After a long winter and an increasingly short spring, the start of summer is marked by full golf courses and tennis courts, lakes filled with boats, and 45-minute lineups for terrasses. You make all these exciting plans. The places you’re going to travel, the friends you’re going to see, all the late nights and lazy days at the cottage. Then, seemingly about a week later, people are already talking about Labor Day.

It doesn’t matter if you spent the summer island hopping around Greece, discovering hidden gems in the Balkans, or chained to your desk churning out PowerPoint decks for your MD while they are busy doing business development in Saint-Tropez. This is a surprisingly universal experience.

You aren’t getting gaslit. At least not about this. There are physics and psychological explanations for why three months can feel dramatically shorter.

First the way we think about time is wrong. Most imagine something resembling a giant grandfather clock in the center of the universe ticking at a perfect Patek Philippe cadence capturing the passing of time. That’s not how time works.

There isn’t a universal clock, time passes at different rates based on a variety of factors such as gravity, velocity or location. A second elapses at a different speed for somebody underground compared to somebody aboard an airplane, on top of a mountain or trying to hold a plank position. The difference isn’t massive so digging a hole and living like groundhog won’t help you outlive Bryan Johnson.

There is not a universal time that everyone subscribes to. Even without Daylight Savings Time or time zones, humanity still would not be on the same time. This is still not an excuse for your friends to be consistently late for everything. The only way to end this, comes from a suggestion from FT. Invoice people when they show up late. People will become punctual very fast or stop returning your calls.

We’ve established that there is not a universal time and it doesn’t move at the same pace for everyone, but our understanding of time is still backwards. Our mental model usually grasps time as the independent variable which causes everything else to happen. Time moves forward which causes ice to melt, grass to grow, the arm of a clock to tick etc. This is also wrong.

We aren’t observing time, but rather how an entity changes. We see grass growing which captures the passing of time. The arm of a clock moving depicts a change which we interpret as time moving forward.

If you were locked somewhere without clocks, sunlight or any other reliable indication of the time, estimating how long you had been there would be surprisingly difficult. French researcher Michel Siffre tested this in 1962 by living alone in a cave without a clock, calendar or sunlight. When September 14 arrived, he thought it was August 20. He lost track of almost a month.

Tldr: Change is what gives time meaning.

(If you find this topic interesting, check out The Order of Time by Carlo Rovelli)

There’s a common belief that the way you experience time changes as you get older. This traces back to a theory from by Paul Janet in 1877. Janet proposed that we experience a period of time relative to how much life we have already lived. The logic is that for a ten-year-old, a year represents 10% of their existence. For a 50-year-old, it represents 2%. Each additional year therefore represents an increasingly smaller proportion of your life.

Additionally since you have more experiences your brain to save space, batches information together it doesn’t think is useful. That’s why you can’t remember every single day you’ve gone to the office, only the days something out of the ordinary happened. Your brain is designed to notice contrast. If every day is virtually the same, it’s as if you are stuck in a groundhog day loop. If every day is completely different, your brain won’t be able to batch things as easily.

This is the disadvantage of a routine. It makes each day more similar because it’s efficient, and reduces decision fatigue. The downside is each day blends together so time feels like it’s passing together and when you look back, you don’t notice how quickly time passes. That’s why when you travel and you are constantly shifting environments, beach, mountains, forest, city etc. Your mind has to process and distinguish the environments creating the contrast. This explains why it’s possible for the paradox of feeling like you’ve been on vacation for a long time while the trip is going by quickly.

This is also why time flies when you are having fun and it can feel like time has stopped when you aren’t doing anything. You have no distraction or any change to observe. If every day felt the same, then your brain will batch them all together.

Which is why whether you had a busy summer or not, it likely flew by.

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Well before TikTok, history has the tendency of being forgotten or dismissed for not fitting present day norms. Each generation is focused on the problems plaguing them, believing their trials are unique and unprecedented. They don’t care about what happened before, only what’s happening today and what they think will happen in the future, not realizing the past is where they will find most answers.

People underestimate the value of history because they don’t see how what’s happened before could possibly apply to them. Whether it’s the narcissism to believe that nobody has ever dealt with a similar situation or the naivety to think there hasn’t been a time like this in history. IE: This time it’s different. This logic is flawed.

You see this in areas as disparate as finance, technology, politics and art. There have been plenty of changes but just as many things that have remained the same.

The recent advances in AI might be unprecedented but this is hardly the first time a Leopold Aschenbrenner type has earned impressive returns in the short run by being aggressive only to blow up at the sign of unexpected volatility. As we discussed last week, Aschenbrenner is knowledgeable about AI but inexperienced when it comes to financial markets. Compared to somebody like a Ken Griffin who’s been a leading hedge fund titan for longer than Leo’s been alive, he’s at a severe disadvantage. Griffin and Citadel have lived through several crisis, understanding volatility can strike at unexpected times. This is scar tissue a fresh faced 24 year old can’t learn from prompting Claude.

This doesn’t mean you need to wait until your 60s to become a great investor or a leading figure in a particular domain. Young people can outperform older peers. What they lack from experience, they usually have more energy, open minds and suffer from less inertia. In some fields like technology, this is a major advantage.

Yet to innovate, you need to understand the current state of things, not to mention what happened before. Otherwise how can you know if what you’re working on is even new? You can be the millionth person to repeat the same mistake with the hubris to believe you’re the first.

There’s plenty of valuable lessons learnt from your own mistakes/experiences instead of just taking information on face value, but it’s also painful. You don’t need to always put your hand on the stove to confirm it’s hot. Sometimes you can take somebody else’s word for it. Given the choice, I’m sure Leopold would have preferred not to get liquidated in such a public and humiliating manner. He definitely won’t forget this episode, but hearing about somebody else’s own folly with leverage and concentration could have saved him a ton of embarrassment.

Books are a codified reflection of somebody else’s own thoughts and experiments. By reading, you can increase your own surface area of knowledge, even if it’s second hand. I probably don’t need to convince you reading is good. However, what you read is what makes the difference between expanding your mind and filling it garbage barely better than what you find on social media.

Some authors are now publishing hundreds of books per year using LLMs. Many of the readers won’t realize they are consuming AI slop. This is an evolution of a problem that has always existed in publishing. Publishers are businesses. Their motivation is to put out books people will buy. Quality helps, but it is hardly their only consideration. Thousands of new books appear every year. Some become bestsellers, fewer remain widely recommended years later and even less say something people find worth remembering decades afterward.

