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

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

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

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

We discuss:

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

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

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

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

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

• becoming the “Venkatesh Rao for tumblr girls”

• how learning makes you live “longer”

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

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

17 Lessons from Celine on Taking Your Intellectual Interests Seriously

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

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

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

Timestamps

• (0:00) Opening Highlights

• (1:35) Intro to Celine

• (4:25) Thanks to Notion

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

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

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

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

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

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

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

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

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

• (2:18:31) Thanks Again to Notion

Episode Links

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

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

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

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

Escaping Flatland

Differently free

Cousin Bichonnade in Flight, Jacques Henri Lartigue, 1905…

Read more

a month ago · 104 likes · 5 comments · Henrik Karlsson

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

Timestamps

• (00:00) Opening Highlights

• (01:28) Intro to Henrik

• (04:05) Thanks to Notion

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

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

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

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

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

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

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

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

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

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

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

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

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

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

• (2:40:49) Thanks Again to Notion

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

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

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

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

Timestamps

• (0:00) - Opening Highlights

• (1:21) - Intro: Charles Broskoski

• (4:00) - Thanks to Notion

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

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

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

• (33:26) - Contextual Patterns and Channels

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

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

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

• (1:22:53) - Aspirational Attention

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

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

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

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

• (1:59:48) - Personal Businesses

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

• (2:28:28) - Thanks Again to Notion

All links available at dialectic.fm/cab.

We discuss:

• Why spreadsheets is always wrong and why

• How he developed conviction on Vanta in 14 seconds

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

• Why craft and design have never mattered more in software

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

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

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

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

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

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

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

15 Lessons from Andrew

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

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

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

Timestamps

• (0:00) - Opening Highlights

• (2:02) - Intro: Andrew Reed

• (3:50) - Thanks to Notion

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

• (19:07) - Investing & Great Founders

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

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

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

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

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

• (1:28:39) - Sequoia Capital

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

• (1:51:29) - Closing Questions

• (1:59:08) - Thanks Again to Notion

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

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

We also discuss:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Bonus:

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

Description

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

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

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

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

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

Timestamps

• 0:00: Opening Highlights

• 1:29: Intro to Molly

• 3:36: Thanks to Notion

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

• 21:36: Agency and Ambition

• 34:45: Commerciality

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

• 59:46: Coaching and Working with Young People

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

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

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

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

• 1:58:58: Thanks Again to Notion

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

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

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

We talked about:

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

• How cultural capital has merged with financial capital

• Why speculation is rational

• The belief economy: from making → framing → predicting

• What he learned working with Kanye for three months

• Finding new subcultures in the dark corners of Telegram

• Why he’s long humanity despite everything

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

Dialectic Ep. 37: Trevor McFedries

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

Timestamps

• 0:00: Opening Highlights

• 1:18: Intro to Trevor

• 4:12: Thanks to Notion

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

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

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

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

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

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

• 58:22: Speculation is Rational

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

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

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

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

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

• 1:52:45: Culture & Business

• 1:54:38: Kanye

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

• 2:17:55: Thanks Again to Notion

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

Thi is focused on a dilemma with scoring systems:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

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

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

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

Timestamps

• 0:00: Opening Highlights

• 1:39: Introduction to C. Thi Nguyen

• 5:13: Thanks to Notion

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

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

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

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

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

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

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

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

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

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

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

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

• 2:18:52: Closing Thanks to Notion

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

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

Please enjoy!

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Description

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

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

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

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

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

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

Timestamps

• 0:00: Opening

• 3:54: Notion

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

• 2:30:07: Thanks to Notion

There’s no better example of his approach to creativity and design than his personal project, ryOS, which he created with Cursor. Take a look, or better yet, give it a try.

Dialectic 34: Ryo Lu - It’s All the Same Thing

Dialectic Episode 34: Ryo Lu - It’s All the Same Thing - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

14 Lessons From Cursor’s Ryo Lu on Iterative Creativity, AI, and Soulful Design

1. It’s all the same thing. Everything—apps, organisms, ideas—is built from simple parts that recombine into complexity. In many ways, design is pattern recognition plus taste in how you remix the fundamentals.

2. Get close to the material. You learn by making, not planning. For software makers, that’s code, at the most basic level. For creatives, it’s testing whatever medium gives feedback: clay, prototypes, rough cuts. Mocks and renders show possibilities. Prototypes show reality.

3. Greatness is emergent. It only looks inevitable in retrospect. You always start with shit. But because it exists, it can be improved. For Ryo, design feels like shaping clay or finding David in the marble. Poke, prod, ship, and quality sharpens into shape.

4. Simplicity is earned, not given. “Simple” design is achieved by wrestling with complexity and compressing it into a digestible form. The swan glides elegantly because it’s paddling like hell underneath. Easy is what comes after hard.

5. Design is making things true. Not polish. Not more details. It’s asking: what are the essential qualities of this thing? And then making them better, continually.

6. Learn to communicate at different altitudes. A prototype and a spec doc are the same thing, just at different levels of abstraction and in different flavors. The fundamental goal is translating ideas into forms people can absorb, and eventually use.

7. Great systems flirt with chaos. Push right up to the edge of collapse, then rein it back. You want weirdness, divergence, slack; just shy of too much. Don’t snuff out the new too soon.

8. AI is raw material, not finished goods. The purple gradient the AI tools give you is just the beginning. The difference between slop and soulful products is iteration and taste. Most people stop at the first output, rather than using it to begin.

9. Don’t dumb things down. Give users pro-grade tools with beginner-friendly packaging. Discovery beats prescription every time. Get out of the way and let users surprise you. Treat their growth as journey you accompany them on, and build affordances along the way.

10. Build bricks, not readymades. AI is really good at composing parts, so build great bricks. Agents without guidance reinvent the wheel, so give them consistent, reliable materials to work with. Remember: There’s no such thing as “the final design.”

11. Tenderness is care made visible. Understand what people need and are frustrated with. Build tools that amplify their strengths while erasing drudgery. Good design is generous.

12. A band of pilgrims, not conscripts. Teams that build greatness don’t hide behind convoluted processes or bloated hierarchies. They’re there because they truly love the work. And you can tell: they talk about ideas and impact, not valuations and vesting cliffs.

13. Become irreplaceable. AI is trained on all public knowledge. You’re trained on what you’ve experienced and how you respond: your taste, judgment, how you feel. That gap is what makes you distinct, and thus valuable.

14. Start anywhere. Compound everywhere. Small ideas stack up. You don’t need permission or a grand vision. Make a choice, observe, then make it better.

Description

Ryo Lu (Website, X) is the head of Design at Cursor. Prior, he was a designer at Notion, Stripe, and Asana, working on some of the most influential software tools of the last decade. He is now focused on building the next generation of tools for making software.

Our conversation is an extensive exploration of Ryo’s design philosophy, which is anchored in his recurring mantra: “it’s all the same thing.” He sees the world as fundamentally modular, where simple rules and patterns endlessly recombine to create emergent complexity. For Ryo, design is consciously participating in this process: seeing through the surface to understand the underlying structure and rearranging it into new forms. This means constantly moving between simplicity and complexity, chaos and order, bare material and highest levels of abstraction.

We discuss how his process has evolved with AI. In the past, designing in tools like Figma felt like painting; now, working in Cursor feels like sculpting clay or finding David in the marble. So much of his philosophy is about getting closer to the material—in this case, code—and letting it provide feedback. There is no better example of this than his personal project, ryOS, a nearly full-on operating system he built entirely in Cursor. It is soulful, deeply personalized, and the opposite of “AI slop.”

This is a philosophical discussion about designing things that feel “true” or even “inevitable,” but it is also a practical one. We talk about balancing agility and quality, allowing for “slack” in systems, and how to create soulful things with AI. Ryo is a profound thinker, but he is also a prolific doer, and it is this marriage that makes him so effective. I hope you are inspired to get closer to your own material, to be more flexible and dynamic, and to expand the boundaries of what you can personally create.

Dialectic is now presented by Notion. I am now focused on Dialectic full-time, thanks to their support. You can read more about why Notion embodies Dialectic’s values and our partnership announcement here.

Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts.

Timestamps

• 0:00: Notion Announcement & Dialectic’s Future

• 4:45: Intro

• 7:46: “It’s all the same thing!”

• 17:25: Technical and Conceptual Readiness and How AI Helps us Deal with Complexity

• 20:58: Designing for true-ness and inevitability

• 27:28: Practicality and False-Compromise

• 33:45: Working with Material and Different Ways of Thinking

• 44:06: ryOS and Designing for the Full Spectrum of Users

• 59:39: Allowing for Slack and Some Amount of Chaos in Design

• 1:04:55: What is Cursor, Conceptually?

• 1:10:33: How Using Cursor Evolves

• 1:15:50: Designing for Power While Not Alienating Users

• 1:19:59: How Ryo Designs at Cursor: Abstractions, Writing, Prototyping

• 1:23:57: Process, Creating Soulful Things with AI, Refining Taste

• 1:31:08: Balancing Agility and Quality, Chaos and Order

• 1:37:00: Great Teams and Great Products

• 1:39:41: Grab Bag: Human Tech, Why Tools Need Stories, Why Cursor Isn’t a Slot Machine, Notion & Cursor, Steve Jobs, Liquid Glass

• 1:56:16: Tenderness & Empathy

Links & References

• ryOS

• How to make something great

• Complexity first, simplicity second

• The Future of Coding

• Making things true

• Notion Seed Pitch Deck 2013

• How to make something great

• Dialectic #12: Che-Wei Wang & Taylor Levy (CW&T) - Iterating Together with Time

• Ryo’s 12 tips for using Cursor (April 2025)

• 21: Geoffrey Litt - Software You Can Shape

• Inside Cursor - Colossus

• in the age of ai, the question everyone’s asking is “will i be replaced?”

