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 entrepreneurial 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.

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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. My “What are You Building This Year feature with Notion on Instagram.

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.

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Dialectic is presented by <...

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.

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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.

Ti...

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.

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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 Agil...

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.

Transcript and all links available at https://dialectic.fm/tbpn

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

Dialectic with Jackson Dahl is available on all podcast platforms.⁠

Join the ⁠telegram channel for Dialectic⁠⁠<...

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
• (1:20): Intro
• (3:42): Coast to Coast
• (12:29): Leaning into Weird & Investing in Fusion
• (24:35): Having People Who Keep You in Check
• (32:00): The Power of Language and Stories
• (1:03:03): Investing, Risk, and Wild Confidence
• (1:27:57): Imposter Syndrome and Making Companies Better
• (1:38:03): Lowercarbon's Team and Culture
• (1:57:47): Chris's Life Chapters, AI, and Creative Outlets
• (2:22:04): Drifting Back Towards Real

All links and transcript available at https://dialectic.fm/chris-sacca

Dialectic with Jackson Dahl is available on all podcast platforms.
Join the ⁠telegram channel for Dialectic⁠
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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.

Full transcript and all linked references: https://dialectic.fm/gabe-whaley

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,...

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.

Transcript and extensive linked references: https://dialectic.fm/david-senra

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) - Intuition
• (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

Dialectic with Jackson Dahl is available on all podcast platforms.
Join the ⁠telegram channel for Dialectic⁠
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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
• 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

Links:

• ‎McCartney 3, 2, 1 (2021)
• The Way of the Tracker: The Path of “not this” - Boyd Varty
• Eddie Murphy Is Tracy Morgan's Favorite | Comedians In Cars Getting Coff...

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

Key Links:

• The Man-Made Miracle of SpaceX - Max Meyer
• Max Meyer Launched a Print Magazine in 2024. Here’s Why. - Infinite Loops Podcast
• Man i...

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 money 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.

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Full transcript and all links: https://dialectic.fm/mackenzie-burnett

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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

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 is available at https://dialectic.fm/cyan-banister

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

We explored Reggie's frame of technology as a mirror and the Kevin Kelly-inspired notion that technology has an agenda of its own. Reggie has a fresh perspective on brand and "feel" as they relate to technology products, why friction can create meaning, and a Naoto Fukasawa-influenced view that design is about communicating values. The latter, for Reggie, originates with writing.

We dipped into a discussion about how hardware and how it shapes our software cultures, and what a world with more basic luxuries like the iPhone might look like. We also discussed "loaded" technologies and the current narratives that are working in crypto vs. what might be idealized.

The conversation concludes with a zoomed out meditation on myth, American western idealism, personal history, and what type of vision is required to create something radically new. This episode is shorter than usual given the live nature, but it's jam packed and I'm thrilled that we were able to cover a lot of ground across many of the ideas that are representative of Reggie.

Full transcript and all links: https://dialectic.fm/reggie-james

Video version from FWB livestream available here.

Timestamps

• 3:05: Technology as Mirror
• 8:04: De-fanging Loaded Technologies
• 12:43: Writing's Role in the Design Process
• 16:13: Affordances, Software, Hardware, and Values
• 22:53: Universal Luxuries
• 25:46: Friction and How Technology Can Make us Feel
• 30:16: The Role Brand Plays in Technology Today
• 34:30: Successful Narratives in Crypto
• 41:30: Crypto as a Mirror
• 44:39: American Myth & West
• 47:56: Personal Myth
• 54:16: Vision

References

• What Technology Wants - Kevin Kelly
• Crying in the Garden ~ Closing Eternal - Reggie James
• Joan Didion on writing to think
• Universals & Luxuries - Reggie James
• Naoto Fukasawa: Embodiment - Naoto Fukasawa
• THE TOKYO TOILET
• ‎Perfect Days (2023)

Previously, Linus held research or engineering roles at ⁠⁠Notion⁠⁠, ⁠⁠Betaworks⁠⁠, ⁠⁠Replit⁠⁠, and others, and has built over 100 personal ⁠⁠projects⁠⁠ on the side--including his own programming language and ⁠⁠most of the tools he uses day to day⁠⁠. Most of his work, writing, and projects revolve around language, knowledge work, thinking tools, machine intelligence, and latent space for creativity.

We begin with how technology can concentrate or distribute power and amplify our diminish our agency. Then he breaks down his framework around instrumental and engaged interfaces, why representation is so critical in tools, and talks through what 'tools for thought' actually means. We also discuss the state of LLM tools and how they can become more robust, as well as how latent space could be codified to help us understand more qualitative domains. This bleeds into his approach to and work at Thrive, which we discuss in detail.

Linus is attuned to the ways technology can make us more or less human, and that's reflected throughout. Technology is not determined: the future we imagine and create is entirely up to us. Will we optimize ourselves into something non-human, or dream our way into something beautiful?

Views expressed here are the interviewee's and not intended as investment advice.

Full transcript and all links are available at ⁠⁠https://dialectic.fm/linus-lee⁠⁠

Timestamps:

• (2:23): Values and Technology as an Amplifier for Agency
• (9:57): Instrumental vs. Engaged Interfaces and Tools
• (20:05): Representations, Abstraction, and Exposing Complexity
• (33:23): Dreaming of Thinking Tools, Especially Beyond Text
• (48:06): LLMs, Mechanical Thinking, and Going Beyond in How We Understand
• (57:42): Embeddings of People
• (1:01:16): Applying Rigor and an Engineering Approach to Working with LLMs
• (1:08:26): Collaborating with AI: Having Agents Work for You vs. Accelerating Your Craft
• (1:11:10): Using LLMs to Explore Latent Space
• (1:14:58): Working at Thrive: building internal tools and taking software seriously at a VC firm
• (1:28:09): What Great Engineering in an Organization Looks Like
• (1:33:50): Humanity, Aliveness, and Technology
• (1:39:41): Dreams, Aesthetics, Imagery, and Intentionally Guiding Technology
• (1:46:09): Lost to Wonder

References

• ⁠⁠What are conference talks about? - Linus⁠⁠
• ⁠⁠Instrumental interfaces, engaged interfaces - Linus⁠⁠
• ⁠⁠What makes a good human interface? - Linus⁠⁠
• ⁠⁠Dialectic Ep. 21: Geoffrey Litt - Software You Can Shape⁠⁠
• ⁠⁠Linus Lee on Representations for MIT Media Lab Lecture⁠⁠
• ⁠⁠On Exactitude in Science - Jorge Luis Borges⁠⁠

"Tammy" worked at the Charter Cities Institute and the Mercatus Center at George Mason University, which is chaired by Tyler Cowen.

Tammy is obsessed with tacit knowledge and the illegible parts of the world that actually support so much of our lives, work, and societies. This includes taste, charisma, relationships, and a wide-range of load-bearing infrastructure that supports healthy and trustful societies, from small-talk and manners to hidden forces that prevent anti-social behavior and maintain safe places to live and work.

We discuss this and more, including how she selects the ideas worthy of Stripe's audience, her unique career path, her refreshing take on agency, her standards for herself, reading and writing, and how she chooses how to spend her time. Above all, Tammy's incredible love of other people shines throughout the conversation.