This is why with few exceptions, you should usually ignore new best seller lists. These lists are usually gamed by the author and publisher anyway. If people are still recommending a book ten years after it comes out, then it’s probably good. If something is still read 20 years after release it’s a classic. Older than that, it’s a foundational work.

Some books have short shelf lives. A book explaining the current capabilities of LLMs in 2022 is already irrelevant. Most political memoirs have always been ghost written slop, whom the only paying customers are the political parties who back them.

Others are timeless, that if anything, get better over time. The longer they are around, the more time there is to survive scrutiny. If a book can get analyzed, dissected for decades and centuries, but people still revert to that, you know it’s more resilient then something fresh off the press.

The Iliad or The Odyssey are better than 99.99% of anything produced afterwards. Not because writing was better 3,000 years ago but because of survivorship bias; everything else from that time and most of that’s come after wasn’t worth repeating or transcribing so it was lost to history. Lots of books go out of print because publishers and the reading public doesn’t feel like they are worth re-issuing. Since most aren’t worth reading when they come out, it stands to reason they won’t be anymore worthwhile years later either. Some are robust, staying as relevant as when they came out, such as How to Make Friends and Influence People.

Others are anti-fragile that become more valuable the longer time goes by, such as Moby-Dick. In either case, if you come across books that came out a long time ago, there’s a decent chance they contain something novel. If you want to have an edge, you need to uncover secrets. Some secrets come from your own experience, others you can uncover by re-discovering what’s been forgotten.

It’s not a coincidence that when you look at a list of Warren Buffett’s recommended books, you’ll notice most are decades old. Few were released recently. Somebody like Buffett has forgotten more about investing than any book author could ever distill but Buffett hasn’t lived through it all. A century is a long time, but he was born after the depression of 1929, and all the preceding market crashes. If he only focused on the financial markets from 1950 and onwards, he probably could have still been a great investor, but he wouldn’t be Warren Buffett. Yet reading old books alone won’t make you the best in your field, you need to earn it.

Knowledge without application has its limits. There’s a scene from Limitless after Bradley Cooper starts taking a nootropic NZT, and he puts up astonishing returns in short order. He attracts the attention of some financial heavyweights, including Robert DeNiro. Bobby D is impressed with Cooper but he points out that these powers of his were not earned. He was a smart kid but he hadn’t lived through tough times, like DeNiro had to get where he has. Cooper has had it come too easily to him, therefore he doesn’t understand what he doesn’t know.

(can skip to 30 seconds)

DeNiro is so convincing Bradley Cooper wasn’t sure if the message was for him or his character.

This is why greats like Warren Buffett and Ken Griffin can master the markets for decades. They are students of history and they have the scares. Leopold is a smart kid but he had not been investing long enough to accumulate the scar tissue. He didn’t earn the success that came to him as quickly as it did, which is why he was unprepared for it. He wasn’t in the game long enough to learn from his own experience, but if he had read What I Learnt Losing a Million Dollars, perhaps he wouldn’t be preparing to write its sequel What I learnt Losing Billions of Dollars.

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The initial instinct is to take the money. With compound interest that will be worth tens of millions by your thirties guaranteeing a level of security few can enjoy. However, this is short sighted. If your goal is to build something enduring, the advantages of intangible assets compound faster than what’s in your bank account.

There are endless personal finance books teaching how to build wealth. Whether they are about how to live frugally, why to invest in real estate, buy ETFs etc. they only talk about how to accumulate tangible assets. Tangible assets are important but they are limited because they can only help you access things money can buy.

How would you feel about one of your children marrying somebody with the surname Hitler? Even if this young Hitler was very wealthy, it would be normal to have concerns with the association. They would need a lot of money to offset the baggage their name brings. For many, under no circumstances would they consort or do business with somebody like this. Money can't buy everything.

Your reputation is what people think of you before you enter a room. If they are primed to like you, it’s easier for you to get along. If they’ve decided you aren’t worthy, you’ll face an uphill battle. The better your reputation, the easier your life will be.

Every promise you keep, person you help and difficult situation you handle enhances the way you are perceived. Every broken commitment, act of dishonesty or bad energy you bring, detracts. If your good deeds outnumber your negative interactions, you will create goodwill. Goodwill, a strong work ethic, talent and experience are all examples of intangible assets. They don’t have a financial value but they are key determinants to success.

People with goodwill have more supporters than detractors. This increases the chances people will want you to win and this extends to the people around you. They too are impacted by your reputation. Have you ever gotten preferential treatment just by saying you were a friend of so and so, or related to such and such? Have you ever had to answer for somebody else’s crimes because of your association?

Your circle is critical to your success. If you hang around bad actors, their stink will get onto you. If the people around you have goodwill, it will extend to you. At a minimum, you should never do anything that will impair your groups reputation, to succeed everybody needs to enhance it.

Groups that could maintain power for many generations could only do so because they understood the value of goodwill and other intangibles are more durable than money. The Rothschilds didn’t become a premier merchant bank because they offered the best prices. They became indispensable to governments, crowns and key corporations, by being consistently reliable. Even when something seemingly impossible was needed. Whether that was raising millions in uncertain conditions or getting gold past naval blockades. Their empire ran on trust, which inspired a level of loyalty an upstart bank with more capital could not quickly replicate.

The more somebody has come through, the more embedded the belief that they will always deliver becomes. This makes them hard to displace and affords them the benefit of the doubt when they can’t. This is why being born a Rothschild or into one of these families comes with advantages that extend far beyond money.

The surname carries with it generations of goodwill, and many potential supporters. This assumes each successive generation can improve or at least maintain the reputation they inherited. Otherwise it atrophies, negating advantages for their offspring. It should be easy but few wealthy families can maintain their fortunes beyond three generations1. This perceived blessing can be just as much of a curse.

If each successive generation is less like the person who made the family noteworthy, the intangible assets will gradually get impaired, which will manifest in the decline of the tangible assets too. Cornelius Vanderbilt had more money than the US treasury, within a few generations, his descendants squandered that fortune. They inherited the financial security without the hunger, drive or business acumen and look what happened. This is a familiar tale.

