11: Eugene Wei - Amusing Each Other to Death
Eugene Wei is a writer, product thinker, and cultural observer best known for his essays on technology, media, and social networks, including “Status as a Service”, “Invisible asymptotes”, and “TikTok and the Sorting Hat.” 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, TikTok's Impact - (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, Luigi Mangione, Death of Community - (1:03:01): Speculation Culture and Playing to the Power Law - (1:08:08): NBA, NFL, Netflix, Power Laws, and Distraction-Friendly Viewing - (1:15:55): Playing for Attention: the Only Goal - (1:18:43): Video and Image vs. Text - (1:20:57): The Subconscious of American Culture and the Decline of Community According - (1:32:31): Terminally Online Culture, Role Models, Evolving Search for Meaning - (1:45:23): Friction and the Internet's Impact on Communities - (1:50:50): AI, "The Most Human Human" and Creativity - (1:56:38): Lighting section: Invisible Asymptotes for Social Media and Eugene, and Writing - (2:02:08): Beginner's Mindset, Film School, What Technologists Could Learn from Filmmakers - (2:06:40): What Idea from a Book Would Be Most Compelling to "Transmute" into an Audiovisual Medium? - (2:08:56): Bezos and Removing Friction - (2:11:09): Left Brain vs. Right Brain, Engineering Problems vs. Human Problems - (2:15:07): Why Film is Meaningful and a Recommendation Episode transcript: https://bit.ly/DLCT11
8: Steph Ango - Tools for Amplifying Our Light
Steph Ango aka Kepano (Website, X) is a designer, writer, entrepreneur,and toolmaker, best known as the CEO of Obsidian, a powerful and flexible writing and thinking tool. 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 is consistent constraint Buy wisely Stadium of selves What can we remove? File over app Obsidian Manifesto In good hands Pain is information Quality software deserves your hard‑earned cash Don't delegate understanding Nibble and your appetite will grow A little bit every day Caloric energy is precious Erewhon by Samuel Butler Earth is becoming sentient Agents of chaos Concise explanations accelerate progress Always learning, always teaching Six definitions of love 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
7: Toby Shorin - The Shapes of Culture
Toby Shorin (Website, Blog, X) is a researcher, writer, consultant, and cultural anthropologist for the internet era. 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. 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
6: Chris Paik - Intentionally in Search of the New
Chris Paik is a General Partner and Co-founder of Pace Capital, a Venture Capital firm in New York City. 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
5: Tina He - Internet Citizen and Philosopher in Action
Tina He (Site, X, Newsletter) is a product designer, entrepreneur, writer, and amateur philosopher. She is a product lead at Coinbase, where she works on developer tools for its network Base. She joined Coinbase through the acquisition of her company, Station Labs. 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 Photo: Eugene Wei
4: Ava - Alive in Writing and in Love
Ava is one of my favorite writers. She writes full-time for her Substack, Bookbear Express and focuses on love, friendship, emotions, culture, and psychology. 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
3: Dan Romero - Why Information Should Flow on Protocols
Dan Romero (Farcaster, X, Website) is the CEO and co-founder of Farcaster, an open Twitter/X-like social network protocol built on blockchain rails. 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
2: Michael Dempsey - The Craft of Investing in the Future
Michael Dempsey (Website, X) is an investor, writer, technologist, and Managing Partner of Compound, an early-stage, thesis-driven, research-centric investment firm. 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
1: Jason Liu - The Freedom in Being Nobody
Jason Liu is a technologist, consultant, teacher, and friend. 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