Full episode transcript with all linked references: https://dialectic.fm/tamara-winter

Timestamps

• 2:09: Taste, absorbtion, and influences
• 10:54: Deploying your taste
• 15:49: Ideas that matter and taking yourself seriously
• 22:13: Aesthetics
• 24:16: Choosing Teachers and Authors
• 28:15: Charisma & delightfullness privilege
• 34:59: Living a relational life
• 44:07: Trust, social scaffolding, and small talk
• 51:01: Erosion of social norms, low-trust environments, and load-bearing infrastructure
• 1:02:17: Cultural arson and the dark sides of "you can just do things"
• 1:15:44: The healthy kind of agency
• 1:20:45: Tammy's N-of-1 path and who she aspires to rhyme with
• 1:28:38: Red herrings of success and focusing on outcomes
• 1:32:22: Assortive everything
• 1:37:52: Personal and professional standards
• 1:43:06: Journaling, great writing, and audience
• 1:57:29: Reading & Biographies

Key Links:

• The Art of Doing Science and Engineering - Richard Hamming
• On Self-Respect - Joan Didion

• Scaling People - Claire Hughes Johnson

• High Growth Handbook - Elad Gil

• Virginia Woolf on Montaigne
• Ava on Tammy
• Old Enough!

Nadia recently published her newest book, Antimemetics: Why Some Ideas Resist Spreading. She explores why consequential ideas, unlike memes and supermemes, fail to spread. She also recounts the last several years of online public and private life and how we're all less naive than we were in previous eras of the internet. Critically, she suggests a path toward poking our heads out of group chats and silos to engage in publicly discussing or promoting the ideas that matter most.

Her first book, Working in Public: The Making and Maintenance of Open Source Software, was published by Stripe Press. Nadia also worked at Substack, Protocol Labs, and Github, and has written extensively on Silicon Valley Culture; the importance of ideas and institutions; consciousness, attention, and meditation; and more.

Nadia's self-described sweet spot is when people respond to her writing by saying,"I read this piece and it gave me words for a thing that I didn't know how to express before." I can attest that is true, both for Antimemetics and for much of her other thinking. And as much as she writes about ideas, I admire how focused she is on how they might produce action.

Nadia believes that important ideas infect us, and the reasonable response to that is to be tremendously thoughtful about our attention. I hope this conversation inspires you to put great care into where your attention goes.

Transcript and all links: https://dialectic.fm/nadia-asparouhova

Timestamps:

• 1:31: Why Ideas Matter
• 9:33: The Last 10 Years of the Internet and Attention Collapse
• 17:07: How The Internet Caused Attention Collapse
• 19:59: Private Coordination in Public Spaces
• 24:01: Legibility and Illegibility as a Tactic
• 28:28: Ideas Are Not Created Nor Discovered; They Infect Us
• 35:17: Defining Antimemes
• 42:00: Ideological Black Holes: Supermemes
• 49:13: Engaging in the Public Square vs. Opting Out
• 54:16: Truth Tellers who Can Bring Anti-Memetic Ideas to Light
• 1:05:06: Champions, or the Great Apostle Theory
• 1:10:57: Institutions, Ideologies, and Movements
• 1:24:51: Attention
• 1:31:30: Jhanas
• 1:38:42: Writing a Book
• 1:46:19: Connecting the Dots in Reverse
• 1:50:29: Lightning Round: Fighting (or Working With) Human Nature, Software as Passion Project, Democracy, Space Away from the Center of Things

Dialectic with Jackson Dahl is available on all podcast platforms.
Join the ⁠telegram channel for Dialectic⁠
Follow ⁠Dialectic on Twitter⁠
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Subscribe to Dialectic on YouTube

Ink & Switch is an independent research lab focused on how computers can help us think and work. While researching and writing, Geoffrey and team also build products and prototypes to explore how their ideas can exist in practice. Geoffrey got his PhD at MIT CSAIL, where he built on his inspiration around computational media like spreadsheets, hoping to push more software toward the ethos of end-user programming, but without the technical complexity. In a sense, why should using software and changing it be any different? Previously, he built software for teachers at Panorama Education, which he joined out of school as one of the first employees.

Geoffrey and collaborators recently published a definitive piece on malleable software and we discussed it in detail. We dig into why most modern apps feel like sealed boxes rather than flexible tools and environments, and what changes when your app, document, or workspace, feels more like Lego than machinery. Geoffrey makes his case that we want software tooling to feel like a chef knife, not an avocado slicer, and we talk about how the best designed tools help users up a smooth slope of learning and ability. He argues in favor of deeper understanding, illustrated by one of my favorite ideas: The Nightmare Bicycle. We talk about how LLMs are enabling malleable software and how local tinkerers might be able to build systems for themselves and their team or communities that understand their needs more deeply than any professional designer could. Finally, Geoffrey lays out a call to arms for founders: build products that treat users as co-authors who understand their own needs, not just consumers.

On one level, this is a conversation about software and design. But it is really about agency. I hope it inspires you to pop open the hood on various aspects of your life, look at what's inside, and trust yourself to tinker. As Steve Jobs said many years ago, "the minute you can understand that you can poke life, and if you push in, then something will pop out the other side; that you can change it, you can mold it—that's maybe the most important thing."

All links and transcript: https://dialectic.fm/geoffrey-litt

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

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Timestamps

• 2:12: Agency in a Digital World and Geoffrey's Creative Medium: Software
...

Yancey's life and work has revolved around what it means to be a creative individual, and how to improve the cultural and mechanical forms that enable artists and creatives.

We talk about how much of modern society is rooted in individualism, how that wasn't always the case, and how the internet is evolving our sense of self. We get into creativity, the term's surprisingly recent origins, and why Yancey believes the 21st will be the "Creative Century." Then, we go beyond the individual and discuss the deeply-rooted longing that all of us have to be a part of something bigger than ourselves. Yancey suggests that is not simply about being subsumed by a collective, but by maintaining our individual star while becoming part of larger constellations—like the labels that have empowered the distribution of ideas for centuries. Finally, we discuss the forms Yancey has or is helping to build and imagine a future where even more of the world creates professionally.

May we all shine more brightly and find others who inspire us to make wonderful things.

Full transcript and all links available at https://dialectic.fm/yancey-strickler.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

---

Timestamps

• 1:41: Individualism, Identity, and the Internet
• 19:13: Creativity — Its Origins, Art, and Reaching Toward Something Deeper
• 33:30: The Creative Century and a Case for the Continued Growth of Professional Creativity
• 38:27: Hampton
• 40:02: Something Bigger than Ourselves — The Post-Individual, Bentoism, Being a Star and a Constellation
• 51:51: Labels & Conspiring Together in Practice
• 1:07:15: New Forms & Kickstarter
• 1:18:44: Metalabel
• 1:31:56: Creativity and Commerce & A Brand New Form: The Artist Corporation
• 1:46:22: The Long Game: Supporting the Artistic and Creative Life

Key Links & References (all available at dialectic.fm)

• YOUTH MODE - K-HOLE

Henrik Karlsson (Substack, X) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently recommended: on designing your life and finding your wife (or husband).

