his telling, that’s why he’s never managed to write “the short, good piece.”

17. The Boy Who Cried Wolf isn’t about wolves. We read novels instead of the dictionary, which holds far more information, because life is fuzzy and fuzzy situations need fuzzy lenses. A great story or essay hands you “a fuzzy thing that represents something much, much larger than itself.”

18. Give your idea a handle. Adam’s goal is to take something fuzzy and make it legible and portable. He knows it worked when readers feel like “you put words to something that I’ve been saying.” He is “bolting a handle onto an idea so you can move it around the world.”

19. Embarrass yourself in the love of something. Every emotion is useful for writing except bitterness, so Adam checks his archive for too many “complain-y posts in a row,” counting how often he’s hit “This is a wrong thing, let’s fix it” versus “This is a right thing, let’s preserve it.” He loses trust in writers who are all criticism, because “if I can’t see you loving something, how do I know you can?”

20. Cowardice is squirming. Courage is relief. Not knowing what’s right feels different from knowing and hoping you won’t have to do it. Dodging confrontation feels like squirreling around, “just really hoping that you will not be asked to be brave.” Accept the consequences, and the freedom is startling: “Oh, nothing can hurt me. I’ve already decided to die. That’s it. It’s easy from here.”

21. The offer to sell out never expires. Asked what he still has to lose after leaving academia, Adam named his integrity, because “there will never be a lack of opportunities to trade in your values for something else.”

22. Pray to be useful. Useful might mean handing someone a new schema, getting them unstuck, or nudging them toward living by their values instead of selling out. Before publishing each post, he says the same prayer: “Let me be useful.”

Nearly a decade in, he hopes to fight decay and build a company that gets better over time, not worse. 1-in-3 startups use Mercury, and he's betting that the next 10 years of entrepreneurship will be greater than the last.

21 of my favorite lessons below. Full episode is available on Spotify, Apple, YouTube, Twitter, and here on Substack. Transcript and all links here. Follow Dialectic on Instagram and Twitter for clips.

Dialectic 57: Immad Akhund - The Art of Irrational Effort

Description

Immad Akhund (X, LinkedIn) is the co-founder and CEO of Mercury. He is also a prolific angel investor and co-hosts the Founders in Arms podcast.

Mercury is a fintech banking platform used by one in three startups. It is Immad’s fourth company in 20 years of entrepreneurship. Mercury is in the process of becoming an FDIC-insured bank and recently launched Mercury Books, AI-powered accounting software.

Immad grew up in Pakistan, moved to London at nine, and left for San Francisco at 23 to become an entrepreneur “for real.” Mercury is built on something rare in finance: a willingness to spend a disproportionate amount of energy on details, the kind of care Immad admits “seems irrational.”

We start with a simple question (what is a bank?) and discuss why banking stayed bad for so long, what stays hard as AI makes software easy to build, and why Mercury’s motto is “be extremely helpful.” Entrepreneurship has shaped Immad’s life, and he hopes Mercury can empower a generation of entrepreneurs.

I hope you come away a little more annoyed by the mediocre things we’ve all learned to tolerate and inspired to put an irrational amount of care into making them better.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. It works with all of your agents and keeps context across them and your team. Check out the new Notion Skills API. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:50) Intro: Immad Akhund

• (4:16) Start: Banks and Why Immad Was Suited to Build One

• (20:30) What Traditional Banks Do Well & What Mercury Got Right

• (29:33) Why Mercury Wants a Bank Charter

• (35:57) What’s Scarce When Software Is Easy

• (49:00) Becoming the Default for New Entrepreneurs

• (53:34) Product: 100 Little Things Better

• (1:06:51) The Right to Win

• (1:09:19) Brand as Care

• (1:15:19) Culture and Being Extremely Helpful

• (1:22:51) Command, Agents, and AI

• (1:34:26) Ambition, Investing, and Leading

• (1:46:54) Family, Pakistan, and America

• (1:52:56) Money, Freedom, and Energy

• (1:59:14) Outro

The Bar Was Not That High: 21 Lessons on Obvious Advantages, Irrational Care, and Fighting Entropy

1. Greatness seems achievable once it’s familiar. Immad grew up poor in London, but twelve generations back, an ancestor ruled the Durrani Empire, so greatness was part of the family story. Later, sitting beside billion-dollar founders at Y Combinator dinners made it feel human-sized: “I don’t think I’m amazing or anything, but I also don’t think everyone else is that amazing either.”

2. Look for risk with a floor and no ceiling. Quitting a $50K job meant $50K of downside, “but I could make a billion-dollar company.” He now teaches his kids to chase capped downside with unbounded upside and to avoid the reverse.

3. Banks are bad at product because the product doesn’t pay. Immad estimates lending supplies 80–90% of most banks’ revenue, making them “mid-market enterprise sales companies selling loans.” This explains their neglected everyday banking interface.

