Lessons from Impro

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Martin Casado has lived through multiple tech waves—first as a founder, now as a16z’s leading voice on AI and infrastructure. He helped pioneer software-defined networking, then moved from academia to entrepreneurship, and today backs founders building at the frontier of technology as a General Partner at Andreessen Horowitz. In this conversation, Martin shares his unique perspective on the AI boom, his market-first investment philosophy, and why he believes we’re still in the early days of AI’s impact.

We explore:

Martin’s path from game engines and simulations to investing at Andreessen Horowitz
Why Martin believes we’re only in “1996” of the AI boom cycle with years to run before any bubble
Why Martin approaches investing “from markets in” rather than “from companies out”
Why the AI coding market represents a potential $3 trillion opportunity
The transformation of Andreessen Horowitz from a small generalist partnership to a specialized 600-person organization
The concerning dominance of Chinese companies in open source AI models
Why Martin thinks AGI discussions encourage “lazy thinking” and obscure meaningful conversations
How World Labs is solving the 3D representation problem that could unlock robotics, VR, and more

Explore the episode

Timestamps

(00:00) Intro

(04:50) Martin’s early career

(08:35) Martin’s shift from academia to founding his own company during an economic downturn

(11:25) The story behind Martin joining Andreessen Horowitz

(17:55) Ben Horowitz’s most impactful advice

(19:49) How Andreessen Horowitz has transformed since 2016

(22:20) Why product experience matters more than technical prowess for infrastructure investing

(26:26) Martin’s market-first investment philosophy

(28:39) Andreessen Horowitz’s framework for assessing founders and startups

(33:14) Why Martin thinks Hock Tan may be the best CEO today

(35:18) The controversy around non-consensus investing in early stages

(38:42) Why today’s AI boom reminds Martin of the mid-’90s tech environment

(44:38) How today’s AI boom differs from 2021’s tech bubble

(47:10) Why the promise of AI in organizations remains largely unrealized

(50:29) How Martin uses AI for coding and as a reading thought partner

(52:56) Why Martin doesn’t use AI for writing

(53:24) Martin’s interest in Eisenhower and historical parallels to today

(55:33) Two equally important paths for AI’s future

(58:33) Why Cursor stood out as the leader in AI coding tools

(01:01:14) The lack of inherent defensibility in AI and how to build moats

(01:03:30) World Labs’ mission to transform 2D images into 3D environments

(01:06:42) 3D’s emerging use cases and why the VR market may expand

(01:11:50) Why Martin isn’t an “AGI guy” and how the term erodes conversation quality

(01:14:59) How seeing AI as a continuum creates room for future products and investment

(01:16:28) The security and regulatory challenges of Chinese open-source AI models

(01:19:23) Final meditations

Follow Martin Casado

LinkedIn: https://www.linkedin.com/in/martincasado/

Resources and episode mentions

Subscribe to the show

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Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Palantir’s Weirdest Book Recommendation

2025-10-02 22:43:50

“Some of the best analytical work out there - we learn something new from every post!” — Peter, a paying member

Friends,

In October of last year, former Palantir employee Nabeel Qureshi reflected on his eight-year spell at the defense giant. It is an intriguing peek at the inner workings of a secretive company. Among ruminations about Palantir’s famous “forward-deployed” model and contentious moral alignment was a list of four books the company used to prescribe to every new employee: The Looming Tower, Interviewing Users, Getting Things Done, and Impro.

One of these is not like the other.

The Looming Tower is a natural recommendation for Palantir to make. Lawrence Wright’s work chronicles the rise of Al-Qaeda, culminating in the attacks of September 11th. Likely no book would do a better job of articulating Palantir’s existence and significance.

The second and third books are almost a little disappointing, a harsh critique from someone who has read neither. Palantir’s culture has always seemed almost gratuitously scholarly. Co-founder Peter Thiel is one of the most reliable sources of off-piste texts, responsible for Girard-pilling half of Silicon Valley. CEO Alex Karp presents an even more professorial image, an eruption of wiry, gray hair confessing the philosophy PhD he earned at Goethe University Frankfurt. Seeing these names on the list feels like Slavoj Žižek handing you a dog-eared copy of Rich Dad, Poor Dad with a glowing endorsement.

Still, both are beloved practical texts, and Palantir is a high-velocity profit-making enterprise, not the Cambridge Apostles. And so, here too, there is an obvious logic.

Which brings us to Impro by Keith Johnstone, a book on improvisational theater techniques that most people have never heard of. What is it doing here?

A few months ago, I became fascinated by this question. Why would a vendor to the military ask its new recruits to study the ponderings of a former associate director of London’s Royal Court Theatre? What possible utility could it possess?

Every week or so, these questions would reappear in my mind like a troop of wasps assaulting a picnic. The downside of focus is that you can bat away these intrusions for quite a while before you realize: Oh, I can just figure this out.

And so, earlier this summer, I bought a copy of Impro and read it. It has stayed with me so fully that a couple of weeks ago, I re-read it with a pen in hand to convey its primary insights to all of you. As you will see, it is a special book with lessons for people across functions and professions. Without exaggeration, it has changed not only how I view investing and building, but every interaction. Though I hope this piece will give you a deep appreciation of Johnstone’s theories, I heartily recommend reading the full book.

50 game-changing startups – all in one place.

A few weeks ago we released the 2025 edition of the Future 50, a database featuring the world’s highest-potential startups, supported by our friends at Brex.

