Sunday, 16 August

Two thoughts from Daniel Kahneman

“If you were allowed one wish for your child, seriously consider wishing him or her optimism.”

“We can be blind to the obvious, and we are also blind to our blindness.”

Monday, 17 August

Two thoughts from Anne Brontë

“But he who dares not grasp the thorn, should never crave the rose.”

“There are great books in this world and great worlds in books.”

Two thoughts from Georg Simmel

“He is educated who knows how to find out what he doesn’t know.”

“One needs to properly possess only a couple of great thoughts – they shed light on many stretches whose illumination one would never have believed in.”

Tuesday, 18 August

Two thoughts from Walter Benjamin

“We collect books in the belief that we are preserving them when in fact it is the books that preserve their collector.”

“To be happy is to be able to become aware of oneself without fright.”

Wednesday, 19 August

Two thoughts from Herbert A. Simon

“A wealth of information creates a poverty of attention.”

“You do not change people’s minds by defeating them with logic.”

Thursday, 20 August

Two thoughts from Keanu Reeves

“The simple act of paying attention can take you a long way.”

“You can’t stop the waves but you can learn to surf.”

Friday, 21 August

Two thoughts from Viktor Frankl

“When we are no longer able to change a situation, we are challenged to change ourselves.”

“No one can take away my freedom to choose how I will react.”

Saturday, 22 August

Two thoughts from Albert Camus

“The need to be right is the sign of a vulgar mind.”

“Those who lack the courage will always find a philosophy to justify it.”

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This week: what shows up when you give things a little more time. Go players realizing the future arrived early, eight episodes of slow-cooked revenge, Theodore Roosevelt before he became Theodore Roosevelt, Four Tet on repeat, and Danny McBride poking around the Criterion Closet and accidentally explaining half his career.

1. AlphaGo : We’re All Go Players Now

I first watched AlphaGo when it came out in 2017. Really enjoyed it at the time. I rewatched it recently, in large part because I read the excellent book The MANIAC by Benjamín Labatut, and the events covered in the film play a big role in the book. I enjoyed it just as much, but it felt like a different film the second time.

Back in 2017, watching some of the best Go players in the world suddenly realize that an AI was much better than they expected felt like a glimpse of some weird future. But in the post-ChatGPT world, it feels a lot more like we’re all the Go players now.

Go was supposed to be safe for a while. Deep Blue beat Garry Kasparov in 1997, but Go is another animal. There are something like 10^170 possible board positions, and good play relies heavily on pattern recognition and intuition, because on every move you can do almost anything. Brute force alone doesn’t work.

Go legend Lee Sedol had seen an earlier version of AlphaGo play. He basically thought: pretty good, but nowhere near me. He predicted he’d win 5–0 or 4–1. The problem was that the games he’d watched were already five months old. He had no idea how much better AlphaGo had gotten in the meantime.

I won’t spoil how the match unfolds, because a big part of the fun is watching Lee, the commentators, and even the DeepMind team keep recalibrating in real time. At one point, AlphaGo plays what became famous as “Move 37,” a move so weird and unexpected that the experts watching initially don’t quite know what to make of it. Lee later said it made him think AlphaGo could be creative.

Director Greg Kohs spent years at NFL Films, and you can tell. He treats this less like a documentary about software and more like a sports film about people under pressure. You really don’t need to know anything about Go to get into it. Half the drama is just watching people’s faces as they try to understand what they’re seeing.

What happened after the film? A 2023 study analyzed 5.8 million professional Go moves from 1950–2021 and found that after superhuman Go AI arrived, human decision quality improved and novel moves became more common. Apparently, getting beaten by a much better player and having a tireless practice partner to learn from can teach you a few things. [Liberty]

• 🎬 AlphaGo Documentary (2017, free on YouTube)

2. The Count of Monte Cristo : Revenge Needs Room to Simmer

Eight episodes is not much time to tell the story of a 1,200-page novel.

But it’s immensely better than trying to fit it into a 2-hour movie.

That’s why I really enjoyed the recent miniseries adaptation of The Count of Monte Cristo directed by Bille August, and starring Sam Claflin as the tortured Edmond Dantès.

I’ve seen multiple film adaptations of this epic story and despite their best efforts, they are forced to either rush through major plot points or cut them out entirely.

This series, while still needing to abridge at times, lets the story of betrayal, adventure, and revenge simmer long enough for you to occupy the headspace of different characters. The web of competing ambitions and desires between Dantes, Villefort, Danglars, and Mondego feels palpable.

My favorite part is how the series handles the change in Dantès over the course of the story. If you’ve never consumed this story, I’ll spare you the details so you can enjoy it fresh. But for those who know, Claflin embodies the arc from young and optimistic to ‘experienced’ and cynical very well, allowing the novel’s message to land.

I think one reason this story is so enduringly popular is that the drama plays out like the world’s greatest soap opera. So if you decide to give it a go, make sure you don’t have early meetings the next morning. Because you’ll be fighting the impulse for “just one more episode.” [Jameson]

• 📺 The Count of Monte Cristo (2024, TV Miniseries)

• 🎬 The Count of Monte Cristo (2024 French film, Original title: Le Comte de Monte-Cristo, 178 min)

3. The Making of Theodore Roosevelt

There was a stretch in my twenties when I was reading everything I could get my hands on about Theodore Roosevelt. I don’t think that’s uncommon among a certain kind of ambitious person. Whatever your views of the man, you cannot help but admire the sheer volume and range of what he accomplished in a single lifetime.

Here was someone who ran the New York City police board, served as Assistant Secretary of the Navy, left civilian life to raise a volunteer cavalry regiment and fight in Cuba, came home to be elected Governor of New York, then Vice President, then President at forty-two, the youngest we have ever had. He wrote some three dozen books, the first of them a serious naval history published when he was twenty-three. He boxed at Harvard. He reportedly read a book a day, sometimes more. Just reading a list that long can make you tired and leave you wondering if he’s from the same species as the rest of us.

That’s why my recommendation this week is The Rise of Theodore Roosevelt, the first volume of Edmund Morris’s masterful three-part life. The book is the story of how that resume began. It’s also the story of the things the resume leaves out: the asthmatic, sickly boy whose father told him he had the mind but not the body, and that he would have to make his body, which the boy then set about doing in a home gymnasium with a grim determination that never really left him. The early political defeats. The years of being underestimated by everyone in Albany. Once you’re done, you feel a pep in your step.

Most powerfully, Morris gives us February 14, 1884, the day Roosevelt’s young wife Alice and his mother Mittie died within hours of each other, in the same house. He drew a large X in his diary that night and wrote that the light had gone out of his life. This is what sent him back west to the Dakota Badlands, far from the politics and the literary world he had known in New York. Then you watch him come back, and everything he goes on to do looks more remarkable for what it cost. Watching Roosevelt move through his grief reminds you that he was a human being, and there is something in the way Morris renders that humanity that makes you respect the man more.

It’s beautifully written and exceptionally well researched, and it won everything when it came out. If you’re just beginning your Rooseveltian journey, this is where to start. But I revisit it regularly, because it always returns me to the person behind the long Wikipedia entry. [Jimmy]

• 📘 The Rise of Theodore Roosevelt by Edmund Morris

4. Four Tet: Electronic Music for Deep Work

As I look back, I see a running theme with some of my Field Notes selections. I covered DJ Padre Guilherme earlier, and Barry Can’t Swim a few issues back. Clearly I’ve been on an electronic music binge lately, and this note is no different.

Lately a friend of mine mentioned the musician Four Tet in passing, and I decided to check him out. Four Tet is the stage name of English electronic musician Kieran Hebden. The kaleidoscopic cover art caught my eye (Jason Evans made the cover by photographing printer-test images on film, hole-punching the film, arranging the tiny discs on glass, and making a C-print), so I picked his 2010 album There Is Love in You. I’ve been listening to him almost non-stop for the past week.

There’s an absorbing quality to the music, and for someone who’s new to electronic music in general, it’s perfect. I don’t quite have the words to describe it, except perhaps to tell you where I listen to it: while in a state of deep work, often when I’m writing, editing a video, or on long drives.

As Pitchfork put it in its review:

“Instead, it’s both heady and physical, subtle but powerful music for thinking and moving or ideally doing both at the same time: It’s been a while since a brisk walk through the city sounded this good.”

A few favourites from the album. First, the opener ‘Angel Echoes’. It’s uplifting and rhythmic, with a soft vocal sample looping through it. It’s awesome. ‘Love Cry’ has these strange industrial hums and buzzes, but then suddenly a wonderful drum loop begins and I’m transported into the world of this song. I can see it playing in a dance club straight out of Mirror’s Edge. When the words ‘Love Cry’ start to repeat, I’m deep in a trance.

The Expanded Edition of the album also has remixes of these songs, and I’ve been really loving Floating Points’ remix of ‘Sing’. [Rohan]

5. The Closet That Became Cinema’s Tiny Desk

In 2010, Guillermo del Toro stopped by the Criterion Collection’s New York office for a meeting. Someone on the social media team suggested taking a picture of him in the closet. Criterion president Peter Becker went one step further: he pulled out his iPhone and filmed him picking movies. That one-off video became the Criterion Closet Picks series, which has since filmed more than 300 episodes featuring everyone from Cate Blanchett to Hideo Kojima to the Slovenian philosopher Slavoj Žižek, and has quietly become one of the most reliably great things on YouTube. Think of it as cinema’s answer to NPR’s Tiny Desk: intimate, unscripted, and revealing in ways that press junkets never are.

The latest episode features Danny McBride, who studied filmmaking at UNC School of the Arts in Winston-Salem. He picks Badlands and explains how Malick’s naturalistic style shaped his own filmmaking instincts. Five Easy Pieces reveals that the cold ending of Eastbound & Down’s first season was lifted directly from Jack Nicholson’s final scene. A Face in the Crowd traces Andy Griffith’s fraudulent-southern-charm performance straight into Kenny Powers’ fourth-season media arc. “It’s funny how much of Eastbound is actually inspired by classic films, but it is,” he says. And he explains that on George Washington he was the second-unit director — his first-ever production job, shot in two weeks around Winston-Salem the day after graduating film school.

The Closet lets you see the invisible thread between the movies people love and the work they make. Three hundred episodes in, and the formula hasn’t changed. Here’s to hoping it never does. [Taylor]

• 🌐 Criterion Closet Picks

• 📺 Criterion Closet on YouTube

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Sunday, 9 August

Two thoughts from Garry Kasparov

“The point of modern propaganda isn’t only to misinform or push an agenda. It is to exhaust your critical thinking, to annihilate truth.”

“Dictatorships must be feared to survive so they cannot bear to be mocked.”

Monday, 10 August

Two thoughts from Rahel Varnhagen

“What am I doing? Nothing. I am letting life rain upon me.”

“Hope for forces which you do not yet have. That is what is most impossible, and nevertheless possible.”

Tuesday, 11 August

Two thoughts from Poul Anderson

“Timidity can be as dangerous as rashness.”

“A fanatic’s willingness to kill or be killed in the service of a cause cannot prove the rightness of that cause.”

Wednesday, 12 August

Two thoughts from Frédéric Gros

“Discipline is the impossible conquered by the obstinate repetition of the possible.”

“The illusion of speed is the belief that it saves time...but haste and speed accelerate time, which passes more quickly, and two hours of hurry shorten a day”

Thursday, 13 August

Two thoughts from Marshall Goldsmith

“What got you here won’t get you there.”

“If we do not create and control our environment, our environment creates and controls us.”

Friday, 14 August

Two thoughts from Paul Erdős

“It is not enough to be in the right place at the right time. You should also have an open mind at the right time.”

“God may not play dice with the universe, but something strange is going on with the prime numbers.”

Saturday, 15 August

Two thoughts from Morgan Richard Olivier

“Your mind is a compass. Wherever your mind goes, your actions or reactions will ultimately take you.”

“When people reveal themselves,

believe them.

Stop painting prettier pictures

with the red flags you see.”

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This week: things that change when you look at them twice. Two songs written 44 years apart that somehow become one, an AI revolution that may not produce an economic one, L.A. history hiding inside freeway interchanges, a 936-page Bombay epic that blurs life and fiction, and David Milch’s damaged characters seen through the man who wrote them.

1. This Bitter Earth / On the Nature of Daylight : The Accidental Duet, 44 Years Apart

In 1959, Dinah Washington recorded “This Bitter Earth,” a blues song written and produced by Clyde Otis. In 2003, a German composer named Max Richter sat down in Edinburgh and wrote a piece for string quintet as a protest against the Iraq war: “On the Nature of Daylight.”

Two songs in two completely different genres recorded forty-four years apart... Then Robbie Robertson put one on top of the other.

Robertson had been telling Scorsese for years that, instead of an original score, they ought to try building a film out of modern classical music. So when the Shutter Island script arrived, he told Scorsese this was the one - and, thankfully, Scorsese agreed. Richter’s strings went in early and became the theme for Dolores, the dead wife. They play every time she appears.

The end credits were the last thing to solve. Robertson had the Richter piece in his head, and he had also been carrying the Dinah Washington song around for years (she had been one of his favourite singers for decades), and something in him kept setting the two of them side by side. So he went and checked. They were in the same key.

The rest he did by hand. He cut her vocal out of the 1959 record line by line, the way you’d chop a rap sample, then laid each phrase back over the strings exactly where he would have sung it himself. He wasn’t sure he was allowed to do any of this, so he sent it to Scorsese with a warning attached. He had taken a liberty; this was the entirety of two artists laid on one another. Scorsese loved it. Somebody then had to ring Max Richter and Dinah Washington’s family to ask permission after the fact. Again, thankfully, both said yes.

I’ve listened to it more times than I can count, and it still sounds to me like one piece of music that was pulled apart at some point and put back together. Her phrasing falls into the gaps in the strings as though she had been in the room while they recorded it, which adds to how haunting it already is. [Dylan]

• 🎶 This Bitter Earth / On the Nature of Daylight (Shutter Island Soundtrack)

2. Why AI Might Transform Everything Without Exploding Economic Growth

You have probably heard both versions of the AI future. In one, the transformation is so fast that if you can just stay alive for the next three years, you stand to increase your lifespan by hundreds of years. In the other, AI is cool and all, but all the talk about hypergrowth is mostly… hype.

Charles I. Jones (a Stanford economist and now an Anthropic employee) explores several scenarios in this recent paper. A graph of the avg. US per capita income for the last 150 years (figure 1) shows a steady growth of 2% per year. That’s 150 years that saw electricity, air travel, antibiotics, transistors, personal computers, and the internet to name a few!

All of these were transformative and yet, they translated to a 2% growth in the long run. So, is this time finally different? Could AI really get us to grow at 10% or more?

Jones looks at the “a chain is only as strong as its weakest link” argument with an economic and mathematical lens. Most of the economy is not about manipulating text files, and there are countless complex human interactions that keep the world running. As we automate one part of the job, the bottleneck just moves to another — making that the new weak link. How quickly can AI automate through the bottlenecks? And that assumes the set of things we do doesn’t expand, which seems unlikely.

In April 2025, while visiting California, my wife and I took a Waymo ride for the first time. It still tops our list of mindblowing experiences. What do you mean that a driverLESS car just arrives, you sit and tap a screen, and it calmly maneuvers through traffic and stop lights and drops you to the destination like a random Uber?!

That moment was us living in the future.

While discussing when we could expect this future to arrive back home, in India, we were reminded of how even something as basic as well-paved roads is currently too much to expect. The knowledge required for building good roads is widely available, the tools are inexpensive, but it’s the human-in-the-loop that has persisted as the bottleneck to something that was solved a century ago. Perhaps that’s why Tyler Cowen calls humans the #1 bottleneck to explosive economic growth because of AI. [Vatsal]

• 📄 AI and Our Economic Future by Charles I. Jones

3. Take THE 405 to THE 10: A Love Letter to L.A.’s Freeways

I grew up watching CHiPs — the late-’70s series about California Highway Patrol officers on motorbikes — and the opening credits always got me dreaming of a place far from my native Midwest.

Those aerial shots of freeways snaking through the L.A. basin, the late-afternoon light catching eight lanes of traffic flowing in formation, made the infrastructure itself look cinematic. So when I stumbled onto the X account Freeways of Los Angeles, it hit my nostalgia and history nerves: a steady feed of archival photos, engineering histories, construction timelines, and route stories drawn from roughly 650 miles of freeway crisscrossing Los Angeles County.

What makes the account so good is that the freeway is almost never just the freeway. You click on an old interchange photo and wind up reading about the political fight that put it there. The account traces all of it: from the Arroyo Seco Parkway, the first freeway in the western United States when it opened in 1940, to the controversies and construction sagas that shaped the system Angelenos navigate today. It’s the kind of niche, deeply regional content I’m a sucker for: the history of a place told through its infrastructure.

My wife’s family is all from L.A. and Orange County, and I love giving them a hard time about route planning. Everyone has a preferred freeway. Everyone has a strong opinion about the 405. And of course, everyone calls them THE Five or THE 10 — a habit that dates back to when the freeways had names instead of numbers, and “the San Diego Freeway” simply became “the 405.” If you’ve seen SNL’s The Californians, where Bill Hader, Kristen Wiig, and Fred Armisen argue about routes in exaggerated Valley accents, then you already understand. [Taylor]

• 🌐 @FreewaysLA

4. Shantaram : Prison, Bombay, Mafia, War

Years ago, during the middle of summer, I read a novel called Shantaram by Gregory David Roberts. I don’t remember how I first came to it. I remember being absorbed from the jump. This despite its length, which clocks in at 936 pages. The heft is worth it, and I recommend it enthusiastically.

The story follows a man called Lin, an Australian convict who escapes a maximum-security prison, buys a false passport, and disappears into the crowds of Bombay in the 1980s. He finds a guide, a taxi driver named Prabaker who has the best smile in the book and possibly in literature. He finds a slum, and in it he builds a free clinic, drawing on his earlier training as a medic to treat thousands. He finds a woman named Karla, who is beautiful and withholding and running from something of her own. He finds a mafia don named Abdel Khader Khan, who becomes a kind of father to him and who will eventually lead him into the mountains of Afghanistan. Along the way there is a village monsoon, a Bombay prison, a Bollywood set, an opium den, and a war.

It is loosely based on the author’s life, but this is one of those books that, whether it’s fact or fiction, it doesn’t much matter. Because the book has a gem of writing or emotion or wisdom on almost every page. Its people and places have stayed with me long after I finished it. Roberts spent years living in Bombay, and you can tell. He knows what the air smells like at four in the morning outside a Colaba bar. He knows how people talk to each other when they have nothing. [Jimmy]

• 📙 Shantaram: A Novel by Gregory David Roberts

• 📺 Shantaram (2022, Apple TV+ adaptation)

5. How David Milch Keeps Looking for the Full Human

David Milch was already one of my favorite writers before I had seen most of his work. Just based on Deadwood, my favorite TV show (which I will tell you more about in a separate note — I’m keeping that one for later as dessert), I knew I loved that man’s mind.

When I first read his Life’s Work a couple of years ago, it completely changed my perception of Milch, and of Deadwood. I realized how much of himself is in his characters. The damaged people that he writes about seem like reflections of his own struggles with addiction, gambling, and being abused as a child.

On my first read, I had not yet seen what made Milch famous, NYPD Blue. For some reason, I expected it to be a vanilla police procedural from the 1990s. I thought maybe Milch started out more conventional, and built up the permission with the TV networks to experiment later. Well, my wife and I have been watching NYPD Blue from the beginning for the past few months, and I couldn’t have been more wrong. This is clearly one of the ancestors of modern prestige TV. Characters are flawed in ways that network TV ‘heroes’ rarely were at the time. Milch loved to deviate from the formula and throw out the outline. He was known to revise and improve scripts until the last second.

We’ve just hit episode 5 of season 6. I went in blind, and it hit me like a ton of bricks. I won’t say more to avoid spoilers. The very next day, I started re-reading Milch’s memoir, and now the section about NYPD Blue is making me see the show in a completely new light.

Milch said the real person detective Sipowicz (played by Dennis Franz) most closely resembles is his father, Elmer Milch, a brilliant surgeon who also was an alcoholic and compulsive gambler. Once you know that, Sipowicz feels different. Milch wanted to portray that kind of person in “full human complication,” capable of ugliness, but not reducible to his ugliness.

Milch writes in the memoir about how things that happen later can change the meaning of what came before. That’s exactly what this reread feels like. NYPD Blue is changing how I read Life’s Work, and Life’s Work is changing how I watch NYPD Blue. [Liberty]

• 📙 Life’s Work: A Memoir by David Milch

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Sunday, 2 August

Two thoughts from Barry Schwartz

“Happiness as a goal is a recipe for disaster.”

“Ninety percent of adults spend half their waking lives doing things they would rather not be doing at places they would rather not be.”

Monday, 3 August

Two thoughts from Patrick Winston

“Your success in life will be determined largely by your ability to speak, your ability to write, and the quality of your ideas—in that order.”

“Salute the audience.”

Tuesday, 4 August

Two thoughts from Marvin Minsky

“In general, we’re least aware of what our minds do best.”

“One can acquire certainty only by amputating inquiry.”

Wednesday, 5 August

Two thoughts from Roger Schank

“Humans are not ideally set up to understand logic; they are ideally set up to understand stories.”

“Learning happens when someone wants to learn, not when someone wants to teach.”

Thursday, 6 August

Two thoughts from Donald Knuth

“The language in which we express our ideas has a strong influence on our thought processes.”

“Premature optimization is the root of all evil.”

Friday, 7 August

Two thoughts from Christopher Alexander

“Making something beautiful is not a new thing or an old thing. It is a constant thing.”

“Simplicity and inner calm are more important than complexity and superficial agitation in architecture.”

Saturday, 8 August

Two thoughts from Annie Dillard

“If you stay still, earth buries you, ready or not.”

“You can’t test courage cautiously.”

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This week: hidden worlds in plain sight. A fake ’60s hit that became real nostalgia, a KGB colonel living a secret double life for eleven years, the Letterboxd for photobooks, twin sisters on a bloody revenge mission, and Delhi as seen from one foot off the ground.

1. That Thing You Do! : The Fake Band That Became Real Nostalgia

It may sound like a good idea to make a film about a one-hit wonder band from the 1960s. But then you have a problem. You have to write the hit song.

Tom Hanks had that challenge with That Thing You Do!, the 1996 movie he wrote and directed about four guys from a small city in Pennsylvania whose band records an insanely catchy song and briefly becomes famous.

To me, the film is pure fun. It follows the Wonders (they’re originally called something else, but I won’t ruin the joke) as they go from playing local talent shows to hearing themselves on the radio, touring the country, and eventually going on national television. Don’t expect evil managers or crazy rock-and-roll excesses. It’s not the Goodfellas arc, where the manic rise is followed by a descent into hell. It’s mostly just four young guys riding a big wave, and then it fizzles out.

Hanks really captures how exciting it must have felt while it lasted.

But for any of this to work, they needed a hit song. So Hanks put out the call: write the song. Around 300 versions came in. One was from a then-little-known songwriter named Adam Schlesinger, who had just co-founded the band Fountains of Wayne (you may know their biggest hit, Stacy’s Mom).

After the film came out, something funny happened: the fake hit became a real one. “That Thing You Do!” reached #41 on the Billboard Hot 100, #22 in the UK, and was nominated for an Oscar for Best Original Song. The soundtrack eventually went platinum.

The Wonders never existed. Play-Tone Records never existed. None of these songs were actually on the radio in 1964. But almost 30 years later, there are people who grew up with this movie. To them, the song is a real hit, and they feel real nostalgia for this fake band from a fake version of the ’60s.

Hanks even named his real production company Playtone after the record label in the movie. I don’t know, I kinda love that. [Liberty]

• 🎬 That Thing You Do! (1996)

2. The KGB Colonel Who Spied for Britain for Eleven Years

Of all the books I have read so far this summer, the one that stands out is Ben Macintyre’s The Spy and the Traitor. I am probably a little late to the Macintyre fan club, but I have joined it now, and I have joined it with enthusiasm.

The book tells the story of Oleg Gordievsky, the KGB colonel who spent more than a decade passing Soviet secrets to British intelligence while continuing to climb the ranks in Moscow and London. Around that story, Macintyre builds a portrait of spycraft itself: the dead drops, the tradecraft, the constant low-grade terror of a double life. Macintyre had more than 100 hours of taped interviews with Gordievsky and interviewed every British intelligence officer involved in his case. You feel that access on every page.

There is enough context to understand the era, but Gordievsky’s story stays firmly at the center. Macintyre has done so much reporting that even the smallest scenes have texture. And the book moves. You just keep turning pages.

I will not say more, because I do not want to spoil how good it is. I will say that it deserves every piece of praise it received, and that it does the thing great nonfiction is supposed to do: it reads as well as fiction.

The book is so good that — just having finished it — I'm starting it all over again. [Jimmy]

• 📘 The Spy and the Traitor: The Greatest Espionage Story of the Cold War by Ben Macintyre

3. The Letterboxd for Photobooks Has Arrived

The photobook is one of photography’s most enduring forms. But discovering a great one has always been a scavenger hunt — trawling used book sales, Instagram rabbit holes, small press websites, and the stacks at bookstores where you overhear someone say “you have to see this one.” I’ve been collecting photobooks for years from all of these places, and I’ve always wished there were one good place to keep track of what I find. Photobookers comes pretty close.

Photobookers was built by Éanna de Fréine, an Irish photographer who founded The Velvet Cell in 2011, an independent publisher that has put out more than 60 photobooks. At its core, the site is a big curated database: search for a photographer or publisher, find their books, save the ones you want, follow people whose work you like. But there’s also an editorial side, with featured books and photographers and longer interviews. I like the way the site describes the idea: “a hub, not a dump.” There’s also an iOS app, and it’s free.

I found it at exactly the right time. Social media has become a powerful discovery engine for photography, and my Instagram and X bookmarks are jammed with photographers and new books I want to track down. The work is easier than ever to stumble across, but keeping track of it is still a mess. Photobookers fills a real need. A few of my favorites are “Dormant Season” by Erinn Springer and “Driving Through Flyover Country” by Lewis Ableidinger. [Taylor]

• 🌐 Photobookers

4. Is God Is : A Revenge Movie Bound by Fury

A combination of the World Cup, work, and that deeply unfortunate side-effect of existence known as “a social life” has taken a sledgehammer to my movie-watching over the past few weeks. But there have been highlights. Modern cinema is back (although I’ve long argued it never really left): any month where you can go see The Invite, The Furious and The Odyssey in packed-out screens is a good one.

My viewing of Aleshea Harris’s revenge-thriller Is God Is was less satisfying. The film never got a theatrical release here, so I was forced to watch it at home: an imperfect solution at the best of times, but doubly so for a film as lively as this one.

Racine and Anaia (Kara Young and Mallori Johnson) are twin sisters who were badly burned in a fire started by their father (a silkily venomous Sterling K. Brown). When their absentee mother summons them and demands they take vengeance so she can die in peace, the sisters hit the road. Bloody hijinks ensue.

Joel Coen once said that a director’s job is “tone management.” This is Harris’s feature directorial debut (she adapted it from her own 2018 play), and her superpower is how delicately she balances the film’s seemingly conflicting sensibilities. There are hints of Tarantino in its bloody set pieces and exploitation-movie DNA, but this has far more on its mind than the subpar Pulp Fiction knockoffs that populated the 1990s, folding in bouts of hyper-earnest melodrama, goofy humour, and magical realism.

Add in the episodic plot and it should all feel overwhelming, but by and large the film holds together, its disparate elements bound by a barely concealed fury. More please! [Ed]

• 🎬 Is God Is (2026)

5. The Cats Who Owned Delhi

I have a weakness for books about, around, based in, or even remotely connected to Delhi. Because Delhi is my city, the city I was born in. So Nilanjana Roy’s The Wildings had an unfair advantage with me from the start.

This novel is about a bunch of feral cats that live in Nizamuddin, among dargahs, ruins, rooftops, drains, and trees, and have their own codes, rivalries, and myths. They call us Bigfeet and share a common language called Junglee (pretty obvious, I know). There is an old Siamese named Miao who teaches kittens to hunt and a tom named Hulo who patrols the territory. Things go sideways when an orange kitten named Mara shows up. She is a special one who can project herself across distances through her whiskers and is what the cats call a ‘Sender’.

Many authors anthropomorphize animals but end up giving them too many human qualities that break character. Roy never pretends to humanize the cats. They remain feral, sweating, mewing, eating rats and doing whatever cats do.

I loved how she built a microcosm of a civilization using the cats’ version of the Nizamuddin neighborhood with its iconic dargahs, canals, lanes and trees. The book gives a strange sheen to the place with the raat ki rani smelling ten times stronger. The shift in perspective reminded me of the Panchatantra tales I read as a child: talking animals making their world feel strange and exciting while smuggling in lessons about our own.

The author was a literary critic for years before she wrote her first novel. The Wildings won the Shakti Bhatt First Book Award in 2013 and also has a sequel, The Hundred Names of Darkness. If you want to see Delhi from a foot off the ground, go for it. [Aashisha]

• 📙 The Wildings by Nilanjana Roy, illustrations by Prabha Mallya

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A few of the references have aged in the years since, but if you’ve joined us recently, it’s a great way into the back catalogue. If you’ve been around a while, we think it still holds up!

Apple podcasts

Sunday, 26 July

Two thoughts from Lenny Bruce

“The only honest art form is laughter, comedy. You can’t fake it...try to fake three laughs in an hour -- ha ha ha ha ha -- they’ll take you away, man. You can’t.”

“I was not born in a vacuum. Every thought I have belongs to someone else.”

Monday, 27 July

Two thoughts from Bill Hicks

“Watching television is like taking black spray paint to your third eye.”

“Listen, the next revolution is gonna be a revolution of ideas.”

Tuesday, 28 July

Two thoughts from Mae West

“You only live once, but if you do it right, once is enough.”

“Between two evils, I always pick the one I never tried before.”

Wednesday, 29 July

Two thoughts from Mort Sahl

“That feeling of hopelessness only serves your masters.”

“One thing about being narrow-minded: you’ll never be lonely.”

Thursday, 30 July

Two thoughts from Friedrich Hayek

“‘Emergencies’ have always been the pretext on which the safeguards of individual liberty have eroded.”

“From the saintly and single-minded idealist to the fanatic is often but a step.”

Friday, 31 July

Two thoughts from Itzhak Bentov

“The more you know, the more ignorant you become, because ignorance grows exponentially—the more answers you get, the more new questions arise.”

“The Soul is repository of information that we gather during a lifetime.”

Saturday, 1 August

Two thoughts from Vernor Vinge

“Intelligence is the handmaiden of flexibility and change.”

“He was guided by what he saw rather than by what he wanted to believe.”

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This week: a 433-mile bike ride that brings small towns to life, a D&D campaign disguised as a heist movie, a Pulitzer-winning book and HBO miniseries about the marriage behind one of America’s founders, portraits staged like tiny theatres, and a documentary about a dump with one of the greatest sounds in music history.

1. Biking Across Iowa: Water Towers, Pie, and Small-Town Hospitality

In 1973, two Des Moines Register journalists wanted an excuse to get out of the office. John Karras, an avid cyclist, suggested they bike across Iowa and write their column from the road. Don Kaul, who authored “Over the Coffee,” agreed, but only if Karras came along. That ride became RAGBRAI, the Register’s Annual Great Bicycle Ride Across Iowa, now the oldest, largest, and longest multi-day bicycle touring event in the world. I just finished this year’s edition — 433 miles by my own tracker, thanks to an optional century loop and a campsite set well outside town — and I’m still feeling it.

Iowa is not flat. That myth dies somewhere around your fourth relentless roller on Day 2. This year’s route was the tenth-hilliest in RAGBRAI history, with over 16,000 feet of climbing. The heat and humidity can be unbearable. But the towns are what make this ride. You spot a water tower miles before you arrive.

Fitting that this year’s theme, “An Iowa Classic,” actually celebrates those beacons on the horizon. Then you roll into a community with a few hundred people and find churches serving homemade pies, kids with lemonade stands, and grain elevators taller than anything else in town.

In Marshalltown, an overnight stop of about 27,000 people, I counted at least four family-owned businesses that have been operating for more than 90 years. A miracle for a town that was practically leveled by an EF3 tornado in 2018.

An estimated 20,000 riders pour through these communities each day, and the money goes directly to local projects: new baseball fields, pool repairs, scoreboards. For towns losing people and businesses, one week of bikes can really help the local economy.

I have been all over this country. The hospitality and friendliness of Iowans remains unmatched. I also fulfilled a lifelong wish and got to take batting practice at the Field of Dreams. Until next time, Iowa. [Taylor]

• 🌐 RAGBRAI Official Website

2. Honor Among Thieves : What if Danny Ocean Played D&D?

A few days ago, Jonathan Goldstein, one of the writer-directors of Dungeons & Dragons: Honor Among Thieves, mentioned that they’ve written a sequel, and that he doubts it’ll ever be shot “for a number of financial reasons.” So there’s a finished script for a movie nobody will pay for. Which is a shame, because the first one is a lot of fun. I watched it again recently with my kids (their first time), and it was a hit with them.

It’s a heist movie in a fantasy setting. Chris Pine plays a bard whose only real weapon is being charming (he’s the Danny Ocean of this film), and he assembles the usual crew of specialists: a barbarian, a sorcerer who keeps flubbing his spells, a shape-shifting druid. The goal is to rob a vault belonging to his old partner, played by a very funny Hugh Grant, clearly having a great time as the smiling con man.

My favorite scene is in a graveyard. The sorcerer casts Speak with Dead, a real D&D spell that lets you ask a corpse exactly five questions. The party immediately starts wasting them arguing about whether asking if something counts as a question counts as a question. The scene keeps finding new ways to make five a very small number, and it pays off later in a way I won’t spoil.

The reason it works, I think, is that a heist and a D&D campaign are the same thing. Both are an elaborate plan meeting reality and failing again and again until it somehow comes together. I’ve played D&D weekly for years, which is the only expertise I bring to this. What the film adapts is the playing, not the lore: somebody always improvises something idiotic, it half-works, and the party spends the rest of the night arguing about it.

You don’t need to have played to enjoy it. Knowing the game gets you extra references, but my wife has never rolled a d20 and enjoyed it as a straight adventure movie.

It’s a well-made crowd-pleaser, which is rarer than it sounds. They did a good job, the hard way. The dragonborn is an animatronic with motors in its face rather than a CGI render, and the directors said they were aiming at Willow and The Princess Bride (see Field Notes #1 for Cary Elwes’ memoir of making that film).

Stay through the credits for a bonus scene. Too bad the sequel will never be more than a PDF on somebody’s hard drive. [Liberty]

• 🏰 Dungeons & Dragons: Honor Among Thieves (2023)

3. John and Abigail Adams: The Founding’s Greatest Partnership

Two of my all-time favorites are really one story told twice: David McCullough’s John Adams and the HBO miniseries it became seven years later. I can’t think of another case where a book and its adaptation actually improve each other, but these two do.

McCullough won the Pulitzer for it, and it holds up.

He spent years in the Adams papers and came out with a portrait that doesn’t sand anything down. The vanity and the temper are all there, right alongside the courage. Adams wasn’t Jefferson and knew it, which is part of what makes him such good company on the page. He was a stubborn New England lawyer with an overdeveloped sense of duty who kept volunteering for the hardest jobs of the founding — defending the British soldiers after the Boston Massacre, arguing independence in the Continental Congress, negotiating the peace in Paris — and got most of them right, including the one nobody remembers to thank him for: losing an election, handing power to his rival, and going home.

The miniseries, directed by Tom Hooper, somehow adds to all this. Paul Giamatti plays Adams squat and twitchy and brilliant, funny and heartbreaking in the same scene. I’ve loved Giamatti in almost everything he’s done, but I think this is the best thing he’s ever done (I think it even edges out Billions!). That said, it’s Laura Linney’s Abigail who holds the seven episodes together.

The two of them wrote each other more than a thousand letters over the course of their marriage. He was gone for years at a stretch, and she ran everything in his absence: the farm, the money, the children, and a good deal of his political thinking. On many questions, she was the sharper politician. Watch Linney and Giamatti argue about slavery, the vice presidency, or the loneliness of Paris, and they stop looking like historical figures. They look married. So much of the founding was really a story of partnerships. This was one of the great ones.

I would say first read the book, then watch the series. And if you’re still not done with the Adamses after that, the letters themselves are in print. Worth a read on their own, as a portrait of what two people can do in a lifetime. [Jimmy]

• 📕 John Adams by David McCullough

• 🎬 John Adams the miniseries (2008, HBO)

4. The Man Who Photographs Actors Like Dioramas

Willem Dafoe has always been one of my favorite actors. As a kid, I remember seeing him in the Spider-Man movies, and he shines in every role. It helps that he has a classic theatrical face, which makes him seem natural as a mad sea-captain or in the many distinct roles he plays in Wes Anderson movies.

A few years ago, this photo of Willem Dafoe started circulating online. It’s part of a GQ Italia photoshoot. I was mesmerized by it. First of all, it’s strange. Why is Willem’s head inside a cardboard house? Why is he posing like that? Every single photo from that sepia-toned shoot accentuated his theatricality.

This was the work of photographer Szilveszter Makó, who I’ve been obsessed with ever since. Aperture magazine recently did a feature on him, and they showcase a lot of his strange work. Makó does not really think of himself as a photographer. He builds the sets, makes the props, and stages his subjects inside box-like rooms. The photographs look less like portraits than tiny theatre productions.

Two details from the Aperture profile stood out to me. One was Makó’s insistence on making sure everything is handmade, to elevate the textures and grain of the image. The other was the feature’s exploration of Makó‘s inner rooms:

“When he speaks about his inner architecture, though, the style morphs into something more intricate. He imagines “lots of little rooms,” each distinct, each filled with carefully gathered trinkets. Every object is collected and stored, separate yet connected in a sort of organized chaos…”

This snippet made me wonder: can we really know what’s going on in our favourite artists’ inner minds? Can we use our own inner chaos and channel it into magic the way Szilveszter does? [Rohan]

• 📷 Szilveszter Makó on Instagram

5. Brown Shag Carpet on the Walls and a Hundred Platinum Records

The Sound City studio opened in 1969 in a former Vox amplifier factory in a Van Nuys industrial park in Los Angeles. Brown shag carpet on the walls, no windows, and everyone who worked there describes it as a dump. It also had a Neve mixing console that cost $75,000, one of only four in the world, and twice what one of the owners had just paid for his own house. He says in the film that his wife never found out.

Neil Young recorded part of After the Gold Rush there. Fleetwood Mac made their 1975 self-titled album. Tom Petty made Damn the Torpedoes. Rick Springfield made “Jessie’s Girl.” Nirvana made Nevermind.

In 2013, Dave Grohl made a documentary about the place, his first time directing. He'd recorded Nevermind there in 1991, and bought that console when the studio closed in 2011 (it reopened in 2017, after the film came out). Then he interviewed forty musicians and staff who had worked in the room. That's the best part: people telling stories about how the records actually got made.

It took four months to dismantle and move the Neve console, and then a few hours for, as Grohl puts it, a guy with a toothbrush to remove all the cocaine and fried chicken from its insides.

My favorite of those stories: in 1974, Mick Fleetwood came by looking for a place to record. Keith Olsen, the house engineer, played him "Frozen Love" to show off what the room could do, a track he'd cut there with a duo called Buckingham Nicks. Lindsey Buckingham happened to walk past while his own record was being used as a sales pitch. Not long after, Fleetwood Mac needed a guitar player, and Buckingham told them they'd have to take his girlfriend too.

This is why I like a good behind-the-scenes documentary. It shows how random life can be. That room turned out to have one of the best drum sounds in the world, entirely by accident, and nobody wanted to make changes to it in case they ruined it.

The second half is weaker. Grohl brings a bunch of musicians to his own studio to write and record new songs on the old console, and it's fine. He’s very likeable, so it’s still fun to hang out with him, but I much prefer the first half.

The place was a dump. But make enough great records in one room and it gets a halo. Even the ugly carpet is part of the legend now. [Liberty]

• 🎬 Sound City (2013, documentary, directed by Dave Grohl)

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We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

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Highlights

$1 million in gross profit, or your money back

Jimmy Soni: And so the audacious bet — the bet you started our conversation with — is you will make a million dollars in revenue by the end of your four years, or —

Nat Eliason: Gross profit.

Jimmy Soni: Gross profit, not revenue.

Nat Eliason: Not revenue.

Jimmy Soni: Wow. Even more audacious. So how does — without giving away state secrets, or anything privileged you can’t share — what was the thinking around that particular set of numbers, that bet, that promise? Because that’s the thing that’s been getting headlined.

Nat Eliason: Yeah, this was something Joe came up with when he came up with the idea for the school […]

Jimmy Soni: A million dollars in profit, or your money back.

Nat Eliason: Exactly. But he knew the same thing I said at the top of the conversation — there are no good entrepreneurship programs out there.

Jimmy Soni: Right, right.