4. When the default is mediocre, doing the obvious is an unfair advantage. Immad assumed a law explained why banks hide transactions older than 90 days. In fact, they all share the same backend software and its 20-year-old limitation. Mercury refused to accept limits like that, and “the bar was not that high.”

5. Enough small improvements can add up to something new. Mercury launched without a novel hook. Just “the thing that you might expect your bank to do, but we did it much nicer.” Immad believes “80% of the fight is doing the little things,” and that doing them consistently compounds.

6. Two percent of a big enough market is a big market. Six months before launch, Immad spoke to 100 companies and found only two that were really excited: a dispiriting result after so much work. His eventual lesson: *“If 2% of people are like, ‘F\*k yeah,’ that’s actually a lot of people if the market’s big enough.”

7. Trust is the foundation of a right to win. Most products don’t begin with “Step one: Send me all your money.” Banking does, which makes trust painful to build. But once customers clear that bar, they’re already in a trusted relationship when the next high-trust product arrives, like accounting.

8. Go long entrepreneurship. Only about a quarter of Mercury’s customers switched from another bank. The rest opened their first account for a new company. Immad wants to compound with them: “The future is defined by those companies, not the existing companies.”

9. Make the product the relationship. “I really hate talking to people if I don’t need to.” While Silicon Valley Bank tracked how often its bankers talked to customers, Immad built Mercury to be “the thing you come to if you don’t want to talk to people,” because it’s so easy to use.

10. You can’t pitch cohesion. You have to show it. Mercury is difficult to sell through one headline feature because “100 different things are better”—search, virtual cards, signup, and how they fit together. So they put the whole product online with fake money at demo.mercury.com, and visitors who click through are roughly 30 to 40% more likely to become active customers.

11. Annoyance is a good product strategy. Mercury runs on Mercury, putting its own builders on the receiving end of their decisions: “I just want (our team) to be clicking around and getting annoyed about things all the time.”

12. Care can look like wasted effort. An elaborate animation in Mercury’s accounting onboarding seems to have gotten an irrational amount of attention. Immad sees art in that excess—“Why did you even do this?”—and a way to show customers how much the team cares.

13. Most products & companies decay. Build one that gets better with age. Products ship and go unmaintained, culture drifts, and focus slides from customer value to customer extraction. His defense is a high bar for everything Mercury launches, plus constant upkeep: “It’s like entropy is sucking it out of you all the time and you got to fight it.”

14. When code gets cheap, look to what’s difficult. Mercury may have started roughly half software and half other moving parts. As software gets 10x easier to build, “then the other part becomes 95% of the hard part”—trust, brand, network effects, and now, the bank charter.

15. Leave culture undefined, and the loudest voice will define it. At his last company, culture came down to whether people stayed for drinks, and it drifted toward “whoever was the loudest voice in the room.” At Mercury, they wrote down the traits they wanted at four people, then hired and managed against those values.

16. If you’re not going to be helpful, what’s your purpose? His older sister asked him that when he was a bratty teenager. It stuck, and Mercury’s motto is “be extremely helpful,” because “just being slightly helpful is not good enough.”

17. Words scale. Context doesn’t. On a three-person team, “I hate this” is candor, because everyone knows how you mean it. At 1,300 people, many of them don’t know him, so the same words can be disheartening. He’s learned to react less emotionally and prioritize context.

18. Don’t fight the future. Speed it up. When COVID shut people out of bank branches, Mercury was already online, and Immad sees AI as “another accelerant.” Other companies will protect their position, but “the worst thing you can do is fight the future.”

19. The best finance tool may be the one you never open. The chat box on Mercury’s AI agent (Command) is only “a stepping stone.” The goal is to cc Mercury on a customer thread and have it get the contract signed and make sure they pay on time, until “people don’t come to Mercury, maybe at all.”

20. Time isn’t about time. It’s about energy. At his first job, Immad showed up at 10 a.m, left at 4 p.m., and still went home exhausted. At his own startup, he worked 9 a.m. to midnight and felt energized. The question isn’t how many hours you have but “am I doing things that give me energy?”

21. Forever is too long to put your life on hold. Wanting to be an entrepreneur forever meant Immad couldn’t sacrifice the rest of his life for it: “I just have to find a way to do this alongside my life.” Family is part of what gives him the energy to keep going.

The first was an new essay from early guest (ep. 7: The Shapes of Culture): Body Futurism (reading, original). The second was Philosopher ’s essay, Art is for Seeing Evil (reading, original).

Today’s reading was actually originally a speech, given by 20th century public servant, educator, and public reformer John W. Gardner. It was delivered to a group at McKinsie & Co in Phoenix, AZ on November 10, 1990. The transcript of Personal Renewal is available at PBS.

Willem Van Lancker shared this with me in 2024, before I’d started Dialectic and while I was trying to figure out what was next. I’m grateful. I’ve returned to it about a dozen times and shared it with more than as many people. Even during this reading, I felt myself getting goosebumps, and I felt aliveness rising in my soul. I hope you are similarly inspired.