The Future 50 is the result of months of collecting nominations from leading VCs, researching different companies, and reviewing private data. You won’t want to miss it. Here’s a sneak peek of the startups you’ll hear about:

The Latin American super-app processing 3% of a country’s GDP
The “AI mirror” poised to change the fashion industry
The crypto company that grew 293% over the last year
The European robotics firm bringing AI to the factory floor

…and 46 others. Each company is accompanied by a detailed description and clear rationale of why we think you should have it on your radar.

Check it out here

Lessons from Impro

An introduction

Before we get to Impro’s lessons, let us set the stage.

Published in 1979, Impro details the philosophies of Keith Johnstone, an English playwright, director, and educator. It draws on his experiences teaching in elementary schools, at the Royal Court Theatre, and at his own theater company, the Loose Moose in Calgary. It runs a little over 200 pages, and is split between five sections: “Notes on Myself,” “Status,” “Spontaneity,” “Narrative Skills,” and “Masks and Trance.” Though some sections build on each other, several feel quite self-contained, more like a separate essay.

For the layperson, not all of these sections are of equal interest. As you’ll see, much of our discussion will focus on questions of status – the heart of Johnstone’s text. Meanwhile, we will make no direct mention of masks. Performers might find this final, 70-page tract valuable (and anthropologists will enjoy Johnstone’s cross-cultural observations), but it is less relevant beyond that.

Throughout Impro, some themes recur: the inherent “competition” in social interactions, the stultifying qualities of traditional education, how ego impedes originality, and the malleability of imagination. We will delve into all of these, and more, but I share these to give a sense of the kind of text we’re entering into. How does your posture influence how others perceive you? What are the necessary ingredients of a good story? Why does traditional school crush artistry? How can you trick someone into being creative? These are the matters of interest in this text.

Every interaction implies a status

If there is one thing to take away from Impro, this is it: status transactions occur everywhere, all the time, and are unavoidable.

While teaching improvisational theater at the Royal Court, Johnstone found his actors struggling to speak naturally. He tried various techniques before landing on his “status transactions.” Actors in a scene were instructed to set their status a bit above or below their scene partner’s. Johnstone asked them to do so as minimally as possible. As he tells it, the impact was immediate:

“[T]he work was transformed,” Johnstone writes. “The scenes became ‘authentic’ and actors seemed marvellously observant. Suddenly we understood that every inflection and movement implies a status, and that no action is due to chance, or really ‘motiveless.’ It was hysterically funny, but at the same time very alarming. All our secret maneuverings were exposed.”

If transactions are so omnipresent, why don’t we notice them more often? In Johnstone’s view, social etiquette “forbids” us from seeing these minor machinations, meaning that we only notice them when in direct conflict.

People play high or low status

It is not possible to be “status-neutral.” In every interaction, you – and those around you – are either playing high or low status. The inflection of someone’s voice, the volume of their speech, the movement of their hands, and the stories they choose to tell about themselves – all contribute to the status they are playing.

How do people play high status? Johnstone provides examples, gleaned from exercises with his students:

Holding eye contact. Actors who do so report feelings of power. It can also feel high status to break eye contact first, provided one does not look back immediately afterward.
Holding your head still while speaking. According to Johnstone, this creates an immediately appreciable difference that others find hard to pinpoint.
Introducing a long pause in your speech. When you start talking, introducing a long ‘errr’ reportedly contributed to high status affect. By doing so, the speaker conveys that others must wait for them. “The long ‘er’ says, ‘Don’t interrupt me, even though I haven’t thought what to say yet.’”

The famous “business card” scene in American Psycho is a fantastic example of what it looks like when multiple people compete to play the highest possible status.

From these examples, you can easily deduce what playing low status looks like:

Breaking eye contact. Specifically, it feels low status when you break eye contact and look back almost immediately. There is a certain insecurity or instability displayed that creates a sense of feebleness.
Moving your head around while speaking. Some people move their head wildly as they speak and struggle to hold it still. If one is playing low status, this is fine, but it can become an issue when the actor must play high status. “You can talk and waggle your head about if you play the gravedigger, but not if you play Hamlet.”
Introducing a short pause in your speech. If you start your speech with a short ‘er,’ you signal weakness. You demonstrate that you don’t know what you’re going to say and invite others to interrupt.

These represent a tiny sampling. Pay attention, and you’ll find status interactions to add to your personal taxonomy everywhere: the way someone reaches for the check, how they sit in the back of an Uber, or queue at the grocery store.

We play status to objects and space

We don’t simply play status with one another but to our surroundings and objects within it. As Johnstone notes, “If you enter an empty waiting-room you can play high or low status to the furniture,” Johnstone notes. “A king may play low status to a subject, but not to his palace.” A high-status person may happily take a couch’s cushy corner seat while a low-status person is squashed in the middle.

The way we use our own “space” influences the status we’re playing, too. Johnstone recounts watching actors move across the stage and imagining force fields around each of them. As they interacted, space from one actor might flow into another, or in a different direction altogether. For Johnstone, “the best actors pump space out and suck it in,” and when this is done in concordance with their other movements, it helps “the audience feel ‘at one’ with the play.”

The high-status player stands with shoulders rolled back and a wide stance to let their space flow into another person. Johnstone gives the example of a sergeant major screaming into a subordinate’s face – their energy flows unfettered into the low-status soldier.

Meanwhile, the low-status player stops their space from flowing into anyone else. They crouch or kneel or cross their arms – defending themselves and blocking direct confrontation.

The way someone sits in a chair or leans against a bus stop conveys status just as readily as words and gestures.

Becoming a status expert

Before you begin staring down strangers or peppering your speeches with interminable ‘errrrs,’ it is neither “bad” to be low status nor “good” to be high status. One should aim to become what Johnstone calls a “status expert.” This is someone capable of modulating their status up and down depending on what the situation demands and the effect they are hoping to solicit.