Nat Eliason: There’s no undergraduate entrepreneurship degree that’s worth it, no graduate one that’s that good either. There are people who go to these schools and become successful entrepreneurs, but there’s really none of these schools that reliably drive outcomes in entrepreneurship. If you just said, “We’re launching a high school for entrepreneurs,” it’s kind of like, okay, right, there’s a lot of places for entrepreneurs — there’s FBLA, there’s all these things that say they’ll teach you entrepreneurship, and everybody kind of knows they’re not going to do that good a job. But if you say, “We’re launching a school for entrepreneurs, and if your kid doesn’t make a million dollars by graduation, we’ll refund you the tuition” — tuition is $150,000 a year, so we’re saying we’ll give you back $600,000 at the end of four years if we don’t get your student to that outcome. There are caveats — we’re assessing students each year, if a student comes in sophomore year they’re not on the guarantee, there’s all the edge cases. But that’s the core promise of the school, and it’s putting the pressure on us to actually figure this out, to make sure we’re delivering on these outcomes, and not playing startup like I was in college, trying to learn this for myself. It’s this incredible forcing function, and it’s the only reason anybody’s talking about this — because we have to be insanely committed to creating the best education experience possible on this topic, one that’s never existed before, that nobody’s made this kind of commitment to before. That’s where all our mental energy is going — we know this is possible, we just have to fine-tune it as we work with the students.

The perks of quitting early

Jimmy Soni: How did you deal with the feeling you described — you’re a year in and you realize it’s not going to work? Did it feel like the sky was falling? Because even at that age, even if you’re not building a business, you’re generally dealing with the challenge of what am I going to do with my earthly time — those are challenges for people who are just going to class every day. You’re building a business and watching it fail. What was your thought process, if you can think back?

Nat Eliason: I usually don’t stay in that headspace very long. I’ll have those feelings occasionally, but it very quickly shifts to: okay, well, there is something to do here. So I’ve never had long periods of wallowing, or being stuck in fear, because I very quickly click into, okay, we need a new plan — what is the plan, let’s focus on that. It shifted very quickly. I literally remember writing this on a whiteboard in my room — I wrote “$2,000,” because it was: okay, this startup is dead, I’m not working on this anymore, these illusions of raising $500,000 and going big — that’s not happening anymore. So what’s the thing I can focus on next? How do I get to this number by this date? That was the new plan. It felt like a very quick shift from focused on the startup to, oh wow, no, this is dead. I think it had probably been bubbling up for a couple of months, what was really going on. I must have spent some time making sure I wasn’t just having a momentary freak-out, because you don’t want to go that route either. But I remember it being a pretty quick and pretty adamant realization and decision.

For better or worse, I think I am good at that — okay, this feels like it’s hit a wall, but there’s this other vector that does have potential, I’m going to go on that one. That’s worked out very well for me. It’s also definitely had the downside of quitting things too quickly, or killing things too quickly, and it can be tough to find that balance sometimes.

Jimmy Soni: When you think back on that — because you’ve written publicly about quitting and talked a lot about it — do you have, sitting here in 2026, any updated thoughts on sort of knowing when to fold ‘em and knowing when to hold ‘em? Any new heuristics, or ways you’re thinking about it?

Nat Eliason: Yeah, I think ultimately — “quitting early” is the wrong term, but I’ve always had this bias toward being willing to kill something and move on to a better opportunity. The issue with that is it’s led to a lot of shiny-object syndrome. Most people, I think, go through a period of that, where they do this thing, then this thing, then this thing, and don’t get anywhere, and they realize, oh, I shouldn’t do that, I should pick something and focus on it. The issue for me is that it’s worked.

Jimmy Soni: Right.

Nat Eliason: Right. And I don’t mean this in a braggadocious way — it’s just, I’ve gotten away with it. I’ve been able to get super interested and fascinated in things, go hard on them for a year, launch these little businesses off my X account or my newsletter, and then they go really well. It’s like, okay, I can just become obsessed with something, dig into it for six months, then launch a course or a product, and it makes a few hundred grand in the span of a couple of months. Great — costs are covered for the next period of getting obsessed about things. That’s a cool ability to have. It’s incredibly powerful, incredibly useful, and I’m very grateful I’ve been able to do that.

But it does lead to not fully committing to things, not seeing where they can go, not living up to my full potential in a lot of those areas — because these breakthrough moments will happen, and instead of saying, okay, the excitement is over, now for the long slow slog to 10x this, it’s, well, I could just goof off for six months and then do this again. That’s been fun, that’s been satisfying. And then, really, last fall, I sat down — I ended up having this conversation with my wife, too — where I was like, I don’t think I should keep doing this. Even though it’s working, even though it’s provided a lot of the sustenance for our life, it feels like I’ve been playing this game a little too long. I really want to focus on something bigger, something serious, that has a meaningful risk of failure — because I think part of it comes from a fear of failure, a fear of trying something big and it not working and being embarrassed, because that means I’m not smart, I’m not capable. But as long as I’m doing these little things, there’s no risk of feeling that way.

Jimmy Soni: Because six months later, something else comes down the road and you figure that out.

Nat Eliason: Something’s going to happen.

Edited Transcript

Jimmy Soni: All right, Nat Eliason, thank you for coming on Infinite Loops.

Nat Eliason: Good to be here. Last time I did this with Jim. Now I got to do it with Jimmy. There you go.

Jimmy Soni: Yeah, we’re just going to continue rotating in people. Jim, Jimmy.

Nat Eliason: There you go. Have a cast of characters.

Jimmy Soni: One of the things that I have — this theory of the case of friendship that is like a contemporary case, or contemporary theory of the case of friendship — before the Internet, it was basically like, there’s less than a 1% likelihood you and I would have ever become friends. Because we grew up in different places. It would have been unlikely. Not impossible, just highly unlikely. And now what happens is you can have all these people who are Internet friends who become in-real-life friends. And so it’s this fascinating thing, because before, you would sort your friendships based on how close my locker was to yours.

Nat Eliason: Right.

Jimmy Soni: Did we grow up playing on the same little league team or something? And fast forward, you and I connected — I believe it was on Twitter, or when it was —

Nat Eliason: No, you emailed me. For the podcast, back in 2017, ‘18. Yeah.

Jimmy Soni: And then you sort of evolve from there, and you follow friends’ projects and you support them along the way. And so it’s a real pleasure to do this, because it actually shows you, I think, what’s different about friendship now — that would have been impossible 50 years ago, or highly unlikely 50 years ago.

Nat Eliason: Even 10, 15 years ago, I feel like a lot has changed. I certainly grew up in the era where “don’t talk to strangers on the Internet” was my parents’ number one concern with me getting on it, for decent reasons. And now at least half of my friends, if not more, I meet online first. I have this very vivid memory of 2018 — my wife, my now-wife, and I had just moved into our first house in Austin, and I invited a friend and his girlfriend over for dinner. About an hour before he showed up, she was like, “Oh, by the way, how do you know Adam?” And I said, “Oh, we know each other through Twitter.” And she was like, “What — you’ve never met this person in real life? Who are you bringing into our house?” And it was great. Adam and I are good friends now. But even then, that was odd — and she was totally fair to have that reaction. Now it’s just like, “Oh yeah, of course, that’s another person we met.”

Jimmy Soni: And it’s funny, because I think you accelerate a lot of friendships that way, right? Because you do feel like you’re kind of in each other’s heads in some way — you vaguely know the projects the other person’s interested in. Whereas with, call it, locker proximity, that still requires a fair amount of investment in a friendship before you know if you’re even interested in the same things. But with online or digital friendships that convert into real-life friendship, you’re like, I already know all the stuff you like. We like all the same stuff.

Nat Eliason: We follow all the same people. Our feeds are the same.

Jimmy Soni: It’s like you were already hanging out with them.

Nat Eliason: Yes. Although it does create these funny circles, where I have a much harder time being friends with Instagram guys than Twitter guys, because I just don’t know what’s in their feed. It’s almost like a relationship strategic thing — Cosette knows what’s going on in a lot of our friends’ lives that I don’t know, because I’m not on Instagram, and I know stuff going on in other friends’ lives that she doesn’t know, because she’s not on X as much.

Jimmy Soni: That’s really funny.

Nat Eliason: It’s strategic, almost.

Jimmy Soni: Do you get a little bit of — I don’t know if you have this — the six degrees of Chris Williamson? Or the problem of everybody consuming the same information?

Nat Eliason: Yeah, right.

Jimmy Soni: A little bit.

Nat Eliason: That’s definitely true.

Jimmy Soni: I think that’s true of all communities, but I think it might be particularly true of friends who are based on Twitter, X.

Nat Eliason: I have a group chat of guys who are also terminally online on X, and I swear, two-thirds of the time someone posts something funny in the chat, I’ve already seen it.

Jimmy Soni: Already seen it.

Nat Eliason: And it’s a weird experience — this world is big, and it’s really, really small.

Jimmy Soni: Well, we’re here to talk about your world expanding a bit and changing a bit. A lot has changed. But just for listeners who aren’t familiar with your particular path — can you sketch out... I think of you as like the Dos Equis guy of the Internet. You’ve had some of the most interesting career shifts, transitions, experiments you’ve run. Can you walk us through briefly — take me from your education at Choate to now, kind of bullet points, so people have a sense of who you are?

Nat Eliason: Yes. So, I guess the way I describe it is that I’ve been very fortunate to have made a career out of getting super fascinated and obsessed by things and diving down these different rabbit holes that have thin relations but not very thick ones. That’s been this fun journey over the last 12, 14 years. I went to high school at Choate Rosemary Hall up in Connecticut, and while I was there I thought I was going to go into physics. Then in the same year I took microeconomics and read Atlas Shrugged and got immediately red-pilled on entrepreneurship and business. So I kind of hard-pivoted — decided entrepreneurship and business was what I wanted to do, applied to really just the top ten business schools for college, went down that list, and then went to the best one I got into, which was Carnegie Mellon.

One year into business school at Carnegie, I realized it wasn’t going to teach me anything useful about entrepreneurship. It was great for learning finance and stuff that would be useful in a management consulting career, things like that — but really not much. There’s not much value in the entrepreneurship degree at almost any college or grad school. I dropped out of that into the philosophy program, because I still had that literary interest, but that was also the lowest-requirement major, so it gave me the most freedom to do whatever I wanted with my college degree. I ended up dropping out for a year to work on a startup, and convinced the business school and the philosophy school to give me credit — kind of independent-study credit — for working on my business, which allowed me to still graduate on time. So I got to hack the system that way.

Jimmy Soni: Which, by the way — just to pause here for a second, because there are either young people listening or parents of young people listening — one of the things I say when I’m speaking, because I did roughly the same thing: I designed my own degree at Duke. Basically, starting sophomore year, I was able to choose all of my classes through senior year. I designed it so I got to do exactly what I wanted, with who I wanted, and then just did a bunch of independent studies to fill in the gaps. I tend to think college — you’re in this business too — is far more hackable than people think it is. There are no rules. There’s nothing they actually have to do. You can make it up as you go along, and, by the way, get money to do it.

Nat Eliason: And once you graduate, no one’s really going to care what grades you got or most of the classes you took. So you either use it to get an extremely deep education on a challenging subject you couldn’t realistically get anywhere else — if you can study physics at MIT or something, you have the potential to get an education you can’t get anywhere else — or you do the bare minimum, get the piece of paper, meet everybody, because those are going to be your friends, possibly your wife or husband, your future business partners, all of that, and then focus on other stuff. I think the bimodal approach is the way to do it.

I ended up getting a lot of value in the sense that I spent that whole year off campus in downtown Pittsburgh, working on my startup with other adults. I went through a startup accelerator downtown — so it was me, the 20-year-old who couldn’t go out to the happy hours, and then all these other adults working on their startups. I was off campus during the day, learning business skills, interacting with people much older and further along in their careers, but then at night I went back to campus, stayed in my fraternity, threw parties, did all the fun aspects of college. That was the best year of college, by far. Best of both worlds.

Jimmy Soni: Did you — how did that business go?

Nat Eliason: Oh, terribly. I mean, it was the classic problem: one, I was a 20-year-old who’d gotten into good schools without herculean effort, and I knew I was smart, so I felt like I knew what I was doing. I’d read a couple of books, like The Lean Startup, and there was nobody around me saying, “You don’t know what you’re doing.” So I just assumed I did. I was able to raise a small amount of money, but I don’t think in that year we got a single paying customer. I was really good at making pitch decks —

Jimmy Soni: Which is a skill.

Nat Eliason: Which is a skill. It’s a skill. I was good at going to networking events, I was good at playing startup, but I did not actually learn how to start a business. About a year in — it must have been a book I read, because it wasn’t somebody who told me — there was this moment of cascading dread, when it all hit me at once: oh my gosh, I’m a fraud, this isn’t working at all, this is making no money, there is no product-market fit here, and I’ve just spent a year on this, and I could have figured this out probably eleven months ago. Very useful.

Thankfully, when I realized that, I very quickly went to: I need to shut this down, and I need to get my act together, because I’m graduating in eight months and I’ve been shirking a philosophy degree. So I have no job prospects that way — my startup has failed, so that’s not going to pay me — and I have about eight months to figure out how to make money or get hired, or else I’m moving back. I didn’t have a fallback plan. I was like, I’m just going to figure it out. And thankfully, I did. That was when I got really into content marketing and writing, because the question I asked myself was: okay, I want to get into startups, I don’t have any useful skills for that right now — I don’t know how to code, I don’t know how to design, I don’t know how to market, I don’t know how to do sales — what is the skill that would be useful to a startup that I’m closest to knowing how to do? I picked marketing, specifically content marketing, because I was a philosophy major, I was writing a lot. I figured, okay, I can figure out how to write good articles for a company blog, a startup blog, and that will get me my first jobs and internships.

So I started my blog, started writing articles on it just to demonstrate I could do content marketing, from what I could piece together from blogs that were out at the time. There wasn’t really — there wasn’t YouTube back then in the educational sense we have it today.

Jimmy Soni: Back in the stone age.

Nat Eliason: Yeah, exactly. There were no Twitter accounts I could follow — people were just posting about pooping on Twitter, there was no real network. But Zapier and Buffer were the two big future-of-content-marketing companies at the time. So I started my blog, posted on it for two months, felt like I was getting good, and then I just cold-emailed both of them and said, “Hey, will you take me on as a freelance writer?” I didn’t say internship, didn’t say college student — I was just trying to pitch them to hire me as a freelance writer. Buffer said no, but Zapier said yes. So by December — this is a two- or three-month period — I’d gone from nothing to: okay, I have my first freelance writing gig with this company I have a lot of respect for. It was $150 an article. I did the math and said, okay, if I do 12 to 14 articles a month, call it three a week, that gets me enough that I could afford to live somewhere like Argentina or Thailand. So now I know I can go do that when I graduate if I need to — I don’t need to take any job I don’t want to take, I can keep focusing on entrepreneurship skills, and I have this as the backstop.

That was really the first — you don’t think of freelance writing as entrepreneurial, but it was a very entrepreneurial thing to do. It was like, okay, I’m going to develop this skill, sell it, figure out my rough P&L to run that business, and go from there. I ended up taking a job for about eight or nine months that didn’t work out very well, but then started a marketing agency right after it, and it all started with making that decision senior year of college. That marketing agency ended up doing a few million a year — I stepped out of it, had another CEO take over, and she ran it for a few years before it was eventually acquired. That was my first entrepreneurial thing that did very well, and it all stemmed from that decision.

Jimmy Soni: Just out of curiosity — did your family, were they nervous? Were there any tough conversations? Because that’s usually the part of the story people leave out, right? One, one has to drop out of college — but the more complicated thing is usually not dropping out, it’s the phone call to the parents to let them know what your plans are. You didn’t drop out, but did they have any concerns — you’ve gone to Choate, you’ve gone to Carnegie Mellon, you’ve been in these worlds that are indisputably prestigious, and now you’re going to go write freelance articles and maybe move to Thailand?

Nat Eliason: Yeah. By that point they’d been warmed up to it from me doing that year off — that was the hardest of those conversations. I don’t think my mom was ever worried — she was like, “He’s going to be fine, he’s going to figure it out.” My dad is much more academic — he went to Harvard Law School, he’s a professor, it’s like, college is important. I think he was very worried I wasn’t going to get a degree. I think he knew, rightly, that as soon as I got a taste of not being in college, I’d never want to go back. It’s sort of a fluke that I ended up graduating, in the sense that if I hadn’t gotten all that extra credit, and if I hadn’t had so many APs from high school, I wouldn’t have finished — there’s no way. But after I shut down the startup and papered out the math with my advisor, we realized we could jam one semester full of kind of BS classes to get me to the finish line and still get the piece of paper. I think if we hadn’t been able to work that out, it wouldn’t have happened. But that satisfied him, at least, that I got the degree.

I think it was clear to them at that point that even if the startup hadn’t worked, I had started something, hired people, raised some amount of money — I was on some path. And I think if I’d said, “After I graduate, I’m going to figure out how to make money doing freelance writing,” that would have been one thing. But going to them and saying, “I’m already doing it, I’m already making it” — that helps a lot. It’s like, okay, clearly there’s a plan here, he’s on some sort of trajectory. Sometimes kids in high school or college reach out to me. They used to more when I was younger —

Jimmy Soni: You’re over the hill now.

Nat Eliason: No, well — I feel like when I was in my mid-20s I was more vocal about the college-alternative-path thing, so I’d get more of that inbound. I don’t get as much of it anymore. But I’d always say: make some money online first, then tell your parents, because they’ll be a lot more amenable to the idea if you have proof of success instead of just hoping it’ll work out.

Jimmy Soni: When you were raising money at 20 years old, how did you communicate with investors? What were those conversations like? Raising money is something even adults obviously struggle with mightily.

Nat Eliason: Yeah. Honestly, it was a lot easier for me, because it was from a local startup accelerator in Pittsburgh, and I was a Carnegie Mellon student. These guys are wonderful — I don’t mean this as a criticism — but they gave me a lot of benefit of the doubt because I went to Carnegie, and I’d just won the Startup Weekend in Pittsburgh with this idea. So I had that kind of charisma, and there was a bit of local excitement around what I was doing. It was kind of a natural fit in that sense. But looking back, if I’d gone out to Silicon Valley and tried to pitch YC, or tried to get in front of an a16z, I think they might have said, “You have no idea what you’re doing, you have nothing here.” That might have been very helpful, honestly. Even when I raised the follow-on money, it was from the same parent fund — a Pennsylvania innovation fund to support job creation within the state. So again, I wasn’t playing in the hardest leagues, and I think they gave me more trust because I went to Carnegie.

Jimmy Soni: How did you deal with the feeling you described — you’re a year in and you realize it’s not going to work? Did it feel like the sky was falling? Because even at that age, even if you’re not building a business, you’re generally dealing with the challenge of what am I going to do with my earthly time — those are challenges for people who are just going to class every day. You’re building a business and watching it fail. What was your thought process, if you can think back?

Nat Eliason: I usually don’t stay in that headspace very long. I’ll have those feelings occasionally, but it very quickly shifts to: okay, well, there is something to do here. So I’ve never had long periods of wallowing, or being stuck in fear, because I very quickly click into, okay, we need a new plan — what is the plan, let’s focus on that. It shifted very quickly. I literally remember writing this on a whiteboard in my room — I wrote “$2,000,” because it was: okay, this startup is dead, I’m not working on this anymore, these illusions of raising $500,000 and going big — that’s not happening anymore. So what’s the thing I can focus on next? How do I get to this number by this date? That was the new plan. It felt like a very quick shift from focused on the startup to, oh wow, no, this is dead. I think it had probably been bubbling up for a couple of months, what was really going on. I must have spent some time making sure I wasn’t just having a momentary freak-out, because you don’t want to go that route either. But I remember it being a pretty quick and pretty adamant realization and decision.

For better or worse, I think I am good at that — okay, this feels like it’s hit a wall, but there’s this other vector that does have potential, I’m going to go on that one. That’s worked out very well for me. It’s also definitely had the downside of quitting things too quickly, or killing things too quickly, and it can be tough to find that balance sometimes.

Jimmy Soni: When you think back on that — because you’ve written publicly about quitting and talked a lot about it — do you have, sitting here in 2026, any updated thoughts on sort of knowing when to fold ‘em and knowing when to hold ‘em? Any new heuristics, or ways you’re thinking about it?

Nat Eliason: Yeah, I think ultimately — “quitting early” is the wrong term, but I’ve always had this bias toward being willing to kill something and move on to a better opportunity. The issue with that is it’s led to a lot of shiny-object syndrome. Most people, I think, go through a period of that, where they do this thing, then this thing, then this thing, and don’t get anywhere, and they realize, oh, I shouldn’t do that, I should pick something and focus on it. The issue for me is that it’s worked.

Jimmy Soni: Right.

Nat Eliason: Right. And I don’t mean this in a braggadocious way — it’s just, I’ve gotten away with it. I’ve been able to get super interested and fascinated in things, go hard on them for a year, launch these little businesses off my X account or my newsletter, and then they go really well. It’s like, okay, I can just become obsessed with something, dig into it for six months, then launch a course or a product, and it makes a few hundred grand in the span of a couple of months. Great — costs are covered for the next period of getting obsessed about things. That’s a cool ability to have. It’s incredibly powerful, incredibly useful, and I’m very grateful I’ve been able to do that.

But it does lead to not fully committing to things, not seeing where they can go, not living up to my full potential in a lot of those areas — because these breakthrough moments will happen, and instead of saying, okay, the excitement is over, now for the long slow slog to 10x this, it’s, well, I could just goof off for six months and then do this again. That’s been fun, that’s been satisfying. And then, really, last fall, I sat down — I ended up having this conversation with my wife, too — where I was like, I don’t think I should keep doing this. Even though it’s working, even though it’s provided a lot of the sustenance for our life, it feels like I’ve been playing this game a little too long. I really want to focus on something bigger, something serious, that has a meaningful risk of failure — because I think part of it comes from a fear of failure, a fear of trying something big and it not working and being embarrassed, because that means I’m not smart, I’m not capable. But as long as I’m doing these little things, there’s no risk of feeling that way.

Jimmy Soni: Because six months later, something else comes down the road and you figure that out.

Nat Eliason: Something’s going to happen.

Jimmy Soni: Why last fall? Was there something going on that occasioned that “maybe I need to stick with one thing for a while”?

Nat Eliason: I think it was a combination of things. One, I’d been doing sci-fi writing for a year and a half, and it was clear that wasn’t going to pay the bills. While that had been going on, I’d been super deep in building with AI, learning how to use these tools, and I launched a course on learning how to vibe code before “vibe code” was even a term — nobody had used that word yet, Andrej hadn’t coined it. It was basically the first big vibe-coding educational thing out there. It did about $250,000 in sales in a weekend, went on to do half a million over the course of the year, with basically no ongoing work after that first set of recordings, plus an update in October — a breakout success. And I’d seen a lot of people who came in after me, some of whom took my course and then actually committed to doing something with those skills, building a product, building a bigger education business — and I realized I’d been so early, I’d established myself in that topic area, and then had just completely let that opportunity go. Maybe there’d never be another opportunity like that in my life — I don’t actually believe that, but it’s a consideration. Looking at that was hard. It was like, wow, I nailed this timing, and then I just did nothing with it, I just let it go. That felt like a mistake.

I think being a parent contributes a lot to it, too — would I tell my kids to treat opportunities that way? Definitely not. If they came to me and said, “What should I do with this?” I’d say, obviously you should keep going.

Jimmy Soni: That’s right.

Nat Eliason: So it’s like, okay, well, why wasn’t I doing that? It made me want to do something bigger, or fully commit to something. That started that thought process last fall, and then I spent the next four, five, six months figuring out what that could be.

Jimmy Soni: Well, we’ll cover some of the other topics from earlier in your adventures, but that brings us to what you’re doing now — which is one of the most interesting things I’ve seen in your career evolution, just the portfolio of stuff you work on. Tell us a little about the result of that soul-searching last fall, and what you’re up to today.

Nat Eliason: Yeah, so I’d basically made this decision last fall — okay, I’m going to put the book work on hold, take something from this interest in technology, and really just go all in on it. So I started spending all of my time going even deeper than I had before on building with AI, using AI — what is interesting here — and had started working on one product, which led to another and another, and was kind of going down that path.

Then there was this tiny trickle of a side quest, where Cameron Sorsby was working at Alpha School and he’d DM’d me on Twitter — all roads lead back to X, all good things come from X — and he said, “Hey, I work at Alpha School, I’m working on this new high school program for entrepreneurs, I want to help the kids level up their AI skills, would you be down to come in and do a workshop for them?” I already knew about Alpha School at that point — part of why I liked being in Austin was knowing I could send my kids to Alpha School. To me, it was, and still is, the most interesting thing happening in education. It’s the one school I’d most want to send my kids to, and I liked being there. Honestly, one of the first thoughts through my head was, oh, this is how I get my kids into Alpha School —

Jimmy Soni: They’ll discount the tuition.

Nat Eliason: Exactly — I get in the good graces now, and then when I apply next year for my kindergartner, I’ll get through the application process because I’m already on the inside. I was literally thinking that. It wasn’t completely selfishly motivated — there was a bit of that, but there was also a bit of, oh, this sounds super fun, super exciting, of course I want to come do an AI workshop for these high schoolers, in part because I was curious to see what an Alpha School high schooler is like, from everything I knew about the school.

So I went and did a modified version of my “building with AI” course for these high schoolers, and was just blown away — they were super sharp. A lot of them had already started working on business ideas or had already built audiences — a couple had over a million followers on TikTok. They were asking better questions than a lot of adults I’d done this stuff with, and they could take feedback extremely well, which maybe stood out the most. There’s a natural fear when working with students that you have to put on kid gloves, but they were very eager to hear, “This part of your landing page is ugly, you can change the copy like this, this is broken, you need to go harder here” — they were super receptive to it. I loved doing the workshop.

Jimmy Soni: And how long was the workshop — a couple hours, a half day?

Nat Eliason: Like a half day, four hours — a little bit of talking, then independent work sessions, then coming back together, then independent work again, so it’s flowing back and forth over the course of an afternoon. After we did that, Cameron and I were hanging out and talking more, and he told me more about what he’d joined Alpha School to do — this new high school for entrepreneurs, what’s now called Founders School — where they’d promise that students would make a million dollars by graduation or get all their tuition refunded. My immediate reaction was, that is the worst business idea I’ve ever heard — do you realize what you’re committing to here? But then I thought about it some more, thought about what I’d seen with the students, and — obviously I was super deep in building with AI, had seen what a lot of other teens out there were doing with AI, what teens were doing starting businesses without this kind of support — and I very quickly got to the point of, oh, this is actually doable.

It sounds insane, but you combine what Alpha’s done with academics, being able to compress the whole high school day to about three hours, which gives you four to five hours of hands-on workshops, instruction, mentorship, and support specifically on entrepreneurship in the afternoon — you take that out across four years, add in what AI lets a teenager do — and you fit all those pieces together, and you realize, oh, this actually makes all the sense in the world, especially if you get the right people in the room to help them, because it can go the wrong way if they have the wrong support, wrong mentors, wrong guidance. But get the right people in there, and this could work.

So he just asked, would I be down to chat with him occasionally as he planned this out. I said, yeah, this sounds awesome, I’d love to come in and talk to the students, be a mentor or whatever. We were just talking about it for the next two, three months, while I was working on all these other AI projects. After a few months, I’d found something that was really taking off with the AI products — stuff related to OpenClaw and agents — and side conversation, and I was basically in the middle of launching that when Cameron and I hung out again. He said, “I think for this school to work, I need somebody who is super entrepreneurial, super AI-driven, good at quickly getting things from zero to one to B, on the ground, working with the students, designing the curriculum, alongside me.” Cameron’s a great educator — he’s been building college-alternative programs for the last ten years, knows all that stuff — but he’s not as deep on the AI side or the hacky-solopreneur side as I am. So he was basically like, “Do you know anyone who’d be good to come do this with me?” And I said, “You’re looking at him.”

It was one of the strangest moments of my life, because I had not thought about it at all before that moment — there was no part of me that was like, oh, I’m going to drop everything and be a co-founder on a high school. But as soon as he asked that, and put that seed of “somebody needs to come do this with him” — it was like, oh, it’s me. I said, “I need to talk about this with my wife.” I think I just went silent for a minute, kind of staring at him as I processed it all. What I said was, “It’s not a no.” And I could see him go, “Wait — what, this is an option?” I went home and told Cosette, “This is happening,” and she said, “You have to do this.” It immediately was like, this has to happen. I think this was a Friday, and I showed up Monday and just started working — didn’t get officially hired for another month, because, you know, it’s a big company, you have to go through HR, other interviews, negotiate comp, do all the big-company stuff. I was like, I don’t care, I’m just going to show up and start doing this with you, we’re going to make this happen. And then I had to shut off everything else.

There was an evolution to the school that we might get into, where at first I thought I’d still do some of my side stuff —

Jimmy Soni: I was going to ask that — did you see yourself doing this as another side hustle?

Nat Eliason: It started that way, because in the beginning this was going to be a program for students in Austin — for students who were already at Alpha School, the Alpha High School in Austin — and then it very quickly evolved into, this should be its own dedicated high school program.

Jimmy Soni: Can you walk us through that evolution? Because when I first heard about this, I thought, oh, Nat’s going to be running programs for Alpha School — and then it was, no, no, there’s a thousand-person high school, the ambition is to build a thousand-person high school in the middle of New York City. And then I texted you and you were like, “I live in New York now.”

Nat Eliason: Yeah, yeah.

Jimmy Soni: You really burned the boats there.

Nat Eliason: Oh, yeah. We had that conversation where I decided to join, beginning of February, and then we were planning out the programming for it over the next six weeks — what would it look like as part of the high school, what would we teach, who are the mentors we want involved — kind of the program-level structure. Then I did a workshop for the Austin students on using OpenClaw — for anybody who doesn’t know, it’s a way of using an AI agent that unlocks it and gives it superpowers in a way you don’t get if you’re using Claude Cowork, or even Claude Code, or the Codex desktop app, or Perplexity Comet — all these other agentic things have a certain amount of ability to act on your behalf, but this is the next step beyond, in terms of what it allows you to do. It brings a lot of risk with it, because you’re giving it a lot of unfettered access to things, but if you build it right, it’s the closest thing to having a human working alongside you. I’d ended up adopting it pretty early, again kind of gotten away with very quickly building a ton of following, just by being excited about it, posting about it on X constantly — not in a malicious way, I was just obsessed with this. The students started asking, “Hey, can we do a workshop on this?” I said, sure, that sounds great. Did a couple of workshops on OpenClaw with the Alpha students, then the Alpha parents in other cities heard about it and said, “Wait, can you come do this with us?” So, beginning of April, we come out to the New York campus to do the OpenClaw workshop with the New York students and their parents.

While we’re doing the workshop, Cameron and I start casually talking about Founders School with the parents, and they’re all like, that’s the most incredible idea ever, you have to come do it here. They started mentioning people they knew whose kids would be a good fit — there was this immediate excitement, interest, and possible students who were a fit for it that we hadn’t run into yet in Austin.

Jimmy Soni: Did that surprise you at all? I would have thought you’d have had to ship out to San Francisco, or stay in Austin —

Nat Eliason: It surprised me at first. But then the reason it ended up making sense is that demand is absolutely there in Austin in five to ten years — Austin is a young, entrepreneurial city, people are moving there earlier in their family’s lives. So the pre-K, first-grade, second-grade, third-grade demand for Alpha is overwhelming. But there aren’t as many people who come from this entrepreneurial background, or ultra-high-net-worth background, with teenagers, who’ve come to Austin looking for this. So there’s a bit more of that demand here. And when you look at the elite high schools we’re competing with — the Horace Manns, the Exeters — much more of those are on the East Coast than in Austin.

That kind of drove the thinking, along with the parent excitement — it became clear that we’re going to have more demand for these students in New York City, initially, than in Austin. But Cameron was living in Austin, I was living in Austin with my three kids, Joe, our principal, is in Austin, and the New York campus is new — New York only started last year, but the New York team was really excited about it. It was this funny thing where I think everybody arrived at the “we need to do this in New York” conclusion at the same time, independently, but nobody wanted to bring it up first. So there was this little dance for about a week, and then we all kind of said it at once, and it was like, oh yeah, obviously that’s what we’re going to do. That was mid-April, and June 1st, I moved here.

Jimmy Soni: All right, so we are in medias res — we’re in the middle of this.

Nat Eliason: Yeah, yeah.

Jimmy Soni: So what is it — how is Founders School going to be distinct from Alpha School?

Nat Eliason: Yeah. The core premise of Alpha is that, one, students should love school, which sounds obvious, but it’s not a given at all — a lot of parents have just accepted that their kid is going to be bored in school and that’s part of life. So we say, no, the number one mission of this school is that kids will love it. One of the main ways you let kids love school is if you give them a good reason to get the academics done besides “I told you to” — because normally you get academics done because otherwise you get in trouble at school, or with your parents, or maybe your parents give you some money for good grades on your report card.

Alpha takes it to the max, where we say we want to make it as rewarding as possible to get your academics done. First, we compress it to two hours a day in K through 8, three hours in high school, through an AI tutor that knows exactly where you are in reading, math, writing, science — everything — and gives you the exact next thing you need to learn to progress toward mastery for your age. You’re never sitting in a lecture, bored, waiting for somebody to catch up. You’re never slowed down if you’re interested in a subject — you’re getting the exact right challenge for where you are. That lets you do the whole day in two hours.

You’ll have people say, “Well, then they’re in front of screens, working with AI” — I understand why people are concerned about that. But then you talk to the students, ask them, and the test scores are better — you could argue it’s the highest-performing private school in the country, for a lot of these measures, especially K through 8. You ask the kids, would you rather sit in classes all day, or do these two hours on your laptop in the morning? Every single one says they’d rather do that. We used to survey our students, “Do you love school?” — that was one of our most important surveys at the end of each session. But we stopped, because 90, 95, 98% would say yes, I love school — it stopped being a useful measure. So now we ask, “Do you like school more than vacation?” And 54% of students say they’d rather go to Alpha School than go on vacation.

Jimmy Soni: Wow.

Nat Eliason: That’s an insane metric.

Jimmy Soni: That’s an NPS any business would be proud to have.

Nat Eliason: Right. But the way that happens is the compressed academics are one part of it — the reward, the benefit of that, is that you’re doing awesome stuff the rest of the day. It’s still a full school day, 9 to 3:30, but the academics are done by 11:30, and then you have three or four hours to do other awesome stuff. Those change throughout the year, and by grade level, but they’re focused on some kind of life-skills workshop where students are doing something fun while building an important life skill — often pretty ambitious for their age group. For example, one of the ones kindergartners do is a two-month session where they climb a 40-foot rock wall.

Jimmy Soni: Wow.

Nat Eliason: They go to a local climbing gym, harness up, and day one they go one step up the wall and they’re all cheering for each other because they got on the wall. The next day, two steps, three steps — you do that over two months, and by the end they’re going 35, 40 feet up this wall, while their friends cheer them on. The parents are terrified, but then they see how proud their kid is, they see their peers cheering them on, and that’s what they’re spending most of their day on instead of sitting in a lecture hall. So you ask a kid — would you rather sit in a lecture for most of the day, or get your academics done and then go rock climbing the rest of the day?

Jimmy Soni: Right. My take on Alpha School — which I’m a huge fan of, I hope my daughter enrolls at some point, she’s taking a different tack at least through middle school, we’ll see what happens with high school — is that some people think it’s a bet on the reinvention of education. I don’t. I think the more accurate statement is it’s a much safer bet on how kids already are wired. My daughter’s creating things all the time — it just doesn’t happen within the four walls of her school. This isn’t a knock on them, it’s their model, but in some ways it’s actively penalized — the things she wants to do to get ahead, to break the rules a little, aren’t encouraged. It feels like what Alpha’s doing is catering to the inborn instincts of children —

Nat Eliason: Right.

Jimmy Soni: — as opposed to reinventing. They’re reinventing the system adults created, but kids are actually very naturally wired for these kinds of environments.

Nat Eliason: Kids are natural learners, they’re naturally curious. This was a really long way of me answering the question you started with —

Jimmy Soni: No, you segued it back perfectly.

Nat Eliason: Because part of Alpha’s ethos is that every kid is naturally motivated by something — there’s something they’re just wired for. There’s this great Slate Star Codex article, “The Parable of the Talents,” where it’s not so much that everybody is born with some innate talent for piano, or running, or writing, but we’re often born with a fascination — something we naturally gravitate toward. And by gravitating toward something you want to do more of, it’s kind of self-rewarding. Most things in your life won’t be that way — that’s why you get paid to work and do all these other things. So if you can find what a kid is naturally drawn to do, and free up their day to do a lot more of that, they’ll get through the academics way more efficiently, with much deeper mastery, than in the normal system.

Alpha School has created all these different schools to cater to different students’ fascinations. Alpha is the one most people know best — it’s the most well-known, kind of the elite private school, and Alpha’s afternoons are focused on these workshops, and when you get to middle school and high school, you get to pick a big passion project to dedicate that time to. But we have other schools, like the Texas Sports Academies, where you get your academics done in the two hours in the morning and then spend the whole day playing sports. For a lot of kids, that’s what makes them perform — it’s like, oh, you just have to get your two hours of math and reading done and then you can play basketball, volleyball, or baseball for six hours.

Jimmy Soni: Right.

Nat Eliason: It’s like, yeah, I’m going to get it done.

Jimmy Soni: So when did the thinking evolve to the point that Founders School was going to be its own entity, rather than simply a track within Alpha School — because you’re going to be admitting students who know they’re going to Founders School, right? Is that correct?

Nat Eliason: Yes, yes. It evolved from this model Alpha had started at K through 8 — Sports Academy is for kids who are into sports, Waypoint is where kids are horseback riding and doing archery and rucking and outdoor activities, GT School is hardcore, more academics in the afternoon. We’d started this model at the younger ages, and we said, okay, what are the high schools that should exist? Alpha High is the one where you can explore anything you’re passionate about — it’s very open-ended. We have a student going for the Olympics in rowing, students writing novels, a student putting on a Broadway play, students starting businesses — and it was actually partially their idea to do Founders School, because the thinking was: okay, if you’re really serious about building a business in high school and want to be held to even higher expectations, but get even more crazy support to go after it — this is the school for you.

So it’s stepping up the expectations — obviously we have a longer school day.

Jimmy Soni: So it’s longer than the usual Alpha School day.

Nat Eliason: Yeah, it ends at 5 instead of 3:30.

Jimmy Soni: Why that choice? That’s an interesting design choice.

Nat Eliason: More time. It’s kind of like — if you were going into an apprenticeship in the pre-school era, you’re deciding at 14, 15, 16 that you’re going to become a master blacksmith, and nobody should be able to say, “No, you have to go do these other things before you become a blacksmith,” if you know that’s what you want to do. Obviously our students are still held to very high academic standards — we’re still doing all the academics, they’ll still be in excellent shape for college — but if they know entrepreneurship is what lights them up, and that’s what they’re going to be doing when they go home anyway after school, they can just stay with us longer.

Because the great thing about how we’ve designed Founders School is there’s programming, curriculum, and structure, but it’s also very heavily tailored to provide the exact support the student needs at wherever they are in their business. So instead of a month or two, or a semester, of tons of classes on Facebook ads, if we see a student is at the point where they might start experimenting with Meta ads, and that’s something they want to explore, we get them one-on-one support with an expert who’s a practitioner in the field — somebody running an ads agency or something — whose time we’re buying each week to work with our students, train them, mentor them, audit their process, and help them learn that specific skill right when they need it. So they’re getting this incredible amount of support for anything they might run into in their business, along with the coaching, emotional support, and encouragement that’s standard for Alpha across both academics and extracurriculars.

Jimmy Soni: Got it. And so the audacious bet — the bet you started our conversation with — is you will make a million dollars in revenue by the end of your four years, or —

Nat Eliason: Gross profit.

Jimmy Soni: Gross profit, not revenue.

Nat Eliason: Not revenue.

Jimmy Soni: Wow. Even more audacious. So how does — without giving away state secrets, or anything privileged you can’t share — what was the thinking around that particular set of numbers, that bet, that promise? Because that’s the thing that’s been getting headlined.

Nat Eliason: Yeah, this was something Joe came up with when he came up with the idea for the school. Remember what I said at the beginning of the conversation —

Jimmy Soni: Can you say a little bit about Joe, so people have context on who he is — there are people learning about Alpha School for the first time.

Nat Eliason: Yeah, okay. Joe Liemandt joined, came in as the second co-founder for Alpha School about five years ago. Alpha was originally started by MacKenzie Price in 2014 — she ran it as a school in Austin using these principles of direct instruction, one-on-one mentorship, spending most of the day on activities, and pioneered the overall structure for the school, with incredible success. Joe founded a software company in the ‘90s called Trilogy — it’s grown, and he’s the sole owner of it now, a multi-billion-dollar company, massive successful tech entrepreneur. His daughter ended up going to Alpha in Austin, and that’s how he found out about it — he fell in love with the model, was amazed by what MacKenzie had figured out about teaching students this way. He’d actually sold one of the first pieces of software that was, like — it was Salesforce before Salesforce, is a way you could describe it, back in the ‘90s — so he’s been obsessed with the potential of AI for 30 years now. When generative AI came on the scene, he basically went to MacKenzie and said, this is how we take what you’ve figured out and bring it to a billion students. That’s the core mission of everything we’re doing at Alpha — how do we bring the best education possible to a billion students around the world? It’s kind of like the Tesla model — we’re starting with the Model S, the Roadster, we need the expensive one first, and then we’re able to bring it down-market to broader audiences. So he brought in the software side, invested a significant amount of his own capital, and started building out the Alpha that more people have heard of today.

He’s obviously an incredibly successful tech entrepreneur — he saw the students at Alpha who are really entrepreneurial, and between the two of them, they came up with this idea for Founders School — the school for entrepreneurs.

Jimmy Soni: A million dollars in profit, or your money back.

Nat Eliason: Exactly. But he knew the same thing I said at the top of the conversation — there are no good entrepreneurship programs out there.