Henrik's always written, but lived a winding path across software programming, music, poetry, biology, an art gallery, and other odd jobs. A few years ago, Henrik and Johanna picked up their life in Sweden to move to a small island farm in Denmark so they could homeschool their daughters. He now writes on Substack full-time and lives an unusual dual-life: one is remote and intimate; the other is connected and wide.

My favorite theme of his writing is self-cultivation: introspection and action, designing a life that fits you by experimenting, how to think and how to learn, embracing being wrong and seeing past your blindspots, and living in concert with past and future selves.

I also love his writing on relationships: how to find your life partner, why writing helps others see the inside of your head, how to use the internet as a serendipity machine for finding your people, teaching and parenting, and what its like to be around exceptional people who make your world bigger.

He also writes about education, self-organizing systems, AI, exceptional childhoods, and more. But I find the topic rarely matters—all of his writing expands me. What a gift. I hope you enjoy the conversation as much as I did. May we all embrace the burden of freedom—freedom to iteratively unfold into a life we never could have imagined. If you enjoy the episode, please consider supporting Henrik's writing, as he is fully reader-supported.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

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Timestamps

• 2:36: Self-Cultivation, Introspection, and Larry Gagosian
• 8:46: Writing to Think
• 16:05: Using Strong Opinions as an Opportunity to Learn (and Willingness to Look Stupid)
• 21:53: "Not That" vs. "Maybe this?": Creativity and Formulating a Positive Possible Future
• 25:12: Self-Criticism and Kindness to Your Past Self and Ideas
• 28:44: Eclectic Interests (Poetry, Programming, Music) and a Winding Path to Becoming a Writer Pulling on the Threads of "Dead Ends"
• 33:10: Introspection, Agency and Being Sentenced to Freedom
• 38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments
• 49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us
• 1:04:16: The Ro...

I first encountered Tom and his ideas during his talk at Sohn on Iain McGilchrist, left vs. right brain, and curiosity. Tom writes about complexity, curiosity, and consciousness, and wades into the deep end of various topics that most of us would place in "woo," mystic, and spiritual territories. He spent most of his career on Wall Street and brings a scientifically-inclined, rationalist approach to researching and amplifying some of the most surprising modern and ancient ideas about the nature of humanity and the universe.

With this conversation, I aimed to create a primer on Tom's writing, approach, and the ideas he returns to most. We discuss following your energy, how curiosity is a guiding force, complexity and emergence, and why the world is overrated toward left-brain rationalism. We explore practical questions—How do you know your gifts? When should you pivot or persevere? What does real exploration look like when the world offers no safety nets? And then we wade into much stranger, or even heretical ideas—at least for a modern, intellectual, western audience—including the notion that consciousness is much vaster than what we've come to understand, and how we are just a small part of a much bigger whole.

I hope you enjoy the conversation and consider some ideas that are much more fringe than you're used to. I definitely left it with more questions than answers. And more than that, I hope you are inspired to attune yourself to your curiosity. Perhaps, you may even have the faith to follow that thread pulling you toward what appears today only to be a wall.

Episode transcript.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net works of $1M-100M to create its 2024 Wealth Report.

They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

---

Timestamps:

• 2:03: Following Your Energy and Positive-Sum Games
• 6:04: Curiosity and Complexity: Differentiation and Integration
• 8:12: Entropy & Syntropy: Unpacking Curiosity, Love, and Desire
• 12:34: Emergence and What All the Mystics Point to: Integration
• 15:14: Left Brain & Right Brain: A Primer on McGilchrist's "The Matter with Things"
• 28:58: Hampton
• 30:34: Discovering Your Gifts
• 37:35: Creativity and Sustaining Curiosity
• 43:12: Life Pivots, Especially When You Aren't 22
• 50:24: A Challenge vs. A Grind: When to Keep Going or Try Something Else
• 56:19: Synchronicities
• 1:00:58: Openness and Wisdom
• 1:04:19: Error Correction, or Something Else?
• 1:06:02: Tom's Mission and The Meaning-Mortgage Question: Can you really do what you love?
• 1:08:45: Fear, Faith, Love, and Seeing Reality
• 1:12:59: "Minimum Viable Woo" and Exploring Out There Topics wi...

This conversation starts with one of Alex's most insightful ideas: that a culture of gift-giving underpins technology, innovation, and creative work, and is the key to solving many of capitalism's coordination problems. We then talk about what businesses will look like in a world of abundance: AI agents, massive and accessible infrastructure, and where moats might actually lie. Alex shares why AI-enabled creativity may resemble musicians finding their sound and how and where we might find internet-native subcultures in 2025. Then he explains what "the medium is the message" actually means across different content formats and why audio continues to thrive. We wrap up with Alex's thoughts on the U.S and Canada as someone who identifies with both places and by taking a peek into some of the books that have most influenced his thinking.

I've read Alex for years and I've always been impressed by how generative he is. That comes through in this conversation and I hope you are inspired to—like Alex—be more curious, creative, and most importantly, generous.

Transcript and all links available at dialectic.fm/alex-danco.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.

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Timestamps:

• (0:00): Intro to Alex
• (1:28): Hampton
• (3:23): Steely Dan Intro
• (5:31): Coordination Problems and Silicon Valley
• (21:55): Girard, Taboos, Priests and Kings, and Magical Enzymes for Creating New Things
• (32:22): How Gifts Underpin New Things — Crossing Thresholds and Listening to Each Other
• (44:09): Gifts vs. Performance, Gifts vs. Slop
• (53:58): Overcoming “The Market for Lemons”: How Gifts and Market Mix and How Silicon Valley Resembles a Music Scene
• (1:02:29): Bubbles and Generosity
• (1:07:07): Patronage & Alignment
• (1:11:37): Coordination in Companies, O-Ring Problems, Michael Scott, and AI
• (1:25:51): Agency vs. Accountability
• (1:31:54): Wide vs. pointy businesses and What Makes a Platform
• (1:39:11): Moats, Leverage, and Figuring Out Your Sound: What Could Sam Altman Not Copy?
• (1:50:06): AI, Originality, and Creativity
• (1:55:15): Subcultures on the Internet and Frictionless Discovery
• (2:00:25): What Does "The Medium is the Message" mean?: Hot & Cool Mediums
• (2:11:57): Nixon-Kennedy Debates, Trump, Podcasts, Fox News, and the Decline of TV
• (2:25:21): Alex's Podcast Diet
• (2:28:52): U.S, Canada, and National Myths
• (2:4...

Having a conversation with Anjan is a bit like trying reign in a wild animal: his horsepower, wide-ranging philosophical interests, and unbelievable depth in the areas he cares about make him one of a kind. Fortunately, all of that energy is being channeled into his life's work, Daylight Computer Company. Daylight's mission is to build a computer that amplifies our humanity. That starts with Daylight's first product: The DC1, a tablet that combines the power and functionality of an iPad with the screen of a kindle. Anjan has been building Daylight for seven years across extensive research on screens and hardware, many near deaths, and mission-driven motivation.

Anjan sees computers as a "magical medium" that we're in relationship with, unlike other tools. Unfortunately, "optimization of the means, yet confusion of goals" has led the technology industry to building hardware and software that sits in what he calls a "messy medium." With devices that can do anything and everything, they often fail to empower us toward the vision Steve Jobs called the bicycle for the mind.