A status expert understands that playing low status can be invaluable. When Johnstone meets a new group of students, for example, they sit in chairs, but he will sit on the floor. Immediately, he plays low status to them physically. He exaggerates this further by telling them that they should blame him if any of their improvised scenes go wrong, since he is the teacher. Though this is, on its surface, low status, it actually elevates Johnstone. Only someone very confident could take on this level of responsibility. As he works through this initial speech, students often slide off their chairs and join him on the floor. As Johnstone notes, “I have already changed the group profoundly because failure is suddenly not so frightening anymore.”

It’s easy to imagine how this might be useful in a business environment. A CEO who wants employees to brainstorm creatively will have much better luck if they lower their status rather than raise it. No one writes poetry in front of a firing squad.

Through a more Machiavellian lens, playing low status may divulge useful information to you. If you cast yourself as unthreatening and hapless, perhaps a competitor will tell you something useful.

Playing low status may be tactically shrewd in situations where all hope seems lost. Johnstone gives a rather brutal example to emphasize his point. Congolese soldiers captured two journalists. After shooting the first, the second began to weep. Rather than killing him, the soldiers laughed at his plight and let him go. “It was more satisfying to see the white man cry than to shoot him.” When you find yourself on the wrong end of a lop-sided status transaction, the best move may be this submissive “non-defense.”

Playing high status can be useful when trying to convince others of your competence. By playing high status to investors, a startup founder may make their business appear more real than it truly is. If trying to partner with a much larger organization, displaying high-status behaviors may convince them to collaborate without steamrolling you.

In moments of crisis, legendary CEOs seem to play extremely high status. Elon Musk, Jeff Bezos, and Jensen Huang are all famous for delivering brutal feedback and falling into fits of rage. Perhaps these are simply the most memorable anecdotes and thus get passed on to biographers or emphasized in the editing process. But it seems equally likely that playing high status helps: it minimizes dissent, creates urgency, and implies competence.

Becoming a status expert is not as easy as it sounds. Johnstone believes that all of us have a preferred status we’ve become adept at. If you’ve spent your whole life playing low status, relying on the benevolence of others to achieve your goals, it can feel jarring to suddenly switch roles. Similarly, if you’ve moved with patrician froideur through the world, displaying vulnerability may seem terrifying. To become a true expert, you will need to overcome such fears and experiment.

Friends play status games

If you were to stop reading Impro after 25 pages, the concept of status transactions would feel quite depressing. Does every interaction really have an implied status? Do I play high status to my baby when I feed them a bottle? What about with my partner I express my love for them? Am I acting low status when I confide in a friend? Life begins to feel false and empty when put in such terms.

But Johnstone’s framing is much lighter than this suggests. He would likely argue that, yes, all of these are status transactions of some kind, but that they are collaborative rather than competitive. For Johnstone, entering into status games is not a mark against friendship or intimacy but for it. “[A]quaintances become friends when they agree to play status games together,” he writes. “If I take an acquaintance an early morning cup of tea I might say ‘Did you have a good night?’ or something equally ‘neutral…’ If I take a cup of tea to a friend then I may say ‘Get up, you old cow,’ or ‘Your Highness’s tea,’ pretending to raise or lower status.”

Status is not a prison to be escaped from, but a game to be played.

Status transactions are at the heart of comedy and tragedy

For Johnstone, both comedy and tragedy work through status transactions.

Comedy operates with a status “see-saw,” in which the players see their positions fluctuate. The king and servant decide to change places, and the audience laughs at the interactions that are created. According to Johnstone, comedians are people who purposefully lower their own status, or that of other people. We can immediately recognize these two kinds of performers: the self-deprecating comic that can’t escape their low status (think: Rodney Dangerfield’s “I don’t get no respect” or Larry David’s endless bumbling) or the flamethrower that lowers everyone around them (Don Rickles’ roasts or the smugness of Ricky Gervais).

For us to find a low-status person funny, we cannot have sympathy for their plight, in Johnstone’s opinion. Henri Bergson argued that a man slipping on a banana skin makes us laugh as it shows someone acting “automatically” with a “kind of physical obstinancy.” Johnstone argues that this alone is not enough – if we feel sympathy for the man who falls, it ceases to be funny. Watching an old, infirm man slip on a banana is tragic, not comic. For us to find the scenario humorous, we must know our sympathy is not required.

Tragedy also works through status transactions, specifically, the fall of a high-status person. The king who loses power, for example, or a revolutionary led to the guillotine. In playing these roles, the actor must continue to play high status, even as the character’s actual status disintegrates. If they were to suddenly become a groveling wretch, the audience would not feel the necessary catharsis. “I’ve seen a misguided Faustus writhing on the floor at the end of the play, which is bad for the verse, and pretty ineffective,” Johnstone writes.

We are all storytellers at one time or another, whether that’s with friends in the park or in the boardroom in front of a PowerPoint. As you consider the narrative you hope to spin, consider the status switches sitting beneath it.

To unlock talent, unlearn your education

Johnstone’s education and experience as an elementary school teacher convinced him of the system’s fraudulence. In his view, education tends to ruin talent, not enhance it. Students are dulled by repetitive, moribund lessons that leave them frightful of failure and devoid of creativity. It is for this reason that Johnstone “began to think of children not as immature adults, but of adults as atrophied children.”

In Johnstone’s view, the reactions of an “untutored” person when assessing a film or play are “infinitely superior” to those of a so-called professional. We are taught in school to approach art and literature dispassionately and remotely – examining with faux-objectivity. This is why the expert leans away from the play they’re working on, while the naif leans in.