Jimmy Soni: Right, right.

Nat Eliason: There’s no undergraduate entrepreneurship degree that’s worth it, no graduate one that’s that good either. There are people who go to these schools and become successful entrepreneurs, but there’s really none of these schools that reliably drive outcomes in entrepreneurship. If you just said, “We’re launching a high school for entrepreneurs,” it’s kind of like, okay, right, there’s a lot of places for entrepreneurs — there’s FBLA, there’s all these things that say they’ll teach you entrepreneurship, and everybody kind of knows they’re not going to do that good a job. But if you say, “We’re launching a school for entrepreneurs, and if your kid doesn’t make a million dollars by graduation, we’ll refund you the tuition” — tuition is $150,000 a year, so we’re saying we’ll give you back $600,000 at the end of four years if we don’t get your student to that outcome. There are caveats — we’re assessing students each year, if a student comes in sophomore year they’re not on the guarantee, there’s all the edge cases. But that’s the core promise of the school, and it’s putting the pressure on us to actually figure this out, to make sure we’re delivering on these outcomes, and not playing startup like I was in college, trying to learn this for myself. It’s this incredible forcing function, and it’s the only reason anybody’s talking about this — because we have to be insanely committed to creating the best education experience possible on this topic, one that’s never existed before, that nobody’s made this kind of commitment to before. That’s where all our mental energy is going — we know this is possible, we just have to fine-tune it as we work with the students.

Jimmy Soni: How do you avoid the undue pressure? You’re in the early innings of this — it’s actually fun to talk about while it’s still being figured out. How have you thought about not putting that pressure on the students themselves, for that gross-profit-or-money-back burden?

Nat Eliason: Yeah, okay. We’ve actually had a couple of parents say they don’t want to do the guarantee.

Jimmy Soni: Oh, wow.

Nat Eliason: Right, for that exact reason —

Jimmy Soni: Okay.

Nat Eliason: They’re like, I don’t want my — I always say “student,” because kids don’t like being called kids — I don’t want my kid to feel like they have to hit this or I’m going to be —

Jimmy Soni: Right.

Nat Eliason: It’s like, yeah, obviously, we don’t want that either. It’s first and foremost an offer to the parents — it is the most expensive high school in the country, aside from IMG maybe. That’s how much we’re investing in the students — there’s no other school that’s going to get your kid on the phone with a top-tier Meta ads expert the next day when they have trouble with their ads account. It’s a huge investment, and we’re saying, this is what we’re willing to commit to. But we don’t want to create unpleasant pressure on the students — and it factored into how we ended up at the gross-profit calculation. We want the most aligned structure —

Jimmy Soni: Yeah.

Nat Eliason: — while creating minimum adverse incentives. So, okay — we can’t do valuation.

Jimmy Soni: Right.

Nat Eliason: Because,

Jimmy Soni: Right, valuations can be made up every day.

Nat Eliason: “Oh, I sold 1% of my company for— Exactly. We’re not going to do that, because then they might not learn anything —

Jimmy Soni: Yeah.

Nat Eliason: — because part of this is how do we make sure they learn the most. So then, revenue — we don’t really want to just do revenue either, because then they could be incredibly unprofitable, they’ve made money, they’ve built some business, but it’s not necessarily a good business. So we went from that to, okay, net profit then — because we want them to not just spend infinite money on ads, spend $10 million on ads to get a million in revenue because mom and dad funded it. We don’t want that. But then we realized the problem with net profit was that we’d create other adverse incentives, where we’d be telling students not to reinvest in their business.

Jimmy Soni: Oh, that’s fascinating.

Nat Eliason: Right — we were like, well, shoot, we don’t want that either.

Jimmy Soni: Them to take money out in order to avoid — for their parents to get back the $600K.

Nat Eliason: Exactly. We didn’t want to be going to the students and saying, “No, don’t run ads, don’t do another production run, don’t hire an employee, because we need to make this number happen.” So that’s how we ended up on this gross-profit calculation — we’re going to factor in a certain amount of cost of goods sold, and — you probably wouldn’t normally put advertising and stuff in there, but we’re going to put that in too — but we’re not going to try to disincentivize you from growing your team or reinvesting in the business, because there might be a student who builds a $10 million business, and — I mean, that sounds insane sometimes when you say it in front of parents, but I think that’s fully possible in four years, just seeing some of the students who are applying, who are already making progress. Zach Yadegari — he’s 19, and he sold Cal AI for fifty million dollars.

Jimmy Soni: Wow.

Nat Eliason: And he was going to a normal school — he had to figure this all out on his own. It’s like, this is possible. The reason we have to put so much thought into it is that we want the best structure possible for everybody — it’s not about trying to get out of something, it’s the thing we care most about, providing the best entrepreneurial education for these students, something that’s never existed before, that they wouldn’t need to go to any of these graduate entrepreneurship programs afterward. One of my personal KPIs is that they could teach a class at places like HBS when they graduate — if they can’t teach a class at HBS, I’ve failed. That’s what we’re aiming for.

Jimmy Soni: Yeah. So — I understand the part of Alpha School that’s about compressing an ordinary school day into two to three hours, that makes all the sense in the world, it’s almost table stakes at this point, because of Alpha School’s success — by the way, that’s not a knock, they did it, they proved it, you kind of accept it, and if you don’t accept it you’re just not looking at the numbers. What’s the program design like for Founders School specifically, after you’ve checked the boxes on academics in the morning?

Nat Eliason: So academics are done in the morning, and then we have the students from basically 12 to 5 for the entrepreneurial section. About 70% of the week is independent work time — or, if they’re working with another student as kind of co-founders, working together — on whatever stage they’re at in their business. One of the things we realized really early and really quickly was that just as Alpha School can’t rely on finding incredible second-grade math teachers in every location — the software needs to provide excellent support — we too, at Founders, need to create the best software to support an early entrepreneur wherever they are in their journey.

A lot of it starts with three axes we think are most important for them to figure out to get started. The first is developing expertise — a fun tie-in for me, because I spent years as a personal-knowledge-management writer, went very deep on this topic, how do you teach yourself things, how do you learn things. Now AI has both given us superpowers in that sense, but it’s also given us this incredible crutch — people will just sling slop.

Jimmy Soni: That’s right.

Nat Eliason: Right — they’ll make a document about a topic and then you ask them a question about it —

Jimmy Soni: And they have no idea what they are talking about.

Nat Eliason: They have no idea what’s in it. So the thing we start every student with is: I know you want to go build a business, I know you want to go work on a business — but you don’t get to do that until you’ve demonstrated you’ve developed some meaningful knowledge and expertise in a subject area, so you can actually build a business there. Because the number-one thing we see with students starting businesses is they start things related to school — sometimes that’s a good idea, sometimes it’s good ed tech, that’s a good business — a lot of times it’s not. Or they start businesses for other teens who don’t have money — just not the right market to go after.

So the first thing we do, the first thing we’re pushing them toward, is: start just thinking of topics you’re interested in, and go through this process of building expertise, building deeper knowledge, teaching yourself, being able to explain what you’re learning, and see where that leads you. Because if you don’t have a somewhat unconventional point of view on a topic, it’s going to be hard to carve out a real competitive advantage in almost any business you’d want to go into. So we start them there.

Jimmy Soni: And what does that look like — do they read, do they talk to people, a mix of both? What does that time look like where they’re developing expertise?

Nat Eliason: So it’s a mix of —

Jimmy Soni: Or what do you want it to look like, since you’re still building it?

Nat Eliason: Yeah, yeah. So this is the tool we’ve gone the farthest on, because it’s the foundational element, and it looks like a mix of reading and talking to people, but then doing their own research and kind of annealing — like sharpening a samurai sword — consolidating their opinions based on these sources into defensible positions on these topics. A little bit like what you might do in thesis research in a PhD program, but with the support of good technology that uses AI to challenge you, help with your research, expose you to new ideas and directions, without doing the work for you. You can almost imagine there’s aspects of Readwise, and of Roam and Obsidian, but in this kind of narrow context — pushing them to focus on one area, so they’re not just sprawling in tons of directions.

Another part is audience and network building, because the second big challenge of becoming an entrepreneur in high school is that not only do you not have any expertise or experience, you don’t know anyone. You might have some family connections, the Alpha connections, but that’s kind of it. So we’re pushing them, in a healthy way, to get online — predominantly X, because that’s where we see the most ROI, or LinkedIn — and find the people who are the experts in this subject area, follow them, engage with them, see what they’re talking about, and try to thoughtfully engage with them while building a bit of an audience themselves by sharing their thoughts. One of the most honest measures of whether you’re developing interesting thoughts on a topic is if you start getting responses — not engagement in a negative, viral way, but if other smart adults are thoughtfully replying, you’re getting somewhere.

So we’re helping them build expertise and actual industry establishment through things teenagers never had access to before — AI, the Internet, social media — but being used in a good, pro-education, pro-learning way, not a slop-and-doom-scrolling way. It starts there, and they’re going to be pissed at me, because they want to vibe-code and I’m gonna say you can do a little of that in your free time, but if you don’t start here, that stuff is never going to work. Start here.

We do that, and then they move into our co-founder tool, basically — working with a mix of that, our guides, our entrepreneurs-in-residence, our mentor network — okay, I’ve developed these points of view, started to make some connections, talked to people in the industry and gotten their perspective, these are some of the ideas I think are interesting. Exploring as many of those as possible at first, being challenged on them by the tool, but also by us and by the people they’ve connected with in the field. We have strong opinions on this, a lot of it influenced by Joe — I’ve had the privilege of spending a lot of time with him, learning how he thinks about business, technology, and opportunities, and we’ve built a lot of that into the product. So the students are almost getting direct support from him through the tools, and from him actually coming to the school and working with them as they form these ideas. It helps them move through this process of getting to the validation phase — you came up with something that’s a good idea, a good plan to get to a reasonable scale in a reasonable amount of time, you’ve validated it, made some kind of MVP, some basic version, you’ve charged money for it, and now you’re set up to do the flywheel — try something, see if it works, hit a bottleneck, ask us for help getting through that, and we’re checking in with you every day, during standups, internal reporting, to figure out where those challenges are and get you the exact support you need for whatever’s next.

Jimmy Soni: Got it. Is it businesses in general — are you thinking about businesses where they’re going to have to hire people eventually?

Nat Eliason: I mean, I love that idea — if we have a 16-year-old with a team of ten people in their 20s, 30s, 40s, oh my gosh, that’d be incredible.

Jimmy Soni: But seriously — are you anticipating that? I guess at the beginning you’re saying a lot of these businesses could theoretically be run with small teams, or one person.

Nat Eliason: Yes. I’d prefer their ideas allow them to get to that million-dollar mark without hiring anybody — ideally clever use of AI, good pricing strategy, good market opportunity, that’s completely reasonable these days. That’s what we’d nudge them toward. I wouldn’t want them to try to do, say, a dog-waste pickup service where you need to hire a bunch of people at minimum wage and monitor them — one, for the legal logistics, because they’re minors —

Jimmy Soni: They’re minors.

Nat Eliason: Which does introduce a lot of real challenges — they can’t open bank accounts, can’t sign legal forms. It’s a conversation we have to have with the parents too — hey, you’re cool with this, right, because they’re going to be building a business and your name has to be on it as well. They’re all cool with it, but it does create these weird bottlenecks, where you do kind of have to bias toward software, certain tech, e-commerce — things where it’s a little easier to get some of that initial scale, than if you have to immediately hire. Also, a lot of people in their 30s probably don’t want to work for a 16-year-old.

Jimmy Soni: Of course not.

Nat Eliason: Yeah, occasionally you’ll meet one, maybe.

Jimmy Soni: I think we’re also in a brave new world, though — you could see a universe where that’s okay.

Nat Eliason: Yeah.

Jimmy Soni: One question I have, among others — are you screening, how are you doing the screening and selection process? This is actively happening now. How do you admit a class of people you think are going to thrive in an environment like this?

Nat Eliason: Yeah, it’s something we had to put a lot of thought into, and are obviously going to keep refining. For this first class, we set the max at 20 — I think it’ll probably be 10 to 12, because we’re being very selective, and we wanted it to be a small enough initial cohort that we could be really hands-on with every student while we run this first year.

The first thing that surprises people is we don’t ask for a transcript, because it doesn’t matter that much what your grades were — basically every student who comes into Alpha, no matter what great school they went to, is anywhere from one to, gosh, five years behind on reading or math or these core subjects — not fully behind, but they have holes in their knowledge we need to fill in. So it doesn’t tell us that much. It gives us some idea of how gritty you are, but even for that it’s not a great measure. What we have is our challenge. There’s a first round of the application that just gets you in the door — short answers on why you want to do this, what you’ve done, entrepreneurship, hardest thing you’ve ever done. Then you get a challenge, where over two weeks you have to go through a baby version of the process I just described — come up with an unintuitive position on something, put together an MVP of how you’d do that, try to sell it to at least 20 people who aren’t your friends or related to you, then make a video and write-up on everything you did and learned, and send us the links so we can go look at it.

Now more people know this is the challenge, but for everybody in the process right now, they didn’t know this, so they didn’t have time to prepare for it. You learn a lot about a candidate with that two-week deadline. Some people just disappear at that point of the application — that tells us everything, it’s like, okay, this isn’t the right program for you. But other students blow us away. We had one student who was having a lot of trouble getting sales during the sales part of the process, and he ended up getting the D list for his entire school, and emailed everyone pitching his app to them. He got in trouble, got sent to the dean’s office. But he’s telling me this, and I’m like —

Jimmy Soni: And you’d like that’s amazing, that’s incredible.

Nat Eliason: Exactly, exactly. Those are the kinds of things we’re looking for — are you fully committed to this. In lieu of the transcript, we have what’s called the CCAT, a cognitive aptitude test. A lot of people don’t know this — Alpha makes every employee take this same test, and if you’re below the 85th percentile, you’re not eligible for any role at the company. So every single person at Alpha — the guides, the admin, everyone — has to be in the top 15% on this cognitive aptitude test. It’s incredibly reassuring for an education institution, knowing every single person interacting with your kids is at this level. We just used the same thing for the students, one because we were doing admissions kind of last-minute — we opened it in May for September — and I didn’t want to make them go do an SSAT. It’s only 15 minutes —

Jimmy Soni: Okay. Oh wow, a 15-minute test.

Nat Eliason: It’s a 15-minute test.

Jimmy Soni: Wow.

Nat Eliason: It’s quick, but it’s 50 questions — a mix of math, reading, spatial awareness, similar-ish to an IQ or workplace-competency test. We have them take that in lieu of transcripts or other standardized tests.

Jimmy Soni: Got it. We could talk about this for a couple more hours — I want to be respectful of your time. How do you treat summers? You’re enrolling kids into a four-year program, presumably, and a business doesn’t stop just because summer starts. How have you thought about that?

Nat Eliason: We’ll keep school hours during the summer for them to come in and work on campus, just without the academic portion. Austin actually keeps their school open all summer too — this was the students’ idea, because they loved going in and hanging out with their friends.

Jimmy Soni: More than vacation.

Nat Eliason: Exactly. Yeah, yeah. So we’ll do the same thing here — we encourage you to keep working on this over the summer, we’ll be here to provide all the same resources and support.

Oh, I didn’t even finish talking about what the rest of their day looks like — it’s that 70% working where they are in their business with us and the apps and tools, but then we’re going to have workshops each month on different themes — a month of leveling up everybody’s AI skills, a month of leveling up sales skills, a month of copywriting, some of these core business concepts. We’ll probably do two workshops a week, about one and a half to two hours, going deep on one skill for the month, with an adaptive structure so you’re not learning beginner material if you’re more advanced. But it creates more community time, interacting, working with each other instead of just working alone in your business, and it lets us help them develop skills they might not get as much exposure to until they need it.

The last part of the week, pretty much every week, we’ll either have an elite, top-tier entrepreneur, founder, or executive come in and speak to the students, especially about their early journey — how they got started, what they learned, doing lunch with a few of them, looking at their businesses, giving feedback — or it’ll be a roundtable discussion on a book. We’ll probably have them read The Founders.

Jimmy Soni: I was going to say, sign me up — because a lot of what I went deep on in that book was the high school years of the people I was writing about. Reid Hoffman, Elon Musk, Peter Thiel, Max Levchin, David Sacks — I’d start my discussions with them way before PayPal ever started. The first conversations were usually around high school and college, because you find that, in many cases, they were living their version of Founders School.

Nat Eliason: Right. Exactly, yeah.

Jimmy Soni: They cobbled it together, often at great personal risk, and in the face of a lot of parental pressure. There was one person — you’re telling a story that reminded me of a gentleman I interviewed who was, I think, the fifth or sixth employee at PayPal, on the engineering team. His name was Tom Pytel. He was this famously, this vagabond, with very dubious footwear — his shoes were ratty — but he was a genius-level coder. It was interesting, somewhat like — you’d admire people who dropped out of college, but he actually dropped out of high school. He decided he was just going to take the show on the road. He was writing code, I think, for video games, dropped out of high school, started working right then, continued that, found his way to PayPal, had no interest in being an employee, but the team kind of coaxed him into it — that was how he got his start. He was the ultimate example of what you’re talking about, without any of the support or structure.

Nat Eliason: I mean, again, going back to why we believe this is possible — people have been hacking versions of this together with way less support. Nobody really doubts that a Stanford sophomore could drop out and start what becomes a billion-dollar business. So what are they getting at Stanford? One, there’s the selection effects; two, some amount of network, from being there, meeting people who come to visit campus, maybe a couple of classes. But a lot of it is just, oh, okay, a 20-year-old can do this, a 19-year-old can do this — so a 16-year-old can definitely start a million-dollar business. It’s eminently reasonable. No one’s tried before.

Jimmy Soni: No one, I think, has sort of — I think one of the things Alpha School has made possible is you’ve just expanded the Overton window on what’s possible in education. A lot of it is you’ve asked the unreasonable question — what if this could be true — and then it becomes true as a result of asking, and then selecting the students, and building the programming. A lot of it, I think, is pushing the boundaries on what seems crazy but isn’t actually all that crazy.

Nat Eliason: No, I think people generally dramatically underestimate, especially teenagers.

Jimmy Soni: Yeah.

Nat Eliason: Because we’ve infantilized teenagers for a long time — you have to go to this place, follow this bell schedule, do what we tell you to do, and then you have to stay close to home, you don’t get to travel much in most places, we’ve gotten afraid of all these things. Then you go to college, and there you have to follow these rules too. So we think of a 14, 15, 16-year-old as less capable than they are. Obviously they’re still children, they still need support, encouragement, a certain amount of guardrails — but also, sometimes you just have to get out of their way and tell them, I believe in you, give them just the right little nudge to get started, and then they do these incredible things.

There was one student at Alpha High, when I was doing the OpenClaw workshop — I asked the group, “Where do you think you fall nationally on AI competence — top 10%, top 1%, top 20%?” The consensus was top 10%. This was toward the end of the OpenClaw workshop. I was like, no, guys, you don’t understand, you’re top 0.01% — people will pay a lot of money for you to help them implement this stuff. I could tell some of them didn’t believe me, some did. So I put it out there — I said, if you want to test me on this, I’ll intro you to somebody who’d probably pay you to help them with that. One student took me up on it, I introduced him to somebody trying to learn OpenClaw and AI stuff, and he made $250 for a two-hour call. He was to the moon — he’d never made money doing something like this before, and he was obsessed with the tech. It was like, oh my gosh, I can make money doing something I really like. We were debriefing afterward, and I said, awesome, super happy for you — next time, try charging four times as much. You could just see — he was like, seriously? That’s amazing. And then he did, and they were like, yeah, sure — they paid him a thousand bucks the next time. After that he just started getting referrals, his business kind of took off, and I did nothing after that. I think he made north of ten grand off doing this over the course of that spring. All I had to do was one little nudge, one intro, and then kind of get out of the way. It’s like, you just have to give them the opportunity.

Jimmy Soni: Yeah, I think what you made me reflect on is something you said at the very start of our conversation — the difference between being entrepreneurial and doing entrepreneurship. You had this line about being entrepreneurial in deciding you could make $250, or $150, an article, and use geographic arbitrage to go live somewhere that would let you actually live a life. That required an entrepreneurial frame of mind, even if it wasn’t big-E entrepreneurship in the conventional sense. As I think back to my own high school years, my first business was building custom-built computers for people. I was doing the other parts of a traditional academic life — getting the grades, went to Duke, did well on the SATs — but what I realized was that it was in building businesses and hacking things together that I actually used those same techniques to hack my education. Whether it was designing my own major, or — this is totally random, but I became obsessed with how you could hack the SAT. At one point I did a deep dive on all these obscure forums about ways people had hacked it. One of the things you discover is, at least in my stone-age era, when you had to fill it in by hand, circling the bubbles — if you put one black mark through the middle of the letter, it counts as that answer, instead of shading the circle. That seems like a small thing, except shading a circle takes three to four seconds, versus a single vertical line through the multiple-choice answer, which is one second. The difference between one and four seconds is three to four seconds — but multiply that across the entire test, and you’ve gained back minutes you can use to do the test faster, because the only reason the SAT is hard is the time pressure. Given infinite time, everybody could theoretically get a perfect score — but the time pressure is what matters. Once I figured that out, I’d just do the vertical-line thing, gain back two to four minutes per section, and that gave me all the time I needed to check answers or go back. But I don’t think I’d have had that ability if I hadn’t also been trying to hack things together on the side, whether on the Internet or in real life with computers. It seems to me what you’re giving these — I hate to say “kids,” students — is the gift of that entrepreneurial cast of mind, the same one that led you to say, I can do Thailand and $150 an article for Zapier and make it work.

Nat Eliason: Yeah. I think some people are certainly wired this way — I actually don’t know the answer of whether this is something that develops, or something you’re born with. Either way —

Jimmy Soni: We’ll find out.

Nat Eliason: I know, right? There are a lot of students who think and feel this way, and they feel like the world and the education system is against them, because they’re told they’re bad, or whatever, if they’re not following this set of rules. This is the one thing I didn’t expect, but it’s ended up being incredibly rewarding and meaningful even at this early stage — talking to some of these students and parents, and them saying, “We never thought there could be a school that said this is okay.”

Jimmy Soni: Wow.

Nat Eliason: That you’re — you’re a good kid, you fit in here, this is a space for you. That’s been really cool to see, because it’s like, I didn’t have that.

Jimmy Soni: Right.

Nat Eliason: And I think a lot of kids don’t have that.

Jimmy Soni: Yeah.

Nat Eliason: I think even just getting a lot of students like that in one room together is going to be pretty incredible.

Jimmy Soni: So excited. You uprooted your whole life for this — in some ways you made the same transition I did, where I never thought I’d have a job, and then decided to run a book publisher. What’s it been like transitioning from that — moving from Austin to New York, but also deciding, no, I’m going to be part of someone else’s ecosystem for a while, and develop and design this, but it’s bigger than me? This gets back to the question of commitment — how has that been for you?

Nat Eliason: It’s been great, actually. I’ve always been interested in this topic, education — one of the first entrepreneurial things I did after college was a podcast for kids who didn’t fit in the normal college-education system, trying to tell their stories and connect with them. I’d sort of assumed I’d never do anything in education — it never felt like something I actively wanted to go after, but I was always interested in it, and hopeful somebody would do something with it. So now, if I were going to say, “I want to make a school for entrepreneurs,” obviously it should be part of Alpha — it just makes so much sense.

To the extent I had reservations about joining a big company — it’s like a startup. I mean, the pace it moves at is incredible. We had 25 schools last year, we’re going to have at least 40 this year, and a lot more next year — growing like crazy. At Founders School, me and Cameron — it feels like we’re co-founders on a startup that, thankfully, is well-funded and has a lot of support around it. But we get to control our hiring pipeline, design our application process and curriculum — it has to fit the Alpha ethos, but we have a lot of freedom to be very entrepreneurial with it. We’re not clocking in, so to speak —

Jimmy Soni: It wouldn’t work if you were.

Nat Eliason: Exactly. So all the things I was afraid of about taking a job — job, yeah — just haven’t materialized. Instead it’s been incredibly fun. Going back to the thing I was talking about at the very beginning, wanting to work on something big and long-term, really fully commit to something — I thought that had to be something 100% my own. But maybe that was also, at least for this phase of life, the thing that was holding me back in some sense — because I’m learning so much from being in a bigger organization like this, from not having some of the immediate profitability pressure I would have had on my own, from getting to work with Joe and see how he thinks about business and learn from him. It made me realize it was actually a big limiting belief for me, that I have to always work for myself, that I have to do this alone. I’m super glad I’m doing this, because the interest has been incredible, and seeing these students applying — it’s so much fun, I’m having a great time with it.

Jimmy Soni: Yeah. I wanted to talk to you about many other things, but this conversation has been utterly riveting, and I think we ought to try to have your students on Infinite Loops in the year ahead — as they’re going through the process, I think it’d be a lot of fun to see what they’re building, how they’re building it, how the school is maturing and evolving, and I hope we can do that.

As you know, having been a repeat guest, we ask a question at the end of every episode. You get the ability to incept an idea into everybody’s mind — two thoughts, whatever they are, you can’t use it for violence, you can’t overthrow governments — I mean, unless —

Nat Eliason: Yeah, I think we could actually sanction that one.

Jimmy Soni: You basically get to be emperor for a day, and everybody wakes up the next morning with these two ideas in their head. It’s an interesting question for you as a guest, because you’re actually molding young minds — what are, off the top of your head, the two ideas you’d incept in everyone’s mind? Or two thoughts, quotes, anything.

Nat Eliason: It’s naturally going to be topical, because this is what I keep thinking about, so much of this is based on it. The first one — what I said earlier, that we take teenagers seriously. I talked about this with Chris Powers when I was on his podcast a couple of months ago. But the more I’ve thought about this and explored the idea, the more it does feel like there might be way more problems than we expect that stem from expanding childhood as far as we have. If you go way back, you actually find versions of something like Founders School in Maria Montessori’s writing — she talked about how the childhood school is this core-life-skills stage, the cleaning and cooking and things everybody should know how to do to operate as an adult, the manners and whatnot. But she never got to fully realize this, because of challenges with how society was changing at the time and her resources — her vision of later-stage education was this Erdkinder, where you were doing a bit of academics but also working on a farm or in some kind of apprenticeship, getting hands-on skills, because she didn’t think teenagers should be stuck in a classroom.

You look at basically every pre-modern society, and there are these significant moments where you transition into adulthood, around age 14 — you think about a bat mitzvah, a bar mitzvah, that’s around that age, a confirmation is around that age. You visit tribes in Kenya, the Maasai Mara, and guess when you become a contributing member of the tribe — it’s around that 14 age.

Jimmy Soni: Right.

Nat Eliason: I actually think a lot of the things we assume are bad about childhood — kids hating school — and some of what we assume is bad about having teenagers, might be because they’re capable of doing more adult things, being more adult, but then heavily constrained by their environment. So they naturally lash out against the things doing the constraining — school, parents, society. Alpha’s done a good job of asking, what if we took students, especially teenagers, seriously and gave them this freedom? And now we’re taking it to the extreme — what if we trusted you as much as a 30-year-old, to run a business? I feel there’s a lot of unexplored opportunity there. And — these are different things, to be really clear — but people getting married much later, starting families much later, the aging population — I think we’ve extended childhood further than we should. It can sound dangerous to say that, because you don’t want to force kids to grow up too fast — I’m not advocating for that either — but I am advocating that if somebody shows the ability to be treated like an adult, to be taken seriously, we should figure out how to take them seriously. I’m excited to see where that goes.

Jimmy Soni: Yeah. Actually, when I was prepping for this, I was looking back at some of what Maria Montessori was writing and thinking about — I think of her as far — even though the brand Montessori is as well-known as it is, a lot of her ideas, and her as a person, are vastly underrated compared to others. She’s so cool. One of my favorite stories: she was one of the first women admitted to medical school in Italy, and they wanted to wash her out — they made her dissect cadavers alone, where the male students all got to be with each other. She had to do that on her own, because they thought it would scare her off medical school — and it did the exact opposite. She was burned in effigy in different countries, because people thought her ideas were too heretical. Now everybody and their brother pays gobs of money to get their kids into Montessori or Montessori-type environments, and a lot of her ideas are being validated by science in 2026, in a way they weren’t even 50, 75 years ago. So I take what you said very seriously, because there are echoes in what you’re trying to do and what she was trying to do.

Nat Eliason: Yeah. There’s this book that got really popular a few years ago, called Hunt, Gather, Parent, that talks about tangential, similar ideas — the most enduring idea from that book, the one you hear parents recite most often, is that how you treat a child who wants to help at an early age decides how much they contribute and feel autonomy and agency throughout a lot of the rest of their life. One of the main things the book advocates, basically the same thing Montessori says, is that if a kid thinks they can do it, you just let them do it. Doesn’t matter if they’re going to break the egg, take four times longer, or fall off the ladder, assuming it’s a reasonable height — you let them do it. The argument was, if you tell a kid, “No, you can’t help me wash the dishes” when they’re offering, they’ll just learn that, and then suddenly they’re a 12-year-old who won’t help when you ask, because they’ve internalized it that way. She was going to a lot of more traditional cultures in that book, and that was one of the big differences she noticed — they were letting kids do stuff they were bad at, that was actually slowing things down, obstructing progress, because they’d internalized the lesson that if you just let them, they’ll eventually figure out how to be very helpful, and those rewards come later.

Jimmy Soni: Exactly.

Nat Eliason: It’s such a fascinating idea that I feel has been lost. But going back to raising kids in the city — it feels like we get some of that here, because my kids are riding scooters through the streets now, through the sidewalks at least. The other day, we were at a coffee shop, and my wife had taken the youngest one home, which was around the corner — a block away. My two older girls, they’re four and three, said, “Can we go see Mommy?” I was still in the coffee shop, and I said, sure, go ahead. They scooted down the block, did the turn, went to the house. I called Cosette and said, hey, by the way, make sure they actually show up, please. She texted me a picture a minute later of them at the door, and I said, awesome. You got that little opportunity for autonomy and independence that, sadly, I think some people probably wouldn’t even let their 9- or 10-year-old have.

Jimmy Soni: And in areas where commuting and everything happens by car, it’s a lot harder —

Nat Eliason: It’s a lot harder.

Jimmy Soni: Can’t get away with it in the same way.

Nat Eliason: Yeah.

Jimmy Soni: What’s your second idea you’d incept everybody with? Your first one was a real banger.

Nat Eliason: Oh, geez. Gosh. Yeah, the second one — that’s a lot of pressure. I’m trying to find the right phrasing, because what we were talking about earlier, doing things that are entrepreneurial even if they aren’t big-E entrepreneurship — that really is agency. I think that’s downstream of this idea that the world is a lot more malleable than you tend to assume. This was another big red-pill moment for me as a kid — I don’t remember exactly when, but there was some point when I realized there wasn’t really such a thing as rules. There’s the way other people want you to do things, the way you should do things to be a good member of society, and then there are things you’re told to do, or should do, or how it’s done, that if you don’t do it, there’s literally no consequence, or a very acceptable consequence, or everybody’s kind of doing it because everybody else is. So whenever you encounter something — could be work, personal life, society, whatever — of how something works, or what you’re supposed to do, it’s literally a suggestion. It’s an idea.

Jimmy Soni: Outside of very few things.

Nat Eliason: Exactly, yeah. And, I mean, that mindset can obviously go in bad directions, but — we had a couple of fifth graders at Alpha who were super into robotics, really sharp, and they came up with this idea for a robotics-security-related startup, and they emailed the FBI to pitch them on it.

Jimmy Soni: Wow.

Nat Eliason: It was fine — nothing bad happened, obviously. But if you asked anybody, “Hey, can you just email the FBI your startup pitch?” they’d say, no, you can’t do that.

Jimmy Soni: Right.

Nat Eliason: But you can. As a ten-year-old.

Jimmy Soni: Exactly.

Nat Eliason: To be clear, it’s not something I’d encourage our students to do, but there’s something really admirable about it too. That’s going to take them far.

Jimmy Soni: Yeah.

Nat Eliason: I think it’s so easy to get frustrated by things not being the way you want, or feeling trapped, like you don’t have options — but you pretty much always have way more than you think you do. You just have to be willing to look for them.

Jimmy Soni: And reality is malleable.

Nat Eliason: Reality is malleable. There you go.

Jimmy Soni: Well, Nat, thank you. We’re going to have you and your students on over the next few years, see how this progresses and continues to develop — I’m personally very excited about it. I’m excited for you, as a friend — I want to see how this affects your life, and I can’t wait to have further conversations about it too.

Nat Eliason: I’m super excited too. And, serious offer — we’re doing these book-club things with the students —

Jimmy Soni: It’s a given.

Nat Eliason: Eric’s going to come do one for The Book of Elon — you should come do one for The Founders.

Jimmy Soni: It’s a hop across the river.

Nat Eliason: Exactly. That’d be super easy, a lot of fun.

Jimmy Soni: Amazing.

Nat Eliason: All right.

Jimmy Soni: Thank you.

Nat Eliason: Talk soon.

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Sunday, 19 July

Two thoughts from Hilaire Belloc

“Any subject can be made interesting, and therefore any subject can be made boring.”

“I have wandered all my life, and I have traveled; the difference between the two being this, that we wander for distraction, but we travel for fulfillment.”

Monday, 20 July

Two thoughts from Lera Boroditsky

“Human minds have invented not one cognitive universe, but 7,000.”

“The language that you speak shapes the way that you think.”

Tuesday, 21 July

Two thoughts from Terry Southern

“The important thing in writing is the capacity to astonish. Not shock—shock is a worn-out word—but astonish.”

“There is no power on earth that can loosen a man’s grip on his own throat.”

Wednesday, 22 July

Two thoughts from Anthony Bourdain

“Skills can be taught. Character you either have or you don’t have.”

“Your body is not a temple, it’s an amusement park. Enjoy the ride.”

Thursday, 23 July

Two thoughts from Lewis Mumford

“Life is an art we are required to practice without preparation, a score that we play at sight even before we have mastered our instruments.”

“Humor is our way of defending ourselves from life’s absurdities by thinking absurdly about them.”

Friday, 24 July

Two thoughts from Alfred North Whitehead

“Civilization advances by extending the number of important operations which we can perform without thinking about them.”

“The guiding motto in the life of every natural philosopher should be, “Seek simplicity and distrust it.”

Saturday, 25 July

Two thoughts from Bertrand Russell

“The fact that an opinion has been widely held is no evidence whatever that it is not utterly absurd.”

“Fear is the main source of superstition, and one of the main sources of cruelty. To conquer fear is the beginning of wisdom.”

Follow Jim on Twitter for a daily dose of Two Thoughts!

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This week: a table-tennis movie that’s really about being made obsolete, the Chappelle special that isn’t stand-up, Borges on whether there’s any such thing as the “real” Odyssey, the strange story of how the world’s best movie projector became impossible to build, and a forgotten book on where ideas actually come from.

1. Marty Supreme : When a Better Tool Changes the Rules

I watched Marty Supreme for the second time a few days ago and liked it even more than the first time, though it still comes close to my limit for how stressful a film can be. It’s less anxiety-inducing than the Safdie brothers’ Uncut Gems, but that’s not saying much.

This time, I noticed the craft more: the period detail, how every background face is interesting. But I also caught something central to the film, a major theme that I had not even noticed the first time.

When Marty plays Japanese champion Koto Endo, he’s completely thrown off. He holds the paddle differently and makes shots Marty can’t anticipate. I assumed it was kind of like a karate champion encountering a jiu-jitsu black belt for the first time.

After losing, Marty throws a tantrum and there’s a throwaway line about Endo’s paddle. It sounds like a sore loser making excuses, and that’s what I thought it was.

Except he was right!

The film is loosely inspired by American table-tennis champion and hustler Marty Reisman. Endo is based in part on Japanese player Hiroji Satoh, who arrived at the 1952 World Championships with a paddle covered in thick sponge.

Traditional “hardbat” paddles had thin rubber attached directly to wood. Sponge compressed and sprang back, producing unfamiliar speed, spin, bounce, and trajectories. It even changed the sound of contact. Players who spent years building finely tuned instincts for how a stroke looked and sounded found themselves with a useless toolkit.

Satoh won the world championship. Sponge spread rapidly. Table tennis became a different game.

That changes how I see the whole film. It goes from a story about Marty vs. Endo to one about the old guard raging against a technological shift.

This pattern repeats everywhere. Someone becomes exceptional under one technological regime, then a new tool changes which skills count. You’re still just as good. It just stops mattering. Silent-film stars when talkies arrived. Hand-drawn animators when the studios moved to CGI.

Marty wants the game frozen at the moment when he is best positioned to dominate it. But he hasn’t just met a better player. He has met the next version of his sport. [Liberty]

• 🎬 Marty Supreme (2025)

2. Dave Chappelle’s Best Special Isn’t Stand-Up

I have been a Dave Chappelle fan for a long time. I’ve enjoyed just about everything he’s done: Killin’ Them Softly, For What It’s Worth, Chappelle’s Show, and the run of Netflix specials. But the Chappelle work I keep coming back to - and recommend to friends, no matter their opinion of his comedy - is not stand-up comedy. It is a forty-minute speech he gave at his old high school in June 2022, released on Netflix the following month as What’s in a Name?, and it is one of the most thoughtful defenses of free expression I have ever heard.

The context matters. Duke Ellington School of the Arts in Washington, DC, is where Chappelle went as a teenager, and in October 2021 the school announced it would rename its theater after him. His special The Closer had come out the same month and drawn intense criticism for some of its controversial jokes. Some students objected to the naming, and the school held a contentious Q and A with Chappelle. And on June 20, 2022, at what was supposed to be a naming ceremony, Chappelle stood in front of the students who had opposed him and made an unusual proposal. “Rather than give this theater my name, I would like to give these students my message.” He asked that the space be called the ‘Theater for Artistic Freedom and Expression’. The school agreed.

What makes the speech worth watching is the elegance with which Chappelle treats his critics. He does not dismiss the students. He remembers being one of them. He tells the room what art is for and what it costs, and he makes the case, without hyperbole or heat, that a school named for Duke Ellington should be a place where the hardest ideas can be tested out loud. Netflix put the speech on the platform in July 2022 without fanfare, and it later won the 2024 Grammy for Best Comedy Album. But at heart it is a working artist explaining to a room that had opposed him why the freedom to say difficult things is worth protecting. [Jimmy]

• 📺 What’s in a Name? (Dave Chappelle)

3. Which Odyssey Is the Real Odyssey?

I went into Nolan’s The Odyssey last weekend knowing almost nothing about Homer’s poem. I came out so enthralled by both the theatrical experience and the story itself that I decided to read Homer’s Odyssey and see the film again in a week.

As I did some brief research into which translation to pick (a customary ritual before reading any ancient text), I came across this essay by Jorge Luis Borges in which he explores the art of translation by comparing several English versions of a single passage from The Odyssey. The differences can be large: Pope turns one ship into an entire fleet, while Butler makes Homer sound like a series of “sedate news items.”

Borges calls the belief that translations are inferior to their originals a “superstition.” The same words, even within one language, can invite different interpretations depending on who reads them, when, and where. A translation is thus one of many possible perspectives on a text, rather than a necessarily inferior copy of it. Borges writes, “To assume that every recombination of elements is necessarily inferior to its original form is to assume that draft nine is necessarily inferior to draft H—for there can only be drafts.” (I think the mismatched ‘nine’ and ‘H’ are deliberate, to avoid any direct comparison or ranking.)

How much of what we call fidelity is really familiarity? How much belongs to the author’s style, and how much to the language itself? Which translation is most faithful: the most literal, the most florid, or the simplest?

I won’t spoil Borges’s answer, but the essay made my search for “the best” Odyssey translation much easier. [Vatsal]

• 📄 The Homeric Versions by Jorge Luis Borges

4. We Stopped Building the World’s Best Projector, and Then Forgot How?!

Unlike Vatsal above, I haven’t seen The Odyssey yet. But I read a fascinating piece about how we’ve lost the knowledge of how to build new 70mm IMAX projectors, so we’ve been repairing and rebuilding old ones, hoping they last.

To open more locations for The Odyssey, IMAX spent over a year tracking down old broken projectors to salvage their parts. Despite this effort, there are still only 25 theaters in the U.S. and 41 theaters worldwide that can do true IMAX 70mm film. That’s 11 more than Oppenheimer had in 2023 (just 30).

How did we get to this sad state of affairs? How did we lose the ability to make more of the very best projection format that humanity has ever created?

The industry’s shift from film to digital is mostly to blame. And sadly, IMAX let that institutional knowledge go. By the time film projection began its vinyl-like revival, the expertise and supply chain had already atrophied. The original design files and manufacturing blueprints were created roughly half a century ago (yes, IMAX was founded in 1967! I didn’t realize this until I looked it up), and they were never properly maintained. The engineers who understood these machines have mostly retired or passed away.

Building another projector today is like recreating an Apollo-era spacecraft. It’s technological archaeology. [Liberty]

• 📽️ Why Aren’t There More IMAX 70mm Screens? (Variety)

5. The Best Book on Creativity Nobody Has Read

In 1940, an English music scholar named Rosamond Harding (better known, if she’s known at all, for writing the standard history of the pianoforte) published a short book entitled An Anatomy of Inspiration. And yet, despite its thinness, this unassuming paperback probably sits at number one on my HPL index (highlights per line). It was basically yellow by the time I was done with it.

Instead of coming up with new platitudes about creativity, Harding did something far more useful. She collected what the people who actually made things said about how they did it -- the letters, notes, and routines of Tchaikovsky, Brahms, Jane Austen, Mark Twain, and dozens more.