In Game of Thrones Tywin Lannister understands the value of intangible assets, but unfortunately none of his children do. They believe gold is the answer to any problem but fail to realize they benefit more from the belief “A Lannister Always Pays Their Debts”. They think they will always be the richest so they don’t do anything to ensure future generations will be afforded the same privilege. Succession depicts this as well. Logan Roy built an empire, but none of his children appear equipped to continue the legacy. The next generation were born with all the trappings of wealth but without his killer instinct. They can’t replace their father.

Tywin and Logan were brutal, ruthless and willing to do things that made them unpopular in the short term to benefit their families in the long term. This has nothing to do with money. Future generations benefitted from their actions, but failed to understand if they didn’t make similar maneuvers, their family name would gradually fade to irrelevance.

People use the term “nepo baby” to dismiss the success or discredit people coming from prominent families. If they aren’t actively trying to enhance their families reputation, they are contributing to its decline. If somebody is born with certain advantages why shouldn’t they use it? Are they expected to nerf themselves and cosplay as pre-batman angsty Bruce Wayne just to prove they are self-made?

Cobb and his crew successfully convince Robert Fisher of this in Inception by preying on his insecurity. They explicitly say the only way he could fail, is for him to decide he needs to become his own man. Fisher decides to break up his father’s energy monopoly, because he didn’t want his dad to perceive him as a nepo baby.

Being born into a prominent family can create advantages but deliberately refusing to use it does not make the system more fair. It’s just wasting an asset created by a previous generation. Should Shaquille O’Neal have pretended he wasn't a giant and insisted on playing point guard? Perhaps people would have thought it was admirable of him not to exploit his size advantage but he would not have made the NBA. Shaq, the Magic, Lakers and Heat franchises would have been worse off for it.

One of Citadel founder Ken Griffin’s most frequently gifted books is Hardball: Are You Playing to Play or Playing to Win? The book’s central argument is that if you are serious about winning in a competitive field, you must exploit every legitimate advantage at your disposal. Not everyone agrees but what’s the alternative? Self sabotage?

Nicolas Cage, Jason Schwartzman and Sofia Coppola grew up as part of the Coppola family. If they wanted to be self-made, they would have avoided the entertainment industry. Whether casting directors chose them because of their family name is irrelevant. The proximity to a Hollywood legend such as Francis Ford gave them access to an invaluable resource few would ever get. When you are watching a Nick Cage film, it doesn’t matter what family he was born into. The only thing the audience cares about is his performance. Cage isn’t the only person that benefits from his acting talent. So does anyone he works with because he elevates the film.

Would Christopher Nolan’s films be worse if his last name were Coppola? Of course not. Undoubtedly Sofia, Nick Cage and Jason Schwartzman had a leg up because of the goodwill created by Francis, but it’s their talent that made Lost in Translation or Leaving Las Vegas successful. No amount of nepotism will get Schwartzman an Oscar2.

This isn’t a defence of nepotism but an acknowledgment that intangible values that get transferred among friends and family are more valuable than material wealth. Spending time with highly successful people, is more likely to help you be successful long term. Even if it isn’t specific tricks of the trade they pass down, seeing what it takes to be great permits others to follow and build off the examples set for them.

The value doesn’t come from your name, you can hail from any family, the company you keep matters more. I’ve been helped by countless individuals who can’t even pronounce my name. Your reputation is a proxy for the intangibles before somebody has met you. No matter how people initially perceive you, it’s possible to win anyone over by building goodwill. Consistently being reliable and delivering when others can’t, builds trust. It’s this trust that bolsters your reputation, making it increasingly easier for more people to want to like you and help you succeed.

The right combination of intangibles is a greater predictor of success than money. Becoming the strongest version of yourself, has a far more enduring impact on your community. You can’t take tangible assets with you when you die. No matter what inheritance tax a government tries to levy on future generations, the reputation, lessons and goodwill you create during your lifetime and pass to future generations will help elevate individuals for far longer than anything money could buy.

Too much attention is focused on building tangible wealth, when the real value is in the intangibles. That is why the value of money is overrated.

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Friday July 17th 2026 marks the worldwide release of The Odyssey which could be the best film in the history of cinema.

Based on Homer’s epic collection of stories, The Odyssey represents one of the most enduring pieces of literature, dating back nearly three millennium. It follows Odysseus as he attempts to return home to Ithaca after the Trojan War, a voyage that should have taken weeks but instead lasts ten years. This wasn’t just bad navigating, he had to contend with mythical creatures, cannibals, monsters and singing women. Meanwhile 100 men have taken up residence in his home and compete to marry his wife. Who can’t relate?

Bringing The Odyssey to the screen is one of the most ambitious projects a filmmaker can make. Trying to give justice to the 24 books, has never been achieved. There have been many adaptions but none have managed to capture the full essence of what makes The Odyssey an incredible story.

This is because this feat has not been attempted by a director worthy of such a challenge. Amongst active filmmakers, Christopher Nolan is currently the undisputed heavyweight champion. One could say this film represents an Odyssey of his own.

Coming off the success of Oppenheimer, Nolan could do any project he wanted. He took the biggest swing he could, adapting a work from Homer, a project that eluded him for 20 years. Nolan was hired to direct Troy in the early 2000s before the studio reversed course and returned the project to Wolfgang Petersen. Warner Bros. offered him Batman Begins as something of a consolation prize.

Now to pull off this project, he boasts one of the strongest casts in recent memory. Matt Damon & Anne Hathaway have headlined major projects for 20+ years. Robert Pattison and Zendaya are amongst the busiest leading actors in Hollywood today. Not to mention usual leads getting downgraded to supporting roles.

Some casting choices have been met with controversy but it doesn’t matter. This film will be a work of art people will still be talking about thousands of years from now.

Keep reading to learn why this will be the greatest film ever!

(*I have not seen the film yet and this does not contain any spoilers beyond what is common knowledge about a story that’s been out for 3,000 years)

Book I’m Currently Reading:

1. 1873: The Rothschilds, the First Great Depression, and the Making of the Modern World by Liaquat Ahamed

Related Reading:

1. The Odyssey by Homer

2. The Illiad by Homer

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In case you missed them, here are some other recent articles to check out:

The Odyssey is The Greatest Story Ever Told

The Lindy Effect suggests the longer something exists, the more likely it will in the future. By that measure, we shouldn’t be surprised The Odyssey is one of the most anticipated films in recent years.

How can a story written 3,000 years ago still resonate with people today? The story is about a universal feeling, about somebody longing to go home.