The American Poet Laureate, Billy Collins, captured this dynamic perfectly in his work, “Introduction to Poetry.” Collins wants readers to “take a poem/and hold it up to the light/like a color slide/or press an ear against its hive.” Instead, “They begin beating it with a hose/to find out what it really means.”

To create great work, Johnstone believes one should avoid learning “how things are done.” When he attempted to learn about the “craft” of playwriting, his work regressed, rather than improved. It’s much better to conceive of solutions from scratch, as the great Stanley Kubrick did. When asked whether it was normal for a director to spend so much time lighting each shot, he replied, “I don’t know. I’ve never seen anyone else light a film.” This dynamic is the key reason why talent seems to come from outside a given field – Johnstone notes that of the British playwrights that emerged in the 1950s, only one had gone to university.

True talent is unselfconscious, and the first step toward unselfconsciousness is unlearning.

For creative work, there are direct lessons here. When embarking on an artistic project, Johnstone would argue that one of the worst things you could do is to study the “craft.” If you want to write a mystery, don’t dissect Agatha Christie. If you hope to paint a sunflower, do not look at Van Gogh. Doing so will curb your creativity, not enhance it.

The more generalizable lesson is that as you go about your work, whatever it may be, consider which parts of it were dictated to you at some point, and which you devised yourself.

Think of creativity as divine inspiration, not self-expression

Interpreting art as a form of self-expression is not only “weird” in Johnstone’s view, but also destructive. The reason an adolescent loses the imaginativeness they displayed in childhood is because they fear grown-ups will read into their creations. As Johnstone explains, a story about being chased down a hole by a spider is innocuous when delivered by an eight-year-old but fraught when coming from a fourteen-year-old. Teachers and parents treat such stories as implicit confessions – indications of sexual frustration or mental abnormalities.

Previous cultures perceived artists as “transmitters” rather than “creators.” Their work was viewed not as an embodiment of their mental or emotional state, but as a message from the divine. According to Johnstone, Eskimo bone-carvers did not try to make a specific shape but to reveal that which was already inside it. Michelangelo classified his work similarly: “I saw the angel in the marble and carved until I set him free.”

As Johnstone explains, this distinction protects the artist. “Once we believe that art is self-expression,” he writes, “then the individual can be criticized not only for his skill or lack of skill, but simply for being what he is.” It is a wonder that anyone is able to create art in such a culture, when one’s very essence is free to dissect.

The way to get people to be creative, then, is to assure them that they are separate from their imaginations. Johnstone has devised many exercises to do exactly that.

When an actor tells him she cannot come up with a story on the spot, no matter how trivial, he asks her to “guess” a story he has concocted instead. She will ask questions to which he will answer “Yes,” “No,” or “Maybe.” What the actor does not realize is that Johnstone has no story in mind and simply answers “Yes” to any questions that end with a vowel. Bit by bit, the actor unfurled a vivid story about a species of insects that devour everything in sight until they grow as large as buildings.

“People who claim to be unimaginative would think up the most astounding stories, so long as they remained convinced that they weren’t responsible for them,” Johnstone writes.

There are countless moments in one’s personal and professional lives when we need to galvanize creativity from those around us. Perhaps we want to while away the time on a long car ride, or devise out-of-distribution ideas for a marketing campaign. If people believe their very self is at stake, it will be nearly impossible to get them to be creative. You must find ways to liberate them from being responsible for their imagination. When you do so, as Johnstone writes, “It’s possible to turn unimaginative people into imaginative people at a moment’s notice.”

For a more interesting life, say “Yes”

Improvisation works through offering, blocking, and accepting.

A player makes an offer to another by asking, “Your name Smith?” If the partner says “No,” they have blocked the offer – and killed the momentum. Any intrigue sparked by the premise has been extinguished, and the first actor “feels fed up.” A block is any action that “prevents the action from developing.”

A more interesting decision is to accept the offer and build on it. From Impro:

ACTOR 1: Your name Smith?
ACTOR 2: Yes.
ACTOR 1: You’re the one who’s been mucking about with my wife then?
ACTOR 2: Very probably
ACTOR 1: Take that you swine.
ACTOR 2: Augh!

The second actor accepts three offers here: that their name is Smith, they’ve been fooling around with the other’s wife, and that they have been attacked by the first actor. They could have blocked any one of these – refusing the name, refuting the allegation, or avoiding the attack – but they didn’t. They helped the action develop and contributed to the premise. Critically, it is possible to accept an offer and act antagonistically.

ACTOR 1: Your name Smith?
ACTOR 2: What if it is, you horrible little man?

Beyond the stage, Johnstone believes that each tends to prefer either accepting or blocking. We favor saying “Yes” or “No” more often. Neither is necessarily wrong. “Those who say ‘Yes’ are rewarded by the adventures they have, and those who say ‘No’ are rewarded by the safety they attain.”

In understanding this, we can choose to make our lives, our peers, and ourselves more interesting.

If your life is dull, you may be blocking too many of the offers you receive. Start saying “Yes” more.

If the people around you are dull, ask yourself how you might be blocking the offers they’re proposing. Do they keep raising intriguing topics only for you to shy away from engaging with them? It’s possible that they are not boring, but that you are inhibiting their imagination.

Lastly, if you find yourself uninspired, assess how this process plays out internally. What are you doing to block yourself and thwart your inner creative talent? “What happens in my classes, if the actors stay with me long enough, is that they learn how their ‘normal’ procedures destroy other people’s talent,” Johnstone writes. “Then, one day they have a flash of satori – they suddenly understand that all the weapons they were using against other people they also use inwardly, against themselves.”