What they had in common surprised her. They described themselves less as inventors than as discoverers. The idea arrives on its own, unbidden. The genius is not in producing it, but recognizing it. Just as a farmer can’t grow a crop himself, an artist can’t have an idea. All either can do is cultivate the conditions for its arrival.

For anyone trying to understand the creative mind, it casts a light I’ve found nowhere else. Why it has been forgotten -- out of print, nine ratings on Goodreads, none on Amazon -- is beyond me. Especially given the slop that usually passes for books on creativity.

Two hundred pages. Hunt down a copy if you can. [Dylan]

• 📘 An Anatomy of Inspiration, and An Essay on the Creative Mood by Rosamond Harding

• 📖 You can borrow an ebook version for free on the Internet Archive

⭐ Explore the OSV Field Notes Archive ⭐

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We discuss why government has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

The Department of Silly Walks is in Charge

Philip Howard
But the reality is, the situation has gotten worse.

Jim O’Shaughnessy
And diagnose it for me — why? I mean, I have pretty strong views on this. I think our current political class is one of the worst, on both sides of the aisle. I’m very bipartisan in my view. But why?

Philip Howard
What no reformer has done yet is take on the underlying operating philosophy of modern government, which is basically that we should replace human judgment with either specific legal rules or objective proof. There was no such thing, until the 1970s, as thousand-page rule books. There was no such thing as having to go to a months-long hearing to prove that somebody doesn’t do their job. The Interstate Highway Act, which was in 1956, was 29 pages long. Within 10 years, over 20,000 miles of road had been built. The last transportation bill was almost 1,000 pages long, and it would take 10 years to get a permit for one stretch of road.

Jim O’Shaughnessy
It’s almost like Monty Python is running the government — the Department of Silly Walks and all that. But again, I’m going to press you: why?

Philip Howard
Well, a lot of people make money on this system. When I went to law school, which was a long time ago, the new orthodoxy was that you can’t trust human judgment. An official might be like Robert Moses and blow through—

Jim O’Shaughnessy
I was going to bring him up.

Philip Howard
Right. And so we were going to create a government better than people. And we have. Take the worker safety rules — there are 4,000 of them. I’m all for worker safety regulation, but the way they do it is they have 4,000 rules, and rules that say things like “stairwells shall be lit by natural or artificial light.” Now, that’s useful. Then the company has to have a compliance inspector who has a checklist for these 4,000 rules, going around checking the boxes that they do this. That’s a person doing really nothing useful. Then there’s another person who checks the checker. So you have all this bureaucracy building up, and Washington becomes this enormous factory for red tape.

And law firms — including the law firm I was a senior partner of — you have these law firms doing really well, making money, and lobbyists, and they all navigate the precise language and they argue over it, and really nothing ever changes. It’s like a perpetual tug of war, and they have no interest in changing it. Everybody’s doing well. I think Washington has one of the largest Lamborghini dealers in the United States — a place where nothing ever happens.

The Freedom to Take Reasonable Risk

Jim O’Shaughnessy
I grew up in the 1970s. We were free-range kids. We could do whatever we wanted, as long as we got home.

Philip Howard
Right. And so what’s happened is... A couple of decades ago there was a terrible accident on a sledding hill in Greenwich, Connecticut.

Jim O’Shaughnessy
I remember it well.

Philip Howard
And someone got a verdict of $6 million. And the result of that was not... I mean, Greenwich is a rich town, it could afford it. The result was that sledding hills across the country closed down.

Jim O’Shaughnessy
Yeah. Including that one.

Philip Howard
Right, including that one.

Jim O’Shaughnessy
I used to take my kids there.

Philip Howard
Right. So all of a sudden, because of a lawsuit brought by one person — no deliberate policy choice — the trade-off judgment about whether the risks of sledding outweighed the fun of going out in the winter and the snow was not being made by anybody who’s politically accountable. It was being made by the fact that somebody brought a lawsuit. And there was a similar case in England around the same time, where somebody — terrible accident — dove in a lake and became a quadriplegic. Terrible accident. But there were no hidden dangers there. Sure, you could run into something if you weren’t watching, but people had sledded on that hill for decades—

Jim O’Shaughnessy
It was a rite of passage for your kids.

Philip Howard
Yeah. And so in England, there was nothing hidden — it was just a freak accident. It was tragic. But the county that owned the lake was so scared of liability, because there were two or three near-drownings a year — a big lake, people swimming, bad things could happen — that they had determined to close the lake down. And then this accident happened. So the court said, “Well, this is foreseeable, therefore we’re going to grant damages to this person.” It goes up to the equivalent of the UK Supreme Court, and they order the case to be dismissed. They say, “It is part of our role” — as the lead judge put it — “to protect the reasonable freedoms of people in society, including the freedom to take risk. Do we require that rivers and lakes close down because of the certainty that some accident will happen? Do we require all trees be cut down because some child may climb one and fall? We will not tolerate a dull and gray safety regime. We are here to protect the reasonable freedoms, including the freedom to take reasonable risk.”

Jim O’Shaughnessy
What a great decision.

Philip Howard
And it’s called the Tomlinson case. And that’s what we’re missing in this country: no one is drawing those boundaries.

Transcript

Jim O’Shaughnessy
Philip Howard. Finally. We’ve known each other forever — I served on your board at Common Good. I discovered you well before I met you, with your first book, The Death of Common Sense, in 1995. Loved it. have loved all of your books. But I’ve got to ask — that’s 30 years ago, 31 years ago, and things have seemingly only gotten worse.

Philip Howard
Right. I had lunch with a tycoon a few years ago, and he said, “I like what you write, but have you ever accomplished anything?” And I said, “Well, actually, now that you mention it, I have a perfect record of failure.” He said, “That’s what I thought. I’m not giving you any money.” That’s not exactly true — I actually have worked on a bunch of reforms with Congress. But the reality is, the situation has gotten worse.

Jim O’Shaughnessy
And diagnose it for me — why? I mean, I have pretty strong views on this. I think our current political class is one of the worst, on both sides of the aisle. I’m very bipartisan in my view. But why?

Philip Howard
What no reformer has done yet is take on the underlying operating philosophy of modern government, which is basically that we should replace human judgment with either specific legal rules or objective proof. There was no such thing, until the 1970s, as thousand-page rule books. There was no such thing as having to go to a months-long hearing to prove that somebody doesn’t do their job. The Interstate Highway Act, which was in 1956, was 29 pages long. Within 10 years, over 20,000 miles of road had been built. The last transportation bill was almost 1,000 pages long, and it would take 10 years to get a permit for one stretch of road.

Jim O’Shaughnessy
It’s almost like Monty Python is running the government — the Department of Silly Walks and all that. But again, I’m going to press you: why?

Philip Howard
Well, a lot of people make money on this system. When I went to law school, which was a long time ago, the new orthodoxy was that you can’t trust human judgment. An official might be like Robert Moses and blow through—

Jim O’Shaughnessy
I was going to bring him up.

Philip Howard
Right. And so we were going to create a government better than people. And we have. Take the worker safety rules — there are 4,000 of them. I’m all for worker safety regulation, but the way they do it is they have 4,000 rules, and rules that say things like “stairwells shall be lit by natural or artificial light.” Now, that’s useful. Then the company has to have a compliance inspector who has a checklist for these 4,000 rules, going around checking the boxes that they do this. That’s a person doing really nothing useful. Then there’s another person who checks the checker. So you have all this bureaucracy building up, and Washington becomes this enormous factory for red tape.

And law firms — including the law firm I was a senior partner of — you have these law firms doing really well, making money, and lobbyists, and they all navigate the precise language and they argue over it, and really nothing ever changes. It’s like a perpetual tug of war, and they have no interest in changing it. Everybody’s doing well. I think Washington has one of the largest Lamborghini dealers in the United States — a place where nothing ever happens.

Jim O’Shaughnessy
Yeah, I was just down there and saw as many fancy cars as one might see in Greenwich, Connecticut. And it seems to me that the source might have been the idealism of the 1960s. And by that I mean: we can make things better. But I think it counted also on this idea that we are born as a tabula rasa — as a blank slate. And we are not born as a blank slate.

Philip Howard
Right. Well, first of all, we are not born as a blank slate. And I think there was some idealism. There was a kind of naïveté that, with modern technology on the rise — and that was the era of IBM 360s, stuff like that — they could do it. But the real driver was guilt. We woke up in the 1960s to segregation, to pollution, to unsafe cars, to locking up disabled children in horrible places.

Jim O’Shaughnessy
We were doing some horrible shit.

Philip Howard
Yeah. And so the establishment had a record of neglect of many groups that should not have been neglected. It was one thing to change the values, which we did do — with environmental laws and civil rights laws, and all that was good and necessary — but they wanted to make sure that they could never happen again. And the way to make sure there were no abuses of authority was to get rid of authority. And so—

Jim O’Shaughnessy
Excuse me — get rid of individual’s authority.

Philip Howard
Individual’s authority.

Jim O’Shaughnessy
The regulation was going to become the authority.

Philip Howard
You’d have a legal system that would tell everybody what to do. Eric Foner is a very distinguished historian from Columbia University. He wrote a book they call The Future of Freedom, where he said that in the 1960s the governing idea was the elimination of all authority — so freedom would be enhanced if no one had authority. Now, it turns out that’s upside down. If the person running a firm, let’s say, doesn’t have the authority to uphold mutual standards and values, then there isn’t going to be mutual trust, and in fact everyone loses their freedom. There’s nobody to go to and say, “I’ve got a good idea, let’s change the way we do things.” Authority is actually critical to everyone’s freedom. You need red lights and green lights in any society and any institution.

But we’re still trapped in this kind of quicksand of law that we created, where no one can make a judgment. And then the result is that people who don’t respect law — like the current president, for example — can get away with murder, because they just simply ignore it.

Jim O’Shaughnessy
And one of the things that I always come back to — you mentioned all of the abuses that were being solved. I was 100% in favor of everything you just mentioned: the Civil Rights Act, the Clean Water Act. The rivers around this city used to be so polluted that you risked your life jumping into them. And they got a lot cleaner. So all of those initial rules and regulations and new laws, I think, actually did really good things. And then what you’re talking about started to happen, and we became a society... I had a guest on who was basically comparing the US and China, and he goes, “The US has developed a lawyer society. China has developed an engineer society.”

Philip Howard
Right. Dan Wang.

Jim O’Shaughnessy
Yeah. And when I was on the board of Common Good, all of the ideas you came up with, and the other board members and associates — I thought they were brilliant. But how do you get that into people? Because I’m not a Democrat or a Republican. Maybe I’m kind of like you: a radical centrist.

Philip Howard
Yeah. Well, again, I’ve been working on specific reforms. I was very involved in a bunch of environmental permitting reforms in Congress a few years ago. We developed this project, you’ll remember, for expert health courts, and got everybody for it. Obama agreed to support it — for medical malpractice, it’d go to an expert court without juries, and it would make health care better and also relief quicker for people who were really injured by mistakes. We had a pilot project in the Affordable Care Act that Obama supported, and funding for it. And the day before the vote, the Democratic leader of the Senate, Harry Reid, had it pulled. Because the trial lawyers — they make all their money on extortion. “You may be liable for $20 million for this tragedy, therefore you’d better pay us 10,” or something. Even though the doctor may have done nothing wrong — it may just have been a sick person getting sicker.

So it’s been hard to make change. But one does feel that times are changing. Politics have become more extreme on both sides.

Jim O’Shaughnessy
Yep.

Philip Howard
The left is more left, and the—

Jim O’Shaughnessy
Yeah, we were just talking about it before you got here. It’s like, wow — when did this happen?

Philip Howard
Yeah. And the right is... So there’s clearly more of a mood for change. Two-thirds of the country is dissatisfied with both parties, don’t like the way things are. Also, close to two-thirds of the country fundamentally agree on basic values — the golden rule, honesty, all that kind of stuff. It’s not like diversity has driven us apart. People still believe in the same things.

It does seem there needs... I’m talking to some former attorneys general now. I just hosted a three-day workshop three weeks ago to try to come up with a new political narrative. The idea is not to start a new party — not even, at least for now, to start a movement — but just to change the conversation. So we’ve come up with an idea for a new narrative. It’s in writing. We’re in the process of trying to get some leading citizens to sign on to it. I was just talking to former governor Mitch Daniels yesterday about it, so he’s on board — and getting a group of people to start talking about it.

This new narrative is not about policy, it’s about how things work: how you run a school, how you get a permit, how you’re allowed to act honestly with each other in the workplace without fearing a lawsuit — that sort of thing. It’s really about operating systems. So we have a name for it, we have a narrative that we’re working out, and I think it’s good. It took a lot — I had a bunch of marketing people and press people in this workshop.

And so we’re going to try to roll it out slowly, with just leading citizens — maybe yourself — talking about it with different groups of people, and begin to say, “Isn’t it time that we actually overhauled the system so that people can act, so that Americans can roll up their sleeves and act like Americans?” That’s what people no longer feel comfortable doing, and the law is what’s gotten in the way. It’s just legal quicksand. So it’s about re-empowering human agency.

Jim O’Shaughnessy
Yeah, which is something I deeply believe in. And also, when you look at the history of this country, you have things like... You have a book on this — I think it was probably your most controversial — and that was public unions.

Philip Howard
Right. Not Accountable.

Jim O’Shaughnessy
Right. Not Accountable. Great book. And as I was reading that book, I remembered that FDR himself said that would be the worst thing to ever let happen. Many people consider FDR one of our most progressive presidents, and yet he was like, absolutely not. And yet it happened.

Philip Howard
Right. Well, it’s funny you mention that. I’m just finishing a book called Burning Money, and it’s a book that tries to describe the harm of government that’s become unmanageable. It’s very hard proving a negative. But I teach at Harvard Business School sometimes, so I have a lot of business school professor friends, and they sort of help me out. It’s funny — there’s a vast library of books on how to manage businesses better. There is not one book on what happens if you lack managerial authority. It’s just like breathing — it’s like what happens if you don’t breathe. If you don’t have somebody who can actually direct resources here or there, decide who’s good at what, adapt when something unforeseen happens — all the things that have to make anything work in any institution require managers. Well, guess what? Government no longer has managerial authority.

So, more or less — particularly in the big cities and big states, New York, Illinois, New York City — we’re getting about half the product at twice the price, and we can’t afford that anymore. There are a lot of public needs, and there are a lot of serious policy issues that need to get addressed — income inequality, all kinds of stuff. Meanwhile, we’re burning money. We’re literally burning money. There’s a school in Chicago that has capacity for 1,000 students that has 27 students in it, and no one has the capacity to close down the school and transfer the students to a nearby school, because the teachers’ unions have made it so that no one can close a school. Half of New York City schools are operating at barely over half capacity because of declining demographics. But the teachers’ unions got a law — called maintenance-of-effort laws — which requires that a district never reduce its budget unless tax revenues go down. Because the teachers’ union got an agreement.

So for 50 years, since they got collective bargaining power, year after year, they’ve gotten more and more requirements like that built into the codes. These are laws now — laws that literally require us to burn money. Almost no one appreciates that. I’ve hired lawyers. I have a partnership with the public interest law firm in Chicago that just won the tariff case against Trump, and also won the Janus case. So we have a draft complaint in federal court to challenge the constitutionality of public union controls, ready to go. But I don’t want to do it until I write this book that explains why it’s so harmful that we can’t manage government.

Jim O’Shaughnessy
And you mentioned earlier that what we really need is a new operating system. And in operating systems, incentives kind of rule everything around us. Right now, as you’ve just outlined, our incentives... For example, if I were the head of the public teachers’ union, man, I would be calling for more of those laws, because I’d be highly incentivized to do so. And so it’s easy and disingenuous, in my opinion — it’s easy to scapegoat everybody. Let’s just stop doing that. Let’s look at the underlying system and the incentives that result from it. That explains a ton. I remember one time you told me about the law here in New York City where a public school teacher may not — if a child is in distress, remember this? — the teacher may not touch the child. In other words, one of the most basic human instincts, if an adult sees a child in distress, is to comfort them. That’s just so part of the human OS.

Philip Howard
Right. But we have this precautionary system of government, of law, now, so that anything that might go wrong is forbidden. So, it is possible a weird person could touch a child inappropriately.

Jim O’Shaughnessy
Yeah, of course.

Philip Howard
Because that is possible, and not that unusual — you know, Catholic churches and priests and all that — so they make a rule that you can’t touch a child. But that’s equally weird. And so the only way to square the circle is to have a system where the people in charge are allowed to use their judgment about who’s a good person, who maybe is a little odd, and be able to remove the odd person from that teaching job. But you can’t remove anybody. I interviewed a former commissioner in New York recently who said that in his 40 years of being a top official in New York City, he had never seen anyone terminated for performance.

Jim O’Shaughnessy
Wow.

Philip Howard
Never. So you have a system where you can’t terminate the weird person just because you say they’re a little weird — you have to prove they’re weird. Well, how do you prove someone’s weird? Most of the things that are... I think it was Einstein, or someone like that, who said if it can be measured, it’s not that important.

Jim O’Shaughnessy
In investing: once a target becomes a measurement, it’s no longer useful as a target.

Philip Howard
So we have this system that assumes that right and wrong can be proved objectively. That is manifestly false. How do you prove someone is selfish? How do you prove somebody has good judgment at this but not such good judgment at that? How do you prove who works hard, who cooperates well? How do you prove what’s a good product, what’s not a good product? None of this stuff is provable. It’s tested in the marketplace of human relations, in the marketplace of values, in the marketplace of products — but it’s not provable. This system is built on a false premise, and we need to basically go back to a human system.

The Constitution, with all amendments, is 7,500 words. It includes principles like no unreasonable searches and seizures, and freedom of speech. It does those things in a couple of words. It doesn’t define them, but they become defined over time as issues come up. People have a general sense, from those principles, of what the boundaries are. And we feel comfortable going to bed at night that the police can’t just arbitrarily barge in and throw us in jail or whatever. The current system of federal law and regulation is 150 million words. It is beyond the capacity of any human understanding. And even AI can’t make sense of it, because it’s not consistent — it’s like a giant short circuit of all these laws piled on top of each other.

Going back to the teachers’ union: a couple of years ago, the Citizens Budget Commission in New York City counted 21 bills that passed the legislature to enhance union benefits and rights in one year — 60 years after they got collective bargaining power. Now, not all of them ended up making it into law, for one reason or another, but they are relentless. And so you pile up all this stuff, year after year, and after a while, government’s unmanageable. It doesn’t deliver. It wastes money. By the way — you’re a money guy, right? 23 million people in the United States work for the government. 23 million people. That’s over one in seven people in the workplace. They are not manageable. They’re not managed sensibly in any way. They cost about $3 trillion — in total comp and benefits. And they spend, in a discretionary way, or oversee, another four to five trillion dollars. So we’re talking about not quite, maybe, a third of the GDP being spent by a system that is no longer manageable — and it’s not delivering public services very well, either. And there are all these new needs. So why do we tolerate that? We tolerate it because we don’t understand it.

Jim O’Shaughnessy
It seems to me — I always argued... I’m a big fan of philosophy, and you don’t need to be a pure Platonist or Aristotelian, you need both. Because if it’s pure Plato, you get the Republic, and you get the philosopher kings, and, oh, they’re going to do a great job. What you need from Aristotle is: wait a sec, that might not work out like that.

Philip Howard
Right. The happy mean, right?

Jim O’Shaughnessy
Yeah. And what I was always struck by in our many conversations is, I just can’t believe... We know that the majority of Americans intuitively understand this. We know, as you mentioned earlier, that if you looked at Americans of all races, creeds, colors, sexes, et cetera, we share much more in common than divides us. And yet here we are.

Philip Howard
Right. So we need a new... And by the way, neither political party will solve this problem. If you project out five or 10 years, there’s nothing on the horizon that is even conceivable that could end up solving this problem. The Democrats get most of their resources from the worst of these groups. By the way, I happen to be a registered Democrat. I’m for environmental protection, I’m worried about climate change, I’m for taking care of people who need help — I’m for all those things. They will never solve this problem. And the Republicans see government as the enemy. Both parties do just fine running against the extremes of the other party.

Jim O’Shaughnessy
Right.

Philip Howard
They collect a lot of money. The Democrats collect it from the people who can’t stand Trump, and the Trump people collect it from the people who can’t stand AOC and Mamdani. So you have this system where both parties are profiting by extremism and leaving the vast middle, as you described, behind. We have to come up with a new narrative first — a new narrative and a vision — and then let it turn into something.

I was talking to a former attorney general — I won’t mention him, because I don’t have permission, but a very prominent attorney general. We were having a discussion. I didn’t know him; he was introduced to me by the president of an insurance company. I said, “Well, do you know why we’re talking?” He said, it was on Zoom, “No, I have no idea why we’re talking.” So I said, “I don’t think either party’s going to solve the problems of this country. We need a new narrative that actually addresses the problems people see with a government that doesn’t function very well and doesn’t let people be themselves. We go to video trainings that tell us, basically, don’t be yourself, don’t tell a joke, don’t be candid.” So after about six or seven minutes, he starts finishing my sentences. And then, at the end of our half hour, he says, “Okay, here’s what we do. You come up with the framework of principles about what this new vision looks like, and we’ll go find 8 or 10 or 12 really prominent citizens to start talking about — we don’t have to agree on everything — start talking about why this is directionally what’s missing in our public discussion. And then we start... maybe we have some public events, then we start talking about it.” And he said, “I think it’s possible that we could get one or more people running for president in 2028 to talk this way. Because everybody, just listening to you — of course you’re right. This is exactly what’s... Of course you’re right. Everybody knows you’re right. Just nobody’s saying it.”

Jim O’Shaughnessy
And that’s the exact point that always frustrates me. There’s that great quote — I can’t remember who said it — but it’s like, “If you give me the ability to write the stories of a country, I care not who writes the laws.” And he was really onto something there. That’s why I’m really happy to hear that you’re developing the narrative. Because the system we operate under right now assigns you the bin you’re going to be in. If you can attribute all of my political or social positions from hearing one of them, I am brain dead. I am flatline. And yet that’s what they do, right?

Philip Howard
Yeah. The thing people don’t appreciate with this modern mutation of law is that law is not supposed to be central planning. Law is supposed to be a framework that protects people from bad things — no pollution, no discrimination, no cheating, whatever. Within that, it’s supposed to safeguard an open field of freedom.

Jim O’Shaughnessy
Yes.

Philip Howard
So what’s happened in the last 60 years is that the open field of freedom has become a legal minefield. Instead of proscribing what was bad, for 60 years or so since the ‘60s, we started prescribing how to do everything — and also giving anybody who doesn’t like your decision-making a legal right to challenge it.

I wrote something for The Free Press recently. I had a series on great Americans who are not political leaders, leading up to July 4th. I did one on an early management theorist named Mary Parker Follett, who died in 1933. She was a prominent management theorist before women could vote, so she was really a rather unusual character. One of her points was that as modern democracy is evolving, we have freedom all wrong. It’s important to have democratic elections, but democracy is all about just going in one direction or another — it’s about the herd, it doesn’t affect your freedom. And then there are other people — John Stuart Mill and others — who talk about the importance of individual rights: you can do whatever you want to do. She said, talking about the individual, that it’s like breaking a branch off a tree and expecting it to live. We don’t live alone, individually; we live in groups. And it’s within groups that people innovate and find meaning and fellow feeling, and develop their values and apply their values. It’s in group activities.

And one of the things I think she could not have foreseen was that this modern, post-’60s idea of law — that tells you exactly how to do everything — means that people really are no longer free, that groups no longer have the capacity to innovate and do things their own way. People running a school can’t run it: “Let’s try this.” Can I tell a regulatory success story? A couple of decades ago, Australia had terrible nursing homes. America, by the way, is terrible — do not go to a nursing home. And they’re regulated by thousand-page rule books that tell you when the meals are and how much they have to weigh and how many ounces of vegetables, and all this kind of stuff — just crazy. But they were terrible nursing homes. So someone had the bright idea of scrapping the rule book and replacing it with what ended up being 31 general principles: have a home-like setting, respect the dignity of the residents, that sort of thing. So they did it. And all the legal scholars had scoffed — “these nursing home operators are going to get away with murder; if you don’t tell them exactly what to do, they’ll abuse the residents.” They went a year later to look at how it was going, and what the scholars found is that the nursing homes were twice as good. They looked into why. One reason is that now the nurses’ aides came to work, instead of with a checklist of a thousand things to check off, having internalized these principles. They looked at what the residents wanted. Instead of telling nursing home owners exactly how to do things, they let them do it themselves. One nursing home has a gardening theme, another one has a different theme — they have completely different themes. They can innovate, they can do it in their own way, and take pride in the uniqueness of their creation. Humans need agency. We need to be able to make a difference. This vast legal system has snuffed it out. No wonder everybody’s going crazy and voting for extremists on both sides — because we’re not allowed to be ourselves.

Jim O’Shaughnessy
Particularly for this country. There’s a book called The Hypomanic Edge — Why America has a Little Craziness But a Lot of Success. The thesis is: well, look at who made up the population of this country. They had to be willing to say goodbye to everything they knew — their families, their friends — often with no money in their pockets, and come over here. And so what do you get? You get that type of person.

Philip Howard
And you get people who have to invent. In the old country, you were born the way you were — and that still, to a certain extent, affects the cultures of the old countries.

Jim O’Shaughnessy
Yeah, I agree.

Philip Howard
You’re the son of a carpenter, you became a carpenter. In this country, you move over to the wilderness, the frontier, and if you don’t watch out, somebody’s going to come scalp you. So you really have to take care of yourself.

Jim O’Shaughnessy
Yep.

Philip Howard
And people just invent. Americans invented themselves. Modern — Elon Musk, or Thomas Edison. Thomas Edison’s so smart about this. Here’s a guy with a third-grade education. Great lines. “Nothing any good works by itself. You’ve got to make the damn thing work.” So you imagine him developing sound, inventing the electric light bulb, and all that kind of stuff — but by tinkering.

There was a great book by Harry Evans — God bless him — who was the former head of the Times of London and then became the head of Random House. He bought The Death of Common Sense when it came out; he ran Random House, which published The Death of Common Sense. Oh, it was so much fun. The first time I met him, I was so scared, because I’d never written a book before, and here’s the editor-in-chief of Random House. And he’d say, “I’m so excited about your project. It reminds me of this and that.” He’s completely into it. And years later — we stayed friends — he wrote a book, a coffee table book, which I really urge people to read. It’s called They Made America. It’s a coffee table book of 5,000- to 10,000-word essays about Americans who innovated one way or another, and what their character was and who they were.

So, the Wright brothers. Everyone knew, with the internal combustion engine and all that kind of stuff, and the idea of wings and stuff, that it would be possible to achieve manned flight. And you had the leading physicists in the world, all over the world, trying for some big prize for who could first achieve manned flight. Literally the smartest people in the world, the most educated — they’re all doing experiments and having these things take off on the Potomac and become submarines immediately, that sort of stuff. And then you have these two bicycle mechanics in Dayton, Ohio, who start pedaling around with little foils to test wind flows on their handlebars to see how they work, stuff like that. It’s like Edison, just tinkering. And these two boys, the bicycle mechanics, do it. And after they do it, no one believes them. No one believes them. So they go to Paris. Nobody believes them — this is five years having gone by since Kitty Hawk. They go to Paris, people still don’t believe them. And everyone fills the big stadium, and the French papers are completely making fun of them. It’s some French phrase — the American bluff, or something. And so their little plane takes off from the infield of this racetrack — it’s like Bourget, I think, Le Bourget — and they take off, and people kind of gasp. And then it starts coming toward the grandstands, and people start to panic — this thing’s going... And then it turns, and people just could not believe it. It is such a great story.

Anyway, Harry has his Goodyear in there — sitting there making his family sick by vulcanizing rubber in his kitchen, stuff like that. So these are all basically predecessors to Jim O’Shaughnessy. All these people in the book, making their family sick by bossing them around and making them do all this stuff. It’s a great book, They Made America. It’s about the American... it’s about “well, let’s try this, let’s try that, let’s do the other.”

Jim O’Shaughnessy
You know, Bill Bryson has a great book, America, One Summer. It looks at the ‘20s, and that was the America you’re describing. Like Coleridge...

Philip Howard
Coolidge.

Jim O’Shaughnessy
Coolidge — I’m thinking of the poet. Coolidge was vacationing near Mount Rushmore when the guy was making it. He had no idea he was doing it. His aide said to him, “Hey, there’s some crazy guy up there who’s carving the presidents’ faces into this mountain.” And Coleridge was like, “Cool, let’s go look.” He didn’t ask for any funding. He didn’t go up there and say, “You can’t do that.” He just was like, “Wow, that’s really cool.”

Philip Howard
Cool.

Jim O’Shaughnessy
And back to your tinkerer thing — like Claude Shannon, one of my heroes. Really, because that’s all he did. For those who don’t know, Claude Shannon came up with information theory. He should be, in my opinion, as famous as Einstein. And yet he was just a really, incredibly colorful character. He worked on whatever was of interest to him. So you got a lot of trumpets that shot fire out when you hit a note, you got mechanical chess games, you got all of that — but also you got information theory. And I definitely think... I’m also vehemently opposed to this whole generational “oh, this young generation doesn’t know anything, blah, blah.” That’s total bullshit. These are incredibly talented people, who I just feel intersect with your thesis, because they’re straitjacketed.

Philip Howard
They are straitjacketed. And I think they’re held back by these conventions. We look back at the Victorian age and laugh at how stultifying it was and stuff. Victorians have nothing on us — I mean, they were like hippies compared to us. We are so much more...

Jim O’Shaughnessy
More brothels per square mile in London during the Victorian age than at any other time.

Philip Howard
We are so repressed by, really, a philosophy — a kind of anti-invention philosophy, where being yourself is a danger as opposed to an opportunity. I was thinking about this. I’m asked sometimes by people, “Well, you’ve been at this 30 years, you’ve really had a lot of failure. So...”

Jim O’Shaughnessy
But you’ve been very persistent.

Philip Howard
Well that’s what they say. “So why are you so persistent?” And this has cost me a lot of money. I deemphasized my law career and everything, because I really believed in it. And it’s not like I’m a saint. I don’t wear hair shirts. I enjoy life. I like — like you — fun. I’m playing in a golf tournament this weekend, or whatever. But the reason is that I know, and you know, and the attorney general I was talking to knows, and a bunch of other people who are on my board now, that I’m right: that we’ve created a system that’s fundamentally discordant to the American spirit.

Jim O’Shaughnessy
Yes.

Philip Howard
When I was in college, I got lucky. My family had no money, and I got a job at a federal poverty program at the Oak Ridge National Laboratory. Somebody saw that there was this kid going to an Ivy League school, and so they plucked me out and made me the gopher to a Nobel Prize winner.

Jim O’Shaughnessy
The creator of the multiple-worlds thesis of quantum physics, right?

Philip Howard
Right. And so I spent three summers as the gopher to a Nobel Prize winner.

Jim O’Shaughnessy
How cool is that.

Philip Howard
I ended up publishing papers when I was a teenager on post-nuclear-war recovery and stuff like that. But the thing I learned — we were in a little small group at Oak Ridge, a civil defense group, about a dozen people, an interdisciplinary group: economists and physicists and chemical engineers. What I learned about them is that they thought things through for themselves. And when they thought they understood something, they didn’t let go of it. It wasn’t a question of whether it was accepted or not; it was whether they felt they understood whatever the issue was, whatever the dynamic was, and it became their truth. And they wouldn’t give it up because somebody disagreed, unless the person who disagreed came up with a compelling reason why it was wrong. And I sort of feel that way. I feel that what we’re talking about is true. So why would I give it up? It’s incredibly important.

Jim O’Shaughnessy
Yeah. The principle of parsimony basically tells us that... It’s Occam’s razor by a different name. It works a lot of the time when you apply it to groups and things like that. I was thinking of somebody I had on in the early days of this podcast — Nick Gruen.

Philip Howard
Yeah, I was just on a Zoom with him.

Jim O’Shaughnessy
Okay. And he really sold me on this whole jury idea, which—

Philip Howard
The citizens’—

Jim O’Shaughnessy
The citizens’ jury.

Philip Howard
The citizens’ assemblies.

Jim O’Shaughnessy
Yeah. Why aren’t we trying those? My attitude is: let a thousand initiatives bloom.

Philip Howard
Yeah. Because it’s going to work, and get new ideas, and create... Another thing about society we don’t really understand is the role of moral authority. Citizens’ assemblies, for example: you don’t have to have power to be influential. You could convene a citizens’ assembly on the issues we’re talking about, and have them come up with their own interpretation and comment and so on. And it would have power — not because somebody can push a button to make it happen, but because real people got together and came up with that conclusion. George Kennan, the diplomat, toward the end of his life said he thought American government needed a fourth branch of government. He called it a council of state, but it was really sort of a council of citizens. His fourth branch would have no power. Its only job would be to comment on how the other branches were doing.

Jim O’Shaughnessy
Yeah. Well, you know, didn’t we used to have that in the so-called fourth estate? Journalism has descended right along with government. Because I was a real junkie for — okay, really outing myself as a nerd here — but during the Watergate hearings, I was 13 years old, and I spent all summer watching them. And that feels like a profound loss to me, because — nothing, of course, was perfect — but journalists sort of became the fourth estate that served that function.

Philip Howard
Walter Cronkite. Chet Huntley. These people had moral authority and credibility. If they said something, you believed it.

Jim O’Shaughnessy
Yes.

Philip Howard
And we just don’t... So we’ve lost the moral authority. One of the innovations that has worked in the last 30 years in America is the idea of base-closing commissions. It was politically impossible to close down unnecessary military bases. So one of the recommendations of the Grace Commission under President Reagan was to create independent commissions, appointed with so many by the minority leader and so many by the majority leader — but they weren’t partisan, they were retired generals and such — and they would come up with a set of proposals about which bases to close. So in the 2005 Base Closing Commission, which happened to be run by a guy I went to school with, they came up with recommendations to close or consolidate 50 bases, saving tens of billions of dollars a year. And Congress had the power to vote it up or down, but that’s it. So there’s none of this bickering going back and forth, and the congressman had plausible deniability: “I’m sorry that the base was closed here, but I couldn’t do anything about it, it’s all part of a package.”

Jim O’Shaughnessy
Yeah.

Philip Howard
Great. That’s kind of an innovation. That’s good. But the base-closing commissions had moral authority — they came up with the right answer. So I think we need... and I want to run it. I want you to appoint me to run it. You run for president, then appoint me.

Jim O’Shaughnessy
What did Sherman say? “If nominated, I will not run. If elected, I will not serve.”

Philip Howard
I want you to appoint me to the Recodification Commission — to methodically go through every area of law and turn 50,000 pages into a thousand pages, and not do away with anything, just make it work. Make it a principles-based system, more like the Constitution. And give people defined authority frameworks. Have courts not second-guess it, but only decide whether someone transgressed their authority. That should be the role of courts — not second-guessing. I mean, are the benefits of the transmission line worth the harm of building it through a pristine forest? That’s not a legal question. That’s a policy question, and ultimately a political question, and somebody has to make that decision. Otherwise, today we don’t have the transmission line, so we can’t get the power from renewable sources to the cities or to the data centers or whatever — because the process goes on for a decade. It’s crazy.

Jim O’Shaughnessy
My company, O’Shaughnessy Ventures, is doing a lot with AI. What do you think about that? What do you think about humans who — as you mentioned, not even AI seems to be able to make sense of all of these laws — but it probably is going to do a better job serving a human? By that I mean: have every regulation put in there, have it translated into English, show where it conflicts with other rules and regulations, so that at least — like a human, not even a committee of humans, could do it, but for AI it’s trivial. But not as a ruling — as in, “Here’s what you’re dealing with. Now, you humans, figure this out.”

Philip Howard
Yeah, completely. So I think the closest analogy I can think of to AI is the steam engine. You went from manual labor to a machine that could really do powerful things, and could be harnessed onto tractors or whatever. I have some senior AI people writing for my Free Press series that’s coming out, called Reboot Almost Everything. It’s a 20-part series, coming out in August. And so they’re talking about uses of AI. Reed Hastings, talking about how every student can now have a tutor — it’s fantastic. There are all these fantastic opportunities with AI. Ultimately, though, someone has to be accountable for tough choices.

Jim O’Shaughnessy
I agree.

Philip Howard
And AI is not accountable. So someone needs to—

Jim O’Shaughnessy
The human running the AI needs to be accountable.

Philip Howard
It needs to be accountable.

Jim O’Shaughnessy
I agree.

Philip Howard
So we’re going to need to come up with... A senior person at Google is writing an article on what they view as the proper AI oversight. It’s really interesting. It really is a brave new world, and the opportunities are fantastic. But the challenges of coming up with human oversight — because values... AI can mimic values.

Jim O’Shaughnessy
Right.

Philip Howard
But it can’t really have values. And there’s a lot of ethical theory about how ethics can’t be applied in advance — you always have to be in the situation.

Jim O’Shaughnessy
Situational.

Philip Howard
It’s always situational. And somebody has to be overseeing AI, and somebody has to make ultimate calls. And coming up with those structures is going to be challenging, too.

Jim O’Shaughnessy
Yeah. I think that one of the things that AI can do splendidly is to take those millions and millions of words and boil them down and put them in plain English. And by the way, I think they should do it for business agreements too. You can’t use anything online without agreeing... I don’t know — do you know anyone who’s read the terms and conditions?

Philip Howard
My favorite is when you go to a doctor’s office and they have a little thing there above the receptionist’s desk, and they say, “Okay, now sign here.” And you never see the agreement. And they say, “Okay, now here comes another one, now sign here.” You never — they don’t even go through the pretense of showing you the agreement. You’re just signing stuff. It’s truly the reductio ad absurdum of modern legal life. Crazy.

Jim O’Shaughnessy
So tell me a little bit about the series that you’re doing for The Free Press.

Philip Howard
So the series is called Reboot Almost Everything. It harkens back to our discussion about the need to change the operating system. So it’s not about policy. We go area by area, and we have an expert set up, in give-or-take 500-word essays — these are like one-page, very short essays — but with prominent people, like Reed Hastings or Mitch Daniels, saying, “Here’s the problem: government has become unmanageable, it has all these harms. Here’s the solution: we have to change civil service systems and get rid of union controls and do this.” I’ve written the introduction, and I’ve written one on litigation. I said, here’s the problem: we have an impartial system of litigation in this country — that’s a good thing, and people trust it to be impartial — but it draws no boundaries of who can sue for what. So where’s the law part? It’s kind of “sue for anything” rather than law — not lawsuits, but “sue for anything.” And so we’re missing something. And the harm of that is not just that you get these occasional crazy verdicts, but that people don’t feel free in daily life. They won’t let their kids go out and play alone, because if there’s an accident, they might be liable.

Jim O’Shaughnessy
Our staff here is quite young, and before you got here we were talking about... I grew up in the 1970s. We were free-range kids. We could do whatever we wanted, as long as we got home.

Philip Howard
Right. And so what’s happened is... A couple of decades ago there was a terrible accident on a sledding hill in Greenwich, Connecticut.

Jim O’Shaughnessy
I remember it well.

Philip Howard
And someone got a verdict of $6 million. And the result of that was not... I mean, Greenwich is a rich town, it could afford it. The result was that sledding hills across the country closed down.

Jim O’Shaughnessy
Yeah. Including that one.

Philip Howard
Right, including that one.

Jim O’Shaughnessy
I used to take my kids there.

Philip Howard
Right. So all of a sudden, because of a lawsuit brought by one person — no deliberate policy choice — the trade-off judgment about whether the risks of sledding outweighed the fun of going out in the winter and the snow was not being made by anybody who’s politically accountable. It was being made by the fact that somebody brought a lawsuit. And there was a similar case in England around the same time, where somebody — terrible accident — dove in a lake and became a quadriplegic. Terrible accident. But there were no hidden dangers there. Sure, you could run into something if you weren’t watching, but people had sledded on that hill for decades—

Jim O’Shaughnessy
It was a rite of passage for your kids.

Philip Howard
Yeah. And so in England, there was nothing hidden — it was just a freak accident. It was tragic. But the county that owned the lake was so scared of liability, because there were two or three near-drownings a year — a big lake, people swimming, bad things could happen — that they had determined to close the lake down. And then this accident happened. So the court said, “Well, this is foreseeable, therefore we’re going to grant damages to this person.” It goes up to the equivalent of the UK Supreme Court, and they order the case to be dismissed. They say, “It is part of our role” — as the lead judge put it — “to protect the reasonable freedoms of people in society, including the freedom to take risk. Do we require that rivers and lakes close down because of the certainty that some accident will happen? Do we require all trees be cut down because some child may climb one and fall? We will not tolerate a dull and gray safety regime. We are here to protect the reasonable freedoms, including the freedom to take reasonable risk.”

Jim O’Shaughnessy
What a great decision.

Philip Howard
And it’s called the Tomlinson case. And that’s what we’re missing in this country: no one is drawing those boundaries. So one of my pieces in The Free Press talks about how you would do that. You could have a state pass a statute that says the judges shall have the responsibility to draw the lines of reasonable dispute in any lawsuit; and in any case that might affect the freedoms of people not in the courtroom, the court shall make a legal ruling on the boundaries of acceptable risk.

Jim O’Shaughnessy
See, I’m a big fan of the book The Beginning of Infinity. And he talks a lot in that book about the precautionary principle, and he links the excesses of the precautionary principle to, essentially, the death of societies, because they can’t innovate anymore.

Philip Howard
What happens if.