Throughout, Anjan and I discuss a philosophy toward life, career, design, and creating meaning that I hope will inspire you, whether you work on technology or not. May we all aim to get closer to ourselves and our humanity.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more.

Visit https://joinhampton.com/community to learn more and apply.

---

Timestamps:

• (0:04): Hampton

• (1:57): Anjan Intro
• (3:54): A Bicycle for the Mind and The Computer: Tool or Medium?
• (13:15): The Core of the Computer as a Magical Medium: Relationship
• (16:39): The Waterslide/fall of Agency and Humanity as Nature's Generalists
• (27:35): What drove Anjan to Computers
• (33:00): Building the Non-Inevitable and Confronting Silicon Valley's "Optimization of Means, Yet Confusion of Goals"
• (39:25): Wandering Toward Daylight: a Computer that Doesn't Feel Like Other Computers
• (51:02): Is Daylight paternalistic? The messy middle and the Case Against "sporks" or Sh*tting Where You Eat
• (59:51): The Ultimate Messy Medium: The Phone as Our Main Relationship to the World and Starting Over with a More Simple Tool
• (1:08:04): A Magical Companion: The Primer, Dynabook, or "Hobbes"
• (1:13:31): Starting with Light
• (1:17:32): Daylight as "basically Just a Screen" & Applying "Lateral Thinking with Withered Technology"
• (1:28:18): High Resolution Decision Making: Designing with Intuition and Developing the Right Kind of "Feel"
• (1:40:24): The Four Dimensions of Daylight's Vision
• (1:58:08): Growing as a Person and a Leader
• (2:07:08): Growing Daylight the Company/Organism: Three Principles
• (2:12:42): Competition, Scaling Daylight, Why Someone Should Work There
• (2:17:45): Lighting Round: Paravel – Interactive Fiction App Developed for Daylight
• (2:19:54): The Evolution of Books
• (2:21:20): Most Influential Books on Anjan
• (2:23:43): Is AI making Us More Human or Less Human? <...

Our conversation moves from engineered serendipity—the art of a well-aimed cold email & surfing the web—to complexity science, the Santa Fe Institute, and what better systems might look like. We dive into markets and medicine: investing with a creative mindset; timing in biotech including CRISPR and GLP-1s; and the tension between free-market innovation and healthcare as a human right. D.A. unpacks how incentives shape everything from venture bubbles to hospital billing and how LLMs might move us closer to a universal standard of care.

In the back half we talk creativity, beauty, art, and performance. We discuss whether AI makes us lazy or amplifies originality, DA's many lives across art, tech, and business, and end on his plea for artists to reclaim their throne of "cool". I hope you're inspired by D.A's combination of curiosity and depth and are reminded that you don't have to stay in one lane, regardless of how impressive it might be.

Full episode transcript and all linked references available here.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.

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Timestamps:

• (0:04) Hampton
• (1:56) Intro to D.A.
• (3:29) Curiosity, Serendipity, and the Power of Cold Emails
• (9:21) Web Surfing & D.A.'s Potential One-Man Show
• (13:28) Learning to Go Deep: Explore vs. Exploit
• (19:18) Complexity Science, EO Wilson
• (29:20) What Makes Santa Fe Institute Special?
• (33:13) Complex and Bureaucratic Systems: How do you design a good system? And how do you change entrenched systems?
• (40:25) D.A.'s Attraction to Markets and the Fed Challenge
• (45:19) What Makes a Good Investor?
• (48:30) Creativity in Investing, Index Funds, Elon's Take on a Great VC, and Venture Capital's Real Customer
• (58:45) What Makes for Commercially Successful Creatives: Doing
• (1:05:24) Gene Editing & CRISPR, What "Early" Means in Biotech, and Isolating the Bet You're Making
• (1:12:48) GLP-1, Slow Burn Technological Innovation, FOMO, and Bubbles
• (1:18:49) Healthcare Incentives: The Tension between Free Market Capitalism and Healthcare as a Right
• (1:24:53) Patient Agency, LLMs, and Shifting Away from Pater...

Alex loves people and curating spaces and experiences for them: whether that means parties, music festivals, or mountain towns. He joined Summit Series out of school, throwing large scale events around the world and working on Powder Mountain, a Utah mountain resort the ownership group had acquired. He then joined one of the first social DAOs, Friends with Benefits (FWB) as Mayor/CEO, after being tapped by its founder Trevor McFedries to scale the tokenized social club beyond a Discord Server. He launched FWB Fest, an annual in-person music festival and crypto conference with past performers including James Blake, Charli XCX, and Caroline Polachek. Most recently, he joined Reed Hastings to return to Powder Mountain after the Netflix co-founder acquired a controlling stake in the resort. Alex leads brand, art, architecture, and marketing.

Blending culture, commerce, and "cool" is anything but a science, but Alex has made a career of it. I've known him for a decade and it's been a thrill to watch him continue to find strange intersections, blending worlds like music and tech, crypto and culture, and skiing and art. We talk about this, how to create spaces and events, living in the mountains, large scale art experiences, Christopher Alexander and Jane Jacobs, challenges in creating new cities, learning from Reed Hastings, and a life of deepening one's taste.

I hope you enjoy and are inspired to life a more connected, playful, and present life.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit joinhampton.com/community to learn more and apply.

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Full episode transcript and links available at dialectic.fm/alex-zhang.

Timestamps

• (0:05): Hampton: Dialectic's First Partner
• (4:09): Commerce & Culture, Patronage, and Constraints
• (12:17): Curating People, Spaces, and Art: "Host Energy"
• (19:44): How to Throw a Party or Start a Scene
• (27:05): Unlikely Intersections and Authentic Marketing
• (35:36): Returning to Powder and Building a Unique Mountain Resort
• (42:31): Utah and Mountain Living
• (47:27): Randomness & Emergence: Christopher Alexander, Jane Jacobs, and Cities
• (52:24): Creating a Digital Feeling of Place
• (55:15): Network States and New Cities
• (1:00:42): "Community"
• (1:08:27): Organic Leadership Opport...

The first half of the conversation focuses on two big ideas. First: the growth of "slop" across media and culture and how "care" is its opposite. Then: how to think, learn, and understand more deeply across domains over a lifetime. We discuss how both of these sit against the backdrop of AI's rapid challenging of what it means to make and what it means to think.

Then we discuss Palantir and "grey areas" that many technologists avoid working on or thinking about, government bureaucracy and DOGE, and how technologists are pursuing and accumulating power. We also chat about Nabeel's idea maze ahead of the new company, art and what it is for, and a range of other topics that showcase how curious, polymathic, and considerate Nabeel is.

As the world changes at a breakneck pace thanks to technology and AI, Nabeel embodies a deeply humanistic approach that also accepts change as the default. This conversation inspired me to embrace surprise and strangeness, especially in creativity; to push through the friction and temptation to accept the answers at face value and instead yearn to more deeply understand; and to pursue a life of growth, practice, and care.

Full transcript with all linked references available here.

