Reggie James (Substack, X) is a designer, writer, and entrepreneur. Reggie previously founded Eternal and recently edited and published Hardware 2024, a book highlighting recent attempts at creating a different hardware future. This conversation happened live on stage at FWB Fest 2025 in Idyllwild, CA.

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)
• The Media Lab: Inventing the Future at M.I.T. - Stewart Brand
• The Near Collapse of the American Myth - Reggie James
• The Timeless Way of Building - Christopher W. Alexander
• ROLE: CREATIVE DIRECTOR || COMPANY: USA - Reggie James

Linus Lee (⁠⁠Website⁠⁠, ⁠⁠X⁠⁠) is a builder, engineer, and writer who explores how software can amplify our abilities, humanity, and agency. He builds, researches, and advises on AI at ⁠⁠Thrive Capital⁠⁠, a venture capital firm, and continues to write and hack on personal projects.

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
• ⁠⁠C. Thi Nguyen⁠⁠
• ⁠⁠The Three-Body Problem - Liu Cixin⁠⁠
• ⁠⁠The British Library⁠⁠
• ⁠⁠Spatial Interfaces - John Palmer⁠⁠
• ⁠⁠Prism: mapping interpretable concepts and features in a latent space of language - Linus⁠⁠
• ⁠⁠Synthesizer for thought - Linus⁠⁠
• ⁠⁠Liquid Art - Kate Compton⁠⁠
• ⁠⁠Thoughts on Loom - Linus⁠⁠
• ⁠⁠Linus on Flora⁠⁠
• ⁠⁠Story of Your Life - Ted Chiang⁠⁠
• ⁠⁠Arrival (2016)⁠⁠
• ⁠⁠Linus's bio, culinary edition⁠⁠
• ⁠⁠Goodfire AI⁠⁠
• ⁠⁠Notion, AI, and Me - Linus⁠⁠
• ⁠⁠Dan Shipper⁠⁠
• ⁠⁠Every⁠⁠
• ⁠⁠Philip Wadler⁠⁠
• ⁠⁠Create things that come alive - Linus⁠⁠
• ⁠⁠A Rant about "Technology" - Ursula Le Guin⁠⁠
• ⁠⁠Radio City - Linus⁠⁠
• ⁠⁠Linus tweet on aesthetics⁠⁠
• ⁠⁠Wonder engines - Linus⁠⁠
• ⁠⁠Seeing Is Forgetting the Name of the Thing One Sees - Lawrence Weschler⁠⁠
• ⁠⁠lost to wonder⁠⁠

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Tamara Winter (X) is the Commissioning Editor of Stripe Press, where she exercises her taste to identify the knowledge and "ideas for progress" that matter most in alignment with Stripe's mission: to increase the GDP of the internet.

"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!
• Sort By Controversial - Scott Alexander (Scissor Statements)
• Scarf tweet

• Tammy's advice to young people

• An Elegant Puzzle - Will Larson

• Interact
• The Making of Prince of Persia - Jordan Mechner
• Frank Sinatra Has a Cold - Gay Talese
• Why not inquire together more? - Tyler Cowen
• The Common Reader - Henry Oliver
• In Five Years - Rebecca Serle
• Walt Disney: The Triumph of the American Imagination - Neal Gabler
• Up from Slavery - Booker T. Washington
• Anna: The Biography - Amy Odell
• The Rise of Theodore Roosevelt - Edmund Morris
• Brian Jacques
• A Pattern Language - Christopher W. Alexander

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Nadia Asparouhova (Website, X, Substack) is a writer and researcher who has spent much of her career in service of the question: 'what's happening here?' across various parts of the internet.

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

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Geoffrey Litt (Website, X) is a designer, engineer, writer, and researcher at Ink & Switch, where he champions malleable software: the idea that ordinary people should be able to mold the digital tools they rely on every day.

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
• 12:17: Intro to Malleable Software
• 20:42: "Popping Open the Hood" & The Nightmare Bicycle: A Case for Understanding How Systems Work
• 27:47: Computational Media, Spreadsheets, and Digital Informality
• 34:01: Legos and Home Cooking as Metaphors for Software
• 42:30: Two Types of Malleable Software: Modular-by-Design and Hacking
• 48:35: Hampton
• 50:13: Designing for a Smooth Slope
• 58:20: Unbundling Apps into Environments and Tools
• 1:17:58: Why Do the Work at All When AI Can Do It? When Should We be in the Details?
• 1:29:22: Empathy & Design: Enabling "Local Developers" Who Know Their and Their Community's Needs
• 1:38:23: A Case for Optimism About Human Agency
• 1:51:09: AI's Impact on Malleable Software
• 1:59:03: Commercial Incentives and Ecosystem Change
• 2:04:17: Research and Ink & Switch
• 2:11:46: ChatGPT as a Muse
• 2:15:34: Working at MUBI and Solving the "Too Many Things to Watch" Problem
• 2:18:27: Japan's Culture of Care
• 2:22:15: Mastery and Variety
• 2:24:34: Joy and Clarity as a Parent
• 2:25:30: Expressing Care Through What we Make

Yancey Strickler (Website, X, Metalabel) is a writer, entrepreneur, creative, and founder of Metalabel, a network and platform that allows creative people to release work together. He is also a board member, co-founder and former CEO of Kickstarter and is currently working on establishing a new kind of corporate structure, the Artist Corporation.