Jim O’Shaughnessy
Yeah, that’s David Deutsch, right. I read it when it came out and I liked it a lot, but then when I reread it, it just mapped over to what you’re talking about. So, okay, let’s play a game. I am not the president — that will never happen.

Philip Howard
Oh, come on. I like it. President O’Shaughnessy. But think of all the trouble people have spelling it.

Jim O’Shaughnessy
Exactly. When I’m in Asia, they just simply call me “mister.”

Philip Howard
Oh, yeah, good.

Jim O’Shaughnessy
But I can influence the president. And he assigns you to this role that you’ve asked me to assign you to. What are your first five... What are the first five things that you’re going to promulgate?

Philip Howard
Well, the first thing would be to liberate people’s freedom to be themselves, by drawing the lines of who can sue for what — and making judges, even though it’s hard, draw these boundaries so people can do that. The second thing I would do is say: for democracy to work, the elected executives — governors and mayors — have to have basic managerial tools. They have to have the authority to decide not only what to do, consistent with the legislation, but who’s good at doing what, how to allocate money, how to adapt to new circumstances — all the managerial choices that I’m writing about in this little book that’s going to come out in January, called Burning Money. So I’d do that.

I would unleash — American infrastructure was built by our great-grandfathers. I mean, literally, water mains and rickety power lines all over the Northeast. It’s crazy. You would unleash that by creating a really simple authority structure. For starters, I’d write a law that says: notwithstanding any other law or regulation to the contrary, for the next five years, transmission lines shall be approved in the following process. There will be a notice of proposal. There’ll be an environmental review of not more than 50 pages, to be completed within three months, only talking about major impacts. There’ll be a chance for the public to comment in a short period. And then these designated officials shall have the authority to make trade-off judgments consistent with this. Their decision can be second-guessed by a designated official — the president, whoever it is. And the role of the courts will only be to determine whether, in any of these steps, they’ve transgressed the boundaries of their authority. So you have essentially a one-page document that allows for transmission lines, or whatever we’re talking about, to be built. It would be a slightly more elaborate process for a new nuclear plant, but it wouldn’t be 30 years — which is more or less what it is today.

So you’d simply go, piece by piece, and create authority structures. And I would also, to the greatest extent possible, re-empower local communities to do things in their own ways — whether it’s running schools or doing their parks — decentralized as much as possible, so that people can wake up in the morning and feel they can make a difference.

Jim O’Shaughnessy
You’ve got my vote. I think maybe we’ll run you for president.

Philip Howard
No, I just want to run this Recodification Commission. I really do. I’m getting a little old, but I’m still vigorous enough for now. Napoleon appointed four judges to redo all the laws of France — criminal laws, property laws, estate laws, tax law, everything. Everything was run by a prominent judge named Portalis. And in six months, they came up with new frameworks for all of the laws that affect France. Then they were debated in the legislature — Napoleon actually presided over a bunch of those — and they were enacted. And the result was the Napoleonic Code, which is still the basis for civilized law in half the world.

In the 1950s, a committee from the American Law Institute, run by a guy named Karl Llewellyn, a very prominent professor, said it’s ridiculous that we have — what was then — 48 different states, 48 different contract laws, so that anyone doing interstate commerce has to hire 48 sets of lawyers to comply with stuff. This is crazy. So let’s create a uniform commercial code. And they devised it. It has all different chapters — to do with security interests and commercial sales, different chapters for each one. It didn’t take them that long. And versions of it were adopted by virtually all 48 states. That was one of the things that stimulated the postwar boom: everybody had the same set of principles when they were doing contracts. Well, we just need that for society in America.

Jim O’Shaughnessy
Yeah. And it’s funny too, because I was thinking a lot about World War II — it plays a part in my fictional thriller that I was telling you about. It spans... it ends in 2027, it starts in 1939, so it’s quite the epic.

Philip Howard
Wow, cool.

Jim O’Shaughnessy
But I was thinking about America back then, and the thought struck me — and then I saw other people talking about it as well: if you buy into this idea of the American empire, which I don’t... the idea that for a brief period at the end of World War II, we had a weapon that could colonize the entire world if we so chose to. What did we do? The opposite. We did the Marshall Plan. We rebuilt Germany, we rebuilt Japan. And so I feel very patriotic about that — that America could have... If you look at every other so-called empire in history, if they had that weapon, they’re going to run the entire world. That was never in our DNA.

Philip Howard
And if Donald Trump had been in charge... So that’s why I think Americans intuitively know that’s bad, too. He really has accurately scoped out many of the idiocies that we’ve talked about. He doesn’t really have a vision on how to fix them, but America is a place where people not only wanted to do good for themselves, and innovate, and have agency — they also wanted to do good. And I think that part of America is really important. Obviously our moral authority is significantly diminished under the current administration. That’s the thing we need to come back to. But part of what I’m talking about — when you have a principles-based operating system, it is activated by people acting on their values and their judgments. Not just using their common sense, which is important, but also their values: what’s the right thing to do here? And so America’s missing that. There’s no reason why we can’t get it back, but we have to have a legal operating framework that allows us to act on our values — that doesn’t tell us how to do things. I think there’s a historic moment. I really believe this. There’s a historic moment waiting for us right now, and it is to correct course and face the future with new tools — AI — but with old values and an old sense of responsibility.

Jim O’Shaughnessy
Yeah. Because the effects of the current system are also not difficult to see. You create a group of people who feel no sense of agency, who feel infantilized, who almost get trained into learned helplessness. And my version of America is the opposite of all that.

Philip Howard
Right. Well, I’m going to speak at Notre Dame in October, to a bunch of people. And I’m going to Purdue at the same time — which Mitch Daniels has gotten roped into running again. I’ve actually been targeting Catholic universities, because I think that what you just said is something that Catholic theology deeply believes: subsidiarity, agency, people own themselves, they own who they are. So we need to build a cohort in support of that.

Jim O’Shaughnessy
And I think, at least in America, it’s “catholic” with a small C. In other words, it’s universal in this country. And I don’t know whether you watched any of the reactions of the Europeans in the United States for the World Cup. They’re absolutely delightful, because they’re like, “I thought America was just crime-ridden and horrible.” And they’re blown away by Costco.

Philip Howard
Right. But I’m blown away by Costco too, by the way. Anytime I can get 50 pounds of crunchy peanut butter, I’m there.

Jim O’Shaughnessy
You’re there. But the point is that when regular people are allowed to experience something and then share that experience, you again are reminded that, for the most part, most of what is the civilized world shares a lot of values in common with one another.

Philip Howard
Completely. So let us be that. Give us a framework that allows us to be ourselves, and allows us to do things in groups differently than other groups — that does not force us into a... You know, I’ve always said, people say, “Well, America’s all about diversity.” Actually, I think America is all about conformity. The Swedes go to Minnesota, and the Hasidic Jews are in Brooklyn, and the intellectuals are on the Upper West Side, and the techies are all in Silicon Valley. It’s about conformity. What America did that was really different is it tolerated a diversity of conformities.

Jim O’Shaughnessy
Yes.

Philip Howard
And so there were all these different communities, but all with these core values that they shared: reciprocity, living together in the same community. Fantastic. It’s a great thing. And all the innovation that comes out of all these different groups doing things in different ways — well, let us do that again.

Jim O’Shaughnessy
Yeah. And I love the line about conformity, because there’s so much truth to it. Of course, in both investment theory and social theory, there is this notion of the clustering effect, and, you know, like seeks like. But okay, fine — let’s grant that as an axiom. You’ve got to allow your view, where, yeah, you can have your values, and they might be very different than this group’s over here, but as long as you have an underlying framework that allows for that to happen, and for people to take control. Like your idea about local city ordinances or state ordinances. And the attempt to create a monoculture — monocultures always die. If you know anything about evolution: monocultures die.

Philip Howard
Right. They don’t grow, they don’t innovate. Whereas when you have these cells of like-minded people — one, innovating in their own way; two, competing with other cells in their own way — then all of a sudden you have this movement all the time, and you get this great stuff happening. So I think the American character is there — obviously you do too — but it needs to get unlocked. And so that’s going to require a new narrative and a new vision. And I’m roping you into it.

Jim O’Shaughnessy
Float like a butterfly, sting like a bee. Well, Philip, I love your work. As you know, I served on your board for many years. I hope this is the time, because I’ve got six grandchildren now, and I don’t want them to grow up in this giant squid of regulatory morass. We had a driver in Switzerland once, and it turned out it was his last day — he was retiring. And sometimes I enjoy just chatting with a variety of different people, so I started a conversation. I’m like, “So, tell me about yourself,” and everything. And the first thing he led with was Switzerland: “I’m born and raised in Switzerland. This is my last day of work, and tonight I’m getting on a plane and I’m going to Australia.” And I’m like, “Wow, okay, why?” And he goes — as beautiful as Switzerland is, as much as he loved Switzerland — he said, “I can no longer be in a culture where that which is not compulsory is forbidden, and that which is not forbidden is compulsory.” And so it made me think... In the old days, and even now — we do a lot of investing in startups and things like that — the number of incredibly talented people, and I mean off-the-charts talent, who still want to move, work, and live in the United States... That, to me, seems like just such a huge, asymmetric, unfair advantage that this country has. And we’re going to squander it. Which is insane to me.

Philip Howard
So, look at what’s going wrong. We have to change it. It’s just so obvious. People just have to wake up to the reality that this framework that we’re laboring under is broken for no good reason.

Jim O’Shaughnessy
And not only broken — it’s the wrong framework.

Philip Howard
Yeah, it’s wrong. So give us back the freedom to be ourselves again, to roll up our sleeves. That’s what’s needed. It’s going to take a new movement. It’s got to be invented. It won’t happen because somebody else does it.

Jim O’Shaughnessy
Right.

Philip Howard
It’s only going to happen because we do it.

Jim O’Shaughnessy
Yeah. Well, as always, I love talking about all of this. I could go on for hours, but I know that we both have other engagements. We have a tradition here, and you’re going to get... You might like this, because you don’t even have to be a czar, you don’t even have to be appointed. We’re going to give you a magical microphone, and for one day you are emperor of the entire world — not just America. But you can’t put anyone in a re-education camp, and you can’t kill anyone. What you’re going to be able to do is incept them. You’re going to speak into that microphone two things, and the entire population of the world is going to wake up whenever their next morning happens to be, and they’re going to say, “I just had two of the greatest ideas I’ve ever had, and, unlike all the other times, I’m actually going to act on these two things.” What are you incepting in the world?

Philip Howard
Oh, interesting. In any free society, you must be free to follow your star. That’s number one. The second thing I would say is: you are not alone. You exist in a community and a culture, and it’s your responsibility to be a responsible member of that culture.

Jim O’Shaughnessy
I love both of those. You’ve written tons of books — you can find them everywhere, Amazon, in bookstores, et cetera. And when is the new book coming out?

Philip Howard
The new book’s going to come out in January. It’s called Burning Money: How Public Unions Made Government Unmanageable.

Jim O’Shaughnessy
That’s a loaded title.

Philip Howard
My most recent book is called Saving Can-Do: How to Restore the Spirit of America. It’s about the whole idea of striving.

Jim O’Shaughnessy
No, I read it.

Philip Howard
The idea of striving.

Jim O’Shaughnessy
Yeah, it’s really, really good.

Philip Howard
But these are short books. I’ve taken to writing 100-page books.

Jim O’Shaughnessy
Just like the revolutionaries, right? They’re more like the…

Philip Howard
Pamphlets.

Jim O’Shaughnessy
The pamphlets, the Federalist Papers.

Philip Howard
Common Sense.

Jim O’Shaughnessy
Common Sense. They had a lot of impact. So, Philip, I wish you absolutely the best of luck.

Philip Howard
Great to be with you.

Jim O’Shaughnessy
Thanks for joining.

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Sunday, 12 July

Two thoughts from Rabindranath Tagore

“You can’t cross the sea merely by standing and staring at the water.”

“We read the world wrong and say that it deceives us.”

Monday, 13 July

Two thoughts from Doris Lessing

“People who love literature have at least part of their minds immune from indoctrination. If you read, you can learn to think for yourself.”

“Parents should leave books lying around marked “forbidden” if they want their children to read.”

Tuesday, 14 July

Two thoughts from Orhan Pamuk

“The past is always an invented land.”

“Censorship should never be allowed. One should be able to say anything. But I refuse to let politics be foisted on me.”

Wednesday, 15 July

Two thoughts from Edmund Burke

“If we command our wealth, we shall be rich and free. If our wealth commands us, we are poor indeed.”

“Rage and frenzy will pull down more in half an hour than prudence, deliberation, and foresight can build up in a hundred years.”

Thursday, 16 July

Two thoughts from W.B. Yeats

“The best lack all conviction, while the worst
Are full of passionate intensity.”

“All empty souls tend to extreme opinion.”

Friday, 17 July

Two thoughts from John Keats

“Beauty is truth, truth beauty,”—that is all Ye know on Earth, and all ye need to know.”

“I feel more and more every day, as my imagination strengthens, that I do not live in this world alone but in a thousand worlds.”

Saturday, 18 July

Two thoughts from Hunter S. Thompson

“A man who procrastinates in his choosing will inevitably have his choice made for him by circumstance.”

“Freedom is something that dies unless it’s used.”

Follow Jim on Twitter for a daily dose of Two Thoughts!

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This week: a British post-punk revival cures an allergy to new music, two books explain why football is the only religion without atheists, Bob Hoskins terrorizes 1980s London, a movie doubles as a history lesson, and the overlooked Bennet sister gets the spinoff she deserves

1. Dry Cleaning: British Post-Punk at its Best

Something no one told me about getting older is how much harder it gets to discover new music. I’m finding new movies, books and art all the time, but despite listening to hours and hours of music a day, I find myself consistently underwhelmed, retreating to the safety of my favorite artists. Why is this? Is it just a skill issue? Or is there something unique to music that makes us more discriminating in our tastes?

Anyway, after a brief interlude in the electronic music I listened to as a student, I’ve been back to bands recently. In particular, I’ve been digging Dry Cleaning, a British outfit headed by the taciturn lyricist Florence Shaw. They’re firmly in the post-punk lineage, with Shaw’s monotone, spoken-word delivery dancing over janky, spiky guitar riffs and moody basslines. There is something profoundly British about their weary, resigned tone (exactly what I need on the morning after yet another crushing World Cup exit).

Shaw’s lyrics - non-sequitur fragments accumulated magpie-like from found text and the dusty corners of her mind - are consistently interesting, just on the edge of amusing without veering over into parody or self-mockery. Take this interlude from Strong Feelings, complete nonsense that somehow makes poetic sense:

Tin blades, earthen ware
Flower brick painted in blue
On the sloping edge of a vase of flowers
On the front, Chinese landscape
On the sides, figures in a Dutch landscape
It’s Europe

Going through their back catalogue has reminded me of how I felt discovering new music when I was younger. I’d suggest starting with Strong Feelings and the slow-building Liberty Log for a good sample of their sound. If you like them, check out their first album and work from there. [Ed]

• 🎧 Dry Cleaning

2. Football is the Only Religion Without Atheists

Good news: it’s World Cup season.

Bad news: it’s nearly the end of World Cup season.

As a football fan for over twenty years, I’ve watched thousands of matches. I could probably have learned another language in the number of hours I’ve spent watching 22 people kick a little ball around a field (no regrets).

But some of my most profound football experiences have come a long way from the stadium or the screen. Two books have taught me more about the art and science of the beautiful game than a TV pundit ever has.

The Art: Football in Sun and Shadow by Eduardo Galeano. This is a collection of vivid, bite-sized vignettes celebrating the “great pagan mass” of the sport. Galeano writes like a poet, and he is better than anyone at articulating the religious fervor that football invokes in its fans.

The Science: My Turn by Johan Cruyff. The Dutch master and architect of modern Barcelona delivers a masterclass on “Total Football,” skipping the ghost-written platitudes common to celebrity autobiographies to explain how he engineered space and rhythm on the pitch. Anyone wanting to understand Spain’s masterclass against France earlier this week should start here.

As the World Cup draws to an end, these books remind us why we care so much about 90 minutes of controlled chaos. As Galeano wrote, football remains “the only religion without atheists.” [Camellia]

• 📕 Football in Sun and Shadow by Eduardo Galeano

• 📕 My Turn by Johan Cruyff

3. Before Guy Ritchie Came the Long Good Friday

Harold Shand (Bob Hoskins, in his breakout role) is a London gang boss with lofty visions of legitimizing his operation by building a Docklands property empire, aided by an impending partnership with the American mafia.

Alas, a lifetime of murder and extortion has a nasty habit of leaving a few loose ends. When a series of attacks from a mysterious adversary threatens to dismantle Harold’s meticulously laid plans, he must threaten, bribe, shoot and slice his way into finding and stopping his enemy before it’s too late.

This film is an urtext for the British crime flicks popularized by Guy Ritchie and Matthew Vaughn in the early noughties. Snatch, Lock Stock, and Layer Cake aficionados will find a lot to love in the acidic script (“The Yanks love snobbery. They really feel they’ve arrived in England if the upper class treats ‘em like shit”), dreary London backdrop and compounding eruptions of eyewatering violence.

Oh, and need I add that there is a sinister mustachioed sidekick called ‘Razors’?

Bob Hoskins is inspired as the unnervingly vulnerable head honcho, imperiously sneering and snarling his way through London’s underbelly like a Cockney Robert De Niro one moment; shedding a tear for the death of his best friend the next.

There are stylistic flourishes aplenty (keep an eye out for the exquisite long take that closes the film), but there is a lot more going on under the hood. Gone are the winking, teenage-boy-coded sensibilities of Ritchie’s films, replaced by a sinking sense of claustrophobic dread as the noose tightens around the impulsive Harold. The script is whip-smart, landing blows on Thatcherist individualism, British exceptionalism and class tensions while still knowing when to shut up and play the genre hits. [Ed]

• 🎬 The Long Good Friday (1980)

4. 1917 : You Only Know What They Know

I’ve started watching war films with my 12-year-old. Not Rambo III or Commando. The more historically grounded ones. It started when I mentioned that something happened “during World War II” and realized the words meant almost nothing to him. How could they? My own love of history began with films rather than textbooks. They aren’t always accurate, but they gave the words meaning. Now I’m trying to do the same for my son.

So I built us a little curriculum: 1917, Saving Private Ryan, and Band of Brothers. They’re more violent than what I usually watch with him, but I know my kid, and the violence isn’t gratuitous. It’s supposed to be horrible.

We started with 1917 because I wanted to begin with the First World War before moving to the Second. I’d already seen it twice, including in the theater, and Roger Deakins is my favorite cinematographer.

Everyone talks about how it's made to look like a single continuous shot, unfolding in near real time. It’s neat, but it's not what I care about. What makes it special is that the camera never leaves the soldiers. You see nothing they don't see, you know nothing they don't know. There are no establishing aerial shots of the battlefield, no cutaways to the Germans setting their trap, no shot of Blake's brother waiting at the other end. That absence denies us the reassurance of knowing more than they do.

In 1917, you're just there. It’s the closest a film has gotten me to what it might feel like to be a young soldier having to cross no man’s land. I pointed out to my son how many of the soldiers looked like teenagers, or barely out of their teens.

The violence happens the way it often does in life: fast, brutal, unannounced, no slow motion.

The filmmaking is incredible. Sequences that would be the highlight of another director’s entire career are just stacked one after another. The ruined town at night, lit by drifting flares and fire, is out of this world.

Being told about a war and seeing one are very different. The next time I tell my son something happened in 1917, he won’t hear only a date. [Liberty]

• 🎬 1917 (2019, directed by Sam Mendes)

5. How I Learned to Love Mary Bennet

Mary Bennet bored me stiff.

Jane was beautiful, Lizzy was witty and Lydia was reckless. When I first read Pride and Prejudice, it felt like all Mary did was give solemn little speeches and play the piano. Dull!

Honestly, given my dislike for Mary, I don’t know why I read Janice Hadlow’s The Other Bennet Sister, a partial retelling of Austen’s novel from her perspective. But I’m so glad I did.

I expected a clever extension of Pride and Prejudice. I did not expect to become so invested in Mary.

The first half revisits familiar territory: Longbourn, assemblies, drawing rooms, exhausting marriage calculations, etc. But now it’s all filtered through Mary’s acute self-consciousness. She is bookish, gauche and overlooked, and she knows it. It’s heartbreaking to sit with her as she watches her sisters attract attention she knows she’ll never get.

But once her sisters are settled and her own future becomes uncertain, the novel expands beyond Austen’s plot and forces Mary to build an identity for herself. A slow-burn reinvention follows (my favorite kind), managing to thread the needle between growing Mary as a person while keeping her recognizably Austen’s creation.

If you loved Longbourn (Pride and Prejudice from the servant’s perspective) or Wide Sargasso Sea (the madwoman from Jane Eyre given her own story), you’ll probably love this too.

It got me thinking about other stories whose side characters we’ve overlooked. Is it time for an Animal Farm from the horse’s perspective? [Aashisha]

• 📕 The Other Bennet Sister by Janice Hadlow

⭐ Explore the OSV Field Notes Archive ⭐

Enjoyed OSV Field Notes? 💌 Forward it to a friend!

Jim and Sangeet discuss AI-native companies, the future of knowledge work, American and Chinese AI models, creative “exhaust,” changing career paths, and how to compete when the rules of the game are constantly being rewritten.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

The Cutting-Room Floor Is the Real Asset

Sangeet: If value chains are moving from output to outcome, then the creative exhaust is going to be worth more than the finished work. Think about writing a book. For every word that makes it in, there are probably ten or twenty words in wasted drafts, and maybe five hundred more sitting in notes that are genuinely valuable but never see the light of day. They only exist to help you get to the output, so we treat all of it as waste. But that is exactly where the learning sits.

For the last sixteen years I’ve captured everything I read, every thought, every connection, in a tool called Workflowy. Every day I’d add to it. Every year I’d take a week off just to move ideas around and see how they connected. I could never really do anything with it, until now. I took the whole thing and turned it into a knowledge graph that links all those ideas together. Now it can tell me where the gaps in my own thinking are, the connection I’ve been circling for years but never actually made. What I used to think of as exhaust turns out to be the most interesting part.

Jim: The analogy I use is what was left on the cutting-room floor.

Sangeet: Correct.

Jim: And I’m a prodigious note-taker. For forty-five years it was all by hand, and now we’re digitizing it. Some of what I’m seeing, I would never have thought of in that particular combination, even though they’re my own notes. The AI can basically go in and say, “Dude, you’ve been saying the same thing for forty-five years, how come you never acted on it?” And out of that come whole new ideas, whole new books, whole new ways of learning.

Sangeet: Exactly.

Don't Think Electricity, Think Agriculture

Sangeet: I think the shift to AI is very foundational. It’s not something you can compare to the shift to electricity. I’d say it’s more like the shift to agriculture, or to wood, or to minerals.

Jim: That’s the argument I’ve been making. Don’t think electricity, think agriculture.

Sangeet: Exactly. Because the fundamental input into the value chain is changing. And when the input changes, an entirely new production system has to be built on top of it. But most of our industrial mindset assumes the input as given and treats the production system as the thing you act on. Now we have a new input, and we haven’t even begun to rethink what the production system should be. That’s really what China is working on, treating both energy and AI as new inputs into fundamentally new production systems.

The point isn’t whether China is right or the US is right. It’s that we’re still incredibly early. We’ve just discovered agriculture. We’ve worked out how to make the ground a bit more fertile. We haven’t yet figured out that one day we’re going to make clothes out of cotton. We’re that far from the whole value chain.

Transcript

Jim O’Shaughnessy

Well, hello everyone. It’s Jim O’Shaughnessy with yet another Infinite Loops. I’m delighted to welcome back Sangeet Choudary, the best-selling author of Platform Revolution and the one I really want to talk about, the newer Reshuffle: Who Wins When AI Restacks the Knowledge Economy. Welcome back.

Sangeet Paul Choudary

Thank you, Jim. So glad to be here.

Jim O’Shaughnessy

I have certain guests who, when I see them on my schedule, I get excited, and I so enjoy talking to you. But for people who might not be familiar with your work, let’s do a bit of a recap of your thesis so we can level-set for our listeners and watchers to understand where you think we’re going.

Sangeet Paul Choudary

Absolutely. The key thesis I talk about in Reshuffle is that when we think about the impact of AI on knowledge work, we often tend to think of AI in the same way we’ve thought of previous forms of mechanization, which have typically impacted relatively more codified, standardized workflow. AI is fundamentally different, because work that was previously considered tacit and bound inside human cognition can now be broken down and taken over by machines in a way that was previously not possible. So one of my key points is that the traditional way of looking at the impact of mechanization on traditional forms of work does not apply when we think about the impact of AI on tacit knowledge work.

What I mean by tacit work is fundamentally this. Take the example of solving any market analysis problem. There is no fully codified workflow. You make up your workflow as you get into the problem. You define it, and you learn from the information you’re gathering. It’s difficult to explicitly codify the workflow, the number of iterations, what good looks like. That’s why traditional forms of mechanization did not apply to tacit work, but today AI does. You can see that with the market analysis example: you can get a really good market analysis report using Claude, which is getting better every few months.

So my key point is that when we looked at previous forms of mechanization, we used to think about the impact primarily in terms of automation or augmentation, because you were taking a predefined way of doing work, looking at different steps in that predefined way, and inserting a machine at specific steps. It was either automating that step or task, or augmenting the human on that task. A lot of us are still taking that same model when we think about AI and applying it. That is what I call the task-centric, automation-based way of looking at AI.

The real story we’re missing in that process is that when previously known, modularizable, non-definable forms of work suddenly become redefined and remodularized in fundamentally new ways, the structure of work changes. Who performs which work changes. Take the example of consulting. The pressure on consulting firms is not simply from model providers. The pressure is also from the fact that model providers now change the division of work between what customers could have done in the past and can do now versus what consulting firms can provide them. When customers take more of the work and model providers absorb some of the other work, the consulting firm in between has to rethink not just what to do with the work that remains, but what new work to go toward.

So the real idea of Reshuffle is that what AI does is unbundle our traditional work structures, whether it’s a workflow or an organization. These are specific configurations, what I broadly call bundles of performing work. It unbundles all of that. It redistributes what machines can do and how humans can reorganize what they want to do based on improving machine capabilities. With that, it creates the possibility for fundamentally new structures to emerge: new workflows, new organizations, new industrial boundaries. So the real impact of AI will not be in speeding up today’s work. It will be in reconfiguring everything that supports work, which is our workflows, our jobs, our organizations, our value chains. All of those are poised for reconfiguration. That’s the real idea of Reshuffle. When AI restacks the entire knowledge economy, the game will change, and hence the winners and losers will change as well. That’s the whole idea of who wins when AI restacks the knowledge economy.

Jim O’Shaughnessy

Yeah, and we are very simpatico on that idea. I think many people are asking the wrong questions and framing it wrong. One of the reasons they’re framing it wrong is because they’re captured by their priors. They’re captured by the old workflows, the hierarchy, the meetings, the departments, the job descriptions. I started thinking about this a while back and called my little thing the great Reshuffle. What I saw coming, and it really is, is changing the routing. AI is really going to change the way things get routed to different nodes. And there are going to be problems. There are always problems. But it could create what I would call a new distributed value mesh network.

If an earnest CEO who really wanted to understand what was going on hired you as a consultant, what would you tell them about how he or she should work to design, maybe from first principles, around the new coordination that AI will allow?

Sangeet Paul Choudary

The place where I would start is how you think about strategy. Today, the typical way you think about strategy is in terms of answering two questions: where to play and how to win. What’s the playing field going to look like, and how do you think about the winning game? The first thing I would talk about is that the playing field within which your firm is playing is fundamentally changing. I’ll give a few different examples. If you’re in the knowledge services industry, the professional services industry, clearly the playing field was structured around the assumption that access to certain forms of knowledge work was expensive and proprietary, and hence you could hold it internally and license it or charge for access to it.

So when access to certain forms of knowledge work suddenly becomes very cheap, because AI does perform certain forms of knowledge work, within limitations of course, but it dramatically reduces the cost of accessing certain forms of knowledge work, how does that then change what is differentiated versus what is commoditizable in your industry logic? Or take it all the way away from professional services to a very physical industry like material sciences, plastics, and compounding. Traditionally, the cost of compounding was that if you had to identify or discover new compounds, you had to go into the lab, run a lot of tests, and come out with compounds. Today AI can generate new compounds from scratch. So the value then shifts to how you match the compound to the process, to the demand profile.

Because alongside that, the number of use cases at the front end is also dramatically expanding. As the supply of compounds increases and the demand for different use cases increases, how do you match the two things really well? That’s where the new constraint sits. So the first thing you would want to look at, if you’re a CEO, is that you have to follow the scarcity, because you can compete on the basis of what’s scarce, not what’s becoming abundant. What’s becoming abundant is going to get commoditized. Margins associated with that particular activity are going to get compressed. So you need to think about where your new scarcity lies, and how you can create defensible business models around owning that scarcity. That’s on the playing field side.

At the same time, you have to think about AI strategically in terms of your organization. Today a lot of CEOs are just focused on: we need to get AI adopted, we need to roll this out, we need to get teams on board. All of that is a good starting point, but it is only that. What we should really be thinking about is that as AI gets adopted in our organizations, there are three things changing simultaneously. One, the capabilities themselves are changing, because Claude, OpenAI, all of these are improving on a daily basis. With every new release, what the machine can do and what humans can do changes. So the capabilities from a pure model perspective are changing.

Which of those capabilities actually get adopted in value-creating workflows in the organization is constantly changing as people learn how to adopt the technology. And as people adopt the technology, how they change their own work is constantly changing. So if you’re a CEO, the biggest thing you need to think about today is how you manage this constantly evolving capability set, because you’ve never had such a constantly evolving capability set before. You had a top-down capability set where you said, we’re going to hire these people, map them into these skills, and keep training them on this basis, so the skills you have access to constantly change but you managed how those capabilities evolved. As you deploy AI in the organization, it’s going to evolve on its own.

And not just the machine capabilities, but how they’re adopted, and more importantly, how your people are changing their work around it and how they are discovering new capabilities or moving to new things. That’s going to change what you can do with this evolving capability set. So there are two things here. One, the nature of differentiation and competitive advantage in the playing field is changing. Two, the capability set with which you can innovate from inside is changing. It’s really at the intersection of these two things, given that they are changing for every company across industries. So your competitors are not going to look the way they used to look in the past.

Because once certain forms of knowledge work that were protected by your industry boundary become available outside that boundary, new competitors can come into your industry where they could not have in the past. I’ll give a very simple example. Think about what’s happening to customer support. Traditionally, customer support was something you performed in a contact center. It was a very closely bound industry boundary in terms of who runs a contact center and what kind of tools are provided to them. Today customer support can be performed by AI agents alongside human agents. So you have companies like Microsoft and Salesforce, completely outside those industry boundaries, now entering the support industry, because they can access the capability of providing support without having to invest in training humans to build that capability from scratch.

So when you think about these aspects, the fact that previously scarce capabilities are becoming commoditized, that ways of differentiating are changing, that who can get access to and enter your playing field is fundamentally changing, and that your capability set internally is changing, that creates a very volatile and dynamic competitive playing field, both in terms of what you can do and where you can play. I think understanding and resolving that is the key challenge for CEOs today.

Jim O’Shaughnessy

Another thing I think we face: the authors of the book The WEIRDest People in the World, I don’t know if you’re familiar with it, make the argument that cultural lag is a real thing, and that it takes humanity a while to adapt to a new way of doing things. I think that’s true. But I also think it provides an asymmetric arbitrage opportunity. The asymmetric arbitrage opportunity is: are you going to be willing to move rapidly to a truly AI-first corporate or institutional structure in everything? If you are, it’s my thesis that you’re going to be able to eat the lunch of the players using the old playbooks. Is that one of the reasons? This is why you see the current top of the hierarchy, let’s look at movies, books, a variety of things, they’re not happy at all.

And yet, much like the movie industry, they tried to suppress VHS for years and years. They spent millions of dollars, they lobbied against it, and of course they lost. And then the wonderful irony is that VHS sales and other such sales ended up being a much larger part of their revenue, the very thing they fought all that time. Do you see something like that happening with traditional dominant companies today versus the upstarts?

Sangeet Paul Choudary

Yeah, I think so. It’s that particular element of a company native to a new technology versus a company migrating to a new technology, and the arbitrage opportunity for the company that’s native to it is not entirely new. What’s new is the rate of change, the speed at which this is happening, which confers a compounding advantage to the native player versus the migrant player. If I were to qualify this, take a different technological shift. Take the shift from desktop to cloud, which happened 15 years back. You had a company like Adobe, which moved to the cloud very successfully. There are Harvard Business School case studies about how well Adobe managed that shift, how well its CEO moved, how the CFO agreed to move from licensing to subscriptions. And yet it struggles today.

It has struggled ever since to compete with the native player, which was Figma. The reason it struggled to compete with Figma is that Figma was architecturally organized around the properties of the cloud. Adobe was using the cloud only as a channel. Figma was using it to redesign and reimagine the product architecture, the offering architecture, and the workflow supporting it around the capabilities of the cloud. To give a simple example, Adobe was built on a file-centric architecture. You had to create the file, and in the past you would send it over email. Now you could be on the cloud and have others coming in and commenting on the file, but it was still centered on the file-centric architecture, and the file was tied to the design division.

So the file-centric architecture preserved a certain logic. Figma, because it’s cloud-hosted, is created on an element-centric architecture, which means every design element the organization uses is managed in a central library. It can be reused across design files. So design files are very often reconstructed using new elements and common elements across the organization. There are two important unlocks because of this, and this shows the difference between the native player and the migrant. The first is that when you manage design elements in an organization-wide library, you’ve moved the value from design only to design and governance. Governance no longer sits inside the minds of designers, which is what was happening within Adobe. Now it’s managed organizationally. So the budgets you can access are fundamentally different.

And when you can represent design in terms of a cloud-hosted graph and not a design file, that allows multiple different players, marketing, sales, product, all of them, to work alongside the designer on the same file without forcing the designer to keep ensuring it is well validated and verified, because all that verification is happening centrally. My point is that Figma realized design was not an isolated activity. It was an activity that fed many workflows across the organization, and the cloud natively allowed that workflow spanning to happen across the organization. No matter what Adobe does, it cannot move in that direction. Ironically, Figma is now facing the same issue, because Figma is sort of an AI migrant.

It’s got this nice file structure, element-based, but then Anthropic, for instance, can infer connections between elements, can identify fundamentally new ways in which design files are being manipulated. It can do a lot more with the entire design system than a migrant like Figma can. So we see this cycle repeatedly: when a new technology comes in, if you have the opportunity to rethink the logic of the product, the workflow, your customer’s workflow, your organization, everything around this new technology, the starting point is whether you can really define what the new unit of value is. If you look at Figma versus Adobe, for Adobe the unit of value was the file; for Figma it was the element. So you could do everything at the level of the element.

Even if you opened up APIs for the ecosystem, your partners could be the same, but with Adobe they could only work on the file. With Figma, they could work at the level of the element and integrate at that level. So it fundamentally changes how companies organize, how they collaborate, how they compete. That is why there’s a huge arbitrage opportunity for players built ground up with the new technology. There is also a significant opportunity for players who are migrating, as long as they have several structural constraints that do not simply get wiped out. As an example, in professional services, you could be a copywriter at one end, or an audit and tax consultant at the other end.

As a copywriter, you don’t necessarily own structural constraints, whereas as an audit or tax consultant, you have the right of final sign-off, which is regulatory protected. So there’s a structural constraint that, even if the work gets taken over or commoditized by AI, you are able to hold on to the value at your end. It’s important to know under what conditions incumbents can retain value because of structural constraints, and under what conditions the AI-native player can fundamentally impose a game that the incumbent simply cannot play. All of those factors become very important when we think about who has that arbitrage opportunity.

Jim O’Shaughnessy

And one of the things, this is my view, I’m not attributing it to you, but I think one of the reasons we’re seeing all of what I view as desperate attempts for regulatory capture on the big frontier model designers and providers is because they understand that if they can’t get regulatory capture, if they can’t make the legal aspect of who gets to do what, then the playing field is truly a different playing field, because you’re not going to be able to be saved through the traditional things like copyright, all of the various legal procedures and protocols that we’ve built up over long periods of time. They’re all under attack, right?

Sangeet Paul Choudary

Yeah. I think there are two different issues, and let me know if I’m approaching this the way you intended it. When we think about copyright and other issues around value captured by AI models, there’s this element of ring-fencing what was previously a public good and extracting it the way you would a private good. AI enables you to create a transformation value chain where the end product is completely untraceable back to the input. Copyright law was built in an era that did not assume that kind of transformation, and essentially because of that it’s difficult to protect what’s happening here. This is not my idea. This comes from a well-known book called Power and Progress.

This has played out over the centuries, where every new technological shift, or many new technological shifts, has created opportunities to extract value by ring-fencing a public good and making it private, essentially because the regulation stayed stuck to the previous model whereas the technology imposed a fundamentally new model. In one way, that’s what we’re seeing here. The other thing that’s interesting in terms of how Anthropic and others, the model providers in general, are calling for regulation is because they also, I believe, realize that the American models and the Chinese models are playing a fundamentally different game. In the American model game, the model is sort of the end. So that is where value is supposed to be captured in the long run.

In the Chinese model, I believe the model is the complement that has to be commoditized in order to capture value at the complementary layers, especially when we think of physical AI and new production systems. The value there to be captured is in the energy system, in the production system on top of the model, which is the physical production system, robotics, and so on, and the overall coordination system in terms of how you build fundamentally new value chains, fusing the knowledge value chain and the physical value chain. So the fact that it’s a fundamentally different race and a fundamentally different game that the Chinese model providers are playing is also driving a lot of this concern around regulation.

Jim O’Shaughnessy

And which model, the Chinese version or the American version, do you think wins?

Sangeet Paul Choudary

I think they’re fundamentally different games. If we believe that eventually the knowledge value chain and the physical execution value chain are not two distinct value chains, the way we’ve been talking about digital and physical for the initial part of the digital era. When the digital era started, we always talked about the digital and physical value chains separately, and eventually we realized they are not really separate. You essentially create value by bringing the two things together. I think the same thing applies when it comes to AI. There’s the knowledge work value chain, and then there’s the physical work value chain, which converge.

I believe the way the model providers in the US in general are looking at it is purely in terms of what AI does to the knowledge work value chain, which is a fair way to look at it, because traditionally most value in today’s industries has moved to knowledge work. If you look at any industry, if you look at mining, or the example of plastics I took, the physical work gets fully commoditized and the value moves to the knowledge work. But if you look at the Chinese model in general, the two things are not fundamentally distinct. I take the example of Shein in the book, which clarifies this really well. If you think of Shein, the fast fashion player, the reason it’s interesting is that it creates a learning architecture that brings the physical and the knowledge value chains together.

It constantly senses new ideas and new trends coming up on social media. Then it converts that into a design using a network of designers, converts it into a small batch of production, tests it in the market, and with all of that it’s constantly training which batches work and hence how its physical production system and its design system should work together. So this idea of creating a learning architecture that spans both the knowledge work and physical execution is, I believe, where things are headed. But because in the West we’ve largely assumed that the physical side of things is commoditized, we tend to see the impact of AI only within the knowledge work value chain.

Jim O’Shaughnessy

Yeah. And I should note that we also have a publishing company, so we’re very concerned about copyright and are looking for new ways that the technology itself can unlock to preserve the author’s right to their work, to preserve the filmmaker’s right to their films, and so on. I think that is going to be a really important topic, because if you can’t cut the creators out, you have to come up with a protocol that works with the new technology. When everything can be digitized and the end product looks nothing like the inputs that created it, you’re going to get a lot of very unhappy people. So I think this is not just a business question, this is a societal question.

Sangeet Paul Choudary

Right, right.

Jim O’Shaughnessy

Because another question I would have for you: I sort of think that distributed value networks, mesh networks, where there is no central authority. So, for example, China had the Gutenberg technology way before good old Gutenberg came up with it.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

But it had a very centralized command-and-control government that suppressed it, because the emperor wasn’t interested in people printing things that might be critical of the emperor. Whereas Gutenberg worked because Germany was not unified. It was a collection of city-states competing with each other. So China had the tech first, but Gutenberg was operating under a distributed network protocol, the protocol won. And I think another one of your points is that the coordination layer is going to be vitally important to determining who’s the winner and who’s the loser. Could you explain that a little bit, because you’re much better at it than me.

Sangeet Paul Choudary

No, for sure. This is one of the things I felt people were missing about what AI can do. The way I typically think of it is that when we think about the impact of AI on the underlying economics of what’s improving, we tend to think about two effects. Predictive AI is collapsing the cost of prediction. Generative AI is collapsing the cost of generation. What happens when the cost of something collapses is that it gets done more, in many more places, and hence it unlocks second- and third-order effects, because those previous constraints associated with those activities go away. Those things get done much more. The third thing these two framings miss is that the cost of translation, or coordination, is also going down with AI.

What I mean by cost of translation is that when a foundation model is trained on the world’s knowledge, it can translate between different domains in a way previous technologies could not. Previously, if you had to translate between different domains, you had to either rely on bespoke integrations, or rely on some form of power structure that was willing to invest in doing that translation so it could extract rents from it. It could be a broker or an intermediary, or it could just be what we call platforms, where they specify the interface, manage some form of the mapping, and then once they get sufficient traction, they force the ecosystem to follow the standard. So the translation happens through that mechanism.