Timestamps:

• (3:21): “The Opposite of Slop Is Care.”
• (4:15): Defining Slop
• (14:17): Do We Decide What We Care About?
• (20:16): Original Seeing and Intimacy as a Path to Care
• (24:05): Creativity, Craft, and Care in the Digital World and Physical World
• (28:24): The Human Moat and Practice
• (32:48): Can AIs Care?
• (35:52): Understanding Things Deeply and “The Will to Think”
• (39:52): School: Getting the Answer vs. Deeply Understanding
• (41:44): High-Dimensional Learning from Simulations (Games) and Reality (the Real World)
• (48:38): Moving Down from Abstraction: Be Specific
• (50:49): Karl Popper, Fallibilism, Tyler Cowen, and Fighting Intellectual Inertia
• (53:00): Slowing Down
• (56:00): Nabeel's Funnel for Information & Retention
• (59:18): Spaced Repetition (Flashcards)
• (1:01:09): Palantir, Duty, and Engaging in Political and Moral Gray Areas
• (1:07:06): Palantir's Culture of Independent Thinking: People Who Speak Their Mind but Aren't Douchebags
• (1:09:38): Government Bureaucracy, DOGE, Power
• (1:14:51): Why Can't Governments Be Better at Error Correction and Healthy Renewal?
• (1:17:02): Technologists and Power
• (1:23:47): Nabeel's Next Company and the Idea Maze: “Context Is That Which Is Scarce”
• (1:27:11): Scientist Brain vs. Founder Brain and Context vs. Details
• (1:30:17): Tolstoy, Shakespeare, and What Art Is For
• (1:34:02): Art for Defamiliarization
• (1:36:00): What Makes Film Special
• (1:37:15): Depth in Text and Other Mediums
• (1:40:32): Patterns Across Nabeel's Taste: The Unfamiliar
• (1:43:11): Lightning Round: Travel
• (1:44:37): Stories Nabeel Tells Himself
• (1:45:31): Agency and Being Told What to Do by AI
• (1:47:49): Negotiation and Creating Optionality
• (1:50:28): Palantir's Vocabulary ...

The husband-and-wife team met at NYU ITP and shares a background across industrial design, architecture, computer science, film, including time at Pratt Institute and MIT. They won the 2022 Cooper Hewitt National Design Award for Product Design. They design and manufacture everyday objects including clocks, pens, tools, and other strange objects that challenge our relationship with time, attention, and materiality. Their most recognizable products include the Pen Type-A, Pen Type-C (my favorite), Time Since Launch (a one-time-use, 100-year timekeeper), and Solid State Watch, a remix of the classic Casio F-91W.

Our conversation explores their fascination with time, their commitment to creating heirloom-quality objects in a disposable world, and how they've built a sustainable creative practice on their own terms. We discuss their prototyping-centered approach, the tension between digital and physical creation, and how they navigate collaboration as partners in life and work.

Throughout, Che-Wei and Taylor reveal a philosophy that treats making as its own reward—they create what fascinates them first, trusting that others will connect with their vision. In a world increasingly dominated by disposable products and digital experiences, CW&T offers a refreshing counterpoint: a workshop where physical objects are thoughtfully conceived, meticulously crafted, and built to accompany us through life's journeys. Their work invites us to reconsider our relationship with the objects we use daily and the passage of time itself, offering a refreshing counterpoint to our increasingly digital, ephemeral world.

Full transcript with all links and references.

Timestamps

• (00:00): Time: a pattern across CW&T’s careers
• (11:21): Time Since Launch: the idea of counting up instead of down, and creating personal epochs
• (14:11): "Good design is long-lasting,” Durability of Electric Objects
• (19:31): Balancing art, product, and design: CW&T's approach to creating strange (but useful) things
• (23:51): First Word vs. Last Word Art: Michael Naimark's essay on innovation
• (28:01): Death by consensus: Why Che-Wei left architecture, and the joy of creative collaboration
• (32:52): Inspiration, Theory, and Self-Evidence
• (38:40): Tools: iPhone world, what makes a great tool, and design that optimizes for joy
• (44:21): The Hi-Tec-C pen cartridge and remixing w...

Eugene spent seven years at Amazon in its early days before following a brief detour to pursue filmmaking at UCLA. He then led product, design, editorial, and marketing teams at Hulu, co-founded Erly, and worked at Flipboard and Oculus. Today, he works on his own ideas at the intersection of media and technology while advising and angel investing.

This conversation explores the evolving landscape of entertainment, social media, community, and humanity in our digital age—topics Eugene has examined deeply. We revisit some of Eugene’s greatest hits on how platforms like Twitter and TikTok shape society and also get into fresh ideas he's yet to share publicly.

We start by discussing how today's social media world compares to the television-centric world that Neil Postman lamented in Amusing Ourselves to Death, and how entertainment-maximizing, adversarial, algorithmic social platforms might lead us to "Amusing Each Other to Death." Eugene unpacks TikTok's profound impact on our "digital nervous system," differentiating between social networks and social media—highlighting the latter's emphasis on frictionless positivity rather than meaningful connection.

Amid rising nihilism among young people, Eugene analyzes how cultural and economic structures contribute to lost hope, exploring social media’s role in exacerbating these trends. We discuss power laws influencing tech, media, sports, and finance, and how that drives pervasive speculation across culture. Then, he traces these themes through American television, from 1960s-1990s sitcoms to shows like The Sopranos, Succession, and Industry, revealing how they reflect the erosion of community and purpose in late-stage capitalism.

Throughout, Eugene offers nuanced observations on how technology's removal of friction has paradoxically weakened our sense of meaning and connection. We wrap up with how AI might shape media and creativity, what elements of humanity may be valued in the future, learnings from Bezos and film school, and a movie recommendation for anyone trying to make sense of it all.

Timestamps

• (02:10): Amusing Each Other to Death and "Frictionless Positivity": Neil Postman, TV vs. Social Media
• (14:35): Dunking, Quote Tweets, and Proximity to the Other
• (19:09): Prisoner's Dilemma of Twitter: Concede or Dunk
• (24:52): Is TikTok the Final Form of Social Media?
• (31:02): Status Games in the Algorithm Era
• (39:02): Technology's Reduction of Friction & Avoiding Confrontation with the Other
• (48:45): The Internet's Reversal of Vita Activa and Vita Contempliva
• (50:53): Growing Nihilism Toward Online Status Games: If You Don't Capture Attention, You Aren't Relevant Anymore
• (55:54): Late State Capitalism's Disappointment, Gen Z Nihilism in US and China, Death of Community
• (1:03:01...

Josh is a masterful storyteller who moves seamlessly between science, culture, and markets. As an investor, he seeks the counter-narrative—what others aren't talking about—and has backed countless breakthrough companies in AI, space, biotech, robotics, defense, and beyond. Beyond investing, Josh founded Coney Island Prep charter school and is a trustee at the Santa Fe Institute.

Our conversation explores the interplay between science and storytelling, the power of belief in both doubters and advocates, patterns in creative rebels, and what makes someone both "arrogant" enough to assert a new reality while remaining grounded enough to see reality clearly. We discuss America's scientific competitiveness, the value of competition in institutions, Josh's voracious appetite for the new, and his personal journey with control, trust, and family.