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
• Adam Curtis on the dangers of self-expression - Yancey Strickler for The Creative Independent
• Inventing the Individual - Larry Siedentop
• The WEIRDest People in the World - Joseph Henrich
• The Second Self - Sherry Turkle

• Dolly Parton meme
• Nine Creative Meditations - Yancey
• The Cult of Creativity - Samuel Weil Franklin

• The Post-Individual - Yancey
• Bentoism
• The dark forest theory of the internet - Yancey
• The Dark Forest Anthology of the Internet

• Our Band Could Be Your Life - Michael Azerrad

• Introducing Metalabel

• New Creative Era with Yancey & Joshua Citarella

• Artist Corporations
• How to long game - Yancey

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Full transcript and all links: dialectic.fm/henrik-karlsson

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.

---

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 Role of Ambitious Goals in the Context of Unfolding
• 1:10:06: Hampton
• 1:11:41: Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible
• 1:26:53: Asking Questions that Push People Past their Cache
• 1:31:12: Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet
• 1:48:55: Ruthless Prioritization and Making Time to Get Better
• 1:57:05: Initial Spark and Connecting with People
• 2:05:58: Collaborating with Henrik's Wife Johanna
• 2:09:46: Living a Barbell Life Inside and Outside of the Computer and Henrik's Scale of Ambition
• 2:16:48: Sacrifice
• 2:18:57: Pseudonymity and Playing with Identities
• 2:20:57: Self-Organizing Systems
• 2:22:51: Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold
• 2:33:13: Writers Who Help Us See Ourselves
• 2:35:13: Writing and Thinking in Swedish vs. English
• 2:37:44: Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves – And Modeling That For Others

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Tom Morgan (X, Substack) is a "curiosity sherpa," writer, and podcaster who runs The Leading Edge, a community for leaders focused on personal transformation and authenticity.

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 with a Pragmatic Lens
• 1:16:10: Stories
• 1:18:51: Love, Emergence, and Intelligence Beyond Us
• 1:22:52: A Looming Meta-Crisis, Global Consciousness, and Earth School: Blowing Out the "Woo" Rating
• 1:33:41: Lightning Round: Pseudoscience as the Streisand Effect, Mystics, What Would Rattle Tom’s Worldview Most, Joseph Campbell, Fred Again
• 1:40:41: Tom's Encouragement for His 20 Year Old Self

Select Links

• Thinking the Unthinkable - Tom
• Exploring Gurdjieff's Mysteries - Tom
• A Transformational Heresy? (Syntropy) - Tom

• The Matter With Things - Iain McGilchrist
• Test Your Network - Tom
• Our Unspoken Future - Tom

• Fred again.. Boiler Room: London

Transcript and all references linked at https://dialectic.fm/tom-morgan.

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Alex Danco (Website, X, Substack) is a writer and Product Director at Shopify. Alex rose to prominence while writing his Snippets newsletter while at VC firm Social Capital in 2015. He wrote prolifically—about markets and financial systems, venture capital, startups, cities, culture, the technology-driven shift to a world of abundance, to name a few topics—through 2020, when he joined Shopify. Since then, he's had his hands full with Shopify and young kids, but recently published a flurry of new pieces on his blog while on paternity leave.

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
• (2:44:23): The Most Influential Books on Alex
• (2:56:47): Learnings from Being in a Band
• (2:59:05): Scammers
• (3:02:55): Being a Dad
• (3:05:24): The Best Gift Alex Has Received and the Gift He Hopes to Give

All references and links, with transcript.

Dialectic with Jackson Dahl is available on all podcast platforms.
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Anjan Katta (X) is Founder and CEO of Daylight, a new type of computer company.

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.

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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?
• (2:29:38): Boredom, Authenticity, and Integrity
• (2:32:06): Faith and Spirituality
• (2:33:04): What Anjan Has Learned from His Parents and What He's Forgiven Them For
• (2:34:38): Lilo and Stitch
• (2:35:50): The Most Important Thing

All links and references and full transcript available at dialectic.fm/anjan-katta.

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