Essentially, what all of that leads to is that there were two primary ways to coordinate multiple actors. You either had to get the actors to agree and reach consensus, and the example I take is the shipping container. Once trains, trucks, and ships agreed on the same format of the container, logistics got unlocked globally. So it’s coordination with consensus, or it’s coordination through enforcement and power, which is what, say, a Facebook or an Amazon or any of these large platforms do, initially heavily funded by venture capital, which allows them to gain scale, and then they enforce the coordination. My point with AI is that it allows coordination without consensus, because it collapses this cost of translation.

The reason that’s important is that today’s power structures are structured around proprietary formats, proprietary ways of doing things, proprietary workflows, proprietary interfaces. Essentially those power structures create walled gardens. If you take any industry, whoever owns the choke point, in some industries that’s the R&D choke point, in others the distribution choke point, whoever owns the choke point enforces the standard, the schema, and the way of working on everybody else. What AI can do is take outputs at every step of a value chain, learn from them, and translate them between different walled gardens in the same industrial system. The example I give is construction. In the construction industry, you have players like Autodesk and Bentley with different design formats.

That’s on the architecture and design side. Then there’s the downstream construction and engineering side. All of these tools and technologies don’t talk to each other, and the players providing these tools create their own islands, or walled gardens. What we’re seeing now with new AI-native construction players coming in is that none of them are trying to do design faster. Nobody’s attacking Autodesk straight up. They’re trying to dismantle the Autodesk logic by creating these translation layers, where they tell the user: no matter where your different teams are working, in which formats, we’ll help you see a unified view of the project. Through that, we’ll create a coordination-without-consensus layer.

Once enough demand moves in that direction and starts using this AI layer to make decisions, they would then want to flip it and enforce the interfaces on the various format providers. That’s the idea of coordination without consensus, where you can dismantle today’s power structures and create an alternate way to span the different formats. I think the new power structures it yields could be a combination of protocols, because you need completely open protocols to get different formats to work together, but then a different form of concentration at different points. It could be just one node that you capture, it could be a combination of different layers, but it would be different from today’s power structure. That’s where, going back to your point about protocols, that’s a fundamental Reshuffle pattern we’ll see as well: enabling coordination without consensus, breaking down today’s power structure, and creating alternate structures going forward.

Jim O’Shaughnessy

Yeah, and that’s where I got really intrigued in that part of your book, because I agree wholeheartedly. But if you study history, it’s really nothing new. By that I mean the distributed value architectures and protocols. The example I always use is the Rothschilds. The Rothschilds were five nodes without a central authority. The father sent each of his five sons to the capitals of Europe of the 19th century, the financial capitals. They had an amazing sub-layer of courier network. They had rented boats, carrier pigeons, ciphers that only they knew. But it was not routed to a central authority to make decisions. It was routed to the brother who could take the greatest advantage of it. And it’s an apocryphal story.

I think historians go back and forth on this, but because of this topology that the Rothschilds had, that was their key advantage over others. They had a better information network than government information networks at the time. Of course, the canonical story is Nathan Rothschild, through this courier network, knowing that the Brits won the battle against Napoleon. Then he took advantage of human psychology, went into the stock exchange, and sold British gilts, or bonds. Everyone thought Rothschild knows things ahead of other people, so everyone just rushed to sell. Of course, he had his agent buying from the plunging prices. And they literally controlled finance in 19th-century Europe until the telegraph destroyed their advantage. I see AI in a very similar role here.

I think it’s hard to articulate just how fundamentally transformational a technology this is, because you’re going to be touching a lot of third rails. That’s going to be messy, and it’s going to be a very difficult fight. What about the idea of measurement capture? You don’t have to control the entire network if you can control what gets counted. Could AI itself, as the new router of all this information, could we see a system where that just gets copied and copied and everyone’s using the same routing system? Or am I off base with that?

Sangeet Paul Choudary

No, that’s an interesting thought. There are a few complementary thoughts I have. One is that we’re clearly moving in a direction where firms are not going to compete on the basis of outputs. At the risk of using the cliché, outputs to outcomes, everybody’s talking about it, but what does that mean? I think that has something to do with what we’re talking about in terms of measurement capture as well. We’ve optimized firms around creating the best output, the most output, and scaling that output. We don’t necessarily know what it means to optimize against outcomes. I believe optimizing against outcomes is about owning a proprietary learning architecture, which helps you own the outcome better than every other firm and hence optimize your entire internal production architecture to improve that outcome better than anybody else.

What I mean by owning that learning architecture is this. When we think about learning, after 10 or 15 years of digital technologies, we still think about learning as what happens on the customer interface, personalization, that the system knows more about you, it’s learning about you. We’ve not necessarily seen learning to the same extent across the entire production architecture. Shein is one of those examples where, because it’s a proprietary architecture, you are fine-tuning every element of it. What should be designed, which kinds of design elements work well with which kinds of production factories, which production factories work well with which markets.

You’re fine-tuning every coupling in the value chain in terms of what works well with what. In new value chains, if you look at something like electric vehicles, you do have that learning architecture, because you’re simultaneously fine-tuning what the battery can do, what your charger can do, what your charging network should look like, and hence what the customer experience looks like as a combination of these three things. So there’s a coupling between battery capabilities, charger capabilities, charging network spread, and so on. Over the last 50 years, we’ve constantly moved away from inefficient vertical integration to modularization, first with outsourcing, then with cloud capabilities. Whichever way you think about it, it’s constant modularization, decoupling, making things more flexible and plug-and-play.

But when you move from outputs to outcomes, you need to own the entire production system in order to guarantee the best outcome. So we’ll see a new form of reintegration happening, structured around defining what should be counted as the right measurement at every stage in the value chain, toward ensuring you are able to guarantee the best outcomes to the end customer. That’s the way I would think about measurement capture: the ability to win the outcome game is determined by your ability to own the learning architecture, which is determined by your ability to dictate what should be measured at every stage, because that’s what guarantees the end outcome in the best possible way. I’ll throw a related idea against it as well.

There’s a recent HBR article I wrote that came out last week, where I essentially make the point that we’ve traditionally seen work and learning and skilling and all of these things as decoupled, in the sense that you go and perform your work, then you go somewhere else to learn, and then you come back and perform your work. With AI, what’s happening is that for the first time we’re working with a technology that’s constantly working alongside us. Hence it’s also measuring how we are working, and transforming how it behaves so that it can give us highly personalized feedback based on how we’re working. So we have created this.

We are moving in this direction where learning, measurement, all of that is going to happen in the flow of work, and hence which kind of measurements matter and what learning path they take you individually down is also going to be determined by AI. So I don’t know if that directly addresses it.

Jim O’Shaughnessy

Yeah. Actually, I’m looking at a question, because I believe pretty deeply in this distributed value chain, where, historically, if you look at all wealth creation, not extraction, but creation, it happens under these circumstances. The Greek city-states, all the way up. For politics and philosophy and all of that. It’s not just business, it’s societal, it’s political, it’s everything, the Gutenberg example. In your answer, I asked you this question that I’ve written down. I’m going to read it, because you answered it very much the way I’m looking at the world. I say: if AI is the new coordination layer, and the distributed architecture is the historical engine of value creation, is the highest value produced by controlling the layer, or by designing a layer that can’t be controlled?

And what you’ve just said is you’ve got to create a proprietary layer of knowledge, reinforcement, learning, all of that. So it sounds like we’re both directionally thinking the same way, right?

Sangeet Paul Choudary

Yeah, and I would agree. When I use the term learning architecture, there are two things I try to reinforce, because people have preconceived notions of what learning means based on how we’ve used the term in the last 15 years when it comes to business models. The first is that people just assume learning happens in the market, not across the production system. I think that’s going to be truly unique and new with AI. That is why, again, I believe the Chinese model of betting on commoditizing the model and capturing value from the production system, the energy system, and the existing coordination system on top of the physical knowledge production system is where value is going to be.

So that learning architecture piece is something I believe is not fully understood to the same extent in the Western paradigm of looking at technology. The second piece is essentially the other reason I use the term architecture. When we use the term layer, and I’m just trying to refine what we’re going back and forth on, the term layer is borrowed from the past several years of modularization we’ve gone down, where we’ve assumed certain layers are going to be commoditized and certain layers are going to be valuable. I believe that’s going to continue happening. That’s just how value migration works.

But in the past, it was possible to be just one layer and not do anything else, or at least be visible as one layer, even if you had adjacent control positions and adjacent points. The classic example being that Amazon has Prime as the visible layer, but it has that price-matching algorithm that runs at the back end which helps it retain the Prime position. But if I take the Tesla and electric vehicle example again, it’s not just what we call a layer today, but the couplings between layers and a proprietary new learning architecture that helps you understand how those couplings behave. As the technologies at each of those layers are improving rapidly, owning those couplings is where advantage accrues.

So those are the two reasons I stress the idea of the learning architecture in a way people have not used it with digital technologies, at least.

Jim O’Shaughnessy

Yeah, and again we are aligned, because we think about it at the architectural level as well. We started at O’Shaughnessy Ventures to be AI-first in every aspect of everything it does. And if you’re 66 years old, that requires a lot of open-mindedness about the way things are going to get done. Luckily, I’m very open-minded about these things. I definitely think you are absolutely right that people are not thinking big enough in many circumstances, because I think you’re spot on about thinking at the layer level. That’s a whole different conversation from the architecture level, and the ability for learning to happen in the workflow, to be reinforced, and all of that changes the way everything is done. My concern is, again, back to cultural lag.

We have been socialized to believe that I’m going to get this job, this is what I’m going to do, and this is how I’m going to be judged, by my outputs, and the whole deal. That is not what the future institutions look like to me at all. And I don’t think there’s necessarily a sense of urgency, like those of us who were early to machine learning and seeing what it could unlock. I hear a lot of people saying, oh, we’ve got to get going, we’re late. I think in the grand scheme of things, we’re still pretty early. Am I off base? Do you think I’m right there?

Sangeet Paul Choudary

I think we’re at that phase where we’ve seen the new capabilities that are emerging, we’ve seen how that could lead to new firms and new architectures. We have not yet seen all possible architectures in all possible contexts through which the capabilities can be used to create advantage. What I mean is that if you think of any of the previous shifts, and I think the shift to AI is very foundational. It’s not simply something that can be related to a shift to electricity. I would say it’s more foundational. It’s probably similar to a shift to agriculture, or wood, or minerals.

Jim O’Shaughnessy

Because that’s the argument I’ve been making. I’m saying, don’t think electricity, think agriculture.

Sangeet Paul Choudary

Exactly, right. Because the fundamental input into the value chain is changing. The previous input used to be very different, and an entirely new value chain has to come on top of it. So both agriculture and minerals are two things I would look at. Most of our industrial production mindset assumes the input as given and assumes the production system as the object of action. But now that we have a new input, we have to rethink what the new production system should be. And I don’t think we are thinking about that. This brings me again back to the China point, where they are working on both energy as a new input and AI as a new input into fundamentally new production systems.

I think it’s less a point of whether China is right or whether the US way of looking at AI is right. It’s more about the fact that we’re still very early. We’ve sort of just discovered agriculture. We’ve figured out how to make the ground more fertile, more arable, and so on. We haven’t yet figured out that we’re going to make clothes with cotton at some point. We’re too far from that whole value chain at this point.

Jim O’Shaughnessy

Yes, and again, I agree completely. The thing I’m struggling with as well, though, is this notion of, if you have this distributed, non-centralized mesh network protocol, a viable mesh should be forkable, it should be auditable, it should be hard to fake and hard to capture. So what happens if AI becomes the ultimate mesh capturer? By that I mean, we have the centralized model that we’re using in America, we have the commodity model that the Chinese are pursuing. It’ll probably be a combination of both. But what happens, if the AI is getting smarter and smarter, are they also compressing toward a middle? That’s a criticism I often hear about AI, that it doesn’t, unless you specifically say, hey, I want to look way out in the tail. What it does is compress all of the knowledge into a standardized common ground.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

I’m being inarticulate about this, but the idea is: is it the ultimate enabler of these hard-to-fork, auditable, hard-to-fake, and hard-to-capture mesh networks, which I kind of think it is? I’ve been thinking a lot, and this is what I was looking forward to in getting your view, because I like to think I might be wrong. What happens if I’m wrong?

Sangeet Paul Choudary

So I’m going to again offer a complementary perspective here. I think what I’m saying and what you’re saying, if you bring them together, we could have an interesting theory. Let’s take the creative value chain. It assumes there’s a certain creative process that’s valuable, and the object of action in that creative process is the output that has to be created, whether it’s a book or a song or whatever that is. In the process of working on that object of action, there’s a significant level of creative waste it is willing to deal with, which is not going anywhere. It just goes out as creative waste. It does not have any place in that value chain. It’s all the unwritten drafts, all the messy notes, and so on.

I believe that if value chains are moving from output to outcome, the creative exhaust is going to be more valuable than the object of action, because the creative exhaust is where the learning architecture sits. Hence I believe everybody who has built a life thinking about perfecting the output should now go back to thinking about what to do with the creative exhaust. I wonder whether the protocol plays out most interestingly at the level of the creative exhaust, where my creative exhaust, what I waste, can be refurbished and reused by somebody else it perfectly applies to, who is at a certain point in their own creative exploration. I’ll try to give a couple of examples to illustrate that, and also share how I’m thinking about my own work with that context.

But the other thing, so there are two points I’m trying to make. One is that if we believe the input is fundamentally changing, which it is, which is what is scaring the creative industries, if we keep focusing on the creative object as the output, as the focus of production and the focus of improvement, if we stay focused on the output-centric model of creative work, I have a feeling that’s a loss. We are moving in the direction of: where does this output move into, what problems does it solve, how can I think about that outcome and create an architecture, a learning architecture, to solve that particular thing?

It’s easier to think about that when we think about electric vehicles, because we’re saying, okay, whether it’s battery technology or charging network, all of these are working toward one outcome, driving range. So you have to keep improving them. You don’t improve only the vehicle. You improve every component that was previously assumed as given, in order to get to the outcome, and the learning architecture is where the advantage is. It’s difficult to apply that directly to creative work today, because we don’t necessarily think of it in the same way. But I’ll try to share what I’ve been thinking about in terms of my work, in case it helps us, first, bring it closer home to something I’m applying this to, and second, help us see if there’s a way to bring it back to creative work.

When I am writing books, for every word I write in a book, there’s probably 10 to 20 words I’ve written in wasted drafts, but there’s probably 200 words, or more, 500 words, that I’ve captured in notes that are very valuable but are never seeing the light of day, because they’re only helping me improve, only helping me get to the output. Over the past 15 years, 16 years now, I’ve captured everything I’ve read, every thought I’ve had, every idea I’ve connected. I’ve captured them in a tool called Workflowy, which is sort of like something before Notion and Roam came in.

It was a way to organize your ideas and do it in a slightly hierarchical but flexible way. I curated that over the years. Every day I would sit on it, put in what I was reading, put in what I was thinking, connecting those ideas. Every so often, when I was in a curatorial mood, I would go into it and move ideas around based on how I thought things connected. Every year, at the end of the year, I would take a week off to just play with the Workflowy for the year and see how it connected with previous years and so on. So that was just me geeking out on something I enjoy doing anyway.

So far, I’ve not been able to do anything with it, but now I’ve been thinking, why should I be looking only at the book? I should be looking at all these ideas that have been there at the back end. So what I’ve done is taken all of that and created a knowledge graph that links all of those ideas and concepts together. Now that the underlying knowledge graph has been created, it’s really powerful, because it can tell me which conceptual gaps the ideas have, because I just never read that. So it’s able to identify what I should be looking at next. It’s able to identify what’s unique about that contribution, and it’s able to show it to me.

For my curation on whether a certain thing should be added to the knowledge graph or not, I can take the same knowledge graph and run an entire case study of something happening in a certain industry through it. It calibrates the knowledge graph to say these concepts are playing out in this format, in this timeframe, in this industry. I’m having a lot of fun with it, because I’m constantly learning where the gaps in my learning are. It’s also opening a whole range of ways in which what I had previously seen as exhaust and waste, and had never seen the light of day, all of that is being converted into a knowledge graph that can be converted into something usable and productizable and interesting for different stakeholders downstream.

So that’s the way I’ve been thinking about it. If you think of the creative process, or the production process in any knowledge work for that matter, the value of that, corresponding to the learning architecture, lies in these learning iterations that lie scattered all over the place, not in the finalized output. I’ve always felt that the finalized output was more of slicing and dicing and providing a certain narrative. But the narrative is only one way of bringing together all those ideas. So if I take back my unbundling-rebundling thesis, the narrative of the book is a bundle. If you unbundle it, there are many concepts, and they can be rebundled in many ways.

But because the book has a certain constraint that forces that narrative, whether it’s attention span or storytelling, that constraint prevented many other components from entering that bundle. So how do you then reorganize all of those components? That’s where a knowledge graph, which can then be transformed into many different products, becomes even more interesting. So that’s been my way of thinking about it. This is something I always think about in terms of where my own work is going. But in general, I think some version of this applies to the knowledge economy and knowledge work in general.

Jim O’Shaughnessy

Again, listeners and viewers are going to get bored, because we’re just going to agree on everything. I think you are absolutely right. The repurposing of, the analogy I use is, what was left on the cutting room floor.

Sangeet Paul Choudary

Correct.

Jim O’Shaughnessy

And I am a prodigious note-taker. For many years over the last 45, it’s been by hand. But we’re digitizing all of this, and some of the things I’m seeing are, I would have never, even though it’s in my own notes, I would have never thought about it in this particular new combination. And it is, for me at least, incredibly exciting and indeed incredibly generative. Because the AI’s ability to go in and say, dude, you’ve been saying the same thing for the last 45 years, how come you never acted on that? That jives with your ability. You can recombine, and then whole new product lines, whole new ideas, whole new books, whole new ways of learning come out of that.

Sangeet Paul Choudary

Exactly.

Jim O’Shaughnessy

But let’s, okay, so we’re both very lucky in that we have the ability to have access. We have our own hardware installation, our own multimodal AI. At OSV, you obviously have access to all of the frontier models. You probably have your own bespoke models as well. What advice can we give to the listener out there who doesn’t have the total access, but some access? How can they start to change their own path? Especially, I’m thinking of younger people. I think the days of “I’m going to go get my degree in X, Y, or Z” are painfully antiquated. What would your advice be? I’ll hire you for a second here as a consultant to our younger listeners. Where would you point them to be able to maximize their ability to thrive in this new economy?

Sangeet Paul Choudary

Okay, so I think the larger question here has different answers when you think about a younger audience versus people like me who are in their 40s, or even people who are in their 30s, who have had a certain run which gives them, not so much a buffer to experiment with, but more importantly, it has helped them cultivate judgment. It has helped them understand what good looks like. And it has helped them see what output to outcome looks like, because even though you don’t measure the outcome, you sort of know the outcome you’re looking for and you tacitly understand it, so you fine-tune the output to get there. I want to come to the younger part, but to the...

Jim O’Shaughnessy

Actually, you know what, you’re going to the right place. Start with the people like yourself who are in their 40s, or even 50s. They have this long history that they’ve habituated in themselves.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

And they’re going to need to be able to change that. So let’s address those folks first, but then get to the younger people who might not have to avoid all the bad habits that we’ve developed.

Sangeet Paul Choudary

Absolutely. There are two very different scenarios between the two. There are people who have been through it. I think the biggest thing to unlearn is that they were told a story, then they saw that story play out, and they now believe in that story. That’s what the youngsters don’t have to worry about to the same extent. They had to worry about a lot of things, but not this. The youngsters already don’t believe in the story they have been told, because they’re seeing it’s not working. But those who have been through some sort of career for 10, 15, 20, 25 years, they were told the story, they saw the story play out, they thought they’d figured out the rules of the game, and now they’re seeing the game change.

So the first thing is that everybody wants to believe the game is changing for others, but not for themselves. That there’s something special about what they’re doing, and not just about what they’re doing, but about how they mastered the game, and that it cannot be taken away from them. I think that is one of the first challenges that anybody with experience has. I’ve gone through that cycle as well, thinking I’ve mastered a certain game, and now, even if AI can do certain things, I should just keep getting better at my game.

It takes a lot of unlearning and questioning, some level of shock to your system, and a lot of reflection for you to come to a point where you realize that, well, it’s all good if the game is not changing and if I’m special, but shouldn’t I be preparing for the reality where the game is changing and I’m not special? And if that doesn’t come through, that’s fine, it was just insurance money. But I should be preparing for that so I’m not caught unawares. So that flip does not necessarily happen for everyone. It happens in different ways for different people.

Some people might realize they’ve sort of come to the end of the road of the previous game, and then realize it’s just not worth moving toward a new game. They’re at a place where they want to stop playing games. That’s possible. Another group might be: we’ve come to the end of the road, but you know what, I can see four more years of playing this game, and I’m going to double down and make as much as I can playing this game, and I’m going to stop after that. So those are very viable scenarios, and those are the classic board-level gotchas.

Every time I speak to a board, the underlying question in the room is: I’m 65 or 75 or whatever, and I’m going to be around in this board seat for three more years and in any board for five more years. Should I really care about AI, if you don’t know when your specific prediction is going to play out? Yes, it’s going to play out, but is it two years or 10 years? So should I then care about it? All those are very viable responses as well.

But if you’re somebody who has taken pride in their craft, if you’re somebody who’s always tried to improve at their game because of your internal ambition and to see the results of that ambition, and you’re not just trying to stay in the game just to stay in the game, I think you should take a hard look at what the new game that’s going to be played is. You should just assume the game is going to change. If you really care about your work, if you really care about getting better and doing better, you should fundamentally assume that everything you know is going to be taken away, and you have to rethink what that is going to look like.

Maybe it’s going to happen in two years, maybe in five years, but instead of betting on the timeline, I would just bet on the outcome, and figure out how to make the most of the lag period while betting on the outcome. So that’s how I would think about people in their 40s, 30s, whatever. Unlearn what you felt you knew. Get over the fact that you felt you had figured out the game and that your game will not change, because it’s actually going to change. Get over that and start afresh.

For the youngsters, I think it’s a lot more challenging. And here I’ll say it’s not just those who are young, but anybody who’s been structurally locked out of an upwardly mobile knowledge economy career and who’s been constantly trying to work their way back into it, whether they got kicked out of a job and entered the services industry, or became an Uber driver or whatever, and they now see that path being locked out even more.

So in general, people who are getting into what would traditionally have been called an upward graph of a knowledge work career, and especially those who are young, won’t necessarily have the on-ramp that allows them to build judgment, because the friction of working with an untrained human in certain cases will be too high compared to the lack of friction of working with a sufficiently trained, highly trained AI. Because of that, firms are going to make choices where they simply don’t go down a path where they need it. So a lot of those on-ramps that helped you fine-tune your judgment, that helped you learn from people who had judgment, all of that goes away. So it’s very easy to say AI will do the execution, humans will retain judgment.

But while there are many issues with that, the bigger issue is who will have that judgment. There’s going to be a significant portion of humanity who might not even be allowed the opportunity to develop that judgment and hence have a unique edge. I don’t have very good advice to give to people who are young. I think the younger you are, the better off you are in a way, because you’re learning that this is happening. I think the transition generation, which went into college in 2020, was stuck at home instead of being at university because of COVID, and then came out of COVID to see ChatGPT launch.

I think that transition generation has it most difficult in a way, because they’ve been told a certain story, they’ve worked their first 12 years of schooling toward getting into that story, and suddenly they’ve seen that whole story break apart. I think if you’re much earlier on, it’s an important time for both students and their parents to realize that the traditional way of optimizing for outputs, optimizing for measurement of output, which is what the education system is based on, is not sufficient. You have to figure out a way to constantly create your own learning architecture, and the only way you can do that is through small experiments, through being entrepreneurial, through gathering feedback.

The answer, again, is not as simplistic as: hard skills are going away, soft skills are important, specialists are not going to be important, generalists are going to be important. This is how we try to bucket solutions, but it’s not quite as binary as that. The only thing we can be entirely sure about is that if you have an iterative, learning-based approach toward your work, if you assume uncertainty as the constant, what that means is you have to have an aim on where things are headed, place a bet on that, think in terms of placing that bet, and constantly update your model of where things are headed based on what you’re learning on a daily basis. That’s the only way you can build your own learning architecture.

You have to constantly assume that where you play is uncertain. It’s not going to be the same as it is today, so you have to bet on that. I would say that’s something that’s true for everybody in jobs as well. Today your company is dealing with uncertainty. Everybody has a view on where AI is taking things, and again, it’s not just AI, it’s many forces. But in the midst of uncertainty, you can’t look at your company as the unit that’s going to guide you on the way forward. You have to bet, you have to learn, and you have to give that learning back to the company to signal that you’ve got it figured out even better than they have.

I think that whole flip, from “I’m going to rely on somebody else to guide my career” versus “I’m going to be at the frontier of betting and learning what’s happening, so that everybody else who’s confronted with uncertainty can see that I’m one step ahead,” I think that flip is going to be really important. So I know I didn’t answer the youngster question really well. It’s a very difficult question. But I believe there’s some version of this that applies at every level, where you have to unlearn the old game, just assume that at some point it’s going to go away from you, and then get comfortable with betting on uncertainty, running experiments, and, based on your learning, constantly changing your roadmap of what you’re betting on and how you’re getting there.

Jim O’Shaughnessy

The thing that is ironic is that, in order to become a great success in the new world, you have to select against the basic coding of the human OS. In other words, what’s one of our biggest biases? Confirmation bias. We seek information that proves, in quotes, that we are right, where we should be seeking information that proves or suggests we are wrong. And high agency versus low agency: expecting tutelage and a coach who’s been through the game to be able to help you is kind of a norm. And yet what you are articulating, and I think correctly articulating, is that we’re going to have to learn to try to unlearn these deeply embedded biases in ourselves. When you were talking about the person who thinks, my game is A-plus and everything else, I’m the exception.

I used to have a GIF that I would put up on Twitter to people who were saying something like that. I said, “This must be your screensaver.” And it was a thing that says, “You are the only exception.” I know that I am not the only exception. I know that I am just as fallible and just as outdated and everything. But it took a lot of time for me to habituate this self-interrogation. For you to be able to continue to iterate and succeed, you have to be able to exit an old mental model. That is really easy to say and it is really difficult to do. So I definitely agree with you that the younger people, honestly, they’re going to be native to this environment, and so they probably will excel.

We have some young, as you know, we do the fellowships every year. And oh my God, the brilliance that is out there among people who are still teenagers. You can literally see it in the way they construct their proposals. They are intuitively doing many of the things you are advocating. Whereas people, well, certainly people of my age, a lot of people who are in their 60s, are like, yeah, I have no incentive to be involved in that. Like your board member. I’m only here another three years. So their incentives are to either be reticent or even to actively push back. Whereas the younger people have no such incentives, and they’re doing fine.

I think you nailed it with the people who really need the advice you just gave, which is people who are already successful in their careers. They got successful in a certain way, you would say, by focusing on the outputs as opposed to the outcomes, inputs, excuse me. But that itself would be incredibly useful. Just that conversation would be incredibly useful, because one of my worries that I’ve expressed repeatedly is there is going to be a cohort of people who, through, and I underline this part, no fault of their own, are just not calibrated or designed for this new world. And I would love to come up with a way where we can do everything possible as a society to ameliorate, to in some way make that blow land less hard.

Because you see all the back-and-forth right now. I did not anticipate the anti-AI response. Well, I did a little bit from the old hierarchical guard, that’s kind of a given. But from younger people as well. Because it’s like, whoa, all the rules are changing, and now you want me to change. And unlearning is hard. The ability to unlearn, I think, is much more important, really, than the ability to learn and then habituate. You’ve got to constantly be unlearning. All models are wrong, some are useful. If you take that attitude, you can switch models relatively easily. You can iterate, you can change. How, in your career, have you changed? I mean, in AI time, your book was published in 2025, that’s decades ago in AI time. How has your own outlook and your own process changed from when you actually published the book to now?

Sangeet Paul Choudary

Well, there are a few different points here. One is that when I wrote the book, I wanted it to be timeless in terms of concepts, if not in examples, because I knew it would not be timeless in examples if I wrote it based on 2025 AI. So I rely a lot on historical analogies and so on. First, over the past year, I’ve tried to constantly calibrate those concepts and see if, with everything that’s happening, those concepts play out reliably. It’s helped me fine-tune where it applies and where it does not apply. It’s leading to an updated version, an updated edition this year, which will talk about things with a lot more nuance.

The first-order effect of that was just that I would have to launch an updated version of the book much faster than I normally would. But then that would be the same output fallacy, right? Because that would mean the faster AI moves, the faster I need to keep writing books, and that’s not going to work. What I’ve tried to do with this new edition, which I’m still working on, is that before I write anything, and this is not why I built the knowledge graph, but now that I’ve built the knowledge graph, I’ve actually calibrated the book through the knowledge graph to see where it’s consistent with what the knowledge graph would predict and where it’s not.

The fun of having this knowledge graph for me is that on a daily basis I’m seeing exactly what you talked about, things that I’ve talked about in the past, things I’ve curated in the past, but where I’m not seeing a certain connection. I’ve seen those connections on a daily basis. Some of them get me excited, so I want to dig down further. So it’s sort of curiosity on steroids. If you’re naturally curious, then having this, it’s one thing to have an LLM that’s constantly finding interesting stuff your way, but you don’t always want that.

For me, the way the knowledge graph has transformed the way I work is that I can just wake up in the morning and ask it to throw me three surprising things, or something that appears a lot in my work but that I’ve not connected to something that appears very little in my work, or it helps me see a lot of gaps in my own conceptual frame. The reason I like it is that I want to keep thinking, and I want to use AI to help me keep thinking even better. When I think, the gaps are very often that I waste time trying to figure out unknowns.

What the knowledge graph helps me do, because it’s structured around knowing what I already know, is that it has pre-scored concepts where I’ve done a lot of my work. It’s able to identify unknowns that are just at the level of the right delta, that stretch me a little bit to connect a well-known concept to an unknown concept, to see it happen in a fundamentally different industry, to connect an unconnected historical precedent to it. So I’ve created it as a way to help me think, which I don’t think I get with an LLM. Because what happens with an LLM is I start with a question, it gives me responses, and in sifting through those responses I learn how to ask better questions. But it’s a very tedious way of learning how to think.

At the end of a long session, I may come out of it having learned something new, but because it doesn’t know what I already know, it doesn’t know how my mind is structured, it’s not able to push me in the right way to increase my thinking. So it may sound a little theoretical as I say it, but only after having created that knowledge graph did I realize how important this idea of identifying the unknowns becomes. The second thing, take away AI and all of these things, one of the things that has really liberated me ever since I decided that my previous game is not going to be worth playing anymore and there’s going to be a fundamentally new game, is that it set me free to rethink things.

If I’m going to find a new game from scratch, I cannot optimize it around anything except longevity and fun. It should be something that is organically fun for me, something I have the incentive and the interest to keep playing long enough. Hence it cannot be optimized around a well-structured game, which was very much optimized around certain markers of success that the game led to. So here, if I don’t know those things beforehand, the only way to keep winning is to stay in the game and keep changing with the game. That has set me free, because if I start with, is it fun, is it something I want to continue doing rather than keep getting burnt out, it helps me take a different approach to my work.

One of the positive outcomes of having to rethink your game has been that the only way you can play a game in a constantly changing playing field, which is what AI and other things are doing to us today, is to ensure you’re in the game long enough and that you’re enjoying playing it. So there are two ways I can respond to what’s happening. I can say I want to play the old game to its maximum for as long as it works, or I want to reinvent myself toward the new game. If I’m doing that, I might as well play it for the next 20, 30 years. In order to do that, I should have fun while doing it.

So what all of this has forced me to think about is, if I’m rethinking what it means to be somebody who has traditionally used, say, books and certain very specific forms of narrative to address this overall point of how things are changing around us, how should industries think about this change, how should companies think about strategy, that overarching question that has always guided my work, which is how does technological change force companies and individuals to rethink how they should compete, if that question continues to be of interest, I would rather create the surrounding infrastructure that helps me stay focused on answering that question, if it’s still relevant, and do it in a way that I continue to enjoy for the long term. So, long story short, the key thing I believe has been really refreshing about having to just stop and forget what I was doing in the past, and the thing I’m doing, is that it gives me the opportunity to build it fun-first, joy-first, rather than speed-first or accuracy-first, all of which actually impose a lot of overheads. I think if I can keep focused on that and the underlying capabilities keep improving, then the notion of scale would also change. You should be in a position where, if you are a fun-first or joy-first company or person or career, you will have the ability, as the underlying capabilities improve, to keep scaling your impact with that. So that’s the way I think about it.

The temptation always is to get faster at what I’m doing today, but I think that just traps you in playing a game that’s going to end soon.

Jim O’Shaughnessy

That’s one of the things I’ve been so excited about, literally because of all these journals. I have been waiting for AI since I was 22 years old in 1982, because the possibility space, learning new things, recombining things, to me that’s incredibly fun and invigorating, and, as you would put it, joyful. I think that the old idea of the nine-to-five job, the whole structure of the way our economy works, is going to change, and I personally think it’s not going to be easy. So I’m not Pollyannish or Panglossian about the whole thing. There’s going to be a lot of disruption, and that’s kind of a given in any kind of transformational technology.

If you can look at it the way you’ve just articulated, I think you’re going to have a much easier go of it than if you’re a type that really believes something because that’s the way it’s always been done here. Because you’re not going to survive in the new environment, right?

Sangeet Paul Choudary

Yeah. I know there’s a certain level of privilege associated with building a fun-first career with constant learning and constant experiments, because we have to think about that alongside this whole point of how there’s growing wealth concentration, there’s growing opportunity polarization, and things of that sort. So that is the context within which it would apply to many people. But the one thing that remains immutable to a large extent is that if you just focus on the fact that the old game is going away, and you either get mad about that or you figure out how to play it better or play it faster, that’s a clear path toward irrelevance.

So given every set of constraints that you personally have, you have to figure out how to get to the new game. Everybody will have their own set of constraints. Some will start from a place of more privilege than others, and that’s to some extent how things have always been. But the one thing I think is going to be common to everyone is that if you keep simply focusing on playing the old game, you’re not going to get to a win that’s going to be significant, because winning the wrong game is actually losing.

Jim O’Shaughnessy

Yeah. So if I were to summarize, it would be: you’ve got to relearn, unlearn. Because so many of us have habituated ways of doing things that we’re not even aware of them.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

And I’ve undertaken a series of new projects, one of which is writing my first fiction book. And boy, when I was starting, I’ve written four non-fiction books, and the correlation between fiction and non-fiction I found is basically zero. So I’ve had to learn it, but it’s been really fun to learn how to do it. And I couldn’t have learned as quickly as I learned without AI. I did the traditional thing and read some books on how to write fiction, and I even read a couple about how to write a screenplay. Then I watched some YouTube videos, and I’m like, I don’t think I’ve learned anything at all. So I just went right to our AI platform and started, and then I designed a very mean but very truthful editor that the AI simulated. And it basically came back, “This is horrible, this is awful.”

But it’s interesting, because it’s a whole different conversation. It’s easier to take that advice from a machine than from another person, because from another person I actually experienced it. The first thing I ever wrote for publication, my wife graduated summa cum laude with a degree in journalism, and I was the editor of my high school newspaper. I thought, oh, I know how to write all this stuff. So I wrote it and said, hey, would you take a look at this? This is back in the 90s. I actually handed her the paper that I wrote, and it came back a sea of red. And I got mad, and it became, how can you say this to me, and all of that. I was recounting it with her. And by the way, she was entirely right.

All of her edits made it a vastly better piece of writing. But the point is, we were chatting about it, and I said, so I modeled you into the AI, and they’re wicked mean to me, but I don’t take it personally. And I just think that your underlying factors of curiosity, the joy of experimenting, and the ability to understand that everything’s an iteration, you’re not going to get the hole-in-one every time on the golf course. It seems like selecting for those, again, is selecting against things that we’ve tried to beat out of children in the previous era. Like what was much of public education in the 19th and 20th century?

But no, installing a correct-answer machine in the brain and driving curiosity and all of that kind of stuff out, because your society wanted you to follow orders. Society wanted you to be able to understand those orders and then execute them. So I definitely think this touches not only business, not only society, but the way we learn. And I think it’s interesting to me, because I think we have to be open to every conceivable permutation here. Most of them won’t work, but we’ll learn from what doesn’t work. Your knowledge graph is a great example. It isn’t the large language model that is really giving you all of these super new ideas, it’s your knowledge graph. And people sometimes forget that part of it.

Who knows, maybe at some point in the future AI will get creative and will get all of those things. I have no idea, and I lack the expertise to even comment on whether that is possible. But for now, that isn’t the way it works. It’s a tool. It’s a tool in the hands of a deeply curious person who is comfortable with uncertainty, the best tool that’s ever been invented, certainly in my lifetime. It’s hard for me to articulate how excited I am by it, because it really leads to a whole new paradigm. How do you deal, because you’re dealing with external institutions, and I don’t have that friction, how do you overcome a very deeply skeptical board? Back to the board. Where the CEO answers to the board, and the board is likely made up of people close to my age whose incentives are very different, as you pointed out. Three years and out. How do you convince them, you really have got to take this seriously?

Sangeet Paul Choudary

Yeah. There are quite a few things there. And I want to reiterate the summary you brought in, which brings together a lot of the points we’ve been talking about. It’s a combination of uncertainty in the playing field, with constantly changing and ever-improving capabilities that are available at your disposal, that allows you to innovate in the center and manage that uncertainty to your advantage. That is what the new game is. The difference between a business and an individual is that an individual has emotional constraints and capacity constraints at a different level. That’s why fun-centric becomes very important. But for a business as well, you have to think about what your constraints are, within which you can operate. You have to know that what you’re really going for is, there’s uncertainty outside.

There’s a new capability set internally that creates the opportunity for you, within the unique constraints of your business, within whatever identity you have created for yourself, first, to potentially question that identity, but second, within those constraints, and I wouldn’t say within those constraints, but in cognizance of those constraints, to think about how you can leverage these capabilities to do something fundamentally new, to create a fundamentally new way to compete in the playing field you define. In general, my point to any of these so-called skeptical boards is, by default there’s a certain filter in terms of what comes my way.

So I don’t necessarily speak to a company that’s at step zero. It’s typically to companies at step four out of five, where they’ve kind of done the adoption, they’ve tried to accelerate things internally, they’ve bought into the hype but not seen the results, and then they’ve realized that what I’m talking about is how to change that game, how to think about strategy in a fundamentally different way. So I don’t necessarily have to go in and tell them that AI is important. They sort of know that, everybody’s talking about it, they’ve seen the value internally. They just haven’t yet figured out what that means for them in terms of whether they should continue doing what they’re doing or fundamentally flip.

So that is where I essentially make the case that you can place a bet on the fact that things are not going to change externally. You’re going to have better capability, you’re already adopting it, so you’re going to improve how you do what you do today. But you have to start placing bets on what if things change externally. And to place those bets, you have to start by saying, what are those scenarios? At the end of it, you could come back and say, it’s not going to happen in my relevant timeline, and that’s perfectly fine, because the difference between having a view on what’s going to happen and betting on it is the risk you are willing to take against the timeline.

So it’s a perfectly valid statement to come back and say, I’m not willing to place that bet, because I don’t believe in that timeline. You’re accepting that risk, and that’s fine. That’s how allocation works in general. But you have to do the hard work of thinking through what all those scenarios are, and what your firm looks like in those scenarios. And be very cognizant of the fact that you have to place those bets. You cannot place those bets by omission, the fact that you did not place them because you did not run the scenarios. So you have to do that. At the end of it, if you still believe it’s not going to play out, that’s just the best bet you’ve placed.

There are going to be many situations where companies optimistically, proactively place bets and they don’t play out. And there are going to be situations where companies do not place bets even after seeing the scenarios. But not placing bets because you didn’t do the hard work of seeing the scenarios, didn’t do the hard work of projecting what’s going to happen, didn’t think through how these shifts are playing out, that is the failure case. Because if you do the hard work of developing the scenarios and placing the bets, you’ve already taken some steps to say this is going to happen, that’s not going to happen.

Which means you’ve already perked your sensors to keep sensing whether those bets are going to play out, which means you’ve already started fine-tuning a learning architecture and a feedback loop to see if that’s going to happen. With that, you’ll keep tweaking your scenarios, you’ll keep tweaking your bets. But if you never did that, you would just be an ostrich with your head in the ground, not thinking about what’s going to happen. And so there is no architecture, no feedback loop, nothing created. So that’s what’s important. It’s less about “be the fast mover, do this, do that.” It’s okay to not be the fast mover if that’s deliberate, but it’s not okay to not be the fast mover if that happens out of omission.

Jim O’Shaughnessy

Yeah. And again, our alignment on how we look at this is strikingly similar. Spending a lot of time thinking about failure modes is, in my opinion, not only required but incredibly instructive. Because if you’re a naturally optimistic person, you might have a hard time thinking about all the ways things could go wrong. And the other thing AI can do is simulate cognitive diversity. I’m constantly playing with coming up with the most pessimistic model I can possibly design, but making it very smart. And what’s really interesting when you do that is your blind spots are revealed. We all have blind spots, every single one of us. Having this kind of red-teaming of our own ideas, I just think that is such a valuable thing to have.

And yet a lot of people look at me like I have three heads when I’m like, no, you’ve got to think about all the, not only that, you’ve got to give it to an intelligence that is going to find those blind spots that you have. So, well, listen, I always love talking to you and admire your work. You’re working on the new version of the book that comes out when? Later this year. Perfect. I would love to have you back on again when that comes out, because a topic we didn’t even touch is, what is going to happen to books, your books in particular? Are we going to move to a new way of packaging a book so that it can be constantly updated, so that it can be interrogated?