How to be Agentic in the Age of AI | Cate Hall (CEO of Astera)

2025-09-30 20:04:16

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Cate Hall is the CEO of Astera, a private foundation focused on AI risk and frontier technology. Before leading Astera, Cate’s unconventional career path took her from practicing law (including work on Supreme Court briefs) to becoming the world’s top-ranked female poker player in 2016. After overcoming personal struggles with addiction, she co-founded Alvea, a biotech company developing shelf-stable vaccines for pandemic response, before joining Astera. In this conversation, Cate shares insights on human psychology, agency as a learnable skill, and why she believes AI’s biggest risk may be a “soft takeover” in which humans gradually lose independence and meaning.

We explore:

How Cate’s approach to poker focused on reading people rather than pure game theory, and why this contrarian strategy worked
Why people who always try to “play” high status in conversations often have psychological issues
The critical difference between ambition and agency, and why they’re often confused
How LSD helped Cate break out of her career path and discover her own agency
Why Cate believes we need a slowdown in AI development to develop the social technologies to manage it
The challenge of maintaining meaning in human life as AI systems increasingly mediate our experiences
How Astera is using investment as a philanthropic tool to help steer frontier technology development

Explore the episode

Timestamps

(00:00) Introduction to Cate Hall

(03:56) Cate’s role as CEO of Astera

(04:52) Cate’s poker career and focus on live reading

(07:02) The intuitive ‘people radar’ Cate has in identifying exceptional talent

(11:16) Status dynamics in conversations

(16:13) The parallel between poker and startup evolution

(19:18) The German wave in poker and game theory

(24:22) Cate’s legal career and Supreme Court experience

(27:05) The difference between ambition and agency

(29:13) How LSD helped Cate discover her agency

(31:26) Leaving poker and dealing with mental health issues

(34:26) The founding story of Alvea

(38:14) The founding story of Astera

(43:15) Cate’s journey into AI risk

(45:50) The concept of a “soft takeover” and how AI might hollow out human experience

(49:46) The overwhelming challenge of addressing AI risk

(51:20) Astera’s approach to steering technology development

(53:15) Astera’s investment in Last Energy

(54:20) How philanthropy and investing work together at Astera

(57:22) Practical ways to increase personal agency

(1:07:20) Final meditations

Follow Cate Hall

X: https://x.com/catehall

LinkedIn: https://www.linkedin.com/in/cate-hall-9a81a35/

Newsletter: https://usefulfictions.substack.com/

Resources and episode mentions

Books

Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296/
Impro: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178
Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834/
The Righteous Mind: Why Good People Are Divided by Politics and Religion: https://www.amazon.com/Righteous-Mind-Divided-Politics-Religion/dp/0307455777/

People

Jed McCaleb on LinkedIn: https://www.linkedin.com/in/jed-mccaleb-4052a4/
Charlie Carrel on X: https://x.com/charlie_carrel
Seemay Chou on X: https://x.com/seemaychou
Ben Kuhn on X: https://x.com/benkuhn

Other resources

Astera Institute: https://astera.org/
Rounders: https://www.imdb.com/title/tt0128442/
Hummingbird VC: https://www.hummingbird.vc/
Palantir: https://www.palantir.com/
Game of Gold: https://www.imdb.com/title/tt34936977/
Alvea: https://www.alvea.bio/
Reviving Forgotten Technologies: How Airships, Supersonic Flight, and Geothermal Energy Could Transform Our World | Eli Dourado (Head of Strategic Investments at Astera Institute): https://www.generalist.com/p/reviving-forgotten-technologies-eli-dourado
Last Energy: https://www.lastenergy.com/
How to be more agentic: https://usefulfictions.substack.com/p/how-to-be-more-agentic
Staring into the abyss as a core life skill: https://www.benkuhn.net/abyss/

Subscribe to the show

I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Maintaining Human Intelligence in the AI Era | David Krakauer (President of the Santa Fe Institute)

2025-09-23 22:03:59

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David Krakauer is a leading complex systems researcher and the president of the Santa Fe Institute, a unique institution dedicated to studying complex systems across disciplines. In this episode, David challenges conventional wisdom about AI, arguing that large language models pose a more immediate threat to humanity than commonly discussed existential risks—not by destroying us directly, but by eroding our cognitive capabilities through addictive, low-quality information.

We explore:

Why David believes LLMs aren't intelligent at all and how the AI community misunderstands emergence
The three dimensions of intelligence: inference, representation, and strategy—and which one LLMs lack
How AI acts as a "competitive" rather than "complementary" cognitive technology, atrophying our thinking abilities
What makes great minds unique, from analogical reasoning to the cultivation of unconscious creativity
How Cormac McCarthy's approach to knowledge and creativity offers lessons for the AI age
Why David believes the greatest threat from AI isn't existential risk but cognitive atrophy
How to protect your mind against AI's addictive pull and maintain cognitive autonomy

Explore the episode

Timestamps

(00:00) Intro

(04:39) The Santa Fe Institute’s approach to complex systems

(06:45) Murray Gell-Mann’s ‘Odysseus vs. Apollonian’

(10:35) How SFI was shaped by the legacy of Los Alamos

(12:45) Traits David looks for in great minds

(14:43) Cormac McCarthy on naivety and how thoughtful people treat knowledge

(19:24) A simple explanation of complexity science

(22:50) Why vantage point doesn’t matter when studying systems

(24:36) Aesthetic preferences among complexity scientists

(26:07) Films and directors with complexity science themes

(29:57) Why David argues LLMs are not intelligent

(32:10) What’s missing in the study of LLMs

(36:40) The three qualities of intelligence and how LLMs measure up

(42:19) Lessons from "The Glass Bead Game"