Available here on Substack, Spotify, Apple, and RSS podcast platforms.

Gardner begins with barnacles, and pleas with all of us to not live our lives so stubbornly and stagnantly:

“The barnacle" the author explained "is confronted with an existential decision about where it's going to live. Once it decides.. . it spends the rest of its life with its head cemented to a rock.." End of quote. For a good many of us, it comes to that.

Then comes one of the strongest cases for fighting inertia that I’ve ever read. He encourages us to pursue continual renewal, by way of recognition, self-belief, and commitments.

By midlife, most of us are accomplished fugitives from ourselves.

Life is an endless unfolding, and if we wish it to be, an endless process of self-discovery, an endless and unpredictable dialogue between our own potentialities and the life situations in which we find ourselves. By potentialities I mean not just intellectual gifts but the full range of one’s capacities for learning, sensing, wondering, understanding, loving and aspiring.

The things you learn in maturity aren't simple things such as acquiring information and skills... You learn that self-pity and resentment are among the most toxic of drugs. You find that the world loves talent, but pays off on character.

“There’s something I know about you that you may or may not know about yourself. You have within you more resources of energy than have ever been tapped, more talent than has ever been exploited, more strength than has ever been tested, more to give than you have ever given.“

You have to build meaning into your life, and you build it through your commitments -- whether to your religion, to an ethical order as you conceive it, to your life's work, to loved ones, to your fellow humans. Young people run around searching for identity, but it isn't handed out free any more -- not in this transient, rootless, pluralistic society. Your identity is what you've committed yourself to.

Meaning is not something you stumble across, like the answer to a riddle or the prize in a treasure hunt. Meaning is something you build into your life. You build it out of your own past, out of your affections and loyalties, out of the experience of humankind as it is passed on to you, out of your own talent and understanding, out of the things you believe in, out of the things and people you love, out of the values for which you are willing to sacrifice something. The ingredients are there. You are the only one who can put them together into that unique pattern that will be your life. Let it be a life that has dignity and meaning for you. If it does, then the particular balance of success or failure is of less account.

Spotify:

Apple

His favorite part: getting to go back down the mountain and begin again.

Now, he faces an existential question: AI is making software creation nearly instant and free. All of the underlying assumptions for venture-backed software startups are in question. What moats will persist? Is software over?

I talked to him about playing infinite games, seeing greatness up close, and endurance in finding the next hill to climb.

Available on Spotify, Apple, YouTube, Twitter/X. If you enjoy it, please share it with a friend :)

Always Another Adventure: 21 Lessons from Miles Grimshaw on Software’s Future, Enduring Companies, and Being Impatiently Patient

Miles Grimshaw is drawn to beginnings: the new country, the unfamiliar market, the next mountain. I talked to him about how he finds and partners with exceptional people, which genetics shape enduring companies, what moats will survive in software, and beginning again, over and over.

1. The reward for reaching one summit is another climb. A coach sent Miles Camus’ classic essay imagining Sisyphus happy. He’s internalized it with regard to his infinite game as a venture investor: “I love going back down and looking at new summits and going, ‘Can we go do that one?’”

2. Courtship starts before the round exists. Miles flew to Ottawa after one call with Turbopuffer’s CEO Simon, offered him a term sheet, got turned down, and spent more than a year helping out anyway. When the call finally came at 9:30 on a Monday night, Thrive was committed by 10:30. “Our challenge is to be impatiently patient.”

3. Underwrite the person before the model. Miles invested in Cursor after getting rough numbers over dinner without ever receiving detailed revenue numbers. “It never starts with a spreadsheet. It starts with that person, the future that they see.”

4. Investing is enlisting. Miles treats early investment like joining the team and working for that ownership over the next decade. After Cursor’s Series A, Thrive went all-in on recruiting for them through the Series B. The relationship is working when a founder thinks, “Sure, I want to raise money from these people, but actually, I kind of want them on the team.”

5. Instinct comes from exposure to the best. Your read on great is only as good as the greatness you’ve seen up close. When Thrive met Mesh Optical (a team who built Starlink’s laser interconnect at SpaceX), they went from first meeting on Friday afternoon to commitment by Monday, all in a domain they “had no business knowing anything about.”

6. Specific optimism is the job. He once told a candidate, “There are infinite ways this can go wrong that I can enumerate. Our job is to figure out the path of it going right.”

7. What is it? And who cares? Two questions underpin Miles’s investment analysis. You can say many words about a company, but if you can’t simply define what the customer is actually buying and who values it enough to pay, nothing else matters.

8. Vision is where the founder is looking. Patrick Collison was looking beyond payments toward the GDP of the internet; Cursor’s Michael Truell was looking beyond the IDE toward new abstractions for coding. “In driving and biking, you go where you look… I think that is really true for companies, too.”

