Dialectic

Nicholas Thompson (Website, X, LinkedIn, Wikipedia) is the CEO of The Atlantic, an elite distance runner, and the author of The Running Ground—a memoir about his father, his life, and the sport of running. Full transcript and all links at 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 and editor of newyorker.com. He also co-founded The Atavist, wrote The Hawk and The Dove, and is a prolific interviewer, including his latest series, The Most Interesting Thing in AI. Nick is also the American record holder in the 50K, which he re-broke 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) things I’ve read in ages. Caity Weaver on The Best Free Restaurant Bread in America. Long live long form writing.

-

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

1:17 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 - Nick Thompson


Why I Run (excerpt from Running Ground) - Nick Thompson for The Atlantic


Not Fade Away book - by Laurence Shames and Peter Barton

Nick Thompson - Timeless (With Guarav Ahuja)


Writer Evan Ratliff Tried to Vanish: Here's What Happened (Wired)

John W. Gardner — "Personal Renewal" Speech


Will the Humanities Survive Artificial Intelligence? - D. Graham Burnett for The New Yorker

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

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

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

Transcript and all linked references: https://dialectic.fm/henrik-2

Henrik Karlsson (Substack, X) is a writer and essayist. His newsletter, Escaping Flatland, explores attention, agency, relationships, and the inner life of making things. He is one of my favorite essayists, and I spoke to him previously on Dialectic 19: Cultivating a Life that Fits in Spring 2025. We met again in Copenhagen, this time on video.

Our first conversation focused on designing your life iteratively and relationships. This time is about the messiness of creativity and problem-solving. We circle a central theme of navigating through the woods of confusion when you are—and must necessarily be to grow—lost, and trusting yourself to reach clarity on the other side. Henrik walks us through how he (and so many of his favorite artists and thinkers, from Brian Eno to Charles Darwin to Ingmar Bergman) smashes apart his mental models in pursuit of seeing things more clearly. Or at the very least, offering up something new.

He also challenges my praise of boredom, describes how a ballerina finding balance in her body mirrors what creatives must do, likens desire to the energetic discovery of wandering (or dérive, like past guest Cyan Banister has spoken about), explains why the best art is like a Jenga tower, and reflects on what he believes in; Henrik’s humanity is on display. He challenged me to think much more ambitiously about the risks I take, the ways I am holding on to faulty models of reality, and how living richly is simply a matter of perspective.

-

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.

Timestamps:

(00:00) Opening Highlights

(01:28) Intro to Henrik

(04:05) Notion

(05:58) Begin: Attention, Boredom, Predictability, Aliveness, and Dérive

(14:52) Confusion and Clarity: Mental Balance, Breaking Mental Models, and Making It Through the Woods

(31:37) Henrik's Notebooks, Personal Constraints

(40:54) Introspection as Subject, Not Object: Nick Cave, Rick Rubin, and Attending Outward

(46:56) Creative Risks, Constraints, and the Labyrinth: Eno, Von Trier, Cage, and Herzog

(1:03:47) Agency, The Right Kind of Risk, and What Else Is Possible

(1:23:29) Desire: Trusting Excitement and "Galloping Down the Street"

(1:30:44) Why Good Ideas Come from the Edges and Keeping the Space to Sit in Your Ideas

(1:44:58) Physical Space and Isolation

(1:51:19) Jenga Towers: Why Great Art Has Space and Spits You Back Out

(2:01:30) Conviction, Belief, Navigating Murkiness with Firmness and Openness

(2:15:54) Short Essays and How Reading Is Like Running

(2:22:27) What Love Is Like and Befriend Those We Read

(2:29:18) Grandfather Nils and a Final Reminder

(2:40:49) Thanks Again to Notion