• SpaceX Raptor engine comparison

• 18 Years of Evolution: iPhone 2G vs iPhone Air internals

• Zhuangzi

• NewJeans

Full transcript available at dialectic.fm/ryo-lu

I’m going full time on Dialectic with the support of Notion.

Please share some love for the announcement here on Substack and on Twitter!

A few thoughts on what the future holds, what Dialectic means to me, and why Notion is the perfect presenting partner:

A year ago, I started interviewing some of my smart friends without much of a strategy. I quickly realized that despite the lack of a grand plan, it was easy for me to care a lot about it, especially the preparation to make sure I could meet the guest deeply in their ideas and push them to go a bit further.

Over the course of the last year, I found Dialectic to be the ideal vehicle for me to (1) commit to something and compound in a specific direction, (2) still maximize serendipity and get to follow my curiosity in many different directions, (3) spotlight people I believe in and want to amplify, and (4) produce something that, in its most aspirational sense, is of service: whether that is to my guests or my listeners, in helping them grow, expand, learn, or shine.

I’m so grateful that I get to pour all my energy into just that. As I look ahead, I’ve been reflecting. Dialectic isn’t always legible, but I’m starting to get a better sense of what defines it.

Not everyone I talk to explicitly makes things, but most of them do. While I don’t deliberately pursue a specific kind of guest, there are a few themes that run across my conversations. I think they explain why Notion is such a perfect partner for me, but I’ll get to that in a moment:

The first is about where ideas meet action. I love ideas, and I love reflective people. But I’ve increasingly come to appreciate the thinkers who make sure all that thinking results in doing. Introspection paired with agency. People who understand the power of ideas, but who care most about the ways they meet reality. People who seek to understand themselves as means toward asserting themselves upon the world.

The second is craft. Craft is always aspirational: it is what appears when we care just a little bit more. When our taste is deployed. A human touch. Craft can be the object of creation but it can also be the way we create. When the creator can really feel the work, they produce something that meets reality where it is, and better yet, where it is going.

The third is soul. There are other words one could use here, like authenticity, aliveness, or originality. The elements that make us human. When someone has found a way to line up their life, creativity, and work in a way that feels distinctly them. When they are willing to reach deep, and then naturally settle into a way of being that is inevitable.

I’m proud that Dialectic’s audience seems to appreciate these themes too, and pursue them in their own lives. One of my favorite parts of all this is the audience -- that it seems like my kind of people are listening to and watching the show. I’ve made new friends amongst listeners, made the show better from their feedback, and I’m even lucky to call several of my guests fans.

I’m fortunate that one member of that audience is Notion’s Akshay Kothari. When I began thinking about what it would look like to double down on Dialectic and make it my complete focus earlier this year, I started having conversations with potential partners. He was one the first people to reach out.

Notion makes beautiful tools for your life’s work. I’ve always been a fan of creative tools (and have talked to several people who make them, including Notion’s own Geoffrey Litt!). The best tools amplify us. They meet us where we are and keep up with us as we grow.

In Notion’s case, it is a tool first and foremost for turning ideas into action. For sharing them, tinkering with them, and building things with them.

Craft has always been an essential word for Notion: how do you build an entire system of dynamic building blocks that still feels cohesive? How do you design details that work for students and giant teams? By sweating every single one, and caring enough to raise the floor.

As for soul: well, perhaps that is in the eye of the beholder. But most software doesn’t give mind to it, or to letting its users pour themselves into the tools they use. The rich and wide world of Notion’s community, templates, remixing, and creative expression is evidence of software that feels alive.

So it really wasn’t a hard decision at all, to team up with an organization, product, and brand that feels a lot like Dialectic.

Finally, looking ahead:

A lot more of the same. But better. It’s simple, if not easy. I think I’m onto something. I want to speak to the most original, creative, inspiring, generative people in the world about the stuff that makes their eyes light up. That means creative technologists, thoughtful writers, pragmatic designers, and authentic investors. But the aperture will widen too! I want to talk to people in 2026 that have me pinching myself, and to talk to people you and I have never heard of (yet). I hope to keep you guessing and nodding your head at the same time.

And there will be a lot more video, for those of you who’ve been asking. I have some other ideas too. I see Dialectic as a world I want to build, and I hope you come spend some time here. I hope I am lucky enough to keep creating this world with you for a long time.

In the meantime, please send me people you think I should talk to. People who love ideas, make things, care a lot, and put themselves into what they do.

And thank you to the wonderful team at Notion for being a partner to me on this journey. Thanks to all of you for reading, listening, and watching. More soon.

Onwards!

As I said recently, My two favorite qualities of John and Jordi are that they are earnest and enterprising. That combines for a playful disposition that learns and compounds rapidly, and enjoys the journey along the way. It makes everyone else want to root for you, help you, and join in on the fun.

We talked all about this, and about how much can happen in a year when you say yes and iterate daily.

We had a ton of fun and laughed a lot too, and I was quite inspired. I included 12 of my favorite ideas from the episode below. Enjoy!

P.S. John’s daily run of show newsletter that covers a topic they’ll discussion on the show is great.

Dialectic 33: TBPN (John Coogan & Jordi Hays) - Inside Tech’s Water Cooler

Dialectic Episode 33: TBPN (John Coogan & Jordi Hays) - Inside Tech’s Water Cooler - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

12 Lessons on Daily Compounding, Chemistry, and TBPN’s Uncopyable Playbook

1. You can’t copy compounding. John and Jordi took a great seed (chemistry and a creative format) and compounded it every day for a year. If you look at a frame from episode one of TBPN and a frame from today, the difference is remarkable. Those are the bookends of daily iteration and hundreds of tweaks. Jordi: “Going from zero to what we are today would be almost impossible, even for us.”

2. Discipline eliminates inspiration as a bottleneck. John and Jordi meet at 6:30am every morning to discuss before the live show. Mental muscles are warmed and arguments are sharpened. The live performance looks “effortless” because they show up. John on writing the TBPN daily newsletter: “I’ve never had writer’s block because I’m just transcribing the discussion we already had.”

3. Entertain, inspire or educate—Simply. Did the audience laugh? Learn something? Feel motivated to act? Jordi: “When people pitch us marketing ideas, I tell them, ‘I have more context on your business than 99.9% of people in the world, and I’m going to need you to repeat that marketing idea back to me because I’m still confused.’” Complexity isn’t entertaining, inspiring, or educational. Simplicity has a much better shot.

4. Go high and low at the same time. TBPN’s set looks like prime network TV: Mahogany desk, cinematic lighting, tailored suits, multiple camera angles. But the content also feels like eavesdropping on a group chat: Memes, live tweets, sarcastic quips, and internet-native humor. Formal enough to feel trustworthy while casual enough to be accessible and fun. Unseriously serious.

5. Borrow laterally, not recursively. When you steal from novel influences, you become original. “My biggest critique of tech is that there’s a really big world, and you can go and borrow from anywhere.” TBPN doesn’t study tech media. They draw from Formula One sponsorships, fashion house campaigns, SportsCenter graphics, and TV newsrooms. When your competitors are iterating on podcast aesthetics and you’re remixing television, you’re playing a totally different game.

6. Your niche is enough. TBPN makes content for about two hundred thousand people: founders, investors, operators, technologists. They could broaden, soften the insider references, explain the basics, but they refuse. Deliberate narrowness creates signal density. The content will feel like it’s specifically made for your corner of the internet, not everyone else.

7. The show is the end, not the means. Many creators use content as a Trojan horse for something else—build the audience, launch the fund, start the SaaS company, sell consumables. John and Jordi reject this premise entirely. The show is the point. Advertising lets them have an awesome business and never charge viewers a dime. No diversification, no hedging, no distractions. As David Senra says, aim to get to your last business quickly.

8. Start with obsession, not opportunity. TBPN didn’t start with a deck or a business model. It started because two people couldn’t stop talking about the business of technology. The show is a natural extension of their offline friendship, and that’s why they can podcast for 3 hours a day and still want to hang out after. Good luck competing with that.

9. Platform-Native or Bust. TBPN fully embraced what making a show built for X might mean. This meant less competition, an audience desperate for more, and content that feels like the embodiment of the platform itself. The water cooler, animated. They’re treating Substack, YouTube, and short form the same way.

10. A brand is what you feel. Jordi: “A great brand is not a logo. A great brand is not a website. A great brand is the culmination of what you make a group of people feel over time. It’s educating the audience. It’s making people feel something over and over and over until you stick in their mind. It’s the average of everything that you’ve made an individual person feel.”

11. Humor is a way in. Jokes let you do low-status things without apologizing. TBPN started as two guys reading printed out niche-vial tweets. They made a trailer about being reach and got their audience celebrating every ad read. “When you start with humor, you can broaden the aperture to get really weird.” Before too long, John and Jordi had Mark Zuckerberg ringing the gong after taking over Meta’s annual event.