9. Ask what a company’s growth is made of. Investors love to use a company’s ARR growth as a scorecard: how fast to $10M or $100M? Miles is less interested: “That’s a phenotypic expression of an underlying set of genetics.” A handful of large contracts or a long tail of small customers might both have strong ARR, but will grow into completely different organisms.

10. Pick the customer that helps you live in the future. For early-stage companies, he cares more about demanding, innovative customers than pure revenue. They force the product and the organization to adapt to a changing market. “I think Stripe would be a very different company if Delta was its first customer instead of Shopify or Lyft.”

11. A great product can outrun its sales team. When he began working with Cursor, it got to tens of millions in ARR with zero salespeople. The sales team remained very small until early 2026. Michael relied on his team’s feedback and individual user conversations because “they had a very strong purity to delivering a great product.”

12. Copy the cause of success, not its privileges. Google’s core business was so powerful that 20% time could look like a management principle instead of something Google could uniquely afford. “In some sense, it was the wrong thing to learn the lesson of from that company.”

13. Software’s hidden moat was wall-clock time. Switching costs mattered, but Miles thinks the undercounted advantage of software was the years spent building a place where customers, integrations, expertise, and mindshare naturally gathered. “The great software companies basically built a city... If you’re Benioff and you’re building a CRM, sure, you’re building a CRM, but you’re kind of building the City of Sales.”

14. Get big or go luxury. AI has compressed the build time that protected incumbents in software, threatening the middle. Miles suggests a lesson from ecommerce: either cover enormous surface area or be nimble enough to build bespoke, white-glove products.

15. Craft creates trust. Customers may not consciously notice every product decision, especially as software becomes more like services. But they feel the accumulated attention to detail and infer that the invisible details have been handled with equal care.

16. “I don’t know” is only half the answer. The follow-up is “I’ll figure it out.” Learning requires enough humility to say “Sorry, I just don’t understand that” and enough self-confidence to believe you can reach the ground truth.

17. Instinct must become legible before it becomes useful. Repetition improves Miles’s intuition, but an investment team cannot act on a feeling trapped inside his head. “If I can’t communicate it to the people who trust me the most… how is the rest of the world going to do that?”

18. Raise the ceiling in good times and absorb the shock in bad ones. A lesson from Sequoia’s Sir Michael Moritz. Success gives a company the capacity for the exceptional recruit, ambitious customer, or defining move: “when things are working, you need to set your eyes further out.” In adversity, the founder has already felt every problem more deeply than the board will, so constructive support is more useful than drilling on known problems.

19. Hold jam sessions, not jury trials. He rejects the investment committee as a jury trial where one person presents, and everyone else looks for guilt. “The best version of investment team conversations… is like being in the music studio making music together.”

20. Stable foundations make larger adventures possible. Miles spent much of his life associating the next adventure with leaving: England, the US, India, China, a new major at the end of college, then Thrive for Benchmark. Returning taught him something else: “I’ve come to find a lot more of the magic that gets unlocked by a strong foundation.”

21. Endurance grows from evidence, not encouragement. Miles ran his first marathon at seventeen because he wanted to do it before turning eighteen; years later, he and his wife completed a 150-mile race in New Zealand that half the field did not finish. Belief follows proof: “Once you know you can, you can.”

Description

Miles Grimshaw (X, LinkedIn) is an investor at Thrive Capital. He’s spent most of his career there, there, partnering with founders at the early stages of company building, including Cursor, Turbopuffer, Chai Discovery, Mesh Optical, Revel, XDOF, Socket, Benchling, GitHub, and many more. Miles was also briefly an investor at Benchmark before returning to Thrive in 2024.

The conversation focuses on Miles’ appetite for change and continuing to begin anew, again and again. That starts with “adventure racing” as a teenager, and continues through his career as an investor in search of world-changing companies.

We talk about how Miles proactively puts himself in position to work with great founders in a style that resembles courtship, his disposition of impatient patience, and why he loves change. The latter includes the dramatic shift in his primary domain: software. As the underlying assumptions for software businesses change due to AI, what traits will great companies have? And what moats if any will persist? Is software investing over?

Miles also talks through how great companies and founders go where they are looking, prioritizing customers that help you live in the future, the learned intuition of greatness, and joining the expedition squad alongside the founders Thrive partners with. Finally, we talk a bit about Thrive, his departure to and return from Benchmark, and endurance.

I hope you are inspired to find an infinite game where you are excited to see the stone roll back down the hill and begin to push again.

Disclaimer: This podcast is for informational purposes only. The views expressed are the speaker’s own as of the recording date and are subject to change. Thrive funds and their affiliates have investments in certain companies discussed in this episode. References to those companies are illustrative, do not represent all investments made by Thrive, and should not be viewed as recommendations or indications of future investment performance. Past performance is not indicative of future results.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion’s custom agents are AI teammates that handle recurring work across your tools. Learn more about their new developer platform and workers here. Notion is hiring across product, storytelling, design, engineering, and more. You can learn more at notion.com/dialectic.

