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Dialectic

Jackson Dahl

Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.


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  • 21 episodes
  • Avg 2 hr 2 min
  • English

Episodes 21

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  • Tuesday · 26 min

    Independent Study: Art is For Seeing Evil by Agnes Callard (Essay)

    “Art is For Seeing Evil” was published by Agnes Callard for The Point Magazine on July 15, 2022. My thanks to Agnes and The Point for permission to share this audio version of her essay on Dialectic’s feed. https://thepointmag.com/examined-life/art-is-for-seeing-evil/ Agnes Callard (UChicago, Substack, X, Wikipedia) is a professor of philosophy at The University of Chicago, focused primarily on ancient philosophy and ethics. She also writes for The Point, The New York Times, and more. I particularly enjoyed her recent conversation with Derek Thompson on her theory of the “uni-context.” This essay was shared with me by Nan Ransohoff, (Ep. 51). I hope you enjoy it!

  • #44
    April 20 · 2 hr 50 min

    44: Jared Weinstein - Within Earshot, Out of Camera Shot

    Jared Weinstein (LinkedIn, X) is an investor, advisor, civic leader, and founder of Overton. This is his first interview. Full transcript and all links at dialectic.fm/jared-weinstein. Jared spent his twenties in the George W. Bush White House, starting as a scheduling intern and rising to become the President's personal aide. He went on to Stanford GSB, consulted for Palantir in its early days, and was a founding partner of Thrive Capital in NYC, helping build it into one of the most respected venture firms in the world over eleven years. After leaving Thrive in 2022, Jared returned to Birmingham to focus on Overton, where he invests in local founders, leads civic initiatives including Small Magic — an early childhood language development program — and works to make his hometown the best version of itself. He also continues to invest in startups, serve on boards, and seed and advise new investors. By his own words, he is busier than ever. Despite his very serious resume, anyone who knows Jared will tell you that he radiates humanity. He has spent his career amplifying people and helping them become the best version of themselves. We trace the arc of his career, talk about what it's really like inside the Oval Office, what he admires about the President, and the unlikely pivots that led him beyond a prodigious start. We also discuss what he and Josh got right at Thrive in the early days, how high stakes environments can be psychologically safe, and how to support incredibly ambitious people. Then we talk about his theory of change for Birmingham, the work he is doing now, and his reflections on where he's been and what he'd like to be known for. I hope this conversation gives you a model for what it looks like to bring your full humanity into high-stakes work and inspires you to commit yourself to the people, institutions, and communities you believe in. - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic. - Timestamps 00:00 - Opening Highlights 01:40 - Intro to Jared 03:32 - Thanks to Notion 04:38 - Start: Being a "Friend" and Bringing Humanity to Serious Work 10:55 - From Duke to the West Wing 31:45 - Riding Shotgun with President Bush 59:27 - Starting Over Out West: Post-WH, Stanford, and Palantir 1:16:05 - Meeting Josh Kushner and Building Thrive Capital 1:44:37 - Founders, Humility, and the Three-Body Problem of Ego, Ambition, and Impact 2:06:41 - Leaving Thrive, Coming Home to Birmingham, and Overton 2:32:40 - Busier Than Ever: Mentors, Life in Acts, and What You Hope to Be Known For 2:49:11 - Thanks Again to Notion

