47: Paul Scherer - A Friend That Brings Us Closer

47: Paul Scherer - A Friend That Brings Us Closer

Paul Scherer (X [https://x.com/paulscherer], LinkedIn [https://www.linkedin.com/in/pescherer/]) is the founder of Eigen [https://teameigen.com/] (check out their beautiful website), where he’s building a mutual friend: an AI that brings people closer together and helps us belong. Paul grew up in a small town outside of Frankfurt, Germany, and dropped out of high school at seventeen to work on startups, including Augment [https://augment.org/]. He recently raised $15M from Benchmark, with legendary partner Peter Fenton comparing him to [https://x.com/peterfenton/status/2044817308343005692?s=20] the founders of Facebook, Twitter, Instagram, and Snapchat. I was introduced to him by Notion co-founder Akshay Kothari [https://x.com/akothari], who is an angel investor in Eigen. Dialectic guest [https://dialectic.fm/brie-wolfson] Brie Wolfson [https://x.com/zebriez] has also been working with Paul [https://earlydaysbymerlin.substack.com/p/meeting-eigen], so I wanted to see what all the fuss was about, and why so many people I respect were so enamored with a kid who has yet to publicly launch a product. We start with Paul’s central influence: Michael Ende’s children’s novel, Momo [https://www.goodreads.com/book/show/1408839], and the little girl who reminds a village to be present in the face of Time Thieves quietly pushing them to be more efficient. Then we talk about how even though the internet has shaped both of our lives and relationships, it increasingly feels that social media is making us feel both more connected and more alone. Paul explains what they are working on at Eigen, why we need an (AI) mutual friend, why it should be a single “person,” and why it feels less like engineering and more like parenting or growing someone/thing you don’t have complete control over. I also ask Paul about the pressures and psychology around being “blessed” by Silicon Valley’s powers that be, and why authenticity, or something like it, is in short supply. I hope you are inspired to be courageous in your convictions, even if they are strange, and to listen to the voice inside that so many of us stop listening to in adulthood. All links available at dialectic.fm/paul-scherer [https://dialectic.fm/paul-scherer] - Dialectic is presented by Notion [https://notion.com/dialectic]. Notion is an AI-powered connected workspace where teams think together [https://x.com/ivanhzhao/status/2038670159259619644?s=20] and create their best work. Learn more about Notion’s new developer platform and workers here [https://www.notion.com/product/dev]. Inside Notion by Brie Wolfson & Camille Ricketts for Colossus [https://colossus.com/article/inside-notion/]. You can learn more at notion.com/dialectic [http://notion.com/dialectic]. Timestamps: * (0:00) Opening Highlights * (1:13) Intro to Paul * (2:33) Thanks to Notion * (3:28) Start: 'Momo', Presence, Friendship, and Time * (11:10) How the Internet Connects Us and Isolates Us, and Conflating Social and Media * (25:12) A Future Where We Talk to AIs * (33:55) Paul and Eigen are Building a Mutual Friend to Help Us Connect with Other Humans * (48:01) Why Do We Need a Mutual Friend? And Making a Friend We Can Trust * (1:16:53) Belonging, Building the team at Eigen, and Inventor as Outlaw * (1:25:38) Managing the Psychology of Being a Promising Young Founder * (1:36:53) Maintaining a High Bar, Fighting Entropy, and Influences * (1:53:50) Self-belief, Authenticity, Seeing the Water * (2:10:30) Courage, and a Final Question from a Mutual Friend * (2:15:04) Thanks Again to Notion