12. Complementary obsessions multiply. John and Jordi are a venn diagram: John ran a YouTube channel before and obsesses over the details of production. Jordi built a digital ad business for years and and drives the commercial side. John loves tech and enjoys business, and Jordi is the inverse. They cultivated the right ingredients individually and are reaping the rewards together: “I feel like we started working on TBPN a decade ago.”

Description

John Coogan & Jordi Hays are the hosts of TBPN (X, YouTube, Spotify, Substack), a daily live show covering the technology business. TBPN was launched only about a year ago, but has become a mainstay in tech culture and a center of gravity forterminally online technologists.

John was previously an EIR at Founders Fund and tech YouTuber. He co-founded Lucy Nicotine and Soylent. Jordi has co-founded and invested in many business including Party Round/Capital and Branded Native, a podcast and youtube ad network.

We cover the origins of TBPN, or the Technology Business Programming Network, from its beginnings as “Technology Brothers” to the interplay between John’s love for technology and Jordi’s for business. They share how they’ve built a media business in an era of infinite competition by leaning into high volume and constant iteration, all while treating media as the “main thing.”

We discuss brand building and innovating on form by borrowing ideas from outside the tech industry—from Formula One and SportsCenter to Hollywood films—to avoid tech’s tendency toward circular references. We also talk about their focus on X/Twitter and a niche, highly informed audience, rather than trying to go too wide. We also chat about what makes their partnership work and how they take the work incredibly seriously while not taking themselves seriously at all.

Timestamps

• 00:00: Opening Highlights

• 03:18: Intro & Background

• 06:08: Technology vs. Business and the Strategy behind TBPN

• 12:08: Building a Media Business when Distribution is not Scarce

• 22:26: Being Entrepreneurs and Talent

• 30:33: Avoiding Audience Capture

• 35:57: Why Advertising is a Good Model

• 44:04: Technology’s Circular References and Borrowing Ideas from New Places

• 53:20: Narrow vs. Wide Appeal

• 59:44: X (Twitter)-First Content and Other Platforms

• 1:14:35: Making Content People Want to Share and Taking Yourself Seriously and Unseriously

• 1:20:28: Valuing Brand

• 1:30:10: Balancing Focus and Iteration

• 1:35:25: Endurance & Evolution

• 1:40:34: A Day in the Life of TBPN & Learning to be Newscasters

• 1:49:59: Jordi & John as a duo, Will Manidis, and the beginnings of TBPN

• 2:02:57: Grab Bag: Bias to Action, 15 Minute Interviews, Not Journalism, Talent, and Domination of Spirit

All links and full transcript available at dialectic.fm/tbpn

You can imagine, then, how much of a full-circle moment for me it was to, almost ten years later, sit down with him and talk about life, investing, risk, writing, and the chapters life holds for us.

Chris is known for having what is probably the best performing venture fund of all time (214x for Lowercase I, which included first checks in Twitter, Uber, and Instagram) or for being provocative on Twitter, Shark Tank, and anywhere else he had the chance to speak.

He’s quieter in public forums these days, and sadly doesn’t tweet anymore, which made this all the more special. The thing I most admire about Chris is not the returns or the strong opinions, though. Its his relentless pursuit toward being true to himself and playing by his own rules. He’s walked away from dream jobs multiple times and keeps score only by what matters to him and small group of people he loves. I wrote about that on this newsletter once before in context of one of my favorite books that Chris recommended, and I’m excited to share a conversation that captures the same essence today.

I hope you enjoy it.

Dialectic Ep. 32: Chris Sacca - Drifting Back to Real

Dialectic Episode 32: Chris Sacca - Drifting Back to Real - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

16 pieces of advice from Chris on stacking the deck in your favor, creating power with words, and remembering who you are and want to become:

1. Only play rigged games. Chris avoids public markets because he’s just a spectator there. In venture investing, he can actually shift the odds. His famous line: it may be lucky, but it’s not an accident.

2. Go long on the weirdos. When his team overlooked a founder trying to make it rain (literally) Chris sent them back immediately: “If we invest in normal people, all this money is going to go away.” Asymmetry lies on the frontier of crazy.

3. Words are the most democratic leverage. Growing up, Chris read his parents’ college textbooks. He realized words are free because you don’t need art supplies, canvases, or capital to get started with them. Language has tremendous leverage and is available to everyone regardless of credentials or status.

4. Stories are how you move people. Chris’s family would sit around the table with friends and swap stories. His Dad taught him how to set up a story, how to prime the punchline without giving it away, and the joy of a hearty laugh from the whole table. His father-in-law’s line reverberates: “every single person has a story; give them a chance to tell it.” We are all hungry for narrative, for tales, for things to believe in.

5. Find someone who calls your bullshit. The most enduring operators surround themselves with truth-tellers—people who’ll call them out. For Chris, that’s his wife, Crystal: “You’re so full of shit“ / “That’s a tired idea” / “Are you f*ing serious right now?” Every leader who goes off the rails invariably has no one around them to push back. Find your Crystal. Be someone’s Crystal.

6. Logic is no match for great metaphor. Chris once watched a federal prosecutor pull out a combination lock to (incorrectly) explain hacking to a judge. The courtroom shifted, all washed away by the right metaphor. “Good metaphor, simile, and analogy are the true weapons of mass destruction.” Once a metaphor lands in someone’s mind, you can’t dislodge it with facts, hard numbers, or cold evidence.

7. Change is driven by incentives, not guilt. “My job is to give you a choice you choose out of pure self-interest.” The soup-throwers won’t fix the climate issue by guilt-tripping people. A better, cheaper, easier product will. People will save the world for profit long before they’ll do it for virtue.

8. Strong negative reactions can be a sign. Anytime you have a disproportionately visceral rejection of something, you should train yourself to lean in. The things that make you recoil often point exactly where you need to go, which is true both in life and in investing.

9. You can become world-class in a year. Larry and Sergey to Chris in 2003: “With the tools available to us today, there is nothing keeping you from being one of the 50 most knowledgeable people in the world on a subject within a year.” Read everything. Listen to everything. Then visit everyone who wrote those things and ask to see their work. No one does this. But you can if you care enough.

10. Risk has a different profile when you’re a live player. “Most risk is mis-priced because it’s rooted in fear, imposter syndrome, and underpricing your ability to impact outcomes.” The “crazy” bets aren’t so foolish if you can impact what happens. Conviction comes from knowing how you can affect the game.

11. Don’t bubble wrap your kid’s life. Chris’s thesis on why kids today struggle: “Good decision-making comes from bad decision-making and feeling the consequences of, ‘whoops, that was stupid.’” He believes we’re raising a generation allergic to mistakes: helicopter parents, screen-addicted childhoods, kids suspended for playground scraps. We overclock for physical safety and underclock for online safety. The result? We’ve robbed kids of the chance to screw up, forgetting that competence requires contact with consequences.

12. Beware the tyranny of relevant experience*.* The most successful people Chris works with have no domain expertise in investing, and that once included him. When an early LP convinced him to launch a venture fund, Chris protested, but Hans Swildens brushed it off. The hard part, he said, wasn’t managing money. It was picking great companies and making them better.

13. Singular focus is the rarest luxury. Most days, the world scatters us into a hundred different directions. On his cross-country bike ride, Chris woke up with just one goal: get to the next town. “I knew my exact purpose. The only thing I had to do was get to the other side.” His mantra—Tonight, I will be in my bed—became a finish line he had to earn, day after day, even when his legs were spent and his body craved nothing but rest. How often do we get to want just one thing—and feel what it’s like to earn it?

14. Burn the boats. Chris searched for the common thread among his most successful founders. Immigrant kids? They have the hunger and the hustle. Single-parent families? Early responsibility, unbreakable resilience. Many hustled young, but not all. The only trait every one shared was that success was inevitable. “Not only did they not prepare for the downside case, it just wasn’t one of the options in the math. Zero was never a consideration or a possibility.”

15. Play by your own scorecard. Chris probably left Google with $100 million on the table. He walked away from Lowercase when everyone wanted in. “The only person who knows your scorecard is you.”

16. Drift back to the real you. “My biggest goal for myself is to drift back to the real me. The me that was covered in layers of pretense or inauthenticity or striving.” At every mountaintop, Chris has found a way to shed his skin and exit the local maximum on the way to becoming more true to himself.

Description

Chris Sacca is an investor and founder of Lowercarbon Capital and Lowercase Capital.

Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown School of Foreign Service; turned his student loans in $12M in the tech bubble of 2000 before losing it all and then some; and broke into Silicon Valley before eventually landing at Google, where he won the founders award. Then Chris started angel investing, which led to his first venture fund, Lowercase I. Lowercase I is one of if not the best performing VC funds ever, by multiple, at 214x, and included Twitter, Uber, Instagram, and more.

Toward the end of Lowercase, I had the pleasure of working with Chris. Around that time, he was also a Guest Shark on Shark Tank. Chris was heavily involved in both Obama campaigns and was a large supporter of Hillary Clinton in 2016. When Trump won, he wound down new investing at Lowercase and “hung up his spurs” to focus on political and democracy related efforts. Then, in 2018, Chris started Lowercarbon Capital to invest in “un-f*cking the planet”: carbon removal, climate science, cooling the planet, and eventually nuclear fusion.

We talked about writing and storytelling, keeping people around who keep you honest, having a good taste in “weird,” playing rigged games, taking the right kind of risks, and how even billionaires have imposter syndrome. We also get into how great founders embody inevitability, what makes the people at Lowercarbon special, how much Chris thinks about AI, and the many chapters of Chris’s life, including whatever might be next.