Odysseus is gone for 20 years. The first ten spent for The Battle of Troy which precedes the events of The Odyssey. It was Odysseus who came up with the idea of the Trojan horse. His side won, although they lost many other great warriors because Helen and Paris couldn’t be discreet.

Odysseus isn’t impressive because he’s the greatest warrior, like Achilles, or the most powerful king, like Agamemnon. He is impressive because he is clever. He can fight, but his real talent is thinking his way out of seemingly impossible situations. Kind of like Jason Bourne if you dropped him in Ancient Greece.

Odysseus is not your perfect fantasy hero either. He’s not Aragorn. Odysseus is arrogant, dishonest and occasionally his own worst enemy. These flaws make his journey more interesting and his character more relatable.

Love him or hate him, Odysseus is ultimately just a guy who left home 20 years ago as a king and now wants to return to his land and his family, unsure of what will be waiting for him when he gets there.

Most of us don’t have to worry about our partners entertaining more than 100 potential suitors whenever we leave town. Yet the yearning to return home, wherever home may be, is a universal experience that cuts across time and space.

Christopher Nolan is the right person to capture that feeling.

Christopher Nolan is The Greatest Director of The 21st Century

Hitchcock, Coppola, Cameron, Spielberg and Lucas dominated the 20th century. Some remained active through the early part of the early of the 21st century, but ever since The Dark Knight hit theaters in 2008, there was a new king of Cinema. Quentin Tarantino and Paul Thomas Anderson battled for supremacy during the 90s and 2000s, and with respect to Dennis Villeneuve none have matched the quantity and quality of hits Nolan has displayed since 2010.

A director could have survived decades from the success of having made just one of Inception, Interstellar, The Dark Knight Rises or Dunkirk. Nolan made all of them, and Tenet for good measure. Although the latter wasn’t as well received, it’s incredible. If you didn’t enjoy it, it’s because you made the mistake of only seeing it once.

At a time when the film industry is dominated by franchise sequels, recycled intellectual property and algorithmically assembled ensemble casts, Nolan has consistently produced original films that perform at the box office without insulting the audience’s intelligence.

Instead of relying on big explosions, CGI and cheap gimmicks, Nolan makes films, that make the audience feel something. Films like Inception, Interstellar and Tenet aren’t linear and formulaic accessible to the lowest common denominator. Not everyone will understand it on the first watch, and that’s ok. Having people need to think about what they just watched after leaving the theater is what good filmmakers should do.

There’s enough mindless slop on Instagram, TikTok, don’t even get me started on Linkedin. It’s great when content is worth reflecting and re-watching. All of Nolan’s work falls into this category. Nolan isn’t mass producing next seasons fashion, like a H&M or Shein. He’s a craftsman, like a Hollywood Hermes.

Nolan insists on shooting in IMAX film cameras, which in 2026 is seen as an insane choice. Remaining one of the very few holdouts while everyone else has moved on to Digital. Nolan can only shoot scenes up to 3 minutes at a time, the cameras make loud noises, not to mention how much harder the entire downstream process becomes.

Nolan uses CGI as sparingly as possible, trying to capture as much as possible practically. He built a rotating hallway for Inception, flipped a real truck in The Dark Knight and crashed a 747 into a building for Tenet. Nolan still uses visual effects, but usually to support something physically captured by the camera rather than manufacture the entire spectacle afterward.

If there were any doubts about his abilities, Nolan followed up Tenet with Oppenheimer, which was among the biggest commercial and critical smash hits of the decade. Earning nearly one billion dollars at the box office and Academy Awards for Best Picture and Best Director. Nolan did this without the usual A-lister leading man films of this scale usually command. Opting for long-time collaborator Cillian Murphy, a respected actor, but not somebody thought capable of headlining a 3 hour, R-rated film about nuclear physics, moral responsibility and government bureaucracy.

Coming off that success, he chose the oldest, largest and most ambitious story he could find. To do this, he needed to assemble a murders row of thespians capable of living up to the epic legend.

This Is One of the Best Casts Ever Assembled

Matt Damon is an all time great. He’s played Will Hunting, Private Ryan, Jason Bourne and Mark Watney among countless others. Damon worked with most of the great directors of his era including Spielberg, Scorsese, Steven Soderbergh and Ridley Scott. His run from 1997 to 2007 is among the greatest decades for any actor ever. During that stretch, Damon made Good Will Hunting, Saving Private Ryan, The Talented Mr. Ripley, all three Ocean’s films, the entire Bourne trilogy and The Departed.

(Matt Damon reading The Odyssey on the set of The Talented Mr.Ripley (1997))

Like any actor with a career that long, he’s had bad films but it never took him long to bounce back. Few movie stars of his stature would have accepted such a small role in Interstellar. What the role lacked in screen time, it made up for in substance. This demonstrated Damon did not need to be the lead. He just wanted to be part of a great film. That choice paid off. Less than a decade later, Nolan cast him as General Leslie Groves in Oppenheimer. Now, at 55, Damon is playing Odysseus and leading the largest production of Nolan’s career.

Anne Hathaway has demonstrated similar longevity. She became a star through The Princess Diaries in 2001 and followed it with iconic films such as The Devil Wears Prada, The Dark Knight Rises, Les Misérables and Interstellar. She has shown she can lead a romantic comedy, anchor a major studio film or enter halfway through a Nolan movie and provide its emotional center. She occupies a rare place in popular culture where Boomers, millennials and Gen Z audiences all recognize her from different stages.

Robert Pattinson is one of the busiest leading men in Hollywood today. It took him years to escape the shadow of Twilight. Instead of immediately chasing another franchise, Pattinson spent the following decade working with directors such as David Cronenberg, James Gray, Claire Denis, the Safdie brothers and Robert Eggers. Performances in Good Time and The Lighthouse proved he was considerably stranger and more talented than his early reputation suggested. He eventually returned to blockbusters with Nolan in Tenet, Bruce Wayne in The Batman and in Bong Joon-ho’s Mickey 17. He now moves between enormous franchises and unusual independent films without seeming out of place in either.

Damon, Hathaway and Pattinson would already constitute an exceptional cast. When you realize Tom Holland and Zendaya, two of the most recognizable actors of their generation, are also in the film, they almost feel like afterthoughts. Other members of the supporting cast includes Charlize Theron, Jon Bernthal, Mia Goth and Benny Safdie to name a few. Actors who regularly headline their own projects, now occupy roles that would normally be filled by much smaller names.