Josh is one of my favorite examples of someone who is radically unhedged on himself: he leans into his genius—and thus sometimes, disfunction—in ways that make him authentically effective. Throughout the episode, he demonstrates his rare combination of wisdom and childlike curiosity, competitive drive, and deep care for the things that matter to him. His ideas on storytelling, science, and human nature offer a guide for thinking about bringing new things into the world.

Episode transcript.

Timestamps

• (2:12): Science & Stories
• (6:30): Are technology outcomes and timelines determined or variable based on cultural movements, societal reaction, and stories?
• (11:14): Who is Imagining the Future of Tomorrow?
• (16:34): Originality, AI, and Everything is a Remix
• (20:52): Improving as a Storyteller
• (23:55): Secrets & Magic
• (31:35): Josh's Biggest Believers
• (34:20): Belief Beyond Capital, Motivation, and Fuel
• (37:53): Patterns in Creative Rebels
• (40:53): "Arrogance of the Highest Order" in Entrepreneurs, Asserting Reality, Great Men of History, and Elon
• (47:02): US Exceptionalism and Celebrating Science & Technology
• (55:23): Institutions, Academia, Government, and Competition
• (1:00:56): Josh: Accomplished Yet Childlike - Finding the Edges
• (1:04:07): Breadth and Depth: a Heat-Seeking Ability to Go Deep
• (1:12:03): Managing Dowsides and Lessons that Could Have Been Learned Sooner
• (1:15:58): Control, Past, and Future
• (1:19:57): Learnings from Mom
• (1:20:57): Trust and learning from Optimistic Partners
• (1:22:54): Legacy

Links & References

• Kevin G's Josh Wolfe Compilation
• Kevin's much shorter twitter thread summary of Josh's spikeyness
• Lux Q3 2024 LP Letter - Four Parables of Four Greek Titans

Jacob started his career at Coinbase where he was a product lead and helped create USDC. Five years ago, he left to wade deeper into the waters of internet and crypto-native coordination and creativity and co-founded Zora.

His central interest is how people coordinate together using the internet—the includes currencies, markets, ownership, art, speculation, and memes. We discuss how memes and symbols enable coordination, "The Meme and the Memo," words, money, and laws, Zora's premise built on Stewart Brand's "information wants to be free but it also wants to be expensive," a case for markets around attention, the new version of Zora and "a coin for every piece of content," speculation vs. gambling, token-powered brands, Ethereum and Solana, Coinbase and USDC, and a wide-ranging personal section that showcases why Jacob is so generative.

The parting prompt I hope this conversation leaves all of us with is this: while information is ~free today (and also abundant, infinite), it is also quite expensive to consume in terms of time. We ought to think carefully about what content we spend our precious time consuming and rewarding. That you would spend some of yours listening to Dialectic is as always a privilege and I hope you find it worthwhile.

Transcript available here.

Timestamps

• (3:03): Obsession with Memes: How do you get people to organize?
• (8:46): The Meme and the Memo via Balaji Srinivasan
• (11:32): Three Fundamental Questions: Words, Money, Laws
• (12:39): The Midwit Meme and other Favorites
• (15:55): What makes media and information valuable?
• (19:26): Zora, Tokenized Media, and Information wants to be Free and Expensive
• (22:53): Provenance
• (28:30): Why Do We Want Markets for Attention?

Deeper Crypto Section

• (37:08): A coin for every piece of content: prediction markets on attention
• (42:49): Investing in People or “Creator” / “Social”Tokens
• (44:14): Not fighting internet gravity: NFTs, “utillity,” 1 of 1s, and skeumorphic ideas along the way
• (47:52): Speaking to potential concerns and incentivizing more durable and useful information
• (52:23): Speculation vs. Gambling: positive sum vs. zero-sum
• (56:00): AI: Market Data as an input for for Models
• (58:56): Speculating on how a future of AI and attention markets will be good for creatives
• (1:04:50): Small market cap content can still be meaningful
• (1:08:11): Crypto-optimism and regulation
• (1:13:52): Saint Fame, Nouns, and Ideas for Future Token-Coordinated Orgs
• (1:22:32): Reflecting on “Hyperstructures”
• (1:28:55): Jacob's shift toward market-oriented thinking for solving coordination problems
• (1:30:40): Ethereum, Solana, and Blockchain Competition

Coinbase

• (1:36:23): The Coinbase Internship that Never Ended
• (1:40:49): Starting USDC
• (1:49:14): Bloomberg Terminal's Design

General Jacob

• (1:50:09): Bezos and adoption of technology
• (1:52:47): Tokenized Identity
• (1:55:41): Matt Dryhurst and Holly Herndon and ...

Steph's education is in biology and industrial design, but he is true multi-hyphenate creative, working across mediums including software, hardware, supply chain and packaging, words, wood, furniture, ink, color schemes, open-source systems, video, podcasts, and more. Above all, he makes tools—deeply opinionated ones—designed to reduce friction for himself and others in the act of creating.

Steph joined Obsidian after initially contributing as a fan and enthusiast and impressing its co-founders, Shida Li and Erica Xu. Under his leadership, Obsidian has grown into one of the most beloved and powerful independent software tools in the world, with millions of users. As a daily user myself, I rely on Obsidian for my research and thinking for this podcast. Before Obsidian, Steph founded Lumi and Inkodye, the former of which was acquired by Narvar.

Beyond design, Steph is one of my favorite writers. His concise, sub-500-word essays have shaped my thinking on design, software, learning, agency, constraints, and creativity. While we couldn’t cover all of his ideas in this conversation, we explored many of them in what became my longest conversation to date—one that is packed with wisdom. I believe these ideas will challenge you in unexpected ways and push you to be more creative, agentic, and optimistic.

Transcript for episode 8.

Timestamps:

• (1:56): Constraints and style
• (11:51): Aggressively planting creative seeds but being patient for them to grow
• (17:42): Stadium of past and future selves
• (22:34): Asking what can be removed and making incremental progress
• (28:47): Building a product and company (Obsidian) with the "constraint" of ideology and principles
• (38:52): Using Obsidian makes Steph better at building Obsidian
• (44:09): What makes for good design and seeing the world as something designed (by nature or man)
• (53:11): What makes a good tool?
• (56:20): Thinking tools and Obsidian
• (1:04:32): "In good hands" and caring more than anyone else
• (1:21:38): Engaging all five senses
• (1:24:46): Creating cohesion or your own cinematic universe
• (1:30:43): How to time travel
• (1:33:08): Designing for digital durability or permanence & "File over app"
• (1:56:46): Investment and "selfishness" in extending your light
• (2:05:54): Choosing problems to work on
• (2:09:10): "Nibble and your appetite will grow"
• (2:12:31): Compounding
• (2:19:55): "Caloric energy is precious"
• (2:26:21): "Earth is becoming sentient"
• (2:39:31): Busy being born and sharing along the way
• (2:42:11): Love and freedom

Links

• Style ...

His interests and work include culture, identity, organizational design, psychology, cryptocurrency and blockchains, brands, health and care, spirituality, and social forms and institutions. Today, Toby works on Care Culture, a community and research platform focused on mental health and spirituality. Toby also co-founded Other Internet, a research institute known for its deep cultural analysis and work with crypto organizations. Conversations with Toby and his work—especially ‘Headless Brands’ and ‘Squad Wealth’—were deeply influential to my interest in crypto and related subcultures and ideologies. Over time, I have been even more energized by his broader thinking and ability to interpret cultural change especially with regard to evolving sources of meaning, identity, and connection.