Timestamps

• (0:00) Opening Highlights

• (1:37) Intro: Miles Grimshaw

• (4:30) Infinite Games, Adventure Racing, and Starting Anew, Over and Over

• (11:01) Staying Hungry: Proactive Hunting and the Turbopuffer Story

• (17:35) Impatiently Patient: Courtship, Cursor, Recruiting, and Joining the Team

• (25:33) Loving Change: London to America, the Himalayas, and Learning New Sports

• (31:36) The Genetics of Companies: “What Is It?” and “Who Cares?”

• (38:08) House Cats & Tigers: Where Is the Founder Looking?

• (47:00) Confidence in Uncertainty and Customers That Pull You Into the Future

• (54:25) What Remains for Software: Moats, Cities, Wall-Clock Time, and the Barbell of Scale & Luxury

• (1:04:54) Craft, Trust, and Why Software Isn’t Over

• (1:11:13) Intuition: Gradient Descent and Seeing Greatness Up Close

• (1:18:07) “I Don’t Know” and “I’ll Figure It Out”

• (1:22:12) Commitments, Not Bets: Closing People and Board Work

• (1:29:06) Joining Thrive, Being a Punk, and Music Studios over Jury Trials

• (1:36:18) Leaving for Benchmark and Returning to Thrive

• (1:43:18) Dream Bigger: Lessons from Josh, Teaching Agency to Kids, and Going the Distance

• (1:51:36) Outro

They aren’t trained engineers, designers, or musicians, and yet have built a platform that hundreds of thousands of artists—from 16-year-olds on their first record deal to Lorde—use to store, listen to, and work with their music.

Lorde also recently released XRAYS on [untitled]: 49 demos, the sonic museum behind her album Virgin.

Dan & José are also childhood best friends. I talked to them about the adventure so far and their quest to build the biggest music company in the world.

Available on all platforms: transcript/links, Spotify, Apple, YouTube, [untitled], X/Twitter.

Dialectic 55: Dan Lilienthal & José Chayet - As [untitled] as it Comes

18 Lessons from Dan and José of [untitled] on Unfinished Songs, Sacred Software, and the Sophomore Album

1. Creativity makes the world bigger. José’s benchmark for novelty is what he felt in Copenhagen in 2006, standing under a shower where the water fell from the ceiling. The best music, design, and technology expand what seems possible: “This was the world, and now the world just got a little bit bigger.”

2. Music is AR, not VR. Much of entertainment is escapism: it takes you elsewhere. Music deepens your experience of where you already are. You can see your own life through a new lens. It’s an overlay, not an exit.

3. The divine can sound like your friend’s demo. A friend described music as the way most humans connect with the divine. For Dan, that connection is most vivid in José’s music, because it connects him to the things his friend is feeling, and taps into something deeper than himself.

4. Creation is becoming a series of choices. José connects Duchamp’s found objects to sampling and found sounds in music: over time, creation concentrates in curation and context. AI is only accelerating this. “What do I want? What do I see? What do I want to see?”

5. The idea never wavered. Everything else had to. They wrote the V1 spec in a single day in 2020 and essentially shipped that document three years later. In between came money raised, a few hundred users, and a decision to restart the team from scratch in New York. “It was an execution story.”

6. Find the person upstream of the ecosystem. Music is a pyramid with the artist at the top: producer, manager, A&R, and publicist all serve whatever the artist wants. One producer admitted to José he doesn’t even like the app, but a big artist insisted he use it. Every category has a central character: GitHub won the engineer, Figma won the designer. Their preferences organize everyone else’s behavior.

7. Fake your way into real empathy. They were not professional musicians, engineers, or pixel-level designers, so they decided to become “method actors.” They made music, studied artists and products obsessively, and treated empathy as a discipline you can practice rather than a credential you’re born with. A big musician’s verdict: “It’s as if you’re in our brains and you know exactly what we want.”

8. One primitive can serve 16-year-olds and superstars. A kid on their first record deal and Lorde both want listening to their own music to feel as good as Spotify. Thoughtful and simple design choices can scale if they meet universal needs.

9. Discovery doesn’t always need to be efficient. Unfinished music is sacred, so [untitled] began with intimacy and has resisted the reflex to build a feed, even six years in. Even the most prolific artists “are still very shielded,” so “you have to start from a place of privacy.” Music spreads person to person through iMessage and WhatsApp instead of an algorithm. And the discovery that does happen is slow and physical: most of the music Dan finds now arrives through whoever walks through their studio: “This building is my algorithm.”

10. A peek behind the curtain can make a fan. José thought the Beatles were plain until Get Back made him ask, “Why does anybody else even make music?” Lorde’s demo drop on [untitled] sent Dan back to an album he’d barely played. Context draws us in, but you have to earn the right: nobody visits the museum of a nobody.