46: Nicole Seah (Nix) - Loving What is Real

Nicole Seah (X [https://x.com/startingfromnix], Substack [https://www.startingfromnix.com/], LinkedIn [https://www.linkedin.com/in/nicole-seah1/]), aka Nix, is a writer at Starting From Nix [https://www.startingfromnix.com/] and investor at Costanoa Ventures [https://www.costanoa.vc/]. She recently launched New Ontologies [https://www.new-ontologies.com/], where she profiles founders and companies thinking ambitiously about the future. Her first piece is live now, on Ando [https://www.new-ontologies.com/posts/Ando]: the team building a chat platform for the era of agents. Nicole balances identities with poise, moving between the literary and the practical. I spoke to her about different kinds of beauty and how it takes us out of ourselves, Nietzsche’s case for tolerating strangeness, and choosing reality over fantasy. Then we discuss duality and balancing intensity and lightness, and talk through Borges, Hesse, Miyazaki, Alyssa Liu, and Joan Didion. Nicole argues that freedom comes from not collapsing yourself into a single identity. I asked her about the drive behind New Ontologies, her obsession with techne, and Rebecca Solnit's "cosmology of self.” We then skate across a range of ideas, including memory, appetite and desire, and friendship and why other people’s unknowability is part of what makes them wonderful. I hope this conversation inspires you to look for and love what is real, to be patient with and attuned to the multiple people inside you, and to give freely with your creative life. Full transcript and all links and references: dialectic.fm/nix [http://dialectic.fm/nix]. - Dialectic is presented by Notion [https://notion.com/dialectic]. Notion is an AI-powered connected workspace where teams think together [https://x.com/ivanhzhao/status/2038670159259619644?s=20] 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. Inside Notion⁠ [https://colossus.com/article/inside-notion/] by Brie Wolfson & Camille Ricketts for Colossus. You can learn more at notion.com/dialectic [http://notion.com/dialectic]. Timestamps: * 00:00 - Opening Highlights * 01:14 - Intro to Nicole * 02:04 - Thanks to Notion * 03:48 - Start: Beauty — Effort, Attention, Strangeness * 19:59 - Fantasy and Reality * 29:41 - Multiple Identities, Intensity, and Lightness * 49:08 - New Ontologies: Profiling Founders Building the Future * 1:08:57 - Memory, Lineage, and Process * 1:18:41 - Appetite and Honesty * 1:23:47 - Friendship, Proximity, and The Unknowability of the Other * 1:41:18 - Closing Notes: Solitude, Noticing, and Generosity * 1:53:40 - Thanks Again to Notion