The clearest indication of his power may be how quickly everyone agreed to participate. Robert Pattinson was reportedly the only actor who asked to read the screenplay before formally accepting. Nolan seemed surprised. Everyone else had simply said yes.

The closest recent comparison might be Once Upon a Time in Hollywood. Quentin Tarantino began with Leonardo DiCaprio, Brad Pitt and Margot Robbie, then filled the smaller roles with Al Pacino, Dakota Fanning and Bruce Dern. The cast looks even better in hindsight because Austin Butler, Margaret Qualley, Mikey Madison and Sydney Sweeney appeared before reaching their current levels of fame.

Some of Nolan’s casting decisions were not without controversy. For months people were up in arms over the rumored casting of Elliot Page as Achilles. Page is a fine actor, but not who comes to mind when picturing the greatest warrior in Greek mythology. Brad Pitt made immediate sense in Troy. He looked capable of defeating an entire army by himself, even if Pitt was never particularly enthusiastic about the film. His indifference helped the performance. Achilles was the best warrior alive, knew it and seemed perpetually annoyed that everyone else was wasting his time. Any actor playing Achilles would inevitably be compared with Pitt, but this was irrelevant since Page is playing Sinon, not Achilles.

The other casting choice that drew the public’s ire was Lupita Nyong’o as Helen of Troy. Helen of Troy’s beauty was deserving of 1,000 ships and the greatest battle the world ever knew at the time. Needless to say, whomever was cast would get a large bill to live up to. Some dismiss the casting choice as a Diversity, Equity & Inclusion (DEI) hire. Others don’t think her beauty reaches the level of 1,000 ships, perhaps 300-400 at the most. Still a lot of ships. Others believe Zendaya could have made more sense. Regardless, this is largely irrelevant to whether the film will be good or not. People forget, there was a massive outcry when Heath Ledger was cast as the Joker in The Dark Knight. That portrayal worked out quite well.

It’s 2026, people spend too much time online. Every major project is met with some backlash. If a film is historically accurate, people whine about lack of representation. If a film tries to represent everyone, others will whine about historical accuracy. The filmmaker and their studio should be less concerned about what a few journalists or people on X say, and focus on making the best film possible. A lot needs to go right for a movie to be good and profitable.

I didn’t have an issue with the casting of Lupita Nyong’o as Helen of Troy up until she said she would ask Homer how he felt about the limited attention given to women in his epics. I’m not sure if this is a PR strategy to help generate more buzz or her own personal views, but these comments come off as somebody trying to gain clout by holding somebody who died thousands of years ago to account for today’s standards. It’s unnecessary and frankly a distraction from what promises to be a historical event.

The film marks Christopher Nolan’s own personal Odyssey, having spent 20 years making incredible films, all so that he can make the Odyssey the way its never been captured on screen before. He has the budget, the cast and goodwill from audiences to permit him to take on such an ambitious trial, to which I’m certain like Odysseus, he will find a way to succeed.

There’s a reason The Odyssey is one of the most highly anticipated films in years and we continue to read Homer’s epics thousands of years later. It speaks to a truth that lives inside all of us, and we can be confident we will still be reading these works thousands of years from now.

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There were only two safe outcomes. He could call off the stunt and stay on his side of the canyon, or clear the gap and land on the other side. Anything in between meant falling to his death. His survival only existed at the extremes, ruin sat in the middle.

Most people’s view on risk is that this is something you should try to eliminate. Variance is bad, regardless of the reward. They only focus on the gulley, ignoring the reward waiting for them on the other side. Others are degens who only focus on the reward, the other side of the Canyon, ignoring the very real possibility of dying.

Neither approach is always right, but at times they aren’t wrong. There are cases when people should try to limit variability and others when they should embrace chaos. At times it’s optimal to combine both.

This applies to investment portfolios, career choices, and even dating. Countless people have earned a living referencing Daniel Kahneman and Amos Tversy research showing how bad people are at making decisions. Much of it stems from a misunderstanding around risk taking.

It’s less complex than people realize. Famed investors such as Nassim Taleb have been giving away the solution for years. It’s called the barbell. Like Knievel, you want to avoid the middle. Embrace risk when the potential payoff is worthwhile, otherwise take as little as possible. This approach lets you chase the upside without compromising your chance of survival. Keep reading to learn how.

Book I’m Currently Reading:

1. The Adventures of Herbie Cohen: World's Greatest Negotiator by Rich Cohen

Book I most Recently Gifted:

1. The 38 Letters from J.D. Rockefeller to his son: Perspectives, Ideology, and Wisdom

In case you missed them, here are some other recent articles to check out:

What is Risk?

Most people’s introduction to risk usually comes from games. Parlor games, board games, wagers that sort of thing. Coin flips are easy enough to grasp. The coin has two sides, which guarantees a binary outcome. Heads or tails, one person wins, one person loses. There’s no skill involved so any player has equal odds.

Outside of these games, life doesn’t work this way. Odds and conditions are rarely known ahead of time and performance can play a role. There’s an expected outcome but if actual results can vary, then there is risk. Some risks you can know in advance, like the odds of the coin flip (known-knowns), others you can be aware of but can’t quantify (known-unknowns), others you can’t even fathom (unknown-unknowns).

In the case of the coin flip, if a stranger wagered you $10,000, a mathematician would say your odds are 50-50. That’s the right way to think about your expected payoff but that 50% probability of losing doesn’t capture all of the risks.

This is a stranger so you don’t know enough about them to determine if they can afford to pay you (default risk). Even if they can, they might decide to break your legs and take the money anyway (counterparty risk). These are harder to calculate.

Risk isn’t inherently good or bad, it’s just an acknowledgement of different outcomes. You can think of risk as the umbrella term containing all of the factors that can influence the result. Something is only risk-free if there is only one possible outcome. Examples include forgetting your wife’s birthday or rooting for the Toronto Maples Leafs; both can only end in disappointment.

When you hear terms such as risk, risky or high-risk, this does not mean these are bad things, rather there is a large range of possible outcomes.

Bad Investors Avoid Risk, Good Investors Consider It

(Not Investment Advice)

A common misconception is that classically trained investors try to eliminate risk.

If that were true they wouldn’t be investors. They would be hoarding money under their mattresses. They try to minimize risks that don’t offer enough upside.