11. Alignment is the best marketing. Other music companies run campaigns about how much they care about artists. [untitled] charges artists for a product they keep choosing to pay for. Dan: “The thing that keeps the lights on is making sure artists love what you’re doing.”

12. Necessity is the mother of recruiting. Neither founder is technical. They once flew hours for dinner with an engineer while pretending they were already in town; Dan approached strangers in Swift shirts on the subway and coders at WeWork. A missing capability can force you to become unusually resourceful at attracting it.

13. QA is the job. They can spend a day arguing over 30 versions of one experience. José says QA has “always been the most important function” they’ve performed. As AI increases everyone’s output, this is only accelerating. Now, the challenge is scaling this intuition and filter beyond just the two of them.

14. “AI” is a big tent. Everyone assumes AI in music means generative songs from products like Suno. They are excited about tools that help artists explore references and search enormous archives of works in progress.

15. The scarce ingredient is surprise. Earlier AI models created stranger music. Now, they sound “better” but are predictable: “It’s too good. It’s too good.”

16. Every artist is trained on someone. They asked a legendary artist about AI models training on his catalog. His response: “I trained on other people’s music.” As for what’s next, he admits he hasn’t made anything with AI that he couldn’t have made otherwise… yet.

17. Work with someone who makes you feel like a kid. Dan thinks creativity depends partly on childlike curiosity, and working beside the friend he has known since childhood keeps silliness, inside jokes, and play within reach. “It’s almost like a hack to tap into your childlike creativity.”

18. Reinvent between records. Fifty thousand paying customers, $5M in ARR, and building the thing they dreamed up. But the next phase will look different. Dylan went electric. “It’s time to make the sophomore album and make the next big one.”

Description

Dan Lilienthal (X, LinkedIn) and José Chayet (X, LinkedIn) are childhood friends and cofounders of [untitled] (X, Instagram), a platform for musicians that they describe as a sacred place for work-in-progress music. It is where a song lives between recording and streaming. [untitled] is closer to the Photos app than to a social network: a private place to store, listen to, and slowly share demos, with no feed.

Dan and José are not trained musicians, engineers, or designers, but they have built a product artists love by “method acting” their way into deep empathy. The platform has grown to 50K paying users and now allows artists to share unreleased music directly with fans. Lorde recently released XRAYS on [untitled]: 49 demos and works in progress from her album Virgin, creating a kind of museum behind the record.

We discuss music as a form of communication and a connection to the divine; why they have resisted adding a feed; product inspirations like the iPod and Snapchat; how empathy and QA underpin their product philosophy; designing for 16-year-olds and superstars; AI as an instrument; which parts of the creative process are worth sharing; what it means for software to be sacred; and building a company with your best friend.

I hope you’re inspired to consider what is sacred, share and live with the things you make, seek out music that inspires you, and stay untitled a little longer than is comfortable.

This episode on [untitled].

Dialectic 55: Dan Lilienthal & José Chayet - As [untitled] as it Comes

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

• (1:24) Intro to Dan & José & Thanks to Notion

• (4:42) Start: Brackets, How Creativity Makes the World Bigger, and Music’s Connection to the Divine

• (20:40) Duchamp, Music as a Set of Choices, and The Museum Behind the Work

• (27:52) [untitled]: A Medium for Music In-Progress

• (45:03) From a Better Dropbox to a Creativity Company

• (52:13) Empathy as a Product Philosophy and The Collaboration’s Origins

• (1:01:04) Scaling the Sacred Place and Product Intuition

• (1:10:33) Lorde’s XRAYS Drop and Designing for a Wide Range of Artists

• (1:17:26) 10K Unheard Songs and Whether Process Should be Seen

• (1:24:10) Brand, Trust, Alignment with Artists and the [studio]

• (1:30:54) The Word “Sacred” and Resisting the Feed

• (1:40:52) AI as an Instrument: Building Tools Artists Actually Want

• (1:49:27) Building a Company with Your Best Friend

• (1:56:31) Closing Questions: Dream Users, Rapid Fire Brackets, and Titles

• (2:08:52) Thanks Again to Notion

Ian has spent his career chasing the technology people are going to hate next: file sharing, streaming, crypto, and AI. But he also knows how to build brands and sell culture, from the Beastie Boys to Beats/Apple Music to LVMH.

Ian’s resume is too long to list, but a taste: Beastie Boys webmaster; Gnutella & Winamp; Yahoo! music; Topspin; CEO of Beats Music, then Apple; Chief Digital Officer of LMVH, and now Chief Human Agency Officer of Ledger.

The thread running through his unlikely career combining tech and cool comes from his punk rock roots:

“You are not a spectator who is meant to buy a ticket and buy merch. You are a participant who is meant to engage.”

I hope you enjoy it. As Ian says, the best way for creative works to spread is through word of mouth. So if you do, please share it with a friend.

Available on Spotify, Apple, YouTube, X/Twitter, and here on Substack.