(44:00) David’s perspective on reinforcement learning

(45:38) The greatest threat of LLMs: overreliance and the decline of thinking

(47:40) Competitive vs. complementary cognitive artifacts

(51:55) Why exposing yourself to quality ideas matters

(54:00) How to derisk LLM use

(58:32) Cormac McCarthy’s legacy at SFI and beyond

(1:02:40) The Kekulé Problem: cultivating the unconscious

(1:05:01) Why David and McCarthy were inspired by Wittgenstein

(1:09:00) What Cormac McCarthy liked to talk about

(1:12:20) David’s questions to a higher being

(1:14:46) Final meditations

Follow David Krakauer

Website: https://davidckrakauer.com/

Resources and episode mentions

Books

“The Hedgehog and the Fox”: https://www.amazon.com/Hedgehog-Fox-Tolstoys-History-Second/dp/069115600X
The Birds and The Frogs: https://www.amazon.com/Aristophanes-Frogs-Birds/dp/B000QBPUTY
The Glass Bead Game: https://www.amazon.com/Glass-Bead-Game-Magister-Novel/dp/0312278497
Frankenstein: https://www.amazon.com/Frankenstein-Mary-Shelley/dp/0486282112
Blood Meridian: Or the Evening Redness in the West: https://www.amazon.com/Blood-Meridian-Evening-Redness-West/dp/0679728759
Stella Maris: https://www.amazon.com/Stella-Maris-Cormac-McCarthy/dp/0307269000
The Passenger: https://www.amazon.com/Passenger-Cormac-McCarthy/dp/0307268993/
Pale Fire: https://www.amazon.com/Pale-Fire-Vladimir-Nabokov/dp/0679723420
Tractatus Logico-Philosophicus: https://www.amazon.com/Tractatus-Logico-Philosophicus-Routledge-Classics-123/dp/0415254086
Ludwig Wittgenstein: The Duty of Genius: https://www.amazon.com/Ludwig-Wittgenstein-Genius-Ray-Monk/dp/0140159959
Ellmann's Joyce: The Biography of a Masterpiece and Its Maker: https://www.amazon.com/Ellmanns-Joyce-Biography-Masterpiece-Maker/dp/0674248392
Moby Dick: https://www.amazon.com/Moby-Dick-Herman-Melville/dp/1503280780
Hyperobjects: Philosophy and Ecology after the End of the World: https://www.amazon.com/Hyperobjects-Philosophy-Ecology-after-Posthumanities/dp/0816689237
The Anatomy of Melancholy: https://www.amazon.com/Anatomy-Melancholy-Review-Books-Classics/dp/0940322668
The Golden Bough: A Study of Magic and Religion: Volume I: https://www.amazon.com/Golden-Bough-Vol-Study-Religion/dp/1480131466
Three Critiques: https://www.amazon.com/Three-Critiques-3-Set-Practical/dp/0872206297
The World as Will and Representation: https://www.amazon.com/World-Will-Representation-Vol/dp/0486217612/

People

Cormac McCarthy: https://en.wikipedia.org/wiki/Cormac_McCarthy
Murray Gell-Mann: https://en.wikipedia.org/wiki/Murray_Gell-Mann
Archilochus: https://en.wikipedia.org/wiki/Archilochus
Fyodor Dostoevsky: https://en.wikipedia.org/wiki/Fyodor_Dostoevsky
Leo Tolstoy: https://en.wikipedia.org/wiki/Leo_Tolstoy
Aristophanes: https://en.wikipedia.org/wiki/Aristophanes
Hesiod: https://en.wikipedia.org/wiki/Hesiod
Homer: https://en.wikipedia.org/wiki/Homer
Eugene Wigner: https://en.wikipedia.org/wiki/Eugene_Wigner
Leo Szilard: https://en.wikipedia.org/wiki/Leo_Szilard
John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann
Michel de Montaigne: https://en.wikipedia.org/wiki/Michel_de_Montaigne
Melanie Mitchell’s website: https://melaniemitchell.me/
Ingmar Bergman: https://en.wikipedia.org/wiki/Ingmar_Bergman
Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa#Legacy_and_cultural_impact
Andrei Tarkovsky: https://en.wikipedia.org/wiki/Andrei_Tarkovsky
John Henry Holland: https://en.wikipedia.org/wiki/John_Henry_Holland
Christopher Nolan: https://en.wikipedia.org/wiki/Christopher_Nolan
Jonathan Nolan: https://en.wikipedia.org/wiki/Jonathan_Nolan
Henry James: https://en.wikipedia.org/wiki/Henry_James
Vladimir Nabokov: https://en.wikipedia.org/wiki/Vladimir_Nabokov
Frank Lloyd Wright: https://en.wikipedia.org/wiki/Frank_Lloyd_Wright

Other resources

The Santa Fe Institute: https://www.santafe.edu/
The Cormac McCarthy I Know: https://davidckrakauer.com/artifacts/2022-the-cormac-mccarthy-i-know
Michel de Montaigne’s quote: https://www.goodreads.com/quotes/6873908-we-can-be-knowledgeable-with-another-man-s-knowledge-but-we
The Seventh Seal: https://www.imdb.com/title/tt0050976/
Rashomon: https://www.imdb.com/title/tt0042876/
Stalker: https://www.imdb.com/title/tt0079944/
Solaris: https://www.imdb.com/title/tt0069293/
The Exterminating Angel: https://www.imdb.com/title/tt0056732/
2001: A Space Odyssey: https://www.imdb.com/title/tt0062622/
Large Language Models and Emergence: A Complex Systems Perspective: https://ui.adsabs.harvard.edu/abs/2025arXiv250611135K/abstract
Kind of Blue: https://www.amazon.com/Kind-Blue-Miles-Davis/dp/B000002ADT
Why neural net pioneer Geoffrey Hinton is sounding the alarm on AI: https://mitsloan.mit.edu/ideas-made-to-matter/why-neural-net-pioneer-geoffrey-hinton-sounding-alarm-ai
Why the Real Computer Revolution Never Happened | Alan Kay & Anjan Katta: https://www.generalist.com/p/why-the-real-computer-revolution-never-happened
Zettelkasten: https://zettelkasten.de/overview/
ImageNet: https://www.image-net.org/
The Kekulé Problem: https://nautil.us/the-kekul-problem-236574/
Robert Frost’s quote: https://www.goodreads.com/quotes/71609-writing-free-verse-is-like-playing-tennis-with-the-net