Given the choice between an investment with a guaranteed 10% return or another with a 50% chance of -10% with a 50% chance of a 30% return, over the same time period, the classical investor would take the first one. The second investment provides the same expected return but it exposes the investor to the possibility of losing money, without any additional compensation.

Returns are not created equal. According to finance theory, investors that can generate the highest return per the lowest level of quantifiable risk are superior. Returns that are greater than they should be, per the implied level of risk is called alpha. If as an investor you are not seeking alpha, you are a degen.

A degen doesn’t think in terms of risk versus reward. They just look at reward/upside. Meanwhile a bad investor, only focuses on downside risk i.e.. the potential to lose money, without considering the upside.

Imagine a third investment, one that offered a 99% possibility of a 20% return with a 1% of -10% return. A charlatan investor would focus on the 1% chance of losing money and cost themselves major upside. Both the degen and the classically trained investor take the third investment and hope they don’t get hit with that 1% scenario, otherwise the charlatan will never let them hear the end of it.

That’s the most math you’ll need to do this article I promise.

Upside vs Downside Risk

(Not Military Advice)

The examples I’ve given so far rely on the assumption that risks are knowable and quantifiable in advance. In most cases, they’re not.

As much as classically trained investors like to make their pretty Markowitz efficient frontier charts, this only works looking at historical results. The basis of their planning is to hope the future looks like the past. Sometimes it does, until it doesn’t.

When most people think of risk, they usually just focus on downside risk, like the charlatan investor. This is because people experience more pain from a loss than pleasure from an equivalent gain (this is called prospect theory via Daniel Kahneman).

This is a bad way to think about risk. There are many instances where it makes sense to want to increase the range of outcomes, where higher variance is good. When you are badly behind in Backgammon, to increase your odds of winning, you need to play more aggressively, even if it means exposing your own pieces. Your only chance of catching up is to slow your opponent down by putting their pieces in jail.

Similarly in the case of a military conflict, the larger army has the advantage. If the smaller army tried to challenge them head to head in an open field, their chances of winning are poor. To increase their chances, they should try to fight many small skirmishes. It’s harder for the larger military to plan for and the smaller army doesn’t risk their entire army in any individual battle.

Most risk management advice can be deduced into this. When you are leading/have more to lose, try to reduce variance. Avoid anything that can upend the apple cart. The odds are in your favor so you want to narrow the set of outcomes. It’s only when you are behind or the underdog do you want chaos. Act like the charlatan investor when you are ahead, and behave like the degen when you are behind. Otherwise act like the classically trained investor.

What if there was a way that offered better returns and let you sleep well at night?

How Does The Barbell Work

(Still Not Investment Advice)

Your first goal should be survival. You can’t succeed if you’re out of the game.

The barbell focuses on maximizing your odds of survival, while permitting maximal aggression. These sound contrary but they can be complementary.

Imagine somebody gave you a bank account with a hundred thousand dollars but with one caveat. You can’t access it unless you start a business and it fails. It’s not enough money to live off for the rest of your life, but it’s enough to support you long enough to get back on your feet. Would you be more or less likely to start a business?

The more secure people feel, the more risk they can accept. The barbell portfolio is constructed with two buckets. A low return/safe portion, this could include money market funds/short term bonds, gold, maybe regulated utilities. Looking at long term averages, all lag stock market index funds, but the probability of default is low.

The other part of the portfolio consists of high upside/risk positions. Speculative stocks, Crypto, derivatives, options, angel investments etc. They all offer far greater upside but most individual positions lose money. There is a way higher loss rate.

A classically trained investor would avoid most positions belonging to the high upside/risk bucket, because their models would decide the risk is too high for the expected return. The high default rate and other possible risks offset the upside. Meanwhile they would consider the overallocation to the low risk/upside bucket as a drag on returns. Nowadays the consensus view is to buy index funds and avoiding individual positions all together. Finance Substack is calling this strategy The Retardmaxx Portfolio (not my verbiage).

This is the lowest effort way to invest, but it’s not the best to minimize large drawdowns, or preserve high upside. It’s simply just mid. Anybody who bought Bitcoin between 2009-2019 and held to today would have experienced a >1,000% return. Depending on when you bought NVIDIA, or some high flying names, you could be up by a similar amount. If you just bought and held the S&P 500 over the same time span, you’d be up about 200% but still lived through volatile drawdowns, such as the pandemic. Bitcoin and NVIDIA are highly volatile assets, but who with the benefit of hindsight would not have bought them in 2015? Still, sitting around buying highly speculative assets is not a risk strategy, it’s simply degen behavior.

Nassim Taleb looked like a both a degen and a charlatan for most of his investor career. His approach was not about finding the next Bitcoin or NVIDIA. He would buy protection against rare, violent market crashes. These bets usually lost money. In normal years, they looked like an expensive drag on returns. However, when markets broke, they could pay out spectacularly. More than enough to offset his drag years.

The barbell is not designed to make you look smart every quarter. It’s designed to keep you alive when everyone else discovers their supposedly diversified portfolio was one big bet in disguise. The safe portion protects your ability to keep playing. The risky portion gives you exposure to outcomes that can matter disproportionately.

Most people are overly concerned about looking good on a month to month or year to year basis. They lack the nerve to accept frequent small losses in the short term to win in the long term. This is why most people opt for the middle. It keeps them from looking foolish at the expense of being exceptional. The barbell encourages risk taking by building a strong margin of safety.

There are many ways to build a margin of safety. Low debt, high savings, rich experiences, a strong network etc. These are things you can always fall back on if you get unlucky. The more safety you have, the more aggressive you can be and the more variance you can tolerate. This allows for incredible outcomes, like jumping the Grand Canyon.

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Was I about to lose to an inanimate object?

There I was, in the gym staring at a 100 pound dumbbell. I had just failed on a chin-up with that thing strapped to my waist. Normally, I would be doing anywhere from 3-5 reps with relative ease but today it wasn’t happening.

I had just gotten back from a 3 week vacation, where I didn’t exercise. The weights were feeling heavier than usual. As I stood there, I contemplated whether to reduce the weight or try again.

Science based lifters would have said I needed to ramp back up to my usual pre-vacation loads, so I should have taken 70-80% of my normal weight. This wasn’t a competition and nobody was watching, these reps had no particular consequence. Yet in a way, they meant everything.