This conversation is primarily about themes I’ve noticed across his work and how those have evolved toward what he is working on now. In many ways, this is the pattern of modern culture “secularizing” more sacred forms—including but not limited to practice, faith, ideology, morality, and religion—and how that happens at individual and collective levels.

Episode Transcript

Timestamps:

(02:26): Post-Authenticity & Romantic-Era Individualism (10:08): Squad Wealth: a seed of collectivism--the collective as the atomic unit (14:40): Other Internet (18:45): Life after lifestyle, headless brands, and new forms of collective beliefs, cults, and religions (30:55):  Toby's pivot away digital to physical social forms; from technology and brands to health (38:51): The body, the will, and new kinds of individualism and collectivism (52:47): Prototyping Social Forms of Care (58:08): The theme of Toby's work: practice-- and new spiritual and religious forms (1:00:50): Secular and Sacred (1:04:35): The social body and the social spirit (1:05:56): Toby's central question (1:10:13):  Observing and Critiquing vs. Prescribing (1:13:03): Innovating on social forms like we innovate with business and technology (1:21:52): Reflecting on time spent in Crypto (1:29:23): Protocols (1:31:50): Social forms in lieu of institutions (1:34:43): Learning about yourself through writing (1:37:44): Spirituality

Links:

Dialectic with Jackson Dahl is available on all podcast platforms.
Join the ⁠telegram channel for Dialectic⁠
Follow ⁠Dialectic on Twitter⁠
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He invests in technology and internet businesses at Pace, and previously did the same at Thrive Capital, which he joined in the earliest days. At Thrive, Chris invested in Twitch, Unity, Patreon, among others. Chris is a profoundly deep thinker who relies on behavioral economics to build robust frameworks for understanding technology, businesses, the internet, and human nature. As we discuss, intentionality runs through Chris's life and actions. While Chris has strong views about incentives and markets that may seem in conflict with some kinds of idealism, he is also strongly optimistic and earnest in his love for the world and its people, and for what we might create for each other.

We discuss Chris's frameworks and approach to explanations, markets and incentives, top-down and bottom-up thinking and companies, approaches to new markets and raising capital, his obsession with discovering the new, how his ideas become published thinking, the positive and negative impacts of the internet, Pace and its values, and the inner-workings of Chris's truly unique and fascinating approach to the world.

Timestamps:

(01:08): What does it mean to be intentional? (05:21): Good Explanations (07:28): Sharing explanations and thinking publicly (14:45): Pendulum Theory (22:14): The efficient market hypothesis (27:34): Top-down vs. bottom-up thinking and companies (48:09): First-to-market vs. best-to-market (55:44): Cost of capital and when venture capital makes sense (1:03:28): How Chris finds new things and how he curates what he consumes (1:07:59): Chris's ideation funnel: thinking > sparring > publishing (1:10:42): Is the internet actually good for us? What about capitalism? What rules above capitalism? (1:18:56): The internet as a lever on agency and ability to take risk (1:23:47): Pace Capital: Values, Brand and Reputation, Truth-Seeking, and People (1:32:20): A pre-mortem on Pace's failure (1:34:06): The first piece for a theoretical Pace Capital art gallery

Questions for Chris about himself (1:36:07): Is Chris's unique set of worldviews and thinking more due to nature or nurture? (1:37:21): What has Chris compounded most continuously (1:38:23): What Chris's best or favorite “investment” in the universe? (1:40:01): How do Chris use laziness as a lever? How might other people? (1:41:50): Meta-analysis and cognitive biases (1:45:11): How Chris hacks his brain: what's at the top of the usuer manual of being Chris? (1:47:51): Where is Chris most confident in the conensus view (1:49:01): How does Chris apply pre-consensus thinking to his personal life?

(1:51:36): Alignment: with Keely in life and Jordan at Pace (1:55:43): Every second counts

Links:

• Frameworks v0.2
• PACE DESKTOP
• The Shadow of Disutility: Technology’s Hidden Cost
• Zen for Film, 1965 by Nam June Paik

Transcript for this episode.

Join the

Tina grew up in China before moving the U.S. at age 14. As an adult, Tina has been a dual-citizen of New York City and the internet. As she has put it, Tina is interested in the culture of technology and the technology of culture. While we share a love of technology and the internet as a "place," Tina is also my favorite person to get reading recommendations from. She studies philosophy, immerses herself in art, film, and fashion, and has been writing online since she was a teenager. I aimed to give listeners a glimpse of the types of wide-ranging conversations that I've enjoyed with Tina over the years.

We cover identity, locality, NYC, the internet, writing and sharing online, finding your people online, her career arc from comparative literature in college to venture capital and crypto, how labor markets and economies lay a foundation for culture in cities and online, what it means to be serious, patriotism and greatness, ambition, philosophy, ideas and action, Benjamin Labatut's When We Cease to Understand the World, her favorite philosophers from Kierkegaard to Wittgenstein to Byung-Chul Han, Beauty, taste, aesthetics, film, fashion, and how love and attention underpin her life.

Timestamps:

• (1:07): Identity & Place: What Does it Mean to be Local?
• (7:46): New York City
• (14:24): Urban Design and Evolution in Cities and Online
• (19:03): Being a Citizen of the Internet & Sharing Yourself Online
• (31:55): Tina's Unique Path: from Comparative Literature & CS to VC to Crypto
• (45:58): Station & Coinbase: Why Economic Systems & Labor Markets are Upstream of Cultural Outcomes 
• (55:22): Being a Serious Person
• (58:53): When We Cease to Understand the World
• (1:02:47): Greatness, Patriotism, and Ambition
• (1:07:00): Reconciling with Obsession and Ambition: Can They Go Too Far? 
• (1:10:13): What is Philosophy For? Refining Realities vs. Asserting Reality
• (1:20:57): The Patterns in Tina's Favorite Philosophers and Writers
• (1:26:04): Making Time for Philosophy and Study
• (1:32:09): Aesthetics, Taste, Beauty, Film, Fashion
• (01:39:58): Love & Attention

Links & Resources

• The New Frontier of Belonging by Tina He
• Order without Design by Alain Bertaud
• When We Cease to Understand the World by Benjamin Labatut
• Tina's "raw thoughts from the journal" post-election

I'm not sure there's anyone I've more consistently recommended to friends and loved ones in recent years, and it seems like the world agrees: Ava now has over 30,000 subscribers. One of my favorite parts of this episode was reading excerpts from Ava's essays over the years back to her. We cover a ton of ground, including writing, consistency, commitment, friendship, authenticity, self-respect, taste, beauty, and much more.