Authenticity is a moving target for all of us, but one of the things I most admire about Chris is his ability and desire to shamelessly play his own game.

Timestamps

• (0:00): Open: The Common Thread Amongst The Best Founders

• (1:26): Intro

• (3:49): Coast to Coast

• (12:36): Leaning into Weird & Investing in Fusion

• (24:42): Having People Who Keep You in Check

• (32:07): The Power of Language and Stories

• (1:03:10): Investing, Risk, and Wild Confidence

• (1:28:03): Imposter Syndrome and Making Companies Better

• (1:38:10): Lowercarbon’s Team and Culture

• (1:57:54): Chris’s Life Chapters, AI, and Creative Outlets

• (2:22:11): Drifting Back Towards Real

All linked references and transcript

Please enjoy, including a list of my favorite lessons and ideas from the conversation.

Dialectic Episode 31: Gabe Whaley: Playing the Crowd and Outlasting the Hype - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

14 Lessons from Gabe Whaley on Going Viral, Reinvention, and the long game of making MSCHF

1. The black box can be a storytelling tool. “We’re not necessarily trying to hide anything; it’s because the mystery lends more to the imagination than reality ever could.”

2. People don’t share other’s content, they share their reaction to it. The early internet was about amplification, but the incentives have flipped. “People don’t share things because they’re interesting anymore; they share things to fuel their vanity. Instead of me sharing a link to something that’s cool, I’ll share a video of me talking about a link that’s cool.”

3. You’ve got to believe in something. “That’s not a thing that’s talked about so much anymore because a lot of it is audience-driven. What are you making for other people? Have you verified it with data? Have you done user interviews? To really make art, don’t let the crowd drag your vision down to the lowest mean. Take the chance. It could be shit, but it could be great. And that is always worth it.”

4. Depth is anti-fragile. When you’re hooked on going viral, the only move is to go bigger, louder, and produce more content to feed the beast. The antidote is to go smaller and deeper. True significance comes from holding a “relationship with a small audience for as long as possible—and then a little longer. Then maybe you have a chance of something with significant staying power.”

5. Novelty comes from cross-pollination. Take an idea from one industry, rip it from its native context, and drop it into another where it doesn’t belong. A good remix often starts with taking a culturally ready-made–something already loaded with meaning—twisting and re-launching until the familiar looks alien. The intersection of two worlds that never talk is the easiest place to make something feel fresh.

6. Creativity can be engineered by hunting for inputs. MSCHF schedules brainstorms and builds their own curriculum of reference material—collecting stray ideas, outsider references, and unrelated topics. Even daily routines become creative assets: public spaces, overheard conversations, or the chaos of a commute are all sources of raw material.

7. Play the crowd. MSCHF’s best work isn’t done when they release it. True spectacle happens when the audience takes an idea and runs with it: “They have consumed the idea, and they have become the idea.” This is how your creations can become truly meaningful, but in that process, are no longer yours.

8. Avoid the tyranny of the now. “We’re all stuck looking at our own faces now. That makes it really hard to see what’s next.  Or even to care about what’s next. That is a golden opportunity because everyone is stuck looking two inches ahead of them. A few people will have the discipline to look 10 years away from now.”

9. Celebrate creation, not response. After you go viral enough times, you will feel nothing. Even the most addictive drugs wear off. MSCHF celebrates before their drops, not after they’re successful.

10. Creating the conditions for others to create is its own kind of art. For Gabe, that means, assembling the right people, engineering ideal conditions, and absorbing the operational hiccups so the MSCHF team can be free to create.

11. Subvert the real. The best material is often real: banks, businesses, marketplaces, legal frameworks. A prank embedded in reality hits harder than any narrative arc because it can’t be dismissed, and more importantly, because it forces a response.

12. Use virality as a Trojan horse for substance. Gabe and the team aim for ideas that “slap in one sentence and slap harder in three.” Let simply appeal or provocation smuggle your idea into enough hands that it can mutate, grow, or crash on its own terms.

13. No black box is interesting forever. MSCHF has begun to peel back the curtain as it evolves. “The doors are open. That puts us in a place where we have no choice but to let the work speak for itself, because the black box is not going to do us any favors anymore. It’s putting our money where our mouth is. No more tricks. No more games. The work will have to be so good. And we’ll die on that sword. If it’s not good, that’s not good.”

14. The physical world awaits. As the internet subsumes more and more of our attention, the real world becomes an increasingly special canvas. A room that holds three thousand people experiencing something deeply is more valuable than millions of scrolls and likes and reactions.

Description

Gabe Whaley is co-founder and CEO of MSCHF (Instagram, Wikipedia), the art collective, fashion and footwear brand, startup, and fill-in-the-blank, famous for its viral products and cultural interventions.

A few notable works include Jesus Shoes (Nike Air Max filled with holy water), Severed Spots (a “decentralized” Damien Hirst print), Museum of Forgeries (One original Warhol and 999 perfect forgeries), and of course the Big Red Boot. This conversation was heavily influenced by MSCHF’s recently released Made by MSCHF, a “textbook,” through which the team peels back the curtain and shows us inside the black box that has produced more viral hits than one can count.

Gabe had a sheltered childhood and went to two years of army academy at West Point before eventually finding his way to New York City to intern at Buzzfeed around 2014. In his spare time, he started releasing weird internet projects under the name “Miscellaneous Mischief.” After tasting virality a few times, he started collaborating with likeminded creatives and eventually formalized MSCHF in 2019.

I’ve known Gabe for many years (and even did a small collaboration with him from my seat at 100 Thieves). We sat down to reflect on the last 15 years and the arc of MSCHF, what made it special, and where one goes next when virality makes you feel nothing and the internet feels mature.

The conversation includes MSCHF’s eye-of-the-beholder legibility, their obsession with value, the power of mystery, and how the product doesn’t culminate with release, but after the audience has made it their own (in MSCHF parlance, “playing the crowd”). We also discuss the creative process behind the hit factory, how acting as a label rather than individuals changes their relationship to the work, whether the cultural future is actually canceled, how the internet has changed, and how real world experiences offer something to the creator and the consumer that digital life simply can’t. We wrap-up by speed-running through many of MSCHF’s internal values, from “always punch up,” to “death is just as importance as birth,” to perhaps its defining frame: “nothing is sacred.”

I hope you are inspired toward play, originality, embracing discomfort, and having the courage to burn it all down and start anew.

Timestamps

• (0:00): Intro

• (2:21): Value and Legibility

• (13:24): Is the Future Canceled?

• (20:00): We Create as a Result of What We Believe In

• (26:11): What Makes a Good Remix

• (29:08): How MSCHF Relates to the Current Thing and Evolves What Game it Plays

• (38:31): Creating Something the Crowd Can Play

• (44:59): Emphasis on Craft and Objects Rather than Creating “Lifestyle”

• (47:27): Keeping Up in a World That Demands Constant Production

• (53:11): Resisting The Internet’s Scale and Lack of Friction

• (1:03:15): Accidental World Building, Process, Creative Inputs, and Focus

• (1:14:09): Creating as a Collective and Gabe’s Role in Enabling the Team

• (1:22:30): Trust, Shedding the Black Box, and Staying Original

• (1:30:35): Applied MSCHF – Doors are Open

• (1:34:21): Sarah Andelman, People Who are Still Excited, and Long Time Horizons

• (1:41:52): Buzzfeed

• (1:44:41): MSCHF Values

Full transcript and all linked references

Dialectic Ep. 30: David Senra -
The Clarity of Commitment

Dialectic Episode 30: David Senra - The Clarity of Commitment - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

16 Lessons from David on Effort, Obsession & Other Competitive Advantages for Building Your Life’s Work

1. Don’t be afraid to repeat the hits. Repetition is persuasive. At church, they don’t talk about Jesus one week and some other guy next time. Elon repeats the same thing so much that the executives in the meeting can mouth the words before he says it. Buffett has been saying the same things for 60 years.

2. The audience is new. Relatedly, Claude Hopkins’ iconic 127-year-old idea: “You’re not advertising to a standing army, you’re advertising to a moving parade.”  You think that every single person is paying attention to every single thing you’re doing. Nobody is. You’re the only person doing that.

3. Don’t underestimate “non-fiction marketing.” Simple descriptions of what you’ve made can be the most effective. James Dyson would write 200 words on a tag about how he made his vacuums special. Claude Hopkins was an ad copy legend with this idea. It can be especially true when you don’t think you’re doing anything special. Pull back the curtain and bring people into how something is made.

4. Study Your Favorite DJ’s Favorite. Most people study Steve Jobs and stop there. But the real insight comes from tracing the entire lineage, often over many decades. What about Edwin Land? When you find the original, you’re operating with the source code. Similarly: check the bibliography of the biography for hidden gems.

5. The best storytellers are the clearest thinkers. Clear thinking produces clear communication, which makes ideas easy to understand and spread. Reduce until clarity is what remains. And when you’re easy to understand, other people find it easy to help you.

6. The words don’t change, but you do. Re-read the best books. Re-visit films that moved you. Re-listen to impactful podcasts. We forget nearly everything and more importantly, we are someone new now, for whom the content has new wisdom.

7. There’s no test at the end of a book. That’s not the point. It’s about understanding. If you understand, then you might actually change your behavior.

8. Trust the ancient algorithms. People underestimate or under-prioritize their subconscious mind. It is much older than language. There is a kind of intelligence much wiser than you, and it takes the form of intuition.