I caught a glimpse of myself in the mirror, it was just me in the frame. It was too late now. If I didn’t complete the set as intended, I would be giving up. If I gave up, I would have allowed the weight to snatch my soul.

This dumbbell had no feelings, and wasn’t trying to actively resist me. My competition, was my own mindset. There are two kinds of people. One group believes that their fate is preordained, and life is something that just happens to them. Others believe their will shapes the universe into what they want it to be. What kind of person did I want to be in that moment?

I strapped the weight back on the belt, and banged out 3 ugly reps.

Anybody who has ever achieved success had moments like these. Faced with an obstacle they could have advanced or retreated. If we know their names, it’s because they chose to advance.

Success largely comes from sticking with your mission until the right opportunity presents itself. Even critics that dismiss success as a function of luck or randomness, must also accept the longer a participants stays in the game, the greater their chances of receiving good fortune. That’s why if you want to succeed, it largely comes down to how long you’re willing to pursue your ambition. This longevity is dictated by two things: morale & pain tolerance. Both are functions of mindset.

Today’s article explains why the greats manage their mindset to spend their life chasing their personal legends and quests.

In case you missed them, here are some other recent articles to check out:

Longevity Matters

Who was the better military commander Napoleon Bonaparte or Joan of Arc?

Nobody would consider this a serious question. How can you compare a military career lasting under two years, against the track record of arguably the most famous military leaders in history? Napoleon went from infantry soldier to Emperor in under 20 years. If he had died two years into his military career, nobody would know his name, and the history of France and Europe would have been very different.

It takes time to do great things, often years or decades of persistent work before the break through arrives. Rome wasn’t built in a day, but they laid bricks every hour for decades and centuries. That’s why it lasted 500 years, 1,500 if you count Constantinople. Centuries later, we still think Rome daily.

Why shouldn’t we? Rome is responsible for many of the underpinnings of Western Civilization. There are still many relevant lessons for us today, such as expansion. How far do you keep pushing after you’ve already experienced success? What do you do once you’re out of Beginner’s Luck and each incremental gain takes pain and sacrifice?

Pain Tolerance

Can you name somebody that reached the top of their domain without pain?

Some make it appear effortless, but don’t be fooled. In any competitive endeavor, nobody that’s ever won consistently did so without countless hours of discomfort. Before he was tennis great or a fashion icon, Andre Agassi, hit thousands of shots each day in his backyard, while his father yelled at him. Andre hated it, but nobody could argue with the end result. Even Federer, who was noted for how smooth and effortless his game looked, couldn’t reach the pinnacle of the sport until he took his training more seriously.

They had to. They were going against other professionals, that wanted to win as much as they did. Differences in natural ability net out, as competition improves. All pro athletes are born with natural athleticism; in some sports that alone is sufficient for a top amateur career. Once you reach the pro ranks, everybody is going to be athletic, and skill increasingly dominates.

This isn’t limited to sports. It’s possible to be a top high school student without studying endless hours if you have high intellectual horse power. Once you reach an elite university, all your classmates will have been top students (besides a few legacy and suspicious scholarship admits). To be a top student at an elite university, the gap in raw intelligence won’t be as pronounced, you will need to work as hard as everyone else.

Elon Musk isn’t the smartest man to have ever lived, but he’s one of the most successful. SpaceX didn’t come to be because he knew more about propulsion. Tesla didn’t become the leader in electric vehicles because Musk had superior insight into the auto industry. Musk was successful because of his ability to tolerate pain. To this day, he works longer hours with more intensity than almost anybody else. If you think this is overblown, I invite you to read Walter Isaacson’s biography, or listen to anyone who has worked with him.

Many of the companies Musk competed against were bloated and led by empty suits/pant suits, not built to handle pain or pressure. In their defense, it’s hard to rally employees. Most big companies aren’t built that way, bureaucracy designed to insulate pain, makes them weak.

You can’t expect even the most motivated employees, to tolerate pain for the same duration as a founder/CEO, it’s not their life mission. A leader’s job is to help their followers tolerate pain. They do this, my maintaining good morale.

Morale

Alexander was defeated without having lost a battle. Despite all the success, his men’s faltering morale is what ultimately ended his campaign. Sure, the copious amounts of wine, poisoned or not, didn’t help but if the booze didn’t get him, his men’s refusal to continue his conquest would have.

Alexander’s pain tolerance was legendary. His track record, unquestionable. Toughness aside, when it comes down to it, as a leader, he needed his men to follow him. He asked a lot, and he got a lot out of them. If they mutinied early in the campaign, Alexander wouldn’t have been remembered. He couldn’t have inspired Napoleon, Charles de Gaulle and countless other military geniuses, that would eventually learn the war ends once their side loses the will to keep fighting.

Some people can maintain good spirits in any conditions but most can’t. Coaches and leaders are valuable if they can motivate people to tolerate pain for extended stretches. Agassi hated tennis for most of his life, his career would have ended early if not for the team around him that kept him from quitting.

I worked with many gifted athletes that never panned out as professionals. Some would blame injuries or bad luck. The honest and introspective amongst them would admit, it’s because they fell out of love with their sport. With the right motivation, you can bounce back from tough breaks, you just need to be willing to keep going in the face of adversity. This doesn’t guarantee success, but quitting guarantees failure.

Great leaders know how to keep their followers motivated. Successful CEOs need their teams to tolerate more pain than their competition. Coaches need their athletes to keep pushing, even when they don’t want to. All political leaders experience setbacks, but they still need to energize their supporters to achieve their agenda.

The best way to do this is to deliver on promises. If you promise your troops glory, you better win great battles. Great employees will always have options, if you want them to stay, you need to give them confidence you can deliver. Nothing kills motivation faster than overpromising and underdelivering. A leader only has so many chances, before their followers decide they can’t trust their assurances.

For individual activities, the follower you need to convince, is yourself. I could have skipped that set of chin ups or took a lower weight, but then I would have been disappointed in myself. The more this happens, the less trust and confidence I’ll have in my abilities, and the worse I’ll be. If your goal is to pursue your life mission for a long time, you need to avoid this line of thinking; it’s a death spiral.

The successful people you see avoided giving up. They were able to keep a long term view, while tolerating pain and maintaining proper morale during their life’s mission.

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If this truism confuses you, it should. This logic only makes sense to con artists. Their act relies on deception, to others but most importantly themselves.