I think all of those things are going to be super useful, and I would love your view on them.

Sangeet Paul Choudary

Yeah, absolutely, I would love to. It’s a topic I’m constantly thinking about. I would encourage whoever is listening to go to reshufflebook.com. It’s the companion site to the book, where what I’ve tried to do is extract the concepts from the book and show them as a navigable graph, so you can see which concept connects to what and work on applying that. I’ve tried to create different narratives, all of which are again generated by the knowledge graph, because once you map all the concepts, it generates different narratives. So for different personas, whether you’re thinking about it in terms of jobs or in terms of how you design the workforce and the organization, there are different tracks in which you can go through the book.

So that’s one attempt to think about how you unbundle and rebundle the book in new forms. But the larger thing I’m really going for, and I’ll just throw it out here and would love to discuss this again, is that the book was not an optimal bundle for a lot of things it was used for. It was just forced on a lot of formats. What I mean is that I still believe a big idea with a persuasive narrative requires a book. It cannot be done with questions to an LLM, where everybody’s going to get a different version of the idea in a different narrative.

But a lot of how-to advice, which has so far been packaged in a book, is much better accessed in the context of your work in an LLM and so on. So we’ll have to really rethink the relationship between the jobs we wanted to do and the formats that were forcing those jobs on us. There’s a lot of discussion there, and I look forward to that topic.

Jim O’Shaughnessy

Yeah, the user interface is going to change, there’s no doubt about that. Sangeet, always a pleasure talking to you. As you might recall, our final question here is: we make you emperor of the world. You can’t kill anyone, and you can’t put anyone in a re-education camp against their will. But what we can do is hand you a magic microphone, and you can say two things into it. And those two things are going to incept the entire population of the world. They’re going to wake up whenever their morning is, and they’re going to think the two things you say now were their own ideas. And they’re going to say, unlike all the other times where I had these ideas, shower ideas or waking-up ideas, I’m going to act on these two. What are you going to incept in the world’s population?

Sangeet Paul Choudary

Assuming that these ideas can be personalized by the individual, I would want to create the drive for every individual to figure out what they are insanely curious about, which they would want to do just for the love of doing it, which they would want to think about just for the love of thinking about it. I think what a lot of us are lacking is that by outsourcing a lot of our thinking, we are not seeing the incentive for getting into training our thinking machine, our brain. So creating an organic incentive mechanism for that, which is why I said it would be personalized. Everybody wakes up figuring out, here’s what I’m insanely curious about, I’m going to start figuring out how to go after this, and here’s how I’m going to.

At the same time, I would want everyone to think about it as, if I’m so curious about this, I want to do it as long as I can. So how can I do it in a way that I create the conditions for me to constantly think about it? Because if my conditions don’t support this kind of curiosity, and if I’m constrained in other ways to do things that are more short-term, that comes in the way of doing it. So I don’t know if that answers the question directly, but that’s great. Leave that with people.

Jim O’Shaughnessy

The way I would rephrase it is, we’re incepting everyone to wake up thinking, I am insanely curious about this, how can I go about satisfying that curiosity, and sustaining it, and building it into something I can continue to do. Okay, so that’s your first one. What’s your second?

Sangeet Paul Choudary

I think the second piece is the sustaining part, in terms of how you sustain it. It’s about being very clear that you don’t simply, it’s easy to be curious about something, it’s very difficult to sustain it. And in order to sustain something, it’s not just about the fun, but about having the discipline to sustain it. So yes, it’s important to find what you’re insanely curious about, but you should be disciplined enough, you should care about your curiosity so much, that in order to protect it and do it on an ongoing basis, you create the discipline and the conditions around it that can help sustain it. So the second piece is really about getting to that point where you know this is not just a passion, it’s a discipline. And how do you bring those two things together.

Jim O’Shaughnessy

I love them both. What’s the old saying about curiosity being the cure for boredom, and there is no cure for curiosity? Sangeet, thank you so much for your time and your ideas, and I can’t wait for our next conversation.

Sangeet Paul Choudary

I look forward to it. It’s been such a pleasure. Thank you once again.

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Sunday, 5 July

Two thoughts from Thomas Paine

“A hereditary monarch is as absurd a position as a hereditary doctor or mathematician.”

“To argue with a person who has renounced the use of reason...is like administering medicine to the dead.”

Monday, 6 July

Two thoughts from J. G. Ballard

“Any fool can write a novel but it takes real genius to sell it.”

“I suspect that many of the great cultural shifts that prepare the way for political change are largely aesthetic.”

Tuesday, 7 July

Two thoughts from Robert Pirsig

“The truth knocks on the door and you say, “Go away, I’m looking for the truth,” and so it goes away. Puzzling.”

“The more you look, the more you see.”

Wednesday, 8 July

Two thoughts from Hermann Hesse

“We are not going in circles, we are going upwards. The path is a spiral; we have already climbed many steps.”

“Learn what is to be taken seriously and laugh at the rest.”

Thursday, 9 July

Two thoughts from Thomas Mann

“Tolerance becomes a crime when applied to evil.”

“Order and simplification are the first steps towards mastery of a subject.”

Friday, 10 July

Two thoughts from Arthur Schnitzler

“To be ready is one thing, to be able to wait is another; but to seize the right moment is everything.”

“Martyrdom has always been a proof of the intensity, never of the correctness of a belief.”

Saturday, 11 July

Two thoughts from Stefan Zweig

“One must be convinced to convince, to have enthusiasm to stimulate the others.”

“Beware of pity.”

Follow Jim on Twitter for a daily dose of Two Thoughts!

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This week: the YouTube algorithm delights us, a Heian-era book feels like X or Threads, C-SPAN gives one author three uninterrupted hours, the world’s largest operating steam locomotive crosses America, and Louis L’Amour lives a life worthy of Hemingway.

1. Barry Can’t Swim & Crate-Digging at The Lot

Sometimes the YouTube algorithm gifts us in surprising ways. I’ve been getting into DJs lately, and after listening to Fred Again and the sets of Padre Guilherme (who I had the pleasure of seeing in Buenos Aires), YouTube started pushing a name onto my feed: Barry Can’t Swim.

I ignored it for a long time. Then one day, I clicked a set of his from Brooklyn and put it on while working through an essay. Within a few minutes, I was on my feet, swaying.

Was I able to finish the essay? No. Was my creative brain on fire? Absolutely.

Right after the Brooklyn set I put on another one, from The Lot Radio, and now I can’t stop listening to the guy. This one was even more surprising. Halfway through, I recognized a classic song of my parents’ generation: Anish Kumar’s Nazia, which samples Nazia Hassan’s 1980s Pakistani pop banger Disco Deewane.

Stuff like this is why I love DJs. The best ones are masters of “crate digging” — going into the musical archives, pulling out amazing tunes, and resurfacing them. And Barry Can’t Swim is really good at it. For example, near the end of this set he plays Midnight or Late Afternoon by Mike Simonetti, which is an edit of a bangin’ 70s disco track titled I’m Your Boogie Man by KC and The Sunshine Band. That’s just a taste of his worldly ear; he’s cited Ravi Shankar and Fela Kuti as inspirations.

It helps that the setting suits him. The Lot Radio is a small 24/7 online station in Greenpoint, built by Francois Vaxelaire in a triangular patch of vacant land he found full of trash. A DJ booth and a coffee kiosk inside a repurposed shipping container, and not much else. It runs live all day and takes no brand money. “We never want to contribute to the noise,” Vaxelaire likes to say. The programming is open format on purpose: techno at noon, a rock band at six, whatever a resident wants at two in the morning.

What a way to experience music. [Rohan]

• 🎧 Barry Can’t Swim at The Lot Radio

• 🎧 Barry Can’t Swim in Brooklyn

2. The Woman Who Noticed Everything

I live for little observations. When someone says something a bit too loudly, the particular way someone pinches their nose, the small irritation that reveals way more than a dramatic confession ever could. That’s probably why Sei Shōnagon’s Pillow Book felt so alive to me.

It read like a diary when I started, but halfway through I realized it was a huge list — a collection of lists, gossip, memories, judgments, court scenes, aesthetic preferences, and private annoyances, written by a court lady in tenth-century Japan. Shōnagon writes about “things that make one’s heart beat faster,” “things that should be short,” “hateful things,” “elegant things.”

I loved how contemporary her lists felt. She was snobbish, funny, observant, vain, tender, and cutting, sometimes on the same page. The best thing about her was that she noticed everything: clothing, handwriting, weather, flirtation, rank, timing, embarrassment. Basically, she’s the Heian-era version of X, Bluesky, or Threads — or, better, an aristocratic WhatsApp group chat.

In one section, usually translated as “Very Tiresome Things,” she writes: “When a poem of one’s own, that one has allowed someone else to use as his, is singled out for praise.” I laughed so hard at that line.

The book can feel fragmentary, but that is also its pleasure. It doesn’t have a plot as such, but if you read it to see what a Heian court felt like, you’ll be fascinated. Read it with a cup of tea and it will feel like Shōnagon is talking to you.

If you like books that preserve the texture of a mind rather than just the events of a life, this is worth reading. Some writers build worlds through plot. Shōnagon does it by noticing what everyone else would have missed. [Aashisha]

• 📕 The Pillow Book of Sei Shōnagon translated by Ivan Morris

3. Three Hours, One Writer, One Camera

I realize I’m going full book nerd on you, but it comes with the territory when you make books for a living. So indulge me: today’s recommendation is C-SPAN’s Book TV.

I stumbled onto it back in 2017, when Michael Lewis came on In Depth, Book TV’s flagship program, for a three-hour interview. Three hours. One writer. One camera. He talked about Liar’s Poker and Moneyball and The Undoing Project, and he took questions from a moderator and, one after another, from viewers calling in from their kitchens and their cars. It was the most unhurried treatment of a working writer I had ever seen on American television. I have been hooked ever since.

Book TV airs Sundays on C-SPAN2 and has run since 1998. C-SPAN founder Brian Lamb once said he got tired of watching authors show up on talk shows and disappear before he could decide whether he wanted to read the book. So he built the thing he wished existed. For years, C-SPAN estimated that Book TV featured roughly two thousand nonfiction authors a year.

In Depth ran monthly from 2000 through 2023, with later episodes shortened from three hours to two. The complete archive remains online. The format was simple: one writer, one moderator, viewer call-ins, no b-roll, no jump cuts. The camera just sits there and the writer talks.

I find the whole thing quietly moving. The writers take the questions seriously. The moderators let them answer at length. And for a couple of hours on a Sunday afternoon, the country’s most patient literary talk show carries on, an artifact of a slower era doing its slow work.

If you love books, spend a Sunday with it. You will not want the show to end. [Jimmy]

• 📺 C-SPAN Book TV

4. Big Boy: 1.2M Pounds of American History, Steaming Across the Country

In 1941, an unknown worker at the American Locomotive Company in Schenectady, New York, chalked the words “Big Boy” on the smokebox door of No. 4000, the first locomotive in a new class so large nobody had a better name for it. The name stuck. Eighty-five years later, one of its surviving sisters — Union Pacific No. 4014 — steamed east from Cheyenne, Wyoming, to Philadelphia for America’s 250th birthday, and thousands of people lined the tracks to watch it pass.

Big Boy is the world’s largest operating steam locomotive: 133 feet long, 1.2 million pounds, sixteen driving wheels, and enough power to haul a 3,600-ton freight train over the Wasatch Range without a helper engine. It was built to move war materiel over the Wasatch Range and logged over a million miles before being retired in 1961. It sat in a museum in Pomona, California, for just over half a century.

Then Union Pacific spent three years taking it completely apart and rebuilding it. In May 2019, it moved under its own power for the first time since John F. Kennedy was president. This summer’s eastern tour — the centerpiece of Big Boy’s 250th anniversary celebration — marks the first time a Big Boy has traveled on eastern rails since 1941, when it rolled off the assembly line. It crossed the Rockville Bridge into Pennsylvania this week and is now making its return westward to Wyoming. Even mega-transportation influencer and new Grand Tour presenter Francis Bourgeois showed up.

You can feel Big Boy before you see it. The ground shakes. The whistle carries for miles. The heat radiates off the boiler and you understand, in your body, why people drove hours to stand trackside in the rain. As lead engineer Ed Dickens told WJAC, “Everywhere we go, we have looks of amazement, some looks of terror when people are too close.” In a country that moves everything by algorithm, there is something deeply right about a machine you can hear coming. [Taylor Pipes]

• 🗺️ Big Boy’s Remaining Summer Schedule (Union Pacific)

5. The Man Who Was More Hemingway Than Hemingway

I won’t say you have to live an interesting life to be a good writer, but I’d definitely say it’s an advantage. That’s why I’ve always been drawn to Louis L’Amour.

He left his small North Dakota home at 15 and took on any job he could find while traveling the world. Miner, fruit picker, elephant handler for a circus — he even had a few stints as a professional boxer. He went to China, Japan, Singapore, Egypt, Europe... I could go on. All of this happened before he made a living as a writer.

Even though none of his books are as acclaimed as Ernest Hemingway’s, and he’s often dismissed as “only” a genre writer good at cowboy stories, L’Amour wrote about 100 novels and hundreds of short stories across many genres. He pushed himself to write every day because he believed that “nature has no place for non-producers.”

I bring all this up because I admire him as someone who wrung every last drop out of life — and lately I’ve been reading a lot of those short stories. Most of them have been collected in seven volumes, and I’ve been working my way through volume one. L’Amour’s straightforward prose is easy to read, and I’ve been struck by how many simple stories have left me with something to think about.

If you’ve got an appetite for short fiction that instills values like bravery and integrity, add L’Amour to your rotation. [Jameson]

• 📕 The Collected Short Stories of Louis L’Amour, Volume 1: Frontier Stories

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Jameson explains why fiction is a compressed human experience rather than mere entertainment, how the story of Hercules at the crossroads guides his decisions under pressure, and why training montages give us the wrong idea about how slow and monotonous real change actually is. They also discuss main character syndrome versus narcissism, the pull of tribalism, what separates heroes from villains and anti-heroes like Walter White, and how William James clawed his way out of a breakdown by choosing to act as if his choices mattered.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

What Training Montages Get Wrong

Liberty: You wrote about the danger of training montages. What do they get wrong about transformation?

Jameson: Yeah, that’s a fun thing for me with this pursuit. I can look at things in stories, or in storytelling formats, and then look at them through this lens of protagonism. One thing I thought was funny is that these training montages are effective at conveying to a moviegoer that they put in so much work, and we’re compressing it into 60 seconds of visual cues. Rocky, or whoever it is, he’s been grinding.

Liberty: The Karate Kid, waxing cars.

Jameson: But it’s dangerous for us to be exposed to that, because it makes it seem like it’s not as big a deal as it really is. Let’s take the Rocky example. It shows him working out, especially in Rocky IV, working out in the snow, pulling logs, whatever, and it’ll show one scene of him drinking raw eggs. It shows a variety of things. But what it doesn’t show is him doing that every single day, for months.

Liberty: And years of grinding.

Jameson: And even when he’s sick, having to do stuff that’s just miserable. So it makes the idea of a training arc glamorous, because it’s only showing you 60 seconds’ worth. Whereas the reality of any training arc in real life is that I’m signing up for a suffer-fest, and what I just watched in that training montage are literally the highlights of it, the best moments. But the truth is that there are times in life where you need something like that. You need to buckle down and say, yeah, I’m going to remove distractions for this period in my life if I really want to achieve this thing. There were a few other things in the article, but the biggest one is just the idea that it doesn’t show how monotonous and boring it is to actually achieve something that great.

Liberty: That’s the counterproductive aspect of this, because it’s fun to watch. But if it sets your expectations so that you think, oh yeah, it’s going to feel so satisfying and I’m going to see the progress, it’s almost like a time-lapse. It compresses time so much that it gives you the wrong impression of how slow real progress is, and how not fun it is as you’re doing it a lot of the time. So if you come in expecting that and you start training and you don’t see much progress, it feels crap. You may stop, if you come in with the wrong expectations. It could actually do the opposite of what you’d think going in.

Jameson: Yeah. It makes you get really frustrated really quickly when you’re not seeing a similar level of change, or you’re bumping into way more obstacles than you thought you would. What I’d love to see is a training montage that shows the person eating their Tupperware of chicken and rice while everyone around them is eating pizza. Just show that scene dozens of times, that would be a more accurate representation of a training montage. Or show them having to wake up to the 5am alarm day after day and dragging themselves out of bed. We don’t need to see the log-pulling or the deadlifting of 500 pounds, because again, those are the highlights. Show me the true lowlights of what this journey is, if you want me to have a more realistic expectation of what it’s like.

NPCs and Tribalism

Liberty: What are the signs that someone is living like an NPC? How could someone realize their own NPC tendencies? How do you fight that? And what are your own NPC tendencies that you’ve discovered and dealt with, to bring that to your own story arc?

Jameson: So one of the ideas about an NPC that I think is very interesting, because it translates to real life pretty well, is that if you find an NPC, most games are only going to program a few lines of dialogue for it. If you keep going back, they’ll end up repeating the same line, because they don’t have more in the tank to share with you. That translates to real life in the sense that an NPC is more likely to be running off of only a few scripts, and they’re not open to new information. They’ve just decided, this is life, I’m 25 years old, I’ve figured out life. And they spend the next 50 years assuming they have a grasp on the entirety of truth and that everyone who disagrees with them is wrong. An important aspect of living a fulfilling life is being open to new information at any given time. It doesn’t matter if you’re old. In fact, one lesson I took away from Dracula is that you have Van Helsing, who is the most educated, the most learned character, and yet he’s the one having to tell the other characters, I need you to open your mind, I need you to consider things you have thought impossible your entire life. So being able to constantly take in new information, and not letting that turn you into someone who thinks they know everything, is a crucial detail of being able to pursue the life of a protagonist, in my opinion. An NPC is incapable of that, because it’s just easier to run on fewer scripts and say, no, I’ve experienced enough to say this is what life is.

Liberty: And if you don’t think for yourself and create your own scripts, there are plenty of people out there who will be very happy to supply you with a script that helps them. Consumerism, politicians, whatever. There’s always someone else who is very happy to tell you how to think if you don’t do it for yourself.

Jameson: Exactly. And that brings up something I did not assume at all when I started this project. It’s been amazing to me how much, as I’m analyzing stories and lessons, this idea has come up: the idea of tribalism, and how it’s ingrained in us. We are all part of tribes, even in the 21st century. You’re part of your political tribe, your cultural tribe, your religious tribe, your neighborhood tribe, whatever group you identify with. The purpose of the tribe in ancient times was, we survive better when there’s more of us together, but we have to make sure the only ones with us are ones we can trust. That’s why, for a long time, being ostracized from the tribe was basically a death sentence, because you wouldn’t have access to their resources. So even though we have grocery stores now, and I can get access to food without some tribe granting it to me, there are still definite needs filled by tribal instincts, social needs, things like that.

I just witness how often people’s choices are dictated by the need to make sure they can maintain membership in a certain tribe. Tying this back to NPCs, part of it is that it is exhausting to actually think through how you feel about every single thing. It is a monotonous and terrifying task to actually think, no, I’m going to decide for myself.

Liberty: And if you’re wrong, so you’re wrong. It’s not someone else’s fault.

Jameson: So it’s easier to just adopt a belief system from a tribe and say, if Democrats think this way, then that’s how I feel. Or if Republicans feel this way. Or, trying to think of others.

Liberty: My family, my whatever.

Jameson: Yeah, exactly. It can be as granular as my family. Whatever tribe you’re part of, if they believe this, it’s easier to just say, okay, I guess I believe this too. And you cling to the parts that actually resonate with you, and you bury the ones that don’t under a rug and say, well, I agree enough that it’s better for me to just say I’m part of this group, and bury the things that are actually friction points for me. So to me, an NPC is someone who has largely found two or three tribes that they outsource all of their thinking to, and they say, okay, if that’s what they believe, then great, that’s who I am.

Transcript

Liberty

Hello, everyone. I’m not Jim O’Shaughnessy, I’m Liberty. Jim is writing a new book, and while he was knocking it out, I snuck into the studio and decided to record this conversation about what we can learn from fiction and fictional characters, because I could use more of that in my life. I think we could all use more of that wisdom. I used to read about 95% fiction growing up, but sometime in my 20s it flipped, and now I’m 90% nonfiction. But I miss it. So who better to talk about this with than my friend Jameson Olsen? He’s building the school of protagonism based on these ideas. It’s a life philosophy built from the mechanics of great stories, and his podcast, Becoming the Main Character, is case studies in that. He’s trying to combine the entertainment of those stories with the learning and growth, drawing on Lord of the Rings, Sherlock Holmes, Moby-Dick, Dostoevsky, Project Hail Mary. Very varied, but the central thesis is always that fiction is not just entertainment, it’s a compressed human experience. Jameson, welcome to the show.

Jameson

Hey, Liberty, it’s great to be here.

Liberty

Maybe we can begin like a good story, at the beginning. Could you tell us a bit about yourself? The Jameson origin story. Why did you need protagonism? How did you arrive at this?

Jameson

That’s a great way to start. Like a lot of people, I found myself years past college graduation, feeling like life wasn’t going where I thought it would be at that point. Until you graduate college, you’re basically told exactly what step to take. As long as you’re getting the grades and hitting the benchmarks you need to make, you just know you’re doing fine. Then you enter the real world and things can go a little differently. So I had a period, a big chunk of my 20s, where I was living a pretty small existence in terms of what I was doing. My career was moving forward, but not nearly as quickly as I thought it would.

In the meantime, I was consuming a lot of self-help content and personal development. I got into philosophy. That was the first time I started reading some of the ancients. So I was feeding my brain all these ideas, and that was all layered on top of my love of stories from the beginning of my life. I’m the youngest of four siblings, and my older brother was the problem child, if you want to call it that. By most standards he really wasn’t even that problematic, but out of the four of us, he was.

Liberty

It’s all relative.

Jameson

Exactly. He’s such a social butterfly that my parents were conditioned to think, to punish him, we send him to his room. That was torture for him, not being able to interact with people. So after him, they just figured, send James to his room. If he’s being bad, put him in there. Problem was, that’s where my Legos were. They were basically condemning me to go into my own little world. I had all the pirate sets. This is before the IP Legos came out, like Harry Potter and Star Wars. It was just the pirates or the others.

Liberty

You had to use your own imagination.

Jameson

And so it started young. I’ve always been very interested in understanding what makes a great story great and what makes others fall flat. Why do you forget some movies as you’re walking out of the theater, whereas others you think about for days after you see them? During that period of my 20s, most of that effort of understanding stories came through film analysis, watching video essayists on YouTube, reading books here and there.

Liberty

If I did my research correctly, you were much more of a film buff and only started reading classic literature when you started your podcast. Is that true?

Jameson

It is. I think that also works to my advantage, because I bring enthusiasm to my episodes, since I’ve just read the book for the first time. But I’ve never claimed to be a trained expert on the classics, because I hadn’t spent that much time reading fiction until the last three to four years. I just watched movies. It’s beginner’s mind, which is perfect. You sit down, turn it on and consume, whereas a book takes effort. So it was a transition, but the opportunity came along, this idea of a podcast to talk about the greatest stories ever written. And I couldn’t go down that road without infusing it with, marrying, my two greatest interests, which are: what makes a good story good, and how can I find a better, more fulfilling existence in my own personal life? It was the fusion of those two things. It was the combination of the years spent reading personal development books and studying philosophy with the years of watching movies and analyzing why the great ones work. So I set my sights on bringing the classics to 21st-century consumption habits through a podcast.

Liberty

I’m curious, because we can have the inverse. I used to be all fiction and moved into nonfiction. You were probably more into nonfiction. What surprised you most when you dove really deep into these great stories? What was your expectation going in, and did it match, or was it something else?

Jameson

I don’t know if I really had severe expectations either way. But one thing I’ve noticed is that I used to carry the pragmatic view that a lot of people who only read nonfiction have: I get real value from nonfiction, whereas fiction is just entertainment.

Liberty

It can’t be profound because it’s fun, right? As if those things are opposed.

Jameson

One thing that surprised me was realizing that my anxiety levels were higher reading nonfiction, because it put more on my plate of “this is what I should be doing” or “this is what I need to fix about myself.” I’d leave with great ideas, but basically I’d leave with homework. Whereas with fiction, partly because it’s more entertaining to consume a narrative, but also because you read about these situations and think, it could be worse, my life’s not so bad. That was one thing I wasn’t expecting to piece together, that reading nonfiction is incredible and necessary. That’s one thing I should get straight right off the bat. I am never taking the stance that fiction is better than nonfiction. I think both are essential to a well-balanced life. I still read a lot of nonfiction now, but most of it these days is less personal development and more narrative theory and understanding how to craft a great story. I think both are essential. And because I’ve been that person, I think there are a lot of people who have boxed out fiction because they think the real value is only in nonfiction, whereas I think both are important.

Liberty

I think the takeaway here is balance. If someone is only reading nonfiction, they can probably get a lot out of even adding a little fiction to the mix. And if someone is only reading fiction, I’d recommend the inverse. Get some nonfiction, some history, some biographies. But both have so much to contribute. I’m curious, because we all have favorites. Is there a fictional character that has changed the most how you think about your life, that has had the biggest impact? Or maybe even someone you first judged, like, that guy’s an asshole, and then later understood better and could get more out of?

Jameson

I’ll share two. The first is the one I resonated with most at a personal level. The second doesn’t really fit any of the setups you just shared, but it’s the one I can’t stop thinking about almost two years later. The first one, ironically, was the very first episode I ever did, which was Hamlet. I read Hamlet in high school, and that’s been part of the fun, because so many of the books I cover, someone had to read in high school.

Liberty

Which is the best way of making you not get it and not like it.

Jameson

Exactly. The problem isn’t the literature. The problem is the way you’re forced to see a certain perspective based on your teacher’s perspective. That’s why, when I present my thoughts and lessons from episodes, I’m very clear: this is what I took from it. If you take the same thing, great. But maybe you read it and get something else. That’s where the real value comes, if a story is so well structured that you take what you need from it at that time in your life, and I may take something slightly different. So, rereading Hamlet as an adult, on my own terms, and for anyone with Shakespeare, I do think it’s very much worth having a side by side of the original with a more modernized version. I was using a service called LitCharts for that, which is basically CliffsNotes on steroids. For the most part they have these massive PDF files of analysis of a book, but they have a whole part of their website that’s Shakespeare with side by sides, where they highlight in different colors exactly which text they’re interpreting with the modern version. That helped me see it more deeply.

I resonated a lot with Hamlet and his overthinking tendencies. That’s always been something I struggle with. I used to frame it in my personal narrative, to use a term that’s used to describe someone like Hamlet, as my hamartia, the Greek idea of your tragic flaw, which is also tied to your greatest strength. I used to try to frame that as, yeah, there are downsides to it, but because I’m an overthinker, there are also these upsides.

Liberty

You talked yourself into thinking overthinking was great.

Jameson

Luckily, in recent times I’ve been challenging that notion. Why do I have to justify that there are strengths to this? Why can’t I look at how to remove it and maintain the strength anyway? In particular, the scene that sits with me so much from Hamlet is, I think it’s act four, and I believe it’s scene four of act four. It’s when he’s traveling and Fortinbras, the Norwegian prince, is marching through with an army of 20,000 men or so, and Hamlet is marveling at the realization that this is an equal to me. We’re both princes of these nations, and here he is leading 20,000 men to fight for a scrap of land that’s not even worth the bodies that will be buried in it from the war. But he’s leading men on this cause, and I have been running around, unable to even stick with one decision I make. How frivolous has my life been? There’s a line where he says something about how, if man is only good to eat and sleep, “he’s no better than a beast.” So Hamlet has really stuck with me at a personal level.

The story I was so surprised by, and think about all the time, was actually Mary Shelley’s Frankenstein. Part of it is because Hollywood has never done it justice. The del Toro one is the best we’ve ever had. It’s better than anything else by a mile. It still makes one little change, that’s classic Hollywood, that I hated.

Liberty

What is it?

Jameson

To me, the beauty of that story is that you have two opposed forces in Frankenstein and his monster. Obviously Victor made choices. He’s responsible for the choices that created the situation, so he’s guilty in a sense. But the beauty of the book is that as soon as the monster wakes up, literally the moment it starts breathing, he’s just, oh no, what have I done, this was a terrible mistake. And he spends the rest of the book trying to grapple with how to live with that. He’s constantly trying to figure out how to stop it. He wants to take responsibility, he just doesn’t know how. Whereas every portrayal makes it seem like he’s running away from his problems, classic white male who causes something, gets chased, and doesn’t want to be responsible. So they paint him as the villain, whereas early Hollywood painted the monster as truly monstrous. We’ve always had one or the other. One of them has to be a villain.

To me, my read on the book, and of course there are a lot of theories, because Mary Shelley was descended from one of the original feminists, so the story has ties to themes of feminism. And again, I’m not here to say definitively. In fact, that’s one of my biggest pet peeves, people who say definitively that a story is about this one thing. Maybe for you it is.

Liberty

It can be many things at the same time.

Jameson

To me, the beauty of Frankenstein is that you have these two opposed forces. You have the innocence of the monster. It’s crazy, when you’ve grown up with the idea of him being this big, slow, lurching guy with bolts in his neck, and then you realize in the book he’s actually like a zombie-looking Captain America. He’s physically formidable, he’s fast, he’s super strong. He’s kind of a superhero, because Victor used all the best parts to build him. So he’s got all that, and he’s got the tenderness. I basically describe him as if you put a three-year-old in the body of that creature, because he’s sweet and innocent, but when he’s hurt or when he doesn’t understand what’s going on, he lashes out. And that is terrifying when he’s as big as he is.

Then you have Victor, who made the choices that created the situation, so he’s responsible, but he’s trying to figure out what to do. It’s the two of them butting heads, and they cannot coexist. That tension is something so unique to me. For me, the takeaway of the book is the double-edged sword of ambition. Victor wanted to do something great, but because he became obsessive about it, he basically wasn’t in control of his actions, because he was consumed by this need to do something incredible. In the same way, Jurassic Park’s biggest moral is that if you’re so consumed with whether you can, you may end up making a huge mistake that you shouldn’t have made. So, because early Hollywood was so simplified, oh, he creates a monster and the monster terrorizes everybody, to realize how much depth and room there is to explore moral complexities in that book really took me off guard. It’s one of my favorites to this day.

Liberty

That’s great. I need to read it. I’ve actually never read that book, and you’re selling it very well. Let’s get deeper into what protagonism is. I love that name, by the way. What is it? And what is it most likely to be misunderstood as by someone who just hears about it? Someone could be hearing this and thinking, oh yeah, main character syndrome. How is that different from narcissism, thinking the whole world revolves around you and you’re the main character? Explain what it is and what it isn’t.

Jameson

I’m glad you bring that up, because main character syndrome, or main character energy, are terms I hate, because they bring these assumptions of people who lack self-awareness, who are narcissistic, who don’t care about anybody but themselves. To that I say, show me a story where that is actually the case, where the main character acts like that. There’s another disclaimer I should put in: I’m not claiming all fiction is incredible, there’s a lot of trash out there. But of a story that resonates deeply with a human experience, and for me that’s most classics, because that’s why they’ve survived where other books didn’t. They resonated on a very deep level with people. So show me a main character who is supposed to be a heroic figure from any of these books who acts like that. That is literally not what a main character does. But it is interesting how the term main character brings this assumption of egoism into things.

When you look at stories, the hero is always somebody who starts from a much more humble or collectivist place. They’re doing something for other people, or they’re just trying to improve themselves. That’s much more accurate of what a main character does. One of the best parts in Lord of the Rings, which the movies cover but change, and I think they’re both good, so I’m not here to dog on it and say the movie version is bad, is near the end of The Two Towers, the speech Samwise gives to Frodo about the heroes from the great tales. He says that when he was younger, he used to think the heroes were the people who wanted adventure, who were seeking after it. And now he knows the heroes are the ones who didn’t choose to end up in the places where they were, but who just decided to keep going. There are plenty of other stories that exist, but because the people gave up, we never hear about them. The ones we hear about are only the ones who kept going. That’s such a beautiful way to frame it, in my opinion. The heroes, the people we uphold as the ones we want to emulate, are not people who acted brashly or disregarded others. They were the ones trying to improve themselves, trying to improve or protect other people. And they were willing to undergo a lot of sacrifice or transformation to do that.

So for me, protagonism. First of all, it’s still very new, and that’s part of the fun. I’m building a school of philosophy as I go. Some people may hear this and think, who is this guy to think he can build a school of philosophy? And I’d say, you’re right. But also, who could stop me? You can tell me you don’t agree with my ideas, but there’s no benchmark of having to hold certain degrees to start a school of philosophy. It all comes down to, do your ideas stick? Do your ideas hold truth in them? It’s just been a very fun way to frame what I’m trying to state or prove.

So, protagonism, and who it’s for is where I’ll start. It’s for people like me, first and foremost, the people who think they’ve got more in the tank, wherever they’re at in life. They think, I am capable of more, but I feel stuck. I don’t know why I’m not where I thought I’d be. I don’t know how to get traction in the direction I want to go. Because when I was coming up with these ideas at the beginning, most of the stuff I saw online went into one of two extremes. Either it was very much a victim mentality, other people are the problem, it’s not fair, other people have to change so I have a fair chance. Or it was the other extreme, the hustle-porn, alpha culture of just do it, like David Goggins. And the thing is, I like to consume some of that content sometimes, because it gets you going.

Liberty

It’s useful, but it’s not enough.

Jameson

It wasn’t actually doing it for me either. So I thought, I need a system for improvement that’s more centrist than either of those, and it’s more about recognizing that it’s on you. The whole “nobody’s coming to save you” idea.

Liberty

Yep.

Jameson

No one else is ever going to make you the main character in their story. At best, you’ll be a side character. So if you really want a fulfilling life, it’s up to you. It’s about taking ownership, accepting that a level of agency is required to get a satisfying life, but then also doing it in a way that accepts you’re probably not Superman. You’re not going to be able to flip a switch and all of a sudden your life is completely different. It’s going to be a journey, a narrative of the ups and downs to get from where you are to where you want to be. People in those extremes may resonate with what I talk about, but I’m not making it for them. So if I ever have some alpha bro who’s just like, I don’t approve of your lesson, you should just whatever, that’s cool, I’m not talking to you. That’s fine.

The actual approach, as you alluded to in the intro, is that my theory is that the same rules authors, screenwriters, any storytellers use to create a great character for a great story can transfer over to how you visualize and execute your life. And my theory, which there’s no way I can just prove now, it’s more an exploration, is that the reason those became the rules for great storytelling is because they represent the greatest and most resonant truths that humans have discovered about a good, fulfilling life over millennia. Because otherwise we wouldn’t care about the movies that use those rules, or read the books that use them. It’s the same reason we put down bad stories now. They don’t connect with us enough, because there’s not enough truth buried in there.

Liberty

This reminds me of something I’ve long believed, that in great fiction you can smuggle in wisdom and lessons that would not stick if they were stated directly. We remember a good story way better than a PowerPoint slide with the lessons as bullets on it. Charlie Munger used to have this anecdote about the shoe button complex. A guy made a fortune during the war selling shoe buttons, and he was so successful at that one thing that it made him believe he was now an authority on everything else, because he was so great at that. You understand the principle as he’s telling the story, but you remember the story, and the payload is in the story. Our brains evolved to sit around the campfire telling each other stories and heroic poems. That’s how ideas and wisdom have always been communicated. And now, nonfiction may be great, but if you look at the best nonfiction, self-help, Morgan Housel, whatever, it’s full of stories. It’s almost like trying to use the same infrastructure. So we may as well go back to the original, or at least use it well.

Jameson

Yeah. Humans are wired for story. There’s no two ways of looking at it. There’s a reason we don’t find cave paintings of Excel sheets. It’s just how we make sense of things. The irony to me is that even the people who claim, I don’t care about stories, I don’t watch movies, whatever, you’re still living a narrative. Your narrative just isn’t as rooted in traditional stories. It’s more, look at Elon Musk, I want to emulate him. You’re picking a real figure and you want to emulate their story. You’re still using stories as the framework, because we just can’t help it.

Liberty

Ironically, you may actually know more about a character in fiction, because you can hear them thinking. You can know everything that goes into a decision. You can live the consequences. You have the whole epilogue, and you can learn from all of it. While in real life, you only have what people will show you. People can fake it, people can lie. When things go badly, they disappear, and you never know it went wrong. You only see the highlights on Instagram. So, ironically, real life is often faker and more curated than fiction, which can show you more.

Jameson

That’s a great point. There are studies that have shown people who read fiction rank higher in empathy. Even for me personally, there are a lot of people who don’t love the idea of empathy, because it feels soft.

Liberty

You’re so weak.

Jameson

Because I talk about it in The Hound of the Baskervilles, which I know is one of your favorite episodes of my podcast, I distinguished that there’s actually what’s called cognitive empathy, which is the ability to understand how someone else thinks differently from you, and to understand why they think differently, without you going to the level of emotionally sympathizing with them. That’s why Sherlock is an empath, which sounds ridiculous if you think of any adaptation of Sherlock Holmes, but he’s a cognitive empath. He’s incredible at understanding, this person, because of their situation growing up and because of their personality, is going to think this way and make this type of choice, but he doesn’t need to bog himself down by feeling what they feel in order to do that.

So there’s incredible value to what you said. Whether it’s because other people are wearing masks and aren’t being truthful in real life, or because we really struggle to truly get outside of our own perspective and see things from someone else’s point of view. We just filter what we see them doing through our point of view. That’s how we arrive at, you’re so stupid, why would you do that? It’s because we’re filtering what they’re doing through our mindset, and that just doesn’t work. When I was young, 19 or so, I heard a phrase at a lecture that stuck with me the rest of my life. It’s so simple, but it’s just that “the things people do make sense to them.” So the people you hate, the people you think have completely lost the plot, the fact is, their life experience has led them to a point where that is what makes sense to them. You don’t have to agree with it. You don’t have to say it’s as true as yours. But you have to acknowledge there is truth for them in that action.

Liberty

If someone’s not a total psychopath, a total dark-triad type of person, the rest of us are doing our best and see ourselves as the heroes of our own stories. Even if from the outside it doesn’t make sense, having this cognitive empathy of placing yourself in other people’s shoes is a superpower, because so many people don’t even take the time to learn that skill.

Jameson

Yeah. Whether you want to get better at your relationships with your spouse, your children, or on the far more tactical side, if you want to become a better negotiator, there are all sorts of skills that will improve if you can develop the ability to truly see through other people’s perspectives instead of filtering them through your own. And fiction is great at that, because you’re forced to not only hear the actions of other people, but to get inside their brain and see how the dots connect from the first time you’re introduced to them to why they take the actions they take later. In that way, it’s the only real format for truly getting inside someone.

There are memoirs, where someone you admire who’s a real person is sharing their experience. But again, the question is, is their memory faulty? Are they covering up the real truth and masking it to make themselves seem better in the story? We can’t fully know. Whereas with a fictional character, the author has full reign of what they say. But again, it all comes down to whether we feel it. You read a character and you decide, this feels accurate, or it doesn’t. That’s where it comes down to whether it feels true. We have a BS meter in our head that says, this doesn’t feel right.

Liberty

Very finely tuned by evolution.

Jameson

As long as the character feels truthful in its portrayal, it’s a good enough representation of a different perspective from our own to use as data to consider. One of the ways I frame it is that every story is a simulation in the Matrix. It’s a way of understanding a potential circumstance without having to physically live it yourself, seeing how choices play out and how a choice draws reactions from other characters. That’s one of the other values of consuming stories. It lets you get a better understanding of people in the world without you having to pay the price of experiencing everything yourself.

But to close up this section, we made fun of the fact that they don’t have cave paintings of Excel sheets. But to me, the best truths are ones that have a narrative that the numbers back up. It’s the two of them combined that create the best. One thing I’ve paid attention to in my own life since I started this show is what comes to my mind when I’m in the heat of a moment, when I’m feeling tension, when I’m feeling pressure, when I don’t know what to do. It’s never statistics. It’s never, if I react this way, then 73% of the time that will be favorable. I may internally know that stuff, but that’s not what comes to mind when your reactions are more emotional.

But because I know the story of Hercules at the crossroads, which is one of the best stories about Hercules in all of Greek mythology. If I were to place it in the Disney animated Hercules, this is the scene that takes place right before he starts singing “I Can Go the Distance,” because that’s what this sets up. When he’s a young man, he’s walking towards a crossroads, and he sees a woman coming towards him from each of the paths. On the left side she’s running towards him. The other one is just walking, taking her time. So when he gets to the crossroads, the one who’s running is there first. Her name is Kakia, who in Greek mythology is the goddess of vice, of moral misbehavior. She gets to him first, and she’s gorgeous. She’s wearing fine jewelry, she’s very made up, she’s a smoke show for all intents and purposes. And she’s telling him, come with me, you’ll never have to work again. Life will be nothing but pleasure and enjoyment, and you won’t have to worry about a thing. So he’s taken aback by this promise. By the time Kakia has finished her pitch, Arete, the goddess of virtue, has reached the crossroads. She’s a beautiful woman, but she’s not extremely made up. Her clothes are much more plain, but she holds herself with a certain regalness. So she makes her pitch: I promise you nothing except a life of the fruits of your labors. I cannot promise you that you won’t experience hardship, but I can promise you that what you do experience will be the highest you can. And there’s one line from whatever interpretation I read that stuck with me. She says, “The gods have set a price on every good and noble thing.” Nothing is free. You have to give in order to receive. So whatever Kakia is telling you, that luxury, that lavishness, comes with a cost, which is that you won’t experience meaning.