9. It’s not for you, it’s for me. Make no mistake: Founders is an act of service for David. But that is only the exhaust of his maniacal obsession with finding the mentors he never had in the entrepreneurs of history. For many this is a joke; David’s most listened podcast is Founders.

10. Optionality doesn’t pair with greatness. Most of us can’t focus on anything for very long. Even when we do, there will only be more options as success compounds. Those who become the best in the world do not mistake the main thing.

11. Your life’s work picks you. Find something you won’t get bored of—especially the traditionally boring parts of it. David enjoys the biographies other people put down, not just the “best” ones. People maniacally obsessed with craft and service often end up wealthy, anyway.

12. Excellence is the capacity to take pain. Your ability to push through difficult & often boring things—reading dense books, enduring back-to-back failures—becomes a competitive advantage. If you apply considerably more effort over a longer period of time, by way of human nature, you will have less competition.

13. Quality trumps speed, always. No one’s going to remember if an episode is five days late, but they’ll remember if it’s great.

14. Get to your last business as quickly as possible. The longer you you compound, the deeper your specific knowledge. The returns to compounding (in money, in knowledge, and in life) are back-weighted. Rather than perpetually looking for the next opportunity, many of the greats got to their life’s work relatively early on.

15. Durability is a first-rate virtue. Charlie Munger’s big idea. We all talk about it, yet nearly everyone seeks growth at the expense of durability, especially in tech. Learn from history: The truly great people, products, and companies optimize for decades, not quarters.

16. Show your kids what it looks like to care about something. Your kids won’t remember your achievements as much as your engagement with work and life. When they see someone going through life genuinely obsessed with something—anything—they learn that level of intensity is possible. Maybe they too will seek to make something truly excellent that makes others’ lives better.

Description

David Senra (Website, X) is a podcaster and loves that title more than anyone. He hosts Founders, where he teaches the lessons of history’s greatest entrepreneurs by way of the biographies he reads of them. This week, he launched a second show, David Senra, where he talks to the greatest living entrepreneurs (often about the lessons from Founders).

The first episode with Spotify Founder & CEO Daniel Ek is available now, and the show is in partnership with Scicomm Media, the team behind Huberman Lab.

David is an enthusiast about four things: entrepreneurship, reading, history, and podcasts. His two shows are the articulation of those obsessions in a form of service for the rest of us. He is following Charlie Munger’s advice: “take a simple a idea and take it seriously.”

David is one of the most energizing people I’ve ever met and has greatly inspired my work. I’ve had several multi-hour conversations with him that left me buzzing afterward, and I’m pleased that this is no exception. We cover many of his favorite lessons and founders, his process, biographies, focus, fear, endurance, service, and legacy.

I hope you are inspired to commit yourself to something worth your days and years.

Special thanks to Josh Kale for producing this episode. Please check out his show Limitless on frontier technology and AI.

Timestamps

• (0:00) - Open

• (1:49) - Intro

• (3:02) - Podcasts are Energy Transmission

• (7:52) - People Buy Simple Stories

• (12:38) - Repetition Doesn’t Spoil the Prayer

• (16:11) - Trust in Brands and Products (and Podcasts)

• (19:40) - Continuous Improvement and Speaking to a Moving Parade

• (26:18) - Confidence and Simplicity

• (34:55) - What Makes a Great Biography and Biographer

• (42:17) - Humanity in Context: Why Biographies are So Practically Helpful

• (48:52) - Fear

• (54:32) - Self Reflection and Commitment

• (1:06:52) - Considering Stuff Beyond Podcasting

• (1:10:40) - Focus and Making Time for Relationships

• (1:14:00) - What Should David Delegate?

• (1:24:36) - Advice for 2017 David

• (1:28:21) - Storytelling and Clear Thinking

• (1:32:19) - Defying Rationality and Creating Magic with Obsessive Details

• (1:38:09) - Self-Deception and Understanding Who You Are

• (1:45:01) - Intution

• (1:48:34) - Being Easy to Interface With

• (1:52:26) - Biography Most Founders Would Benefit From: James Dyson’s Against the Odds

• (1:57:05) - Simplicity and Edit Before You Make

• (2:02:42) - Lesson for Tech People: Learn from History

• (2:06:14) - What David Hopes His Kids Say About Him

Referenced Links

There are many, many links, so please check out my site for all of them.

Billy is a writer and researcher who works with Ryan Holiday and Rick Rubin, and he moves at a different pace than the terminally-online, frantic, instant-gratification culture that dominates today. Spending time with him and circling a small set of timeless truths is remarkably grounding. I hope that comes through as you listen.

If you want to give the episode some love on twitter, it’s here!

I also included a couple of other recs below this week — on The Making of the Prince of Persia and a scene from Good Will Hunting that you need to rewatch.

Dialectic Ep. 29: Billy Oppenheimer -
Attuned to Clues

Dialectic Episode 29: Billy Oppenheimer - Attuned to Clues - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

18 Favorite Lessons from Billy on Process, Attention, and Becoming

1. The Work is the Win. Billy’s big idea. In another form, via the Bhagavad Gita: " you have the right to action, not the fruit of that action." Another: ****utterly dedicated and utterly detached. Jerry Seinfeld: “all art is disguising work” and find the struggle you’re comfortable with.

2. Creativity starts with clues. Rick Rubin’s creative process often begins not with genius inspiration, but by gradually collecting “clues.” Notice what catches your attention, collect them, and give them time to simmer, and see what happens.

3. Let inputs guide outputs. Similarly, Billy’s newsletter is just the public exhaust of his research work: “I identify and feel more like a reader and researcher. The writing is kind of like: “Here's some cool things I found. Does anyone else think they're cool?”

4. Be thoughtful with your future self. When highlighting, Billy leaves notes in the margins as affordances for his future self to easily have context on why it was memorable, rather than assuming he’ll remember. Niklas Luhmann calls this “making notes for an ignorant stranger.”

5. Time is the true filter. Billy: “Whenever someone says, ‘I was reading this morning about…’ I’m like—immediately—I’m out.” He deliberately leaves time between finishing a book and returning to review his highlights, and seeks out idle time to let ideas percolate and linger.

6. Reading is a divining rod for hidden interests. Joseph Campbell’s line fits Billy’s experience: a paragraph, name, or footnote grips his attention and a path appears that he hadn’t planned. You can't predetermine what will capture your attention. All you can do is follow the clues when they appear.

7. It’s okay to put a book down for now. Billy’s mindset is: I’m not quitting, “it’s just not for me right now.” Sometimes he’ll come back to it a year or two later, and he’ll be in a different headspace, connecting with it then, often due to personal growth or other reading.

8. Novelty can be overrated. There is more here, still. As painter Eugène Delacroix said, “What moves those of genius, what inspires their work, is not new ideas, but their obsession with the idea that what has already been said is still not enough.”

9. Be careful underestimating “little” ideas. One of Billy’s favorite ideas from Mike Nichols: “We don't know what things are. Big things often turn out to be little things, and little things don't walk around with a sign that says, 'This is a big thing.’”

10. Respect long arcs without comparing timelines. It’s easy to misread someone else’s decade-long competence as destiny or genius and your first-year incompetence as failure. The truth is slower and less theatrical: your talent forms with reps; judgment improves by tossing away what doesn’t hold up. When some performs what seems like magic, ask about their history of compounding.

11. A bad plan beats no plan. Even failed attempts return data, while analysis paralysis returns nothing. Run a modest plan, make contact with reality, and adjust accordingly. The information you receive from taking action is worth way more than hypothetical, perfect planning. He who hesitates is lost.

12. Get to boring. The fantasy version of any craft is a highlight reel. Adam Mastroianni’s "coffee-beans test" is a good litmus for whether you really want to do something. Say you want to open a beautiful cafe? What kind of coffee beans are you going to use? What POS system? This applies broadly too; Ben Gibbard, reflecting on his divorce, realized they never got to the boring parts before they got married.

13. Be great regardless. Harry Belafonte wanted to be an actor, but got stuck singing between scene changes instead of a “real” role. Instead of phoning it in, he "acted as a singer" and took it seriously. Jazz musicians from a local club happened to see his show, stayed after, and brought him to perform at their venue. Be great at whatever you're doing on the way to where you're trying to go for your own dignity, and maybe you’ll get lucky on the way.

14. The goal post never stops moving. Daniel Day-Lewis nailed this tension while describing his There Will Be Blood character: "You get there and, of course, the world is round. The horizon just keeps receding and receding." The people who've reached what everyone else chases still do the work because they know the satisfaction was never at the destination.

15. Avoid the catastrophe of success. Tennessee Williams called success "a catastrophe" because comfort removes the very resistance that made you sharp. You must love the process, otherwise, you’re just going through motions in a life drained of necessary friction, like “a sword cutting daisies."

16. Question your own folklore. Steve Jobs called arbitrary industry norms “folklore” that hold us back. Your personal methods can become a prison. The way you've always done things almost surely contain local maximums, and you most go down to go up.

17. Work with people whose lives you want yours to resemble. Ryan Holiday looked at people 10-15 years ahead in Hollywood and didn't want their daily chaos. He chose Robert Greene's life instead - reading, writing, and pursuing his specific curiosities. Billy has done the same.

18. You can choose who you’d like to become. David Whyte says you’re harvesting your identity in how you spend the hours of the day. You're not born to be a director, writer, or anything else. Billy's days are now filled with reading and writing, the very things that once felt like his weaknesses. Who are you becoming?