  • #43
    April 7 · 1 hr 48 min

    43: Mario Gabriele - Reality is Story-Shaped

    All links and transcript at dialectic.fm/mario-gabriele Mario Gabriele (X) is a writer, investor, and analyst. He is founder of The Generalist and Partner at Hummingbird. He aims to bring the rigor of investment analysis with writing quality and style that is closer to the New Yorker. His profiles, deep dives, and briefings are amongst the highest quality writing in the technology business, and he interviews practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled Microsoft’s Satya Nadella. I spoke to Mario about stories and the truths they hold or reveal. He is a writer first, and it shows in his prose, style, and depth. We also discussed the evolution of The Generalist’s content and business model, both of which he has experimented with ruthlessly. The subscription counts 160,000+ readers / listeners and is currently ranked as the #7 bestseller in Substack’s business rankings. He is also an investor focused on the technology world’s heroes: founders. Hummingbird, which he joined earlier this year, is known for its obsessive approach to understanding the minds, motivations, and worlds of the entrepreneurs it backs. We dive into the under-discussed elements that shape world-beaters, including the notion that ambition almost always comes from some level of pain. Across the conversation, we talk about how authenticity and evolution run across his career, and how he is at peace as someone who doesn’t know exactly who he is becoming. That generalist orientation continues to produce unlikely paths that surprise him. I hope this conversation inspires you to take stories seriously, to look for what's true beneath the polished surface, and to trust paths you didn't plan for. Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic. Timestamps: (0:00) Opening Highlights (1:13) Intro to Mario (2:49) Thanks to Notion (3:58) Start: Stories, Truth, Writing, and the Story Beneath the Story (23:39) Failure, Authenticity, Comparative Advantage, and The Most Annoying Aphorism in the World (35:55) The Generalist's Style (45:20) Process, Goals, Vision, Experimentation, and Business Models (57:52) Investing: Energy, First Checks, Notecard-level Clarity, and Peter Thiel (1:07:46) Understanding Founders, Motivation, Good and Bad Fuel, and True Ambition (1:17:47) Hummingbird: Seeing the World as it Actually Is and How Stories Reveal Truth, Linguistics, Observation, Deciding to Join, and Evolution (1:29:32) Motivation, Raising the Bar, Ongoing Learning and Teachability, Status, Unlearning, Generous Products, and The Reward of Not Knowing (1:47:15) Thanks Again to Notion

  • #42
    March 30 · 2 hr 19 min

    42: Celine Nguyen - Nurturing Your Mind in Public

    All links and transcript available at dialectic.fm/celine-nguyen Celine Nguyen (Website, Substack, X) is a writer, software designer at Watershed, and literary critic. She writes personal canon, a newsletter about literature, design, art, and technology that has grown to tens of thousands of subscribers. She has also written for The Atlantic, Asterisk Magazine, and more. I discovered Celine with her reflection on two years of writing her newsletter, where she made the case for living a life of the mind, reading great things, and writing online: "After 2 years, I’m convinced that reading and writing are the most dignified and worthy activities that anyone can do—and, in fact, are activities that everyone should do." She also has written viral essays on research as a leisure activity and a case for reading Marcel Proust’s 3,000 page novel, In Search of Lost Time. In another favorite, she critically analyzes the mechanics of how great writers begin. Celine makes intellectual life and very serious books feel accessible and exciting rather than obligatory. We spoke about much of her writing, taking your intellectual growth seriously outside of academia, and how she has become an influencer in a good way. She believes you can expand the market for what you love, and her success is evidence that there is a market for more than the low-hanging fruit that dominates much of the internet. Celine sees reading and writing through the lens of becoming, and I was inspired to raise my own bar. I hope you can say the same. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic, and check out their latest round of updates here. --- Timestamps: (0:00) Opening Highlights (1:35) Intro to Celine (4:25) Thanks to Notion (6:18) Start: Pursuing a Life of the Mind, Personal Curriculum, and Contextualizing the Present in History (24:53) Research as a Leisure, Self-Cultivation, and Calibrating Rigor (39:59) Effectiveness, Tools & Process, and Letting Output Drive Your Learning (59:35) Parasocially Influencing People to Do Good Things (Like Reading and Writing) (1:09:39) Drawing the Reader in and Expanding the Market for What You Love (and for Proust) (1:24:07) Aspiration, Posing, and Pretending Your Way into Enthusiasm (1:34:37) Preparation is Not Progress (1:46:07) Copying, Writing Process, Mechanics, and Design (1:57:25) Commitment, Finishing, Substack, Life Extension and Closing (2:18:31) Thanks Again to Notion

  • March 15 · 34 min

    Independent Study: Body Futurism by Toby Shorin (Essay)

    A new experiment: I thought it would be fun to share audio versions of essays or writing from past or future Dialectic guests. Toby Shorin (ep. 7: The Shapes of Culture) recently published 'Body Futurism,' a piece based on a talk I heard him give in 2024 and that I loved. You can read this piece at https://writing.tobyshorin.com/body-futurism/. It is provocative and feels increasingly prescient. Toby suggests that we must return to the body—and not just bodies in theory but quite literally your, my, our physical bodies, as the starting point for how we think about what is good for how we live and how we design and improve our societies. It was published Feb 25, 2026. I'm calling this format Independent Study. You can think of it as curated audiobook versions of internet writing. We'll see if I do more of these, and feedback is welcome. But let me know what you think!

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