Dialectic 54: Ian Rogers - Never a Spectator

20 Lessons from Ian on Hunting the 1%, Selling Culture, and Being the Human in the Loop

Culture & Taste

1. Don’t spectate. Participate. At fifteen, Ian went to a punk rock show and realized Henry Rollins was standing to his left and a band he loved to his right. That is the spirit of punk rock, and has motivated him throughout his life: “You are not a spectator who is meant to buy a ticket and buy merch. You are a participant who is meant to engage.” He’s reminded of Ted Nugent’s line: “I’ve got news for you. I don’t watch anything. I do shit.”

2. A Louis Vuitton bag and a Slayer shirt do the same job. Each tells the world, I belong to that tribe, not this one. Ian thinks the internet created an extraordinary market for anything that helps people define themselves as individuals.

3. Find the 1%. Anyone can point at what sucks. Ian’s response is “shut up and do your job… 99% of every genre and every scene is garbage. Your job is to find the 1% of everything that’s amazing.” This year, his musical 1% is Twisted Teens: “Greatest band I’ve heard in 10 years. New Orleans steel guitar punk rock. Are they a part of a scene? Are they even a part of a genre? I don’t know, but it’s awesome.”

4. Kill the three-star review. What frustrates Ian about legacy critics is that they hedge. He wants only two things from a review: a tip on something great he doesn’t know about or a warning that something will waste his time. Ian says the lukewarm middle is useless. “Don’t tell me something is mediocre. What’s the point?”

5. Culture isn’t dead. You stopped digging. When someone insists music was better in their day, Ian has a move. Ask them what year, pull up that year’s Billboard Hot 100, and watch them backpedal, “oh, but that’s not what I was listening to.” Exactly. Back then they dug for the good stuff underground, and now they judge the whole world by the popular charts.

6. Escape the box. “As soon as you could say, 'Oh, that's not hip hop,' well, now actually you've made a box and you tried to put the art in a box." He watched it happen up close when Kanye told him he was done after Dark Twisted Fantasy and Watch the Throne left him nowhere to go but down. What came out the other side was Yeezus. To Ian, "Yeezus is punk rock.”

7. The feed is not the world. When a town had two newspapers, each had to appeal to nearly everyone. Infinite choice rewards the opposite: take an extreme position just to get noticed. Neither the centrist media of scarcity nor the extreme polarization of abundance are representative. When Ian’s daughter said everyone was furious about Bad Bunny playing the Super Bowl, he stopped her: “But are they?” Ask someone on the street and they’ll probably shrug: Bad Bunny’s cool.

Attention, Brands, and Building

8. Quality—not marketing—compounds. Ian leans on Umair Haque’s 2003 essay ‘The Blockbuster versus the Snowball.’ Under scarce distribution, a movie studio spent its marginal $2 million on marketing to beat a limited field. With unlimited distribution, that money is better spent on the product, because “quality is hyper-efficient, not marketing… the only thing that actually works is word of mouth.”

9. “Everyone” never applies. He quotes Seth Godin: “you should find yourself a nickel anytime you use the word ‘everyone’ or ‘nobody,’ because the moment you say it, every word that comes after it is wrong.” Nothing’s for everyone; nothing’s for nobody. Bernard Arnault is the richest man in Europe and 85% of the population are not his customers. “The goal is not to appeal to everyone; the goal is to appeal strongly.”

10. The front of the box is for the heart. Ian has told people for years to never forget they’re selling culture before they’re selling product. With technology products, via David Sloo, “The front of the box is for the heart, the back of the box is for the head.“ The heart wants the shiny thing on sight; the head hunts for specs to justify the $500 purchase it already decided on.

11. A brand takes a generation, not a venture timescale. Advising a friend starting a label, Ian warned: “Fashion brands are not venture businesses.” By his rough figures, Golden Goose spent 12 to 15 years reaching its first $15–20 million, then another 15 reaching $500 million. A brand has truly arrived when someone can say, “That was my shit when I was fifteen.”

12. The greats lend you their belief. Jimmy Iovine, on the phone, while Ian was mid-startup: "You're a major league player. Why are you playing in the minors?” Bernard Arnault gave John Galliano the same tap on the shoulder, hiring him on the spot in a leather vest, no shirt, and flip-flops. The greats see promise in people and get them "to do things that even they didn't know they were capable of.” “Jimmy saw something in me that I didn't see."

Agents and Humans

13. An agent should suggest. A human should decide. Ian’s job at Ledger is focused on a single rule: every action an AI takes gets approved by a human, or by a policy a human set. He likes Balaji’s framing — “AI is middle to middle, humans are end to end” — and the failure mode is dropping in a task and never returning to take responsibility for the end. The rule has a practical payoff, too: “you get a transaction record of what was approved and by whom... Now you’ve got an audit trail.”

14. Every new technology redraws the security perimeter. PCs required antivirus; the internet, network security; digital ownership, hardware wallets. AI agents create the next perimeter: we’ve given systems built to accept arbitrary commands access to our computers and information. “Prompt injection is a feature, not a bug… Don’t handicap them. Let them be great at that. But don’t give them secrets.”