Timestamps:

• (1:09): What makes for good writing & what Ava writes about
• (5:49): Flow, Writing Practice, Consistency, Commitment, and Maintenance
• (14:08): Audience Consideration, Vulnerability, Sincerity, and Ava's Readership
• (26:30): Feedback Loops, Getting Better at Writing
• (28:51): Distribution and Growth; Writing Online vs. Making a Living with Writing
• (34:39): Social Psychology and Seeing People More Clearly
• (36:21): Do People Change?
• (42:44): Relationships & Helping Others Find Love
• (44:32): The Friendship Theory of Everything
• (1:00:35): Consistency, Self-Respect, and Self-Trust
• (1:03:45): Frames: Consistency in Our Relationships with Others
• (1:08:21): Authenticity and Honesty
• (1:15:12): Taste & Interiority
• (1:24:14): Two Core Interests: Relationships and Technology
• (1:26:12): San Francisco
• (1:29:48): Writing in the Second Person
• (1:31:52): Substack Recommendations and a Novel
• (1:33:07): Motivation & Energy
• (1:33:50): 10 Years Back, 10 Years Ahead
• (1:35:46): Uselessness
• (1:39:06): Beauty

Links & Resources:

Ava's Writing:

• protecting flow
• on maintaining attention
• is everything copy?
• december

• what's up with modern love?
• the friendship theory of everything
• everything I know about love
• frames
• the girl the internet made me (Authenticity)
• taste
• what we talk about when we talk about taste
• in praise of uselessness
  

Others:

Before co-founding Farcaster in 2020, Dan previously worked at Coinbase as a Vice President, among many other roles. He joined the company as the 20th employee in 2014 and left in 2019. He's thought about and used Twitter-like networks for nearly two decades and is passionate about open information flow, market-enabled progress, and individual freedom.

Timestamps:

• (01:39): We were promised flying cars and all we got was 140 characters
• (8:48): Bring Your Own Algorithm (BYOA), RSS, Elon, and The News Channel-ification of Social Networks
• (35:54): The Field of Dreams Fallacy: If You Build It, It Doesn't Mean They'll Come

[Farcaster & Crypto-Focused Section Begins]

• (44:25): Status as a Service and Building the Home for Crypto Status
• (55:03): What is Farcaster?
• (59:34): Why not counter-position against Elon?
• (01:03:42): Programmable social and “Open APIs”
• (1:14:22): The Future of Farcaster
• (1:18:01): Farcaster's Value Capture 
• (1:25:01): Sufficient Decentralization
• (1:28:44): Why Dan has created NFTs but not tokens

[Farcaster & Crypto Focus Ends]

• (1:29:53): Product Market Fit, Focus, and The Idea Maze
• (1:37:01): Dan's career arc, contrarian paths, distributed systems, and creative destruction 
• (01:44:09): Coinbase: pre-2017 learnings, hypergrowth, comparisons between building a culture and social network, and anti-lessons
• (1:49:20): Brian Armstrong and fostering repeatable innovation
• (1:52:24): What do you wish Balaji [Srinivasan] could work on?
• (1:53:20): Group Chats and the pendulum between private and public discourse
• (01:58:55): Power: Elon, Zuck, Trump? 
• (2:00:24): Politics, Populism, Going Direct, and the Podcast Era
• (2:08:48): What have you changed your mind on this year? 
• (2:10:22): Final Questions

Full transcript.

Links & Resources

• RSS+ by Dan Romero
• The Rise and Demise of RSS by Sinclair Target
• Status as a Service (StaaS) by Eugene Wei
• The idea maze by Chris Dixon
• Balaji Srinivasan's paper on the idea maze
• The only thing that matters by Marc Andreessen
• v2 frames
• FC AI/zk trends

Michael and Compound invest in seed and pre-seed science and technology companies in categories like healthcare and biotech, machine learning and AI, robotics, and crypto. He writes prolifically across a range of topics and I've always admired his ability and tenacity to think about the future and paint an optimistic, yet grounded view of where things are going. He's deeply reflective and wise, and I've known both his dedication to craft and the size of his heart for nearly a decade as a friend.

Timestamps:

• (0:00): Technology, Science, and Cultural Change
• (08:37): Inflection Points and seeing the present vs. predicting the future
• (13:00): Being original and/or contrarian; what is "alpha"
• (16:58): "Post-science projects"
• (21:54): Technological timing and false inflection points
• (34:44): Heroes, Talent, Elon, and Zuck
• (45:30): Founders of the future will spike on creativity
• (49:46): Fighting decay
• (55:53): Future shock: "time is collapsing"
• (1:06:56): The future of humanity and our biology
• (1:12:16): Bryan Johnson and biological experimentation
• (1:14:48): AI Therapy
• (1:19:38): Vtubers, digital influencers, and pseudonymity online
• (1:26:19): Authenticity online: "Being known is being loved
• (1:31:57): Discipline, Curiosity, and Writing
• (1:36:29): Inertia and Friendship
• (1:44:44): A life of Craft

Resources & Links:

• On Inflection Points

• Signal vs. Noise, Market Efficiency, & Evolving Alpha
• Power & Technology
• Moral obligations when investing in the future & The Vulnerable World Hypothesis
• Serendipity in Venture Capital is BS…(and other views on the seed VC landscape)
• Being Known is Being Loved
• Inertia, mortality, & Friendship
• A Biohacker Future by Compound

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

Dialectic is available on all platforms.

He spent the first part of his career as a machine learning engineer, mostly at Stitchfix, only to run into a wall: a hand injury that prevented him from being able to write any software for over a year. Fortunately, he's not so one-dimensional, and spent time reclaiming somatic experience in learning to free-dive, train Jiu-Jitsu, and return to the pottery practice he developed in art school, all while reckoning with big questions of ambition, purpose, and self-fulfillment. Since then, he's built a consulting practice helping modern AI companies better implement RAG (retrieval-augmented generation), avoid system design mistakes, hire elite talent, and build for an LLM-centric world. He maintains a large structured output library called Instructor with about 1m downloads per month, writes prolifically (which he does entirely via voice input with LLM editing, as we discuss), tweets semi-manically (he's grown to 30K followers on X with the simplest strategy I've ever heard anyone articulate—tweeting 30K times), and teaches courses on RAG and online consulting. Finally, my man can yap. He was a perfect first guest because he has no shortage of ideas but comes at nearly everything with a beginner's mindset.

Timestamps

• (0:00): Intro to Dialectic
• (2:55): Brick laying vs. capital allocating
• (6:04): Acid Story: Trying so hard to be a somebody
• (9:20): Planning, judgement, elasticity, and abundance
• (11:28): Ambition and Trusting your future self
• (14:20): Fear; Confidence is the memory of success
• (18:46): Compounding psychology of risk taking
• (21:30): Do you get what you deserve?
• (22:32): Playing life on hard mode
• (27:22): Agency, Taking Accountability, and becoming essential
• (35:58): Consulting and Independent Contracting
• (39:52): Ambition and “Manhattan Project” Appeal
• (42:30): What are you motivated by?
• (44:36): Challenge runs and side quests
• (46:39): How to be prolific
• (53:46): Mastery, complex games, and creative fingerprints
• (57:47): Programming, animation, and style vs. cohesion
• (1:07:56): Jason only writes with his voice--with some LLM help
• (1:12:47): Flooding the airwaves with content
• (1:14:10): Twitter growth: simple math
• (1:19:49): Using the “sawdust”
• (1:23:30): ELI5 RAG (Retrieval augmented generation)
• (1:27:39): A final rant against couches

References

• Losing My Hands by Jason
• Advice to Young People, The Lies I Tell Myself by Jason
• A Critique on Couches by Jason
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