Description

Billy Oppenheimer (Website, X) is a researcher and writer who works closely with Ryan Holiday and Rick Rubin, and publishes the “Six at 6” newsletter. Billy is also working on his first book, The Work is the Win.

We kick off by discussing one of my favorite new ideas: "looking for clues," a process and philosophy for creativity that Billy learned from Rick Rubin. He shares the story Rick told him when he learned and adopted this language, which is so representative of how Billy (and I!) research in our work.

From there, we talk about Billy's robust research process and how he has created an external brain of the ideas and patterns that inspire him rather than relying on memory. We also talk about the importance of time as a filter and a series of maxims that underpin his work and creativity. We discuss the importance of inputs over outputs and his big idea and book title, "The Work is the Win," as well many related ideas on success, complacency, compounding, standards, initiative, local maximums, and more. We finish with some lessons from Billy's favorite people.

This conversation is a field guide for making things, pushing through the messiness of progress, and attuning yourself to the richness of the world that often takes the shape of clues.

Full transcript and all links: https://dialectic.fm/billy-oppenheimer

Timestamps

• 0:00 - Intro

• 1:20 - Looking for Clues with Rick Rubin

• 17:42 - Billy's Own Clue-Seeking

• 24:26 - Balancing Listening to the Market and Finding Unique Influences

• 31:17 - Memory, Notecards, and Billy's External Brain

• 37:13 - Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self

• 45:09 - Lingering and Time as a Filter

• 52:51 - Billy's Book and Big Idea: "The Work is the Win"

• 1:00:07 - Be Great Regardless

• 1:04:31 - Following Up Even When Your Abilities and Standards Don't Match

• 1:10:10 - Fending Off the Wolf at the Door (The Comfort of Success)

• 1:15:55 - Unfolding and Planting Seeds

• 1:18:17 - Taking Initiative and Opening Doors: "He Who Hesitates is Lost"

• 1:24:58 - Stupid Bravery and Getting Past the Sewage

• 1:30:16 - Local Maximums and Resisting Personal "Folklore"

• 1:36:14 - Some of Billy's Favorites: Ryan Holiday, Rick Rubin, Steve Jobs, John Mayer, Greta Gerwig, Jerry Seinfeld, Ralph Waldo Emerson

• 1:56:45 - Side Quests

• 2:02:26 - "I Know What We Do Here" and Creative Environments

• 2:05:28 - Bringing Familiar and Unfamiliar Together

• 2:09:26 - Mastery and Compounding

• 2:12:44 - The Real Life of Appearances

• 2:15:43 - "Ton-goo-ey" and The Gifts We Give Ourselves

The Making of The Prince of Persia: Journals 1985-1993 - Jordan Mechner

I just finished 'The Making of the Prince of Persia' by Jordan Mechner, published by Stripe Press.

I wrote some thoughts about why I loved it, and why it's such a rare, raw look into the creative journey:

It’s great to read about the nitty gritty of creating something new as it is happening, rather than with the revisionist narrativization that so often comes with memoirs and biographies. Jordan Mechner’s journals are full of personality and life, and yet often substantive on the process too. It’s also a case for the wonders of consistent journaling. Just writing for yourself, having a conversation forward and backward in time, and maybe one day for the world too.

I couldn’t help but laugh at the constant neuroses and yearning to be on another path, whether it be game development and screenwriting or San Francisco and New York and Paris or sequels and new games. It’s a lovely intimate look at the messy progress of becoming, and how sometimes we see things with remarkable clarity, and other times with hilarious hyperbole (to the positive or negative).

Toward the end, I appreciated Jordan’s realization that he has rarely if ever regretted his mistakes of commission (taking too much risk), but has plenty of regrets about his mistakes of omission (being too passive). Jordan's reflection rhymes with what Steve Jobs ends his Palo Alto high school speech in 'Make Something Wonderful' with:

"Now, as you live your arc across the sky, you want to have as few regrets as possible. Remember, regrets are different from mistakes. Mistakes are those things that you did and wish you could do over again. In some you were a fool (usually concerning women). In others you were scared. In others you hurt someone else. Some mistakes are deep, others not. But if your intent was pure, they are almost always enriching in some way. So mistakes are things that you did and wish you could do over again.

Regrets are most often things you didn’t do, and wish you did. I still regret not kissing Nancy Kinniman in high school. Who knows what might have happened? Maybe she regrets it too …"

There’s a funny line toward the end where Jordan almost literally writes, “you can just do things.”

This book is, of course, about the long and winding road of doing just that: creating something from nothing—not because you were given explicit permission or because you were confident you could pull it off (although Jordan is often remarkably sure of Prince’s inevitable success)—but because every person has inside them a bottomless well, waiting to be put to page or code or film.

This is a book that peels back the curtain on the magic and says, why not you, too?

Good Will Hunting (1997)’s Park Bench Scene

I recently rewatched Good Will Hunting after told me he memorized his favorite scene that happens on the park bench. I love the film but I typically think of "Them apples" or "it's not your fault," or even the ending when I think about the best parts. David is right though. The bench scene is the one:

Sean (Williams): Thought about what you said to me the other day, about my painting. Stayed up half the night thinking about it. Something occurred to me… fell into a deep peaceful sleep, and haven’t thought about you since. Do you know what occurred to me?

Will (Damon): No.

Sean: You’re just a kid. You don’t have the faintest idea what you’re talkin’ about.

Will: Why thank you.

Sean: It’s all right. You’ve never been out of Boston.

Will: Nope.

Sean: So if I asked you about art, you’d probably give me the skinny on every art book ever written.

Michelangelo, you know a lot about him: Life’s work, political aspirations, him and the pope, sexual orientation, the whole works, right? But I’ll bet you can’t tell me what it smells like in the Sistine Chapel. You’ve never actually stood there and looked up at that beautiful ceiling; seen that.

If I ask you about women, you’d probably give me a syllabus about your personal favorites. You may have even been laid a few times. But you can’t tell me what it feels like to wake up next to a woman and feel truly happy.

You’re a tough kid. And I’d ask you about war, you’d probably throw Shakespeare at me, right, “once more unto the breach dear friends.” But you’ve never been near one. You’ve never held your best friend’s head in your lap, watch him gasp his last breath looking to you for help.

I’d ask you about love, you’d probably quote me a sonnet. But you’ve never looked at a woman and been totally vulnerable. Known someone that could level you with her eyes, feeling like God put an angel on earth just for you. Who could rescue you from the depths of hell.

And you wouldn’t know what it’s like to be her angel, to have that love for her, be there forever, through anything, through cancer. And you wouldn’t know about sleeping sitting up in the hospital room for two months, holding her hand, because the doctors could see in your eyes, that the terms “visiting hours” don’t apply to you. You don’t know about real loss, ’cause it only occurs when you’ve loved something more than you love yourself. And I doubt you’ve ever dared to love anybody that much.

And I look at you… I don’t see an intelligent, confident man… I see a cocky, scared shitless kid. But you’re a genius Will. No one denies that. No one could possibly understand the depths of you. But you presume to know everything about me because you saw a painting of mine, and you ripped my fucking life apart.

You’re an orphan right?

[Will nods]

Sean: You think I know the first thing about how hard your life has been, how you feel, who you are, because I read Oliver Twist? Does that encapsulate you?

Personally… I don’t give a shit about all that, because you know what, I can’t learn anything from you, I can’t read in some fuckin’ book. Unless you want to talk about you, who you are. Then I’m fascinated. I’m in.

But you don’t want to do that do you sport? You’re terrified of what you might say. Your move, chief.

Max is sharp and quick with words, but also deeply thoughtful and big hearted. I compiled 17 of my favorite lessons below, along with all the episode details. Transcript here.

Dialectic Ep. 28: Maxwell Meyer -
Starships & Road Trips

17 Lessons from the Conversation with Max

1. America’s lodestar is the Declaration of Independence. The founding myth (all men are created equal…) it represents is unique in history, and upstream of everything else.

2. Risk tolerance is an American advantage. Silicon Valley lets people fail hard and come back again, and that spirit is worth defending.

3. The pendulum swings. Alleged one-way trends (political cycles, birth rates, concentration of power, etc) turn out not to be true as most things tend to be cyclical. We, like many who came before, can be prisoners of the moment.

4. Be careful with cliché. Clichés are the lowest hanging fruit when telling stories. The modern media loves them, but describing things as they are is much more important.

5. Markets make us better. The number one rule of capitalism is: you can’t kill your counterparty. This forces you to negotiate instead.

6. We need markets most for basic needs. Many tend to invert this, thinking: capitalism is fine for luxury sports cars, but we need to regulate grocery prices.

7. Good writing is fundamentally good description. Good writing paired with a good reader is two people thinking, even though they've never met one another.

8. Americans are movers. Everyone in America left somewhere for somewhere else within the memory of 10-20 generations.

9. You can't claim to love America if you hate half of the country. Both sides need a lot of humility here.

10. Progress requires dialectic (😏). You need to go back and forth between ideas to move forward, and most important is taking the other side’s premises seriously.

11. Progress is fragile. Growth and abundance, when taken for granted, can lead to regression. Strong times create weak men…

12. It’s easy to overestimate individual leverage. Elon spent millions on a Wisconsin election to no avail. The FBI director may in fact be more powerful than Sam Altman.