15. Build AI for humans, not to be human. Ian is less worried about AI becoming human than about humans treating it as if it were. We’re easily seduced by things designed around our appetites—doomscrolling, sugar, nicotine. As AI becomes more flattering and emotionally responsive, it becomes easier to mistake imitation for personhood and surrender our agency to it.

16. Don’t let your process get one-shotted. After months of using AI to build materials, Ian “hit the nuclear reset button” and wrote an important presentation entirely by hand. Then he let AI back in: first for a narrative pass, then word by word. This wasn’t abstinence; he was still “working with it,” the way he would with Pro Tools or any other technology.

Living Well

17. Learn to fall well. Watching pro skateboarders taught Ian “the number one thing they are better at than you is falling.” Ten feet above an eleven-foot ramp, upside down, they make a split-second call: ride it out, or knee-slide to the bottom and climb back up the ladder, unbothered. “Once you’re skilled at failure, you are untouchable… because now there are only two outcomes: you win or you learn.”

18. Everyone is magic and imperfection. Choose which to see. Hunt for flaws and you’ll find them: “I’ve been divorced twice. If you’re looking for something, you’re going to find it.” Look for the magic and it is just as available—in a partner, a teammate, or a stranger at the coffee shop. “One of my practices in life is to see the magic.”

19. If the cat is bigger than the shit, keep the cat. Ian’s favorite rule for love comes from Jimmy Iovine’s dad. There’s never a perfect relationship because there’s always some shit. Love survives less by locating perfection than by deciding whether what is beautiful remains larger than what’s difficult.

20. Participation has no expiration date. Mike D at 60, on stage in Paris playing an amazing show with his kids. Paul McCartney in his 80s, still curious, still pushing. Henry Rollins and Ian MacKaye putting out The Cramps’ archive. “It’s just this reminder that as long as we’re breathing, we can still create and participate.”

Description

Ian Rogers (X, LinkedIn) is Chief Human Agency Officer of Ledger, the Paris-based security company whose hardware wallets secure much of the world’s crypto. He now focuses on how Ledger can enable us to work with AI agents while maintaining our secrets and value.

His career has spanned music, culture, brand, and “the technolog(ies) people are going to hate next.” He built and ran the Beastie Boys web presence in the 90s before working on music on the internet for over a decade: file sharing Nullsoft (Gnutella and WinAmp), early streaming at Yahoo!, direct-to-fan commerce at Topspin, Beats Music, and finally Apple, as an abbreviated list. He then joined LVMH as its first Chief Digital Officer, working with Bernard Arnault and its many Maisons to bring them into the internet era. More recently, he joined Ledger to improve its product experience, including collaborating with Tony Fadell to create Ledger’s flagship form factor, Ledger Stax.

Ian’s roots are skateboarding and music, which formed alongside a punk rock ideology while growing up in Indiana in the 1980s. I am glad to have captured a long conversation that covers the many flavors of Ian, and the threads that have persisted through his many lives. That includes: individuality; being a participant, not a spectator; what makes a scene; building brands; trying to help Kanye; and why new culture is always being made—it’s just that you have to find the 1% that’s awesome. Also: ushering forward and translating frontier technologies; being pushed by Jimmy Iovine; why security matters in the AI era; why AIs aren’t people; what he wants to automate; learning to fail; advice on relationships across work, parenting, and love; and a whole lot of love for music—from his 2026 pick Twisted Teens to his desert island albums to tea with Paul McCartney.

I hope you’re inspired to participate in the world and make great things.

Thanks to our friends at Ledger for hosting me.

Ian and I made a playlist with albums/songs mentioned here (Apple, Spotify).

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

• (1:37) Intro to Ian & Thanks to Notion

• (5:22) Start: Tattoos, Individuality, and Punk Rock: Spectator vs Participant

• (16:44) What Makes a Scene?

• (25:24) New Culture, 99% of Everything is Garbage, Finding the 1%

• (40:09) Niche, Quality, and The Blockbuster vs. The Snowball

• (53:35) Brand, Selling Culture Before Product, and The Age of the Individual

• (1:08:12) Aggression, Patience, and Being Pushed

• (1:16:52) Translating New Technologies, Empowerment, and Agency

• (1:25:19) Interfaces, Ledger, Security, and Ideology

• (1:39:56) Ian’s New Role: Chief Human Agency Officer

• (2:06:03) Seeing What is Real, Comfort Being Wrong, Chasing What’s Fun and Cool

• (2:13:45) Lessons from Skateboarding and Favorite Albums

• (2:22:56) Working with Your Friends, Parenting, Love, and Remembering to Stay a Participant

• (2:35:47) Thanks Again to Notion

Links

Transcript & links: https://dialectic.fm/ian-rogers

Spotify:

Apple

YouTube:

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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YouTube:

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