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Leading Through a Crisis with Ryan Petersen

2025-09-18 21:48:52

"The Best Venture Firm You've Never Heard Of is the best piece of writing I've ever read online, and I read a lot of stuff. Personally recommend it to all my friends." — Kaan, a paying member

Friends,

No company follows precisely the same path as another. But certain patterns repeat. One is the Napoleonic Return: a CEO leaves the company they have founded – either by choice or force – only to reclaim their position after a period away. After being forced out by Apple’s board in 1985, Steve Jobs spent 12 years in the wilderness, building NeXT, before returning to power. Howard Schulz stepped back from leading Starbucks at the turn of the millennium, reappearing eight years later when the financial crisis roiled the coffee maker. In 2004, Michael Dell passed the reins to his COO before seizing them back three years later.

Few have pulled off the Napoleonic Return quite as quickly as Ryan Petersen. (His only better in this regard is Sam Altman, whose coup lasted a mere five days). In March of 2023, former Amazon exec Dave Clark became the sole CEO of Flexport, taking over from its founder. Just seven months later, he was out.

Much was written about the move at the time, but not since. In today’s final letter with Ryan Petersen, he shares what happened from his perspective, walking through what went wrong, why he needed to return, how he stabilized a flagging organization, and the hard decisions made in the process. It’s an intimate look at the strategic and emotional impact of a founder reclaiming control over their company – invaluable for entrepreneurs and investors.

To hear the full story and unlock the rest of The Generalist’s exclusive interviews, case studies, and databases, join our premium newsletter, Generalist+. You'll get unfettered access to our best work for $22 per month or $220 per year. Level up your investing and operating for the price of a business lunch.

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Mario’s letter

Subject: Leading through crisis
From: Mario Gabriele
To: Ryan Petersen
Date: Monday September 1 2025 at 10:02 AM GMT

Hi Ryan,

I’m sure I’m going to be sending your previous letter to many founders in the years to come. It was full of so many interesting lessons about fundraising, finding talent, and thinking through acquisitions.

I’m especially grateful for the frankness with which you share the challenges Flexport has endured to reach its current position. The more companies and CEOs I study, the more I learn that these moments are not simply commonplace, but inescapable. It seems to be one of the prices you pay in pursuit of greatness.

That brings me to the subject of today’s correspondence: leading through a crisis. Though some of the episodes discussed in our last letter certainly sound troubling, Flexport’s most significant crisis seems to have been the unsuccessful appointment of Dave Clark as CEO, and the associated fallout.

You will need no reminder of the particulars of this story, but I’ll give a brief recap for the benefit of readers. I apologize for having you relive what may not be your favorite period to reflect upon!

Here we go: On June 8, 2022, Flexport announced that Dave Clark would be taking over as CEO starting in September. It was seen as a strong fit given Clark’s 23 years at Amazon, where he’d been pivotal in building out the company’s fulfillment network. He’d ultimately risen to become CEO of Worldwide Consumer.

You had a thoughtful plan for the transition: Clark worked alongside you as co-CEO for six months before he officially took the reins in March 2023. At that point, you moved into an Executive Chairman role, and not long after, you also became a Partner at Founders Fund.

Shortly after the official hand-off, Clark made a few significant changes, acquiring Shopify’s logistics business (including Deliverr) and adding senior executives from his Amazon days, like Teresa Carlson.

He did not last much longer. As the story goes, at least, Clark submitted his resignation on September 5, 2023. Flexport’s board then rejected Clark’s resignation, preferring to fire him for cause the very next day. You stepped back into the CEO role, and the next few days (and weeks) got a bit messy with some back and forth in the press.

I can’t imagine how intense that period was from your perspective. You had to step back into the breach during a period of chaos, stress, and disharmony. You had new employees to win over, and old ones to re-align. I would imagine that you had customers confused by the change, and perhaps a few fractious investors breathing down your neck.

What did it feel like? How did you protect your clarity and decision-making? Given that you’d intended to take a less active role for the foreseeable future, was it difficult to ramp back up as CEO? What was the state of the company that you inherited?

Tactically, what did you prioritize upon your return? Which steps did you take immediately, and which did you have to delay? As much as possible, I’d love to understand what you did to pull the company through this crisis and the lessons you learned from it. Has it changed the way you lead today?

I’m grateful for your willingness to discuss this with me, and I'd like to thank you very much for taking part in this series. I’ve really enjoyed it.

Best,
Mario

PS – Given the omnivorous learning habits you mentioned in our last letter, I wondered if there was one book, or piece in particular, that you refer back to most often?

Ryan’s letter

Subject: Leading through crisis
From: Ryan Petersen
To: Mario Gabriele
Date: Tuesday September 9 2025 at 7:38 PM GMT

Hi Mario,

It was a tough period.

I realized we had to make a change when I started hearing from people at Flexport. There are a lot of people that love this company and want it to succeed, and they weren’t happy with the way things were going under Dave. I started getting dozens and dozens of phone calls and in-person meeting requests from employees wanting to talk to me.