13. When being optimistic, be specific. Focusing on the things that are already happening is good way to make people optimistic about the future, rather than promising things that are difficult to falsify, concretize, or are abstract.

14. Pursuing quality leads to universal luxuries. Quality goods make everyone richer because they're made to last. In a sense, they turn everyone into an aristocrat.

15. Remember the back half of the brain. There's a constant push and pull between the rational and irrational parts of your brain. Don’t forget the quieter, “irrational” side. It is wise.

16. Don’t forget the places between places. The most underreported American story is the quiet prosperity of small, uncelebrated American towns.

17. American beauty, big and small. America is great because of our wild ambitions — rockets and markets and science — and because of the huge, little lives that everyday people live.

Description

Maxwell Meyer (X, Newsletter) is the founder and editor of Arena Magazine, an "American Propaganda" print and digital publication focused on technology, capitalism, and civilizational progress. Max also works with Joe Lonsdale at 8VC and is the proprietor of his Iowan farm, Henry Hills. He was previously the editor of the Stanford Review.

Our conversation is about ideas Max is most interested in across storytelling and media, American values, technology and progress, capitalism, writing and craft, and deep love for his country.

We start with critique, the media's tendency toward cliché, and defending the new while building trust with readers. Then we talk about American ideology: its radical founding myth, collective enterprise, and a nation of movers. Max makes a case that national character ought to be lived and formed bottom-up, and repeatedly argues that cultural pendulum swings are as old as time and we need not overreact to the swings of the day. He describes tech's brief abandonment of the rest of America and talks through how we might export Silicon Valley's outcome-oriented culture to government and other industries. Max argues that the foundation of capitalism is simple: "you can't kill your counterparty." We of course discuss Arena, magazines, writing, editing, and his ambitions there too.

Above all else, Max makes the case for America, big and small: the beautiful, always-changing, rarely-agreeing, perpetually striving amalgamation of souls that stretch from sea to shining sea.

You can subscribe to Arena here: https://arenamag.com/subscribe

Full transcript and all links: https://dialectic.fm/maxwell-meyer

Timestamps

• 00:00: Intro

• 01:14: Elon, The Media, Cliché, American Collectivism, and Cultural Pendulum Swings

• 09:07: Media, Criticism, and Defending the New

• 17:49: American Ideology: The Declaration, Communal Enterprise, Americans as Movers

• 28:20: Patriotism

• 33:36: Learning from the Rest of the World

• 40:27: A Case for Progress

• 49:38: Tech's Separation from American Culture in the 2010s

• 58:44: Tech Accountability and Engaging Normal People on their Premises

• 1:15:23: Silicon Valley's Tiny Nations and Alex Karp's "The Technological Republic"

• 1:21:19: The Frontier and the Core: Exporting SV Engineering Culture to Government

• 1:28:46: Principled and Unpredictable Thinkers

• 1:34:06: The Case for Capitalism

• 1:43:07: Defending Critiques of Capitalism and Concerns of Concentration of Power

• 1:49:37: Arena, Good Writing and Editing, Magazines as a Medium, Durability, Influences

• 2:02:19: Big and Small America

• 2:06:16: Joe Lonsdale

• 2:06:50: Upholding Abundance

• 2:11:39: Cooking and Bringing People Together

• 2:12:38: The Back Half of the Brain

• 2:14:02: The Places Between Places

Links & References

• The Man-Made Miracle of SpaceX - Max Meyer

• Max Meyer Launched a Print Magazine in 2024. Here’s Why. (Ep. 245) - Infinite Loops Podcast with Jim O'Shaughnessy

• Man in the Arena Speech - Theodore Roosevelt 1910

• Flying Machines Which Do Not Fly - The New York Times | October 9, 1903

• Declaration of Independence: A Transcription

• Democracy in America - Alexis de Tocqueville

• Homestead Act (1862)

• William Jennings Bryan

• America against America - Wang Huning

• The Artificial Intelligence Revolution: Part 1 - Wait But Why

• How United Became an Airline - Wall Street Journal

• The Gentle Singularity - Sam Altman

• Playing With Guns (and Phones) - Nadia Asparouhova | Arena Magazine

• Jonathan Haidt on Adjusting to Smartphones and Social Media (Ep. 209) | Conversations with Tyler

• The Emerging Democratic Majority - John B. Judis

• A Techno-Republic, If You Can Keep It - Maxwell Meyer | The Republic

• The Tinkerings of Robert Noyce - Tom Wolfe | Esquire

• Brian Schimpf: Engineer at War - Maxwell Meyer | Arena Magazine

• To Save America, Restore Our Frontier - Joe Lonsdale

• Pace Layers - Stewart Brand

• Palantir’s Alex Karp Talks About War, AI and America’s Future - Maureen Dowd | The New York Times

• The Earthly Miracle of the Grocery Store - Maxwell Meyer | Arena Magazine

• A More Perfect Mediocracy - Leo Leibovitz | First Things

• Meditations On Moloch - Scott Alexander | Slate Star Codex

• This is Water - David Foster Wallace

• California Sublime | Love Letters to America

• The Magic Water of Hot Springs | Love Letters to America

• Welcome to the MAGA Hamptons! - Max Meyer | The Free Press

• Joe Lonsdale

• The Green Counter-Revolution - Max Meyer

• How To Kill A Country - Samantha Power | The Atlantic

• I Bought an Iowa Farm at Age 22 After my Brother Died

• Places Between Places | Love Letters to America

It’s also the first video episode I’ve actually produced (with some serious help from Josh). It’s set in Mackenzie’s beautiful New York apartment and I’m happy with how cozy the conversation feels.

Mackenzie’s ambition and care for America in big and small ways is an inspiration. See the substack-specific notes and highlights below, along with description and more. Full transcript available on my website.

Dialectic Ep. 27: Mackenzie Burnett - Accounting for America

Highlights & Notes from an episode on pragmatic idealism

• The American Dream is optimism that your children’s future will be better than yours. Optimism is the leading indicator of economic cycles.

• The American Dream also requires plurality because not everyone’s dream is to be a millionaire. Holding space for multiple futures makes a stronger society.

• The government isn’t all good or bad; rather, it’s a slow-moving ship steered by millions of people responding to incentives. Too much faith or too little faith in it misses the point.

• Climate change sits in the worst box of human sensitivity (for acting on): long-term, abstract, and thus difficult to prioritize.

• People only change their minds when they see tangible impacts, like melting Arctic ice, rising seas, and wrecked bases.

• Ideological climate policy backfires. Pragmatic, win-win solutions (like cheaper solar-powered alternatives) actually stick.

• Farming is America’s first entrepreneurship story.

• Farms are biological factories with multiple P&Ls. Managerial accounting—not vibes—tells you where the margin lives.

• Great tools let people engage with intellectual complexity instead of completely avoiding it.

• Average teams will use AI to ship fast but decelerate over time. The best teams will use AI to compound and accelerate over time.

• True independence is not just about money. It’s ownership of your time, work, and, in some cases, physical space/land.

• All roads lead to accounting. Without it, you’re guessing. With it, you reduce anxiety and promote long-term thinking.

• Founders aren't risk-tolerant—they're just better at de-risking potential failure points before they become full-blown problems.

• A CEO’s job is to make the intractable tractable by breaking down overwhelming problems until they can be solved by the team.

• Stay illegible until you're ready to be interpreted by the world and society at large.

• Making something, either creatively or building a business, is the ultimate manifestation of agency.

Description

Mackenzie Burnett (Website, X) is the co-founder and CEO of Ambrook, financial software for independent businesses starting with farms and ranches. We trace her arc from a policy-first upbringing (USDA household, Congressional internships, climate-security research at Stanford) to a building software for rural America.

We talk about why Mackenzie loves America and cares about agriculture, the challenges of aligning sustainability with business and government, and pragmatically building resilience. Mackenzie talks about the American Dream and why independent small businesses are the foundation of it in many ways.

Then we get into Ambrook’s product philosophy: why “all roads lead to accounting,” how multi-P&Ls and biological inventories make farms deceptively complex, and why understanding bookkeeping and move movement enables better decision making and understanding over the long run for big and small businesses.

We also talk through Mackenzie's broad ambition for Ambrook; her growth as a leader; brand, aesthetics, and environment; Ambrook's editorially independent research division, Offrange, and more. Mackenzie is one of the most quietly ambitious and focused people I've met, and yet under her impressive and serious exterior is a life and love for America and its people that is all heart.

Special thanks to Josh Kale for his help producing this episode.