45: Nicholas Thompson - A Life of Long Form

Nicholas Thompson [https://www.notion.so/LINK] (Website [https://www.nickthompson.com/], X [https://x.com/nxthompson], LinkedIn [https://www.linkedin.com/in/nicholasxthompson], Wikipedia [https://en.wikipedia.org/wiki/Nicholas_Thompson_(editor)]) is the CEO of The Atlantic [https://www.theatlantic.com/], an elite distance runner, and the author of The Running Ground [https://goodreads.com/book/show/224082600]—a memoir about his father, his life, and the sport of running. Full transcript and all links at dialectic.fm/nick-thompson [dialectic.fm/nick-thompson]. Nick has led The Atlantic to tremendous subscriber growth and profitability since joining the then-money losing publication in early 2021. He was previously editor-in-chief of WIRED [https://www.wired.com/] and editor of newyorker.com [https://www.newyorker.com/]. He also co-founded The Atavist [https://magazine.atavist.com/], wrote The Hawk and The Dove [https://www.goodreads.com/book/show/6460337-the-hawk-and-the-dove?from_search=true&from_srp=true&qid=3IQzWHIIn6&rank=4], and is a prolific interviewer, including his latest series, The Most Interesting Thing in AI [https://www.youtube.com/@NicholasThompson/videos]. Nick is also the American record holder in the 50K, which he re-broke [https://x.com/nxthompson/status/2043314323817148760?s=20] two days after we recorded this conversation (Exhales). We talked about the future of words in the age of AI, what makes a journalist, why legacy media institutions like The Atlantic are worth fighting for, and what great editing and coaching have in common. Then we turned to running and life: the small tailwinds that compound beyond what we can imagine, Nick’s trajectory—through a prodigious start, early career failure and African kidnapping, cancer at 30, and wild success since—to name a few beats, the trials and blessings of inheritance, and the versions of himself he may no longer have time to find. To close, Nick honors Scott Thompson’s memory by sharing how we might all be more like him and reflects on what drives aliveness. I hope you are inspired to get started, feel the wind at your back, clear unexpected hurdles, savor great words, raise your bar beyond what is reasonable, be grateful for those who came before and pay it forward to those who are next, and remember that there is always more waiting—for you, for me, for us. P.S. It’s unrelated to this conversation, but please read The Atlantic’s latest cover story and one of my favorite (and funniest [https://x.com/jacksondahl/status/2045517778061594904?s=20]) things I’ve read in ages. Caity Weaver on The Best Free Restaurant Bread in America [https://www.theatlantic.com/magazine/2026/05/best-free-restaurant-bread-america/686582/?gift=DSG3Tuza1E1plW5tLvZKU4CmLYLSUSjfOxVxXRJ-YKY]. Long live long form writing. - Dialectic is presented by Notion [https://notion.com/dialectic]. Notion is an AI-powered connected workspace where teams think together [https://x.com/ivanhzhao/status/2038670159259619644?s=20] 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 [http://notion.com/dialectic]. Timestamps: * 0:00 Opening Highlights * 1:17 Intro to Nick * 2:24 Thanks to Notion * 3:30 Start: Words, Reading, and Writing in an Automated World * 18:39 Why Stories Matter and What Makes a Journalist * 28:22 Media Institutions, The Atlantic, Democracy, Tech, and Power * 44:21 Retaining Great Writers and The Virtues of Editors (and Coaches) * 57:44 Magazines and America * 1:05:57 Running, Motivation, Momentum, and Tailwinds * 1:16:08 Aging, Fathers and Sons, Inheritance, and a Mother's Grace * 1:31:00 Merging Machine-like Discipline and Wild Curiosity, The Boat that Never Touched Water, and Who We Might Still Become * 1:44:11 Gratitude, Stalin's Daughter, Scott Thompson's Verve, and Feeling Most Alive * 1:52:40 Closing and Thanks Again to Notion Key Links: * The Running Ground [https://www.amazon.com/Running-Ground-Father-Simplest-Sports/dp/0593244125/ref=sr_1_1?dib=eyJ2IjoiMSJ9.43iOd_n8pEyZxwdi6f5hNA.ctqPLi4gdbBcgp8_qFN1NkTZUm2nWCIgoDLFyUfbyws&dib_tag=se&keywords=nick+thompson+running+book+the+atlantic&qid=1777131862&sr=8-1] - Nick Thompson * Why I Run (excerpt from Running Ground) [https://www.theatlantic.com/magazine/archive/2025/12/the-running-ground-memoir/684633/] - Nick Thompson for The Atlantic * Not Fade Away book [https://www.goodreads.com/book/show/137554.Not_Fade_Away] - by Laurence Shames and Peter Barton * Nick Thompson - Timeless (With Guarav Ahuja) [https://www.timelesspartners.com/journal/conversations/nicholas-thompson?ref=thediff.co] * Writer Evan Ratliff Tried to Vanish: Here's What Happened [https://www.wired.com/2009/11/ff-vanish2/] (Wired) * John W. Gardner — "Personal Renewal" Speech [https://www.pbs.org/johngardner/sections/writings_speech_1.html] * Will the Humanities Survive Artificial Intelligence? [https://www.newyorker.com/culture/the-weekend-essay/will-the-humanities-survive-artificial-intelligence] - D. Graham Burnett for The New Yorker

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

Jared Weinstein (LinkedIn [https://www.linkedin.com/in/jared-weinstein-3b22b538/], X [https://x.com/JaredBWeinstein]) is an investor, advisor, civic leader, and founder of Overton [https://www.overton.ventures/]. This is his first interview. Full transcript and all links at dialectic.fm/jared-weinstein [https://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 [https://en.wikipedia.org/wiki/Palantir] in its early days, and was a founding partner of Thrive Capital [https://www.thrivecap.com/] 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 [https://www.overton.ventures/], where he invests in local founders, leads civic initiatives including Small Magic [https://smallmagic.org/] — 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 [https://notion.com/dialectic]. Notion is an AI-powered connected workspace where teams think together [https://x.com/ivanhzhao/status/2038670159259619644?s=20] 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 [http://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: Mario Gabriele - Reality is Story-Shaped

All links and transcript at dialectic.fm/mario-gabriele [https://dialectic.fm/mario-gabriele] Mario Gabriele (X [https://x.com/mariogabriele]) is a writer, investor, and analyst. He is founder of The Generalist [https://www.generalist.com/] and Partner at Hummingbird [https://www.hummingbird.vc/]. 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 [https://www.generalist.com/] practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece [https://www.generalist.com/p/founders-fund-1] on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled [https://www.generalist.com/p/satya-nadella] 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 [https://www.generalist.com/p/infinite-games], 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 [https://notion.com/dialectic]. Notion is an AI-powered connected workspace where teams think together [https://www.notion.so/E43-Mario-Gabriele-Reality-is-Story-Shaped-33346137d588806cb064d9cb32da41e6?pvs=21] 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 [http://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