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22: Nadia Asparouhova - Ideas that Infect
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-asparouhovaTimestamps:1:31: Why Ideas Matter9:33: The Last 10 Years of the Internet and Attention Collapse17:07: How The Internet Caused Attention Collapse19:59: Private Coordination in Public Spaces24:01: Legibility and Illegibility as a Tactic28:28: Ideas Are Not Created Nor Discovered; They Infect Us35:17: Defining Antimemes42:00: Ideological Black Holes: Supermemes49:13: Engaging in the Public Square vs. Opting Out54:16: Truth Tellers who Can Bring Anti-Memetic Ideas to Light1:05:06: Champions, or the Great Apostle Theory1:10:57: Institutions, Ideologies, and Movements1:24:51: Attention1:31:30: Jhanas1:38:42: Writing a Book1:46:19: Connecting the Dots in Reverse1:50:29: Lightning Round: Fighting (or Working With) Human Nature, Software as Passion Project, Democracy, Space Away from the Center of ThingsDialectic with Jackson Dahl is available on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube
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21: Geoffrey Litt: Software You Can Shape
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---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.---Timestamps2:12: Agency in a Digital World and Geoffrey's Creative Medium: Software12:17: Intro to Malleable Software20:42: "Popping Open the Hood" & The Nightmare Bicycle: A Case for Understanding How Systems Work27:47: Computational Media, Spreadsheets, and Digital Informality34:01: Legos and Home Cooking as Metaphors for Software42:30: Two Types of Malleable Software: Modular-by-Design and Hacking48:35: Hampton50:13: Designing for a Smooth Slope58:20: Unbundling Apps into Environments and Tools1:17:58: 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 Needs1:38:23: A Case for Optimism About Human Agency1:51:09: AI's Impact on Malleable Software1:59:03: Commercial Incentives and Ecosystem Change2:04:17: Research and Ink & Switch2:11:46: ChatGPT as a Muse2:15:34: Working at MUBI and Solving the "Too Many Things to Watch" Problem2:18:27: Japan's Culture of Care2:22:15: Mastery and Variety2:24:34: Joy and Clarity as a Parent2:25:30: Expressing Care Through What we Make
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20: Yancey Strickler - Constellations of Creativity
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.---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.---Timestamps1:41: 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 LifeKey Links & References (all available at dialectic.fm)YOUTH MODE - K-HOLEAdam Curtis on the dangers of self-expression - Yancey Strickler for The Creative IndependentInventing the Individual - Larry SiedentopThe WEIRDest People in the World - Joseph HenrichThe Second Self - Sherry TurkleDolly Parton memeNine Creative Meditations - YanceyThe Cult of Creativity - Samuel Weil FranklinThe Post-Individual - YanceyBentoismThe dark forest theory of the internet - YanceyThe Dark Forest Anthology of the InternetOur Band Could Be Your Life - Michael AzerradIntroducing MetalabelNew Creative Era with Yancey & Joshua CitarellaArtist CorporationsHow to long game - YanceyDialectic with Jackson Dahl is available on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube
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19: Henrik Karlsson - Cultivating a Life that Fits
Full transcript and all links: dialectic.fm/henrik-karlssonHenrik 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.---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.---Timestamps2:36: Self-Cultivation, Introspection, and Larry Gagosian8:46: Writing to Think16:05: 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 Future25:12: Self-Criticism and Kindness to Your Past Self and Ideas28:44: 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 Freedom38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us1:04:16: The Role of Ambitious Goals in the Context of Unfolding1:10:06: Hampton1:11:41: Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible1:26:53: Asking Questions that Push People Past their Cache1:31:12: Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet1:48:55: Ruthless Prioritization and Making Time to Get Better1:57:05: Initial Spark and Connecting with People2:05:58: Collaborating with Henrik's Wife Johanna2:09:46: Living a Barbell Life Inside and Outside of the Computer and Henrik's Scale of Ambition2:16:48: Sacrifice2:18:57: Pseudonymity and Playing with Identities2:20:57: Self-Organizing Systems2:22:51: Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold2:33:13: Writers Who Help Us See Ourselves2:35:13: Writing and Thinking in Swedish vs. English2:37:44: Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves – And Modeling That For OthersJoin the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on Instagram
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18: Tom Morgan - Wisdom in the Woo
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.---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 Games6:04: Curiosity and Complexity: Differentiation and Integration8:12: Entropy & Syntropy: Unpacking Curiosity, Love, and Desire12:34: Emergence and What All the Mystics Point to: Integration15:14: Left Brain & Right Brain: A Primer on McGilchrist's "The Matter with Things"28:58: Hampton30:34: Discovering Your Gifts37:35: Creativity and Sustaining Curiosity43:12: Life Pivots, Especially When You Aren't 2250:24: A Challenge vs. A Grind: When to Keep Going or Try Something Else56:19: Synchronicities1:00:58: Openness and Wisdom1:04:19: 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 Reality1:12:59: "Minimum Viable Woo" and Exploring Out There Topics with a Pragmatic Lens1:16:10: Stories1:18:51: Love, Emergence, and Intelligence Beyond Us1:22:52: A Looming Meta-Crisis, Global Consciousness, and Earth School: Blowing Out the "Woo" Rating1:33:41: Lightning Round: Pseudoscience as the Streisand Effect, Mystics, What Would Rattle Tom’s Worldview Most, Joseph Campbell, Fred Again1:40:41: Tom's Encouragement for His 20 Year Old SelfSelect LinksThinking the Unthinkable - TomExploring Gurdjieff's Mysteries - TomA Transformational Heresy? (Syntropy) - TomThe Matter With Things - Iain McGilchristTest Your Network - TomOur Unspoken Future - TomFred again.. Boiler Room: LondonTranscript and all references linked at https://dialectic.fm/tom-morgan.Dialectic with Jackson Dahl is available on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube
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