Timestamps

• 00:01:11 Intro

• 00:02:51: The American Heartland

• 00:05:21: Agriculture, Policy, and Government

• 00:12:29: The Challenges with Prioritizing Climate Risk: "Long Term and Abstract"

• 00:18:04: Pragmatic Environmentalism and Resilience that Drives Business

• 00:21:49: The American Dream

• 00:25:52: The Importance of Independent Small Businesses

• 00:28:58: Entrepreneurship on the Frontier: America's First Entrepreneurs and Ambrook's First Customers -- Farmers

• 00:36:28: Biological Factories: Why Farms are Complex Businesses

• 00:40:41: Why Everything Goes Back to Accounting

• 00:44:30: Why Money Movement Matters

• 00:51:13: Ambrook as a Twenty-Year Container

• 00:57:27: The National Importance of Agriculture

• 01:00:49: The Features of Illegibility

• 01:04:49: Ambrook's Long Term Vision

• 01:10:17: Making the Intractable Tractable (And Doomscrolling Your Company's Slack)

• 01:14:42: De-Risking and Becoming Friends with Anxiety

• 01:17:26: Building Something That Takes on a Life of its Own

• 01:20:07: Ambrook's Culture in Three Words

• 01:21:26: Brand and Storytelling

• 01:26:11: AI Enabling the Middle Class

• 01:30:57: California History and J.G. Boswell

• 01:34:05: Niche Subjects and History and "The Land Where Lemons Grow"

• 01:36:46: Disney's Magic Band

• 01:39:15: Strange Math and Happiness and Sadness in Parallel

• 01:41:31: Aesthetics, Beauty, and Physical Design Systems

• 01:47:31: The Draw to Start Things

Links & References

• America, the Beautiful - Mackenzie Burnett

• The Founder's Letter: Mackenzie Burnett, Ambrook

• Disposable Cameras

• A “precariously unprepared” Pentagon? Climate security beliefs and decision-making in the U.S. military (Mackenzie's Thesis)

• The Land Where Lemons Grow - Helena Attlee

• Dubai Chocolate Made Pistachios Viral, But Are Small Farmers Winning? - Offrange

• sam altman: “honestly, i feel so bad about the advice i gave while running YC i’ve been thinking about deleting my entire blog”

• affinity - Ava

• Lunch with the FT: Novak Djokovic

• Ambrook Series A Announcement

• Offrange (Fka Ambrook Research)

• AI Could Actually Help Rebuild The Middle Class - David Autor

• The King of California - Mark Arax | Goodreads

• Tulare Lake

• Tweet on The Land Where Lemons Grow

• MagicBand

• Leaders in Tech

• Interact

• Jane Jacobs

• From plows to platforms: how Stripe is powering modern agriculture

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Also—Long have we waited: Dialectic has video. It’s far from perfect but it’s a start. You can expect some episodes to be in full visual res, although travel means not every one will be. Feedback is welcome.

Dialectic Ep. 26: Cyan Banister -
A Fool’s Dérive

Dialectic Episode 26: Cyan Banister - A Fool’s Derive - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

13 Lessons from the episode on a life of wonder:

1. Everyone wants their childhood back. “Like a flame to moths,” that's how Scott Banister, Cyan’s husband, describes people's attraction to Cyan. Cyan suspects people are drawn to her because she reminds them of something they’ve lost: their childlike wonder. At a young age, she decided never to give up her sense of wonder. So, while everyone else learned to separate "real life" from play, she refused that division. Wonder became her companion through childhood trauma, loneliness, investing in companies, meeting new people, and a recent illness.

2. Fear is the mind-killer. The more comfortable you become with death and change, the more freely you can experiment with life/living. Most people are imprisoned by fears that will never materialize, which prevents them from acting or truly living.

3. Every stranger is a portal. Cyan actively talks to everyone because she understands that human beings are a portal into your inner world. They’re like mirrors showing you something about yourself, and each interaction is a chance to discover hidden parts of yourself.

4. Everything is your fault (and that's wonderful). Not in a self-punishing way, but more like asking: What role did I have to contribute to this difficult situation I’ve found myself in? Once you see how you created the situation, you also discover the levers to change it.

5. Collect rare minds. Cyan maintains a mental space where she summons models of people she knows to workshop knotty problems. "What would X person do in this situation? How would Y person approach this problem?" Each collected mind becomes a permanent advisor in her toolbox to be called upon whenever she feels stuck.

6. Intentional drift > boredom. Cyan's mastered what the French call dérive, the act of intentional drifting. Rolling like a tumbleweed, wandering without a fixed destination but with complete presence. Following signs. That randomness combined with attention allows you to see incredible things. And if you’re truly tuned into what you see, it’s nigh-impossible to be bored.

7. But also make your bed. Despite hating routine "like an allergy," she makes her bed every morning after monks in Bhutan told her she needed consistency. She frames bed-making as setting an intention for your future self. Morning Cyan creates something evening Cyan will appreciate while setting an intention for the day. She thinks of it as a love letter to her future self.

8. Humans are mechanical 99% of the time. It’s scary to think that most human beings sleepwalk through life, operating on autopilot, and reacting automatically to stimuli. 99% of the time, we don't know what we're doing. But in those rare moments of consciousness, mindfulness, and presence—where we pay attention or make stuff happen—we just might have free will.

9. Observe your thoughts instead of fighting them. The mistake most people make in meditation is trying to quiet their minds. Better approach: observe your thoughts and ask, "Are these even my thoughts? Who is the 'I' that's thinking them?" This shift from controller to observer changes everything. When you say "I am happy," try reframing as "it is happy." Suddenly, you realize the difference between temporary emotional states and the awareness that comes from observing them.

10. It's nice to try another personality on. Cyan rigged a party where everyone got "magic glasses" with roles written on them, but she made sure each person got the exact opposite of their natural personality. What happened? People leaned in. A people-pleaser cosplayed as a critic, and a grown man acted like he was a five-year-old and demanded bowls of sugar. Give people space to step outside their default programming, and you'll see how much of what we call "personality" is just the most familiar mask we've learned to wear.

11. You can make a profound impact on people in small, silly ways. Cyan thinks you should never throw an event if it doesn’t change people and give them a memory that will last for the rest of their lives. A high bar for sure, but it’s one Cyan swears by. When you become a prankster for good, you can jolt people out of their defaults and help them see themselves and the world in new ways.

12. The age of the artisan is coming. In a world of AI abundance, human creativity becomes scarce and valuable. Hand-made, human-touched work will be like "organic" food—premium because it carries the irreplaceable, imperfect signature of humanity.

13. "It just doesn't matter.” Bill Murray's phrase, from the movie Meatballs, isn't a call to Nihilism. Instead, Cyan interprets it as a call to radical prioritization. Put differently: Let go of what doesn't serve you so you can hold on to what does.

Description:

Cyan Banister (Website, X, Substack) is an investor, artist, and co-founder and General Partner of Long Journey Ventures. Previously, Cyan spent four years at Founders Fund and has a legendary angel investing track record alongside her husband, Scott, including early rounds in SpaceX, Uber, and DeepMind.

Cyan is as original as they come: she grew up on a Navajo reservation and was homeless by 15, with a series of unlikely serendipitous moments combined with optimism, agency, and love of capitalism taking her to a very different life than the one she grew up with. I focused this conversation not on Cyan's work, but her unique approach to living.

We begin with Cyan’s “church”: a weekly visit to see Bobby McFerrin and co. do live, jazz acapella in Berkeley, CA. We discuss how this space ties to presence, openness, and play, and then talk about the tension between novelty and consistency as she continues on her own path toward self-love and mindfulness. She also tells me about her radical approach to accountability and the empowering results of assuming that everything is her fault.

One of Cyan's favorite words is the French dérive, or an intentional drift, and it embodies her approach to the world. She moves with childlike wonder, seeking to see things and people from new perspectives and challenging others to react beyond their default settings. She daydreams about the outcomes she wants and has remarkable conviction and faith even when others do not believe her.

We wrap with a grab bag representative of Cyan's diverse interests, from filmmaking and performance art to the US Constitution to Bill Murray. Cyan manages to combine randomness and intentionality, naiveté and sober-minded awareness, humility and conviction. I hope you are are as inspired as I am to live more playfully, seriously, and courageously.

Full transcript.

Timestamps

• 0:01:23: Intro

• 0:03:45: Cyan's "Church"

• 0:16:21: Stillness, Mindfulness, and Introspection

• 0:28:47: Learning to See in Original Ways

• 0:39:38: People: When the "Light is On," "Collecting Minds," and Conjuring Friends

• 0:46:55: Cultivating Childlike Joy and Refusing to be a Victim

• 0:52:30: Radical Accountability

• 0:56:28: Randomness, Faith, and Experimentation

• 1:06:22: Conviction and Peter Thiel

• 1:12:54: Returning to Seed Investing and Long Journey Ventures

• 1:18:23: Thoughts on Art

• 1:23:42: Performance Art

• 1:26:37: Cyan's Creative Projects

• 1:32:51: Boredom

• 1:36:06: Living Around Elderly People

• 1:42:14: Pete Buttigieg

• 1:45:57: Being a Role Model

• 1:48:26: Young People's Future

• 1:52:46: Scott Banister and Lessons for Her Kids

• 1:55:35: "It Just Doesn't Matter" And Who Pulls the Strings

Key Links

• Cyan - by Kevin Gee and Dan Scott - Cloud Valley

• Cyan Banister — From Homeless and Broke to Top Angel Investor - Tim Ferriss

• Investing for a Higher Purpose - Invest like the Best

• Bobby McFerrin

• University of Texas at Austin 2014 Commencement Address - Admiral William H. McRaven

• Example of Motion and Bobby's performance

• The Magic Glasses - Frank Harris

• My Life and Loves - Frank Harris

• The cart path with Lawrence Krauss - Cyan Banister

• Lee Jacobs

• The Constitution of the United States: A Transcription

• The Song of the Lark - The Art Institute of Chicago

• BILL MURRAY TALKS ABOUT THE PAINTING THAT SAVED HIS LIFE

• The Diamond Age: Or, a Young Lady's Illustrated Primer - Neal Stephenson

• It Just Doesn't Matter! - Meatballs (1979)

• ‎The Razor's Edge (1984)

• Bill Murray gives a surprising and meaningful answer you might not expect. (Charlie Rose)