Liberty

Right.

Jameson

Noble things. And so, ultimately, Hercules chooses to follow Arete, and that’s how he became the hero he became. I share that whole story, because if I find myself in a situation where I’m being offered two paths, one that seems easy and way more lavish, and another that feels like a lot of work but has a lot of potential upside, I’m not going to remember statistics, but I may remember Hercules at the crossroads. All of a sudden that story races through my brain, and it makes the choice a lot easier, because that story rang true with me when I read it. The recall I have of that story in my moments at the crossroads makes it a lot easier to think, of course, this is the path I have to take. There are other situations where a lesson or a quote I took from a book comes to mind in key decision moments, in emotional or stressful situations. Not every book I cover sticks with me that much. I’d have to go back and look at my notes to remember the lessons I took from a certain book. But every few books, there’s one that just hits.

Liberty

And that can be life-changing. One can be enough. The right one at the right moment can alter the course of a whole life.

Jameson

And that’s the same with nonfiction.

Liberty

Right.

Jameson

You’ll read 10 books, and maybe two of them really have any impact on you, but you have to go through them to know which ones will. I’d say that’s the same for fiction as well.

Liberty

And speaking of cognitive empathy, I can hear the listener wonder, okay, that sounds good, but is it about great ambition? Do I need to be a hero to do this, to be a protagonist? Is it about great courage and all that, or can it take other shapes? Can it be a smaller-scale version of that?

Jameson

That’s an incredible question, because it’s one I think about a lot. People I know in my own life have different visions of what our best life looks like, and I see no reason to label one as better than the other. The commonality between them is that they both take intention. Neither will happen by just existing. So whether you want to be the CEO of a billion-dollar company, or some sort of celebrity, or, on the other end, you just want a job that pays the bills and lets you have plenty of time with your family because your ultimate goal is to raise kids you’re proud of, those are both incredible aspirations. I’ve tried to come up with a way to distinguish the two types without one sounding lesser than the other. A type A protagonist versus a type one protagonist. I haven’t come up with terms I feel good about, because if I just say A and B, then everyone thinks B’s not as good.

Liberty

It’s almost like once you’ve picked what you want to do, whatever that is, then these tools can help you live the fullest version of that, the best version, be the best protagonist for that story. But the story itself is for you to choose. And if you try to live someone else’s story and it doesn’t sync up with who you really are, that’s another problem. Having someone else’s ambition sounds great in theory, but you can’t borrow someone’s ambition or someone’s confidence. You have to live your own thing. But then I think these things can help you take that to where it can go.

Jameson

I 100% agree. In fact, one of the foundational principles that came from my studies before I was building this is a concept from Carl Jung, where he talks about the only two things any person needs to be happy. The first is to define your values. Maybe you grew up with a value system from your culture, your religion, your political affiliation. You’ve definitely had values imprinted on you. Some of them will resonate, some probably don’t. So we all need to do the work of actually defining our personal values. They’re nobody else’s. This is what I believe makes a good life. This is what I want from life. Then the second part is living in accordance with those values. That’s all it takes to have a happy life.

Liberty

Easy, right?

Jameson

The problem is that most people never sit down and define their personal values. And even those who do, a lot of them aren’t living up to that expectation. That’s where all the discord, the despair and the lack of satisfaction come from. Either you’re living someone else’s code, or you know what your code is but you keep making choices that violate it. So to me, protagonism is very much rooted in taking control of your story by defining the code you live by. And then the harder part is making sure everyday choices are in line with that. That opens the field wide up in terms of what the end results can be. It doesn’t have to fit one specific type. It doesn’t have to be heroic in the sense of looking at an action hero and thinking, I’ve got to be this macho, Jason Bourne, Ethan Hunt kind of guy.

But one of my favorite books that’s informed the way I talk about protagonism, and I reference it on the podcast all the time, is a book by Donald Miller called Hero on a Journey. It’s one of the only books I’ve come across that does the same thing I’m trying to do, where it uses story principles to map a real life. He talks about how there are villains, victims and heroes, and the similarity they share is that they all experience pain, which is an absolute truth about human life. It doesn’t matter if you’re impoverished in a war-torn nation or born with a silver spoon in your mouth, you will experience pain.

Liberty

The human condition is inescapable.

Jameson

The difference comes in how you respond to pain. A victim feels powerless to do anything about it. They just accept that this is all my life is, unless someone else steps in and takes care of it for me. A villain becomes obsessed with making someone else feel their pain, whether that’s the person they blame for it, or they’re just passing it on to other people. Their whole thing is, I feel pain, others need to feel pain as well. And the hero, the only real difference, is that they decide, I don’t want to feel this pain again, and I don’t want the people I care about to ever have to feel this pain. So I will take on the sacrifice. I will transform into what I need to be to make that happen.

There are so many examples of this story in real life. The parents who grew up pretty impoverished and had a rough life because of it, and they say, I don’t want my kids to live like this. So they work two, three jobs so they can send their kids to college and break that cycle of poverty for their line. That’s an amazing example of a hero saying, this is the pain I felt, I don’t want my kids to have to feel it, I’m going to do whatever it takes to fix that. That’s as much a story of a hero to me as someone who’s actually a war hero, or someone who has created a massive industry benefiting millions of people. The scope is different for everybody, but the same principles are true of everyone. To be heroic, all it takes is saying, this is the pain I feel, I don’t want to feel it again, and I don’t want anyone I care about to have to feel it, so I will take on the responsibility to become the person who stops that pain from happening.

Liberty

That’s a perfect segue, because I want to ask you about what you call the principle of becoming, and how all of this sounds like a verb, a journey. It’s not a destination. One of the main differences between a story in a book and real life is that in the book it’s very clear where the beginning, the middle and the end are. And you know that if the hero is suffering, it’s for something, it means something. In real life, sometimes it’s a lot harder to find a meaning. It’s a lot harder to know where the end is, to have a clear moment where, okay, we’ve won, let’s wrap it up, let’s have the epilogue party, it’s done, we’ve won. Life just keeps going on. So whatever this is, I think it has to be more of a constant thing, a never-ending, infinite game, so to speak. So tell me about this. I think it’s fascinating.

Jameson

Yeah. The principle of becoming is the first and, at this point, the only principle I’ve codified as an official principle of protagonism. It’s just the idea that this isn’t about setting a standard of, I’m trash unless I reach this, that I have to do this or else my life is worthless, because that’s such a burdensome way to live. Thinking that I don’t have value unless I do X is a really rough way to live. And the thing is, there’s always going to be great achievers who talk about how that’s how they live, how they lived with constant insecurity. Again, if the hustle-culture people resonate with my stuff, awesome, but I’m not making it for them. I’m making it for the people in the middle who think, I know there’s more in me, but I don’t know how to go about it.

So the principle of becoming is just the idea that you’re approaching life with almost a curiosity above anything else, of just, what am I capable of? If I got rid of a couple of vices that take up a lot of my time and applied that to a couple of hobbies or skills I’m curious about, what could I become? What is the highest version of me that I could achieve? And approaching that with a patient love for yourself, knowing you’re going to trip up, knowing you’re going to make mistakes, but never yielding that curiosity that asks, whether you’re 20 years old or 60, I still have decades left, what can I do with that? What can I achieve? What kind of existence can I create? What kind of legacy can I leave in terms of my descendants? Are they going to look at me and think, all he did was slave away for the man to make a buck? Or are they going to think something else?

Liberty

I love the idea of being a good ancestor. I don’t remember who said it. Maybe Alex Petkas, maybe someone else. But I love looking at your life from the point of view of someone in the future looking back: was that person a good ancestor? That feels a lot healthier as a drive. It comes from a place almost of peace, of aspiration, rather than insecurity of, I set this goal and I’m a failure until I reach it, and the moment I’ve reached it I need to set another goal and be a failure again. I think it’s better to be a vector going in a direction rather than just looking at this point on the line and, in the meantime, feeling bad. I love that.

Jameson

Yeah. The last thing I’ll say about the principle of becoming is that it’s about not living in a deficit where you feel like I am not whole yet until I achieve whatever. It’s about living in a place of contentment: hey, I’m where I’m at because of my choices, for better or worse, but this isn’t the finish line. So if I apply myself a little more, or just focus, it may not be about what skills I can learn at night so I can start a business. It doesn’t have to be something like that. It could be, how can I be more present in my children’s lives? Or how can I be a better contributor to my community? Again, it comes down to you defining what matters to you and what you want out of life, and then having a curiosity you take with you to the grave of, how can I dive a little deeper into this? How can I become a better version of what I think is important in life? There will be seasons where you’re more doggedly attacking that and trying to achieve something, and seasons where you’re resting a bit more, but you’re always thinking about it: what can I do to get a little bit more out of this? Instead of living the life of an NPC, which, for any listeners who aren’t familiar, is a video game term, non-player character, a character that you, as the player, interact with, but they don’t do anything on their own. They’re just there. So to me, the people who aren’t pursuing a protagonism life are kind of NPCs. They’re just clocking in and out of life, because they’re not holding the pen of their story. They’re just, well, this is what life dealt me, so I’ll follow that script. Whereas a protagonist is always curious about what am I capable of becoming if I just am intentional about how I live my life.

Liberty

Yeah, I have a lot more to ask about NPCs. But first I want to ask about something else you wrote about. You wrote about the danger of training montages. What do they get wrong about transformation?

Jameson

Yeah, that’s a fun thing for me with this pursuit. I can look at things in stories, or in storytelling formats, and then look at them through this lens of protagonism. One thing I thought was funny is that these training montages are effective at conveying to a moviegoer that they put in so much work, and we’re compressing it into 60 seconds of visual cues. Rocky, or whoever it is, he’s been grinding.

Liberty

The Karate Kid, waxing cars.

Jameson

But it’s dangerous for us to be exposed to that, because it makes it seem like it’s not as big a deal as it really is. Let’s take the Rocky example. It shows him working out, especially in Rocky IV, working out in the snow, pulling logs, whatever, and it’ll show one scene of him drinking raw eggs. It shows a variety of things. But what it doesn’t show is him doing that every single day, for months.

Liberty

And years of grinding.

Jameson

And even when he’s sick, having to do stuff that’s just miserable. So it makes the idea of a training arc glamorous, because it’s only showing you 60 seconds’ worth. Whereas the reality of any training arc in real life is that I’m signing up for a suffer-fest, and what I just watched in that training montage are literally the highlights of it, the best moments. But the truth is that there are times in life where you need something like that. You need to buckle down and say, yeah, I’m going to remove distractions for this period in my life if I really want to achieve this thing. There were a few other things in the article, but the biggest one is just the idea that it doesn’t show how monotonous and boring it is to actually achieve something that great.

Liberty

That’s the counterproductive aspect of this, because it’s fun to watch. But if it sets your expectations so that you think, oh yeah, it’s going to feel so satisfying and I’m going to see the progress, it’s almost like a time-lapse. It compresses time so much that it gives you the wrong impression of how slow real progress is, and how not fun it is as you’re doing it a lot of the time. So if you come in expecting that and you start training and you don’t see much progress, it feels crap. You may stop, if you come in with the wrong expectations. It could actually do the opposite of what you’d think going in.

Jameson

Yeah. It makes you get really frustrated really quickly when you’re not seeing a similar level of change, or you’re bumping into way more obstacles than you thought you would. What I’d love to see is a training montage that shows the person eating their Tupperware of chicken and rice while everyone around them is eating pizza. Just show that scene dozens of times, that would be a more accurate representation of a training montage. Or show them having to wake up to the 5am alarm day after day and dragging themselves out of bed. We don’t need to see the log-pulling or the deadlifting of 500 pounds, because again, those are the highlights. Show me the true lowlights of what this journey is, if you want me to have a more realistic expectation of what it’s like.

Liberty

And in this world of social media and influencers, people are getting advice from every direction all the time. Tell us about advice with unshared consequences, or why we should be careful with advice from very confident people.

Jameson

So this was a lesson I took from True Grit, which I covered recently. There’s a scene about halfway through the book, so it is a spoiler, but not necessarily a big plot spoiler. They’ve cornered these two outlaws, and in a scuffle Rooster has shot one of them in the leg, and he’s bleeding out. The other outlaw is telling the wounded one not to say anything. Rooster is dangling this in front of him: tell me where your boss is and I’ll get you to a doctor, you won’t die. But the other outlaw is just telling him to can it, don’t say a word. It got me thinking about how it’s easy for him to say don’t talk, because he’s not going to die regardless of the choice. In fact, he benefits more from the other one not talking, because then the boss won’t be angry at him. But this poor kid who was shot is portrayed as maybe 18 or 19 years old. He’s scared and wide-eyed and doesn’t know what he’s gotten into by working with these outlaws. He’s panicking, and he’s impressionable. So when this colleague of his is yelling at him, you shut it, don’t you dare say anything, he’s kind of believing him, even though his life is draining from him as he does it.

That got me thinking about this idea that people will always give you advice, and there are a lot of times when they’re giving you advice that’s only beneficial to them, because they won’t share the consequences of you following it. Unless it’s from a source you completely trust, a mentor, a family member, your oldest friend, if you’re getting advice from someone who isn’t that deeply connected to you, someone you trust implicitly, you have to think through what their motivations are. What do they get out of me following the advice they’re sharing that might benefit them regardless of what happens to me? Because this world is a tough place, and there are people who will take advantage of you at the drop of a hat if it means them getting what they want. So being able to sit back for just a moment and think, okay, why is he telling me to do this, or why does she want me not to do this thing I was talking about? Sometimes you may not come up with anything detrimental, and you think, okay, maybe they just really meant that. But there might be times where you think, oh yeah, they would look really good if I did that, but I’m carrying all the risk for them. It was such a random thought. The actual lesson isn’t connected to any of the main characters in that story, except that one of the main characters shot the kid. But that’s one of the reasons this project has been so fun for me, that the lessons can come out of nowhere. They aren’t necessarily, oh, the main character did this and then that happened, so here’s a lesson. Just inhabiting the world of that story exposes me to thoughts and ideas that I can extrapolate, concepts that are important to think about in modern life.

Liberty

Let’s get back to NPCs. I think this is another great mental model to have. You mentioned it’s from video games, but I think before that it was from role-playing games like Dungeons and Dragons.

Jameson

That’s true.

Liberty

You get to some inn somewhere and there’s a bunch of people there, but they’re all NPCs. They’re not fully fleshed out. They’re just there for a small purpose. They’re not actively changing the story. So that’s the way to think about it. How do you transfer that to real life? What are the signs that someone is living like an NPC? How could someone realize their own NPC tendencies? How do you fight that? And what are your own NPC tendencies that you’ve discovered and dealt with, to bring that to your own story arc?

Jameson

So one of the ideas about an NPC that I think is very interesting, because it translates to real life pretty well, is that if you find an NPC, most games are only going to program a few lines of dialogue for it. If you keep going back, they’ll end up repeating the same line, because they don’t have more in the tank to share with you. That translates to real life in the sense that an NPC is more likely to be running off of only a few scripts, and they’re not open to new information. They’ve just decided, this is life, I’m 25 years old, I’ve figured out life. And they spend the next 50 years assuming they have a grasp on the entirety of truth and that everyone who disagrees with them is wrong. An important aspect of living a fulfilling life is being open to new information at any given time. It doesn’t matter if you’re old. In fact, one lesson I took away from Dracula is that you have Van Helsing, who is the most educated, the most learned character, and yet he’s the one having to tell the other characters, I need you to open your mind, I need you to consider things you have thought impossible your entire life. So being able to constantly take in new information, and not letting that turn you into someone who thinks they know everything, is a crucial detail of being able to pursue the life of a protagonist, in my opinion. An NPC is incapable of that, because it’s just easier to run on fewer scripts and say, no, I’ve experienced enough to say this is what life is.

Liberty

And if you don’t think for yourself and create your own scripts, there are plenty of people out there who will be very happy to supply you with a script that helps them. Consumerism, politicians, whatever. There’s always someone else who is very happy to tell you how to think if you don’t do it for yourself.

Jameson

Exactly. And that brings up something I did not assume at all when I started this project. It’s been amazing to me how much, as I’m analyzing stories and lessons, this idea has come up: the idea of tribalism, and how it’s ingrained in us. We are all part of tribes, even in the 21st century. You’re part of your political tribe, your cultural tribe, your religious tribe, your neighborhood tribe, whatever group you identify with. The purpose of the tribe in ancient times was, we survive better when there’s more of us together, but we have to make sure the only ones with us are ones we can trust. That’s why, for a long time, being ostracized from the tribe was basically a death sentence, because you wouldn’t have access to their resources. So even though we have grocery stores now, and I can get access to food without some tribe granting it to me, there are still definite needs filled by tribal instincts, social needs, things like that.

I just witness how often people’s choices are dictated by the need to make sure they can maintain membership in a certain tribe. Tying this back to NPCs, part of it is that it is exhausting to actually think through how you feel about every single thing. It is a monotonous and terrifying task to actually think, no, I’m going to decide for myself.

Liberty

And if you’re wrong, so you’re wrong. It’s not someone else’s fault.

Jameson

So it’s easier to just adopt a belief system from a tribe and say, if Democrats think this way, then that’s how I feel. Or if Republicans feel this way. Or, trying to think of others.

Liberty

My family, my whatever.

Jameson

Yeah, exactly. It can be as granular as my family. Whatever tribe you’re part of, if they believe this, it’s easier to just say, okay, I guess I believe this too. And you cling to the parts that actually resonate with you, and you bury the ones that don’t under a rug and say, well, I agree enough that it’s better for me to just say I’m part of this group, and bury the things that are actually friction points for me. So to me, an NPC is someone who has largely found two or three tribes that they outsource all of their thinking to, and they say, okay, if that’s what they believe, then great, that’s who I am. Because I just want to be a part of the tribe in a way that I can lie low, that I don’t have to worry about tension in my key relationships, and I don’t have to worry about my ability to keep moving forward. That’s easiest done if I just partake in a certain number of tribes and play by their rules.

I’m not saying that’s bad. What I am saying is that you can’t have that mindset and at the same time complain about how you’re not getting what you want out of life, because you’re not living according to what you want or what you believe. So there is a certain amount of isolation that comes with truly pursuing your path. Whether it’s the famous CEOs who talk about their years of no one believing in them, or whatever it is. Tying this again to true storytelling frameworks, the hero’s journey, Joseph Campbell’s, one of the most foundational concepts of what a good story is, one of the first steps is leaving the tribe. It literally is leaving the tribe. You have to separate yourself from the people doing the normal thing in order to go do something extraordinary. So there is a conflict. While I’m not here to say an NPC life is bad, there is an inherent conflict that cannot be avoided between you trying to fit into your tribes perfectly, in a way that doesn’t rub anyone the wrong way, and you actually going out and achieving what you think you’re capable of becoming.

The trick, again using the hero’s journey as an example, is recognizing that if you don’t want to be completely ostracized from the tribe, your journey out has to come back to somehow benefit the tribe in the end, or else they’ll decide he’s a liability, get rid of him. So whether you went and slayed the dragon that was threatening the crops, or whatever it is, the only way to maintain relationships within your tribe but also do your thing is that your journey out has to somehow come back to benefit them. Maybe your family is very traditional and they don’t like that you want to go off to a big city and have a big career. If you do that long enough, they may think, yeah, he’s not really as dialed-in a family member as the rest of us. But if you do it so that you can then come back and elevate the existence of your family members, all of a sudden you’re the hero. All of a sudden you’re the one who makes everyone proud. But there are some people who go out on the journey, achieve the great thing, but don’t make the loop back. And then they wonder why everyone hates them.

Liberty

Yeah. And to be clear, being an NPC, or borrowing ideas and values from the tribe, is not all bad. It’s kind of a floor, because some of these ideas are probably great, and it’s better to have that than nothing. But it’s also a ceiling, because if you do like everybody else, you can’t expect to have outcomes too different from everybody else. But one question about this. The flip side of this mental model is, is there a danger that it could be a little dehumanizing, that you could look down on other people, oh, they’re all NPCs, and I’m not? How do you avoid this turning into something negative, or a bad way of interacting with others?

Jameson

I guess the first thing I’d say is that every belief system comes with the risk of downplaying the other, of categorizing the people who don’t see things the way you do as lesser than. So yeah, I definitely think there are risks with it, but it’s not like other, more traditional ways of thinking aren’t this way too. This is a great question. I haven’t spent a ton of time thinking about this before, but from the thoughts I have had, I guess I’d say that part of the way I try to frame this ties back to the thing I said, that what people do makes sense to them. So if they’re not living as purposeful and particular a life as me, someone who’s trying to pursue greatness in one way or another, that’s because their life experience hasn’t taught them that they’re capable of it, or they genuinely may just not desire it. That’s a huge thing that honestly freed me up in my personal life, just recognizing that if people see the world so differently from me, and they’re not doing something detrimental, they’re not harming other people, that’s an important caveat, then it’s no skin off my nose. I don’t have to hold it against them.

What’s funny is that I’d say I’m actually a very judgmental person, in the sense that I do look at people’s situations and make a judgment on them, but I don’t then carry this extra layer of, and therefore they are bad. I make the judgment, but it’s just saying, oh, that’s what they’re up to, that’s their situation, that’s what they think is important. It may be frustrating if I need something from them that they’re not willing to give because of their worldview. There are definitely situations where I wish they’d see the world a little differently, but it’s accepting that they’re living their story. I can’t control that. They wouldn’t want me to control it for them, the same way I wouldn’t want anyone else writing my story. So you try to elevate, you try to assist where you can, but ultimately your story is the only one you have a modicum of control over. So you should focus on that.

One idea to tie in here, and this connects to several things I’ve said, including coming back around to the tribe at the end of the story, is that I do believe truly heroic figures, in one way or another, are always doing what they do for more than themselves. We like to idolize a lot of people who are truly just out for themselves, at least from the outside, and there’s a lot that’s admirable about what they achieve. They accomplish incredible things. But at the end of the day, we don’t revere them the same way we do people who have sacrificed, who have done a lot for the benefit of others. So I think that’s an important way to evaluate what’s worth pursuing with your protagonist life. What are your goals? Purely to make you rich, or famous, or whatever it is you say you want? Or is it because you have a vision of how you can help other people by achieving these things, so you’re doing it for something bigger than yourself? Not only is that a more harmonic ending to the story if you benefit others, but it can also be the motivation to stick through the hard times, if you know other people are being impacted by your success or your failure.

Whether it’s your family, I try to categorize the main characters I talk about into different clusters. I have this matrix that’s partially the Donald Miller framework I talked about, are they a hero, villain or victim, based on how they respond to their pain. And the thing I added to it is, who does this person care about? The three categories that create this matrix are, first, someone I call a champion, and this is Captain America, someone who thinks everyone is worth protecting, I will put myself on the line for anybody. Then there’s the guardian, who has a select group of people they care about. Maybe that’s their family, maybe their city. It’s Frodo caring about the Shire. The guardian has a certain number of people they care about, whereas the champion is just, I am here to defend everybody, to serve everybody. And then the maverick. I used to keep it on the same level as the other heroes, but I’ve ultimately separated it, because I thought, this is not the same thing. The maverick is someone who’s willing to undergo transformation, but ultimately they only care about themselves. So this isn’t truly heroic, but at the same time these characters do the things heroes do. They make self-sacrifices, the same way you can learn from a villain in certain regards. So they’re worth analyzing, but it’s just worth pointing out that this person only cares about themselves. They are burning bridges left and right. They will ultimately only have themselves, or the people they can pay to be around them, at the end of the day. So it’s worth evaluating, who is it that I care about, and how is that motivating me to go down the path I want to go down, to transform into what I need to be to serve this group of people?

Liberty

Beautiful. As I was thinking about NPCs, it reminded me of something I wrote a while ago, about how there’s an asymmetry there. Because you can’t see into other people’s heads, but you can see into yours, you should treat others and yourself differently. I have different expectations. You should never expect others to change. If they do, that’s great. But you should always remember that you can change, and always try to. You should filter what other people say through the most charitable interpretation, but you should pre-filter everything you say through the least charitable interpretation. I think this asymmetry, if you think about the NPC principle that way, means you should always look for your own NPC tendencies and try to fix them. And if you notice them in others, you should be very charitable with it, and say, it may look like that from the outside, but I can’t know what’s going on inside. I think that’s one way to balance it out.

Jameson

Yeah, that’s a great point. The only layer I’d add is that, to me, there’s a certain layer of, I can’t know for sure their intentions. And even if I had the ability to be positive about their intentions and it is a bad interpretation, so what? As you said, you can’t change them. So a lot of being willing to transform is accepting the truth of your circumstances. If that means you have an unsupportive spouse or unsupportive parents, there’s no need to villainize them to be able to say, this is the reality of my situation, so I have to factor this in. If I want to achieve this thing, I have to assume I’m not going to have the support of these people. That’s just how it is. A big key to being a high-agency person is being willing to 100% accept the reality of where you are. Because it’s only then that you can start making the choices to change that situation.

Liberty

Yeah, looking at hard truths and being lucid about it is part of agency. If you have your head buried in the sand and you pretend everything’s okay, are you going to make the decisions, the sacrifices, that cause change, if you think they’re not needed?

Jameson

Yeah, totally. Because, going back to the start of this conversation, that chunk of my 20s, I was very much, oh, this isn’t fair, my boss isn’t giving me the opportunities I deserve. I was very much playing that victim mentality, that NPC mentality of, it’s out of my hands, so what’s the point? It’s such an unhelpful mindset. You’re asking me what the traits of NPCs are. I think it’s that they have a backpack full of limiting beliefs, things they’ve assumed to be 100% true and 100% unchangeable, whether that’s about themselves. Oh, that’s just the way I am, which is one of the most annoying phrases for me to hear, because that’s the way you have been. There’s nothing that says you have to continue to be this way. So they have limiting beliefs about themselves, or limiting beliefs about the opportunities they can expect to find out in the world. I’ve definitely had my fair share. All of us do. Even people who, if we wanted to, could claim we’re enlightened enough to see that the world is more under our control than we think, we all still carry limiting beliefs that we need to challenge on a regular basis. But there’s a big difference between saying, I have limiting beliefs and so I try to catch myself and work through them when I see them in action, and not recognizing that they are limiting beliefs and instead labeling them as concrete truths you have no say over.

Liberty

Yeah. That’s why it’s a journey. That’s why it’s not a destination. How about villains and anti-heroes? Protagonists are not always good people. Walter White is a protagonist. What separates a hero from a villain with tons of agency? And what about admiring characters for their intensity or their cleverness, rather than their wisdom? How do you think about learning from people you may not want to be like, or wouldn’t want in your life?

Jameson

Yeah, that’s another area where there’s so much more to mine than I’ve had time to so far. I cover a lot of characters who fit into the anti-hero category, or even just very compelling villains. Walter White’s a great example. He’s a perfect example of the Greek term I used earlier, the hamartia, the tragic flaw. At the surface level, people think it literally just means tragic flaw, but the deeper meaning of a hamartia is that your tragic flaw is actually tied to your greatest strength as well. It’s the downside of your greatest strength. Walter White is a great example, because his greatest strength is his genius with chemistry. He’s able to do things that have never been done before, and he creates a product that’s worth more than anything that’s ever been on the market. But that makes him pretty prideful, to the point where he creates unnecessary risk, because he’s unwilling to have his genius go unrecognized. And there are so many Shakespearean characters. Macbeth was very ambitious, and because he didn’t have the value set in place, when opportunities to achieve ambition through shady means came around, he jumped on it, even if it took his wife convincing him to. And that led to his downfall.

So to me, anti-heroes, or villains who had a more promising start, whether we hear about that in the story or it’s just assumed, they’re beautiful ways of doing what I described before, simulations of the Matrix. In fact, I love stories where the hero and the villain have similar origins, because then you can track which choices separated them.

Liberty

Especially if they’re best friends.

Jameson

It really is. So if you have characters, especially in a story where the hero and the villain were on the same side and experienced the same thing. One principle of stories is that there’s always the inciting incident. The first bit of the story establishes the world as it currently is, and then something happens that changes everything. A lot of the time it may be the pain point, the thing that creates the pain that starts them on a journey. So if you have a story where the hero and the villain start on the same side, and then the inciting incident impacts both of them, but it’s their responses that really diverge, that’s a really fascinating case study, in my opinion, because you’re witnessing in real time how you end up on different paths.

So I think they’re very valuable, because they serve as warnings. Especially in old Hollywood and a lot of dime-store novels, which stick to higher-level themes, they simplify the villain by just making them truly evil. They’re mustache-twirling, they just love being evil. They wear black, they only talk disparagingly to everybody under them. So they simplify the villain by giving them no redeeming qualities, which for the most part is not true of real life. Everyone we struggle with or see as a bad person, in our personal lives at least, there’s more to them than that, but we’re just honing in on the things we don’t like or disagree with. So I do love that evolution of Hollywood, where we’re getting more complex villains and seeing the backstory. One of the best examples was the first Black Panther movie, where we see, I can’t remember the character’s name, it’s Michael B. Jordan’s character, but we see his origin, we see the pain that he felt. So even if we think, okay, but you took some really radical choices and ended up on the wrong side of stuff, we at least understand, oh, look, this is where things happened to him that led to him feeling betrayed, that led to him feeling like justice was not done unless he took these actions.

Those stories are really interesting to me, because they serve as way better litmus tests. Okay, where was the key choice that he made to end up on this path? Versus someone like, the one that came to mind is Darth Vader. Well, the prequels actually do show his journey, but if we take just the original trilogy.

Liberty

Yep.

Jameson

Darth Vader is just, I mean, he does redeem himself at the very end, but up until the end of Return of the Jedi, it’s just, I am here to do my master’s bidding, rule the galaxy. So that type is just more flat. A cardboard character is a term I hear, not so much authors, but critics of writers use. Oh, his characters are so flat, they’re made of cardboard. So now, the funny thing is that we have so much of a push to show the depth and complexity of villains that when we get a more traditional one, and at the same time we have to show the flaws of our heroes and elevate them and show how complex they are, which, again, there’s value to it, it’s really important, but it’s funny how we’ve pushed so much in that direction that now, when we get a more straightforward story of just a good guy trying to do the right thing, it feels like a breath of fresh air. You and I recorded, as we’ve discussed, on your podcast, A Knight of the Seven Kingdoms and…

Liberty

Project Hail Mary…

Jameson

Yeah. Where it’s just, oh man, he’s not a perfect being, but his intentions are a hundred percent good. That was my favorite thing about that story, compared to the other things we’ve gotten in the Game of Thrones universe, where we’ve got to have 50 different characters and we’re showing all their motivations, and they’re all corrupt in one way or another.

Liberty

Yeah, exactly.

Jameson

So to me, we need both. You need the complex characters so you can see how you may have been headed in the right direction but slowly start to drift. Speaking of Game of Thrones, Daenerys really impressed me in the mid seasons, where we see her transformation from being this savior of the enslaved, out here to right the wrongs. In her mind, her vision hasn’t changed, she’s still doing the same things, but we see how her choices and her tactics evolve into much more sinister paths. So that’s a great example of the evolution of a villain, or just a character with villainous traits. But at the same time, we need the more pure examples as well, as something aspirational. If we’re only given stories of, oh, everyone’s flawed, then we don’t have the inspiration of, but I could be more than I am. We just think, well, I’ve got good qualities and that’s good enough, I’m going to settle where I’m at, there’s no need. Whereas we have Hercules at the crossroads, and we have these other characters who are fictional but are idealized versions of what a human could be. They give us something to aim for.

In fact, one little fascinating thing for me is the way terms are used to describe things. Fiction. We just naturally assume that means fake, that’s what it means, it’s fake, it’s not real. But several of these terms, their origins aren’t nearly as simple as that. They have a better purpose than just saying, oh, this is not real. Recently I learned that the etymology of “pretend” is actually tied to the idea of stretching forward. It’s about reaching. So to pretend is, okay, this is what we know, but let’s imagine, let’s stretch forward a little bit and visualize what could be.

Liberty

Speaking of stories as simulations.

Jameson

Yeah, exactly. So to me, having the perfect hero characters is something that needs to be in the rotation, because they give us the visual so that we can pretend, we can extend forward our assumptions about ourselves. Okay, but what if I could embody that more than I currently do? What if I could approximate this character more than I am now? How much better off would I be? So the same way I say fiction and nonfiction are both necessary, I think we need the complex stories that show that heroes have flaws and that villains had, at some point in their life, better intentions than they’re showing now. But we also need stories that just give us that gold, that shining star of, how cool would it be if I could become more like this?

Liberty

And as we approach the ending of today’s story, someone who’s been listening to this and it sounds good, but they feel like they’ve been drifting, maybe they’ve been hearing about this NPC stuff and thinking, oh yeah, that’s a little too close to home. What is the first small protagonist move they could make today? What are the small first baby steps towards higher agency? What would you recommend they think about? Or maybe don’t think, just do, and then as you do, you start to integrate it.

Jameson

Yeah. In one of the more recent episodes I covered, one of the takeaways I had was the idea of, don’t try to think your way into becoming. Just start making the choices, and then the becoming is what follows. It’s the same concept as, you don’t learn your way into being brave, you take some courageous actions, and then once you’ve got those in your bag, it’s, okay, I guess I am more courageous. But a specific exercise for people who are as overthinking and neurotic as I am: sit down, preferably with pen and paper, and preferably without any device that could distract you. Just sit down and challenge the assumptions. What do I value based on the tribes I’m a part of, and what are the sticky points of those assumptions of my tribe where maybe I need to make a choice that’s more personal to me? Sit down and decide, what is it I want from life? I feel the pull to be uber-successful and make tons of money, but is that really what I want? Because if you’re just chasing money because you know it’ll give you a more comfortable lifestyle. You know the old proverb of the fisherman, where some guy comes to him and says, you should start a fishing business and keep scaling it, and the fisherman says, why would I do that? And it comes full circle, back to saying, well, if you make all this money and have other people do it, then you can take the day off and just go fishing.

Liberty

Retire and go fishing.

Jameson

So the modern life of social media, which is only projecting these shiny versions of life, the 24-hour news cycle, everything in our existence is working to pressure you into thinking the good life is only a certain selection of pathways, and that may not be true for what you want out of life. So I think the number one thing is that you need to decide, what is it that I think I would be most fulfilled by in life? And if that’s becoming an entrepreneur, awesome. If that’s finding how to retire early so you can spend more time with the people you love, equally awesome. The only thing that matters is that you have decided this is what the best version of your story is, and you take the responsibility to recognize that it’s up to you. I will never be the main character in someone else’s story. I’ve got one shot at this. Just because I’m not there yet, and maybe I’m even in a much worse spot than I thought I would be at this point in my life, it’s never too late to take some control back, if you just grab the pen and start rewriting the script you’re currently living.

It’s not easy. The thing I’ll share, and maybe this is how we wrap up, I’ve talked to you about how I recently discovered William James, and I’ve become obsessed with him. He might be on what I’d call the Mount Rushmore of protagonism. So, the brief concept. William James, interestingly, is the brother of the novelist Henry James. He was an American psychologist from, I believe, the late 19th century into the early 20th century. He had a lot of philosophies that are very in line with protagonism, of agency and deciding what to make of your life. But what makes him so fascinating to me is that he’s not some academic who just wrote about this from a cushy life. He actually had a complete breakdown himself, where he spent years bedridden, questioning existence, sometimes considering ending his life. So he went through it personally. And then one day he just decided, because one of the things he was struggling with was, do I have free will, or is it determinism, am I just destined to do what I do? So he was struggling with these thoughts, and one day he just decided, “You know what? I don’t know which it is, but I’m just going to act like my choices do matter, and if that’s determinism, I don’t care.” I love that, because I’ve literally said that in one of my episodes. You could argue either one. As long as I, in my consciousness today, can look at my options and say, I have the choice to do something I think is a better choice than another, that’s all that matters. It doesn’t matter if I was predetermined to do this or not. All I care about is that in the here and now, I can look at my options and I have the option to choose what I think is going to contribute to a better life.

So, William James decided to do that, and he eventually built himself up into one of these very prominent psychologists and philosophers who had a very meaningful life. The detail I haven’t shared with you yet, that ties into it being a journey, is that I learned about that story, and then I learned there was controversy about it. And I thought, oh no, is the controversy that this never happened, that he never had a breakdown? But no, every source agrees he had a breakdown, he went through it. The controversy comes from the fact that some versions romanticize it, that he had that thought one day and boom, his life was changed. And people are saying that’s not true. The only contention is that they’re saying it took him a while to figure it out. He had that thought, he wrote it down somewhere, but he stumbled his way to what we eventually see him as. When I learned that, I thought, that’s even better.

Liberty

That’s more relatable.

Jameson

That’s a much more relatable story. The whole point is that he got there because he just decided, it doesn’t matter how low I am right now, or where I’m at in life, my choices from here on out matter, and I’m going to live under the assumption that I can impact where I end up based on my choices. Because I will never say, oh, everyone can be billionaires if you just choose. Your circumstances do have certain limitations. But within your fixed circumstances that are truly outside of your capability, there are millions of possibilities of how your life ends up that you do have some sway, some control over, as long as you decide that your choices will impact the way your story plays out.

Liberty

You’ve been dealt a hand of cards. How you play them is what matters. We all have a different hand, but then, what do you do with it?

Jameson

Yeah. I can’t remember the exact phrasing, but for the most pessimistic that someone could be about these ideas, my answer is actually something I’ve thought about, and I was validated by it when Matthew McConaughey was on Hot Ones. He talked about this idea that you have desires, you have these things, and, man, I’m really butchering trying to remember it. I just remember the zinger, the line he said where I thought, yes, this is exactly what I’m trying to say. He just points out that it doesn’t matter how bad things are for you right now, “what else are you gonna do?” Are you going to just sit there and do nothing and be like, well, this is life, I’m just going to survive for the rest of my existence on this planet? Or are you going to say, what can I control, what can I become? I may have robbed myself of certain opportunities because of choices I made 10 years ago. I may have certain limitations purely because of where I was born, my parents’ socioeconomic status. Yeah, but so what? What are you going to do about it? What are you going to try to create with your beautiful life? No matter what hand of cards you’ve been dealt, there are people who have been dealt an almost identical hand who have turned it into something amazing, and there are people who have been dealt an almost identical hand who have just suffered through the rest of their life. And that is the difference between being an NPC and choosing to see your life as a story that you can actually impact with the choices you make.

Liberty

I think that’s as good a place as any to close it. We’re going to put all of your links in the show notes. For people who want more, check out Becoming the Main Character in your podcast player. I’m going to steal Jim’s question. If you could be made emperor of the world, you’re the cosmic writer of the novel of life, and every human is a character in it, and you could incept two things in all those characters, two things that they will believe and act on, what would those two things be? And they can be from what we’ve discussed. What stands out?

Jameson

I would instill that the two most important things any person can have to achieve a meaningful life are curiosity, both about what am I capable of becoming and about why do people act differently than me, being willing to see things outside of yourself. So, curiosity. And then grit, the grit to grind out the vision you have, to actually live the painstaking training montages that are glamorized in 60 seconds in a movie. Those two things combined, the curiosity to explore what’s possible and what you’re capable of, and the ability to stick it out when it’s not fun, when it might feel like it’s not going to work out, but you know that the only way to find out if it works out is to stick with it. Grit and curiosity. I think if people just held those as important virtues, it would be an incredible place to live.

Liberty

I love that. Thank you, everyone. Goodbye.

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O'Shaughnessy Fellow Jan Jedryszek has cofounded Biotic, a public-benefit nonprofit working to ensure that all people and the planet benefit from world‑leading biotechnologies.

Biotic launches alongside SpudCell, a cell built from scratch out of non-living chemicals that can grow, copy its DNA, and divide. SpudCell was created by fellow Biotic cofounder Kate Adamala and her team at the University of Minnesota. The breakthrough was featured by The New York Times this week.

Read more at biotic.org.

Sunday, 28 June

Two thoughts from David Cronenberg

“Technology is us. There is no separation. It’s a pure expression of human creative will. It doesn’t exist anywhere else in the universe. I’m rather sure of that.”

“Everybody’s a mad scientist, and life is their lab.”

Monday, 29 June

Two thoughts from Michael Crichton

“If you don’t know history, then you don’t know anything. You are a leaf that doesn’t know it is part of a tree.”

“Men under stress are fools, and fool themselves.”

Tuesday, 30 June

Two thoughts from Michael Connelly

“What is jealousy but a reflection of your own failures?”

“It’s only a wonderful world if you can make it that way. There are no street signs pointing to Paradise Road.”

Wednesday, 1 July

Two thoughts from Leo Tolstoy

“Everyone thinks of changing the world, but no one thinks of changing himself.”

“The only thing that we know is that we know nothing — and that is the highest flight of human wisdom.”

Thursday, 2 July

Two thoughts from Jim Morrison

“A friend is someone who gives you total freedom to be yourself.”

“Keep your eyes on the road, your hands upon the wheel.”

Friday, 3 July

Two thoughts from Carrie Jones

“The secret of happiness is freedom, the secret of freedom is courage.”

“It’s hard to save the world when you can’t save yourself.”

Saturday, 4 July

Two thoughts from Patrick Henry

“Give me liberty, or give me death!”

“The liberties of a people never were, nor ever will be, secure when the transactions of their rulers may be concealed from them.”

Follow Jim on Twitter for a daily dose of Two Thoughts!

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