Their concerns went beyond the P&L, which was ultimately the main driver of the board’s decision to change Dave out. The board’s rationale was clear, they said “Hey, you guys have to change direction here. You have to both cut costs and grow.”

That’s a very difficult maneuver. It’s not just about firing people, you have to let the right people go. It’s really hard to do that without the right context on the company and the team. No one has more context than the founder; I’m fused at birth with Flexport. The board wanted someone to do this surgery, and it became clear it had to be me. It actually wasn’t my decision to come back – the board unanimously voted.

By the time that all happened, I’d already spoken to a lot of the employees who had come forward. I’d heard that our quality had fallen off, that we weren’t growing, and that things were going wrong. So I had some context, maybe even before the board.

Dave is a very credible and very certain person. He was also wrong about important parts of the business. But because of that credibility and certainty, it was hard to know he was wrong. Even if you think something’s off, when you talk to him, you allow your anxiety to get tamped down.

Coming back was incredibly hard and incredibly rewarding at the same time. We had to figure out how to cut costs and improve quality simultaneously, get a culture back that had been put through so much change, let customers know that we were going to stick around, and manage a PR disaster.

That last part was a totally unforced error that didn’t need to happen. A former employee made up lies about Dave, which they shared with a reporter. When the reporter told Dave that “someone close to Flexport” had said these things, he thought the company was making things up about him, got mad, and started trashing the company. Suddenly, we had the kind of story the media loves, with people talking shit about each other.

Building Beautiful Homes with Robots: The Future of Construction | Salar al Khafaji (CEO and Founder of Monumental)

2025-09-16 20:03:48

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Salar al Khafaji is the CEO and founder of Monumental, a company building autonomous robots that assemble buildings, starting with its bricklaying system. After selling his previous software company to Palantir, Salar took time to explore big industries ripe for disruption before landing on construction—a sector that represents a significant portion of GDP yet has seen decades of productivity stagnation.

We explore:

Why construction represents a massive opportunity for technological innovation
How Monumental's system of three robots works together to lay bricks autonomously
Why Europe's severe bricklayer shortage has created wages as high as €80/hour
The post-WWII shift away from beautiful architecture and how to bring it back
Why operating as a subcontractor rather than selling robots makes business sense
The challenges of building a hardware startup in Europe's tech ecosystem
How Palantir's "cult-like" culture influenced Monumental's approach to company building
The balance between structure and productive chaos in scaling a startup
Why the best robotics companies solve specific problems rather than building general-purpose machines
How to foster ambition in Europe's startup ecosystem

Explore the episode

Timestamps

(00:00) Introduction to Salar

(04:44) Overview of Monumental’s work and mission

(06:25) Salar’s journey after selling his company to Palantir

(11:46) Stagnation in the construction industry

(14:21) The mental shift from software to hardware entrepreneurship

(16:10) Salar’s funding framework

(18:21) The post-WWII decline in constructing beautiful buildings

(20:23) Choosing bricklaying as the first construction trade to tackle

(25:20) Why Monumental operates as a subcontractor

(28:38) The limitations of 3D printing and prefab construction

(33:15) The technology and pricing bets Salar made

(33:45) Lessons from Palantir's culture

(39:35) Monumental's company culture

(42:31) An overview of a construction job from start to finish

(45:50) Precision and tolerances

(47:50) Surprising challenges in the construction industry

(49:10) The current state of Monumental and what’s next

(54:00) Why humanoid robots don’t make sense for Monumental

(56:16) Building an ambitious company in Europe

(01:00:56) Monumental’s approach to hiring

(01:03:10) The state of European tech and what needs to change

(01:06:00) Salar’s optimistic take on the current state of tech in Europe

(01:10:46) Final meditations

Follow Salar al Khafaji

LinkedIn: https://www.linkedin.com/in/salark/

X: https://x.com/salar

Website: https://sal.ar/

Resources and episode mentions

Books

Impro: Improvisation and the Theatre: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178
Liftoff: Elon Musk and the Desperate Early Days That Launched SpaceX: https://www.amazon.com/Liftoff-Desperate-Early-Launched-SpaceX/dp/0062979973
Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed: https://www.amazon.com/Seeing-like-State-Certain-Condition/dp/0300078153
The Little Big Number: How GDP Came to Rule the World and What to Do about It: https://www.amazon.com/Little-Big-Number-World-about/dp/0691166528

People

Émile Durkheim: https://en.wikipedia.org/wiki/%C3%89mile_Durkheim
Torsten Reil on LinkedIn: https://www.linkedin.com/in/torstenreil/

Other resources

Monumental: https://www.monumental.co/
Palantir: https://www.palantir.com/
Palantir acquires data visualization startup Silk: https://techcrunch.com/2016/08/10/palantir-acquires-data-visualization-startup-silk/
Waymo: https://waymo.com/
Bauhaus: https://en.wikipedia.org/wiki/Bauhaus
Art Deco: https://en.wikipedia.org/wiki/Art_Deco
How Anduril Is Reimagining the Defense Industry: Faster Tech, Ethical AI, and a New Kind of Deterrence | Trae Stephens (Co-Founder & Executive Chairman, Anduril): https://www.generalist.com/p/how-anduril-is-reimagining-the-defense-industry-trae-stephens
1X: https://www.1x.tech/
Optimus: https://en.wikipedia.org/wiki/Optimus_(robot)
Helsing: https://helsing.ai/
Europe’s Great Founders Must Unretire: https://www.generalist.com/p/europes-great-founders-must-unretire
There’s no speed limit: https://sive.rs/kimo

Subscribe to the show

I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.