Deception happens everywhere. In the dating world, on social media, in professional settings but the highest stake deception relates to financial fraud to the tune of hundreds of billions each year.

You don’t understand banking or fintech unless you can identify all the ways a malicious actor can exploit them. Few people understand the financial system.

Most remember the film Catch Me If You Can as a cat-and-mouse game between two men who get it. Frank Abagnale Jr., played by Leonardo DiCaprio, is a teenager who manages to defraud banks of millions of dollars before his 19th birthday. Carl Hanratty, played by Tom Hanks, is the FBI agent assigned to track him down.

At its core, the film is about duplicity. Abagnale is the walking embodiment of the George Costanza maxim: “It’s not a lie if you believe it.” Combined with a strong instinct for identifying vulnerabilities and a burning desire to succeed where his father failed, he is a dangerous and highly successful con artist.

Outside of duplicity and the relationship between Abagnale and Hanratty, the film is a lesson on how the banking system works and how it used to rely on trust. As banking has gone global, fraud has become more widespread and it has become harder for financial institutions (FIs) to trust customers.

The late 20th century was centralization. Taking individual discretion out of local branch managers hands, instead putting it in software credit scoring systems (mostly just Excel). The crypto solution is decentralization and transparency. Both approaches have failed thus far, because fraudsters keep finding new vulnerabilities.

As long as money, incentives, and human weakness remain part of the system, there will always be Frank Abagnales. This article is about why fraud never disappears, despite the financial systems best efforts.

In case you missed them, here are some other recent articles to check out:

What are Con Artists?

While often depicted as attractive and oozing with charisma, confidence men and women come in various forms. Methods can vary but con artists look to exploit vulnerabilities, often psychological, to manipulate people.

To run a successful con, the victim needs to buy into the story they are being sold.

If you saw a beggar on the street asking for money while dressed in designer clothing, it wouldn’t align with your mental model of what a beggar would look like and you would question their legitimacy.

On the flip side, in Tenet, The Protagonist needs to convince people he’s a billionaire but as Michael Caine points out, Brooks Brothers won’t cut it.

Like an actor, con artists needs to walk, talk and dress the part. The better you do this, the more believable you will be, making it easier for people to accept your story.

There are countless complicated schemes, hustles and plays they might run to achieve this aim but it all comes down to deception, in order to manipulate.

In the case of Catch Me If You Can, Abagnale’s schemes are fairly straightforward. He identifies easy marks, often young single women and distracts them with his charm. At first he poses as an airline pilot with the aim of cashing fraudulent checks, amassing millions of dollars (in 1960s dollars). Then he decides to pose as a doctor then later a lawyer, all to impress a girl he meets.

In reality, the facade he’s creating is not to impress her, but to feed his own growing ego. The more his schemes work and he evades capture, the more infallible he believes he is. Fraudsters and liars never quit while they’re ahead, they just keep building more elaborate lies until they eventually blow up and get caught. This is true for Frank Abagnale, Elizabeth Holmes, Sam Bankman-Fried and countless others.

Common Types of Financial Fraud

Abagnale engaged in cheque forgery, Elizabeth Holmes lied to investors and customers, SBF used customer deposits to fund trades made by his hedge fund.

The application is different but these are all examples of financial fraud. They deceived and manipulated people to enrich themselves. To perform their heist, they all told stories their victims wanted to hear. Bank tellers want to provide fast and efficient service to wealthy bank customers. Investors want to back category defining companies. Abagnale, Holmes and SBF all walked, talked and dressed the part of somebody that fit the model of what their victims believed they would be like.

Abagnale wore fancy clothes and drove expensive cars. Holmes did a creepy Steve Jobs impersonation while SBF positioned himself as the young math genius, saving humanity from the evils of capitalism with effective altruism.

These crimes happened in different decades, and despite the banking system getting increasingly strict on fighting fraud it didn’t matter. Although regulations and technology has changed, at the end of the day, human judgement comes into play and this can be manipulated.

Banking Then, Now and In The Future

Banking has always been less about moving money and more about trust. The old system relied heavily on paper trails, local knowledge, and human discretion. Checks moved through routing systems and branch staff knew their customers, because suspicious activity had to be caught before it was processed. It was very high touch and personal but unfortunately slow, inefficient, and vulnerable to manipulation. In Catch Me If You Can, Hanratty explains in the 1960s, if somebody cashed a cheque in New York assigned to the California Federal Reserve, it would take two weeks to confirm the money was actually there. All Abagnale had to do was change a digit in the routing number and charm a leggy bank teller.

Modern banking replaced much of that with wires, ACH, card networks, and digital payments. Money moves faster, at a larger scale with less friction, but to enable this trust was industrialized. Instead of a branch manager making a judgment call, software scores the risk, compliance teams review the flags, and customers are forced through KYC, AML, and endless verification steps. Banking became more efficient by centralizing decision making to fewer people and financial actors.

This didn’t eliminate fraud; there’s an estimated ~$500 billion committed each year. It can take years to uncover these criminal actions, the real number can be much higher. Even if they’ve reduced paper, scammers have adjusted by hacking software systems or convincing gullible people to pay money for useless online courses, often taught by young dudes living in their parents basement. Fraud and Social engineering lives on.

The next shift is trying to further automate trust. Born out of dissatisfaction with the banking sector, Crypto aims to decentralize financial actors, and eliminate the need for trust, via transparency. Crypto and stablecoins promise faster settlement, at lower costs, on programmable rails. Stablecoins are quickly becoming must haves for financial actors, with many large players trying to quickly offer them to customers.

Now autonomous payments aim to take that further, with software agents transacting directly on behalf of users or businesses. This theoretically further reduces the need for individual trust, but so far Crypto has not managed to eliminate fraud, and it’s only a matter of time before somebody figures out how to hack autonomous payments.

This is because wherever money moves, someone will try to game the system.

Why Fraud Will Never Disappear

Every financial system is, at heart, a machine built to process trust at scale. That was true during Abagnale’s time and it’s true now. The infrastructure changes. The game does not.

Catch Me If You Can endures because it captures something permanent. Abagnale is not just exploiting a flaw in 1960s cheque processing. He is exploiting a flaw in human beings. People want the story to be true. They trust uniforms, credentials, status, confidence, and whatever best fits their mental model of legitimacy. That was true for bank tellers then, and investors in Theranos and FTX now.

Despite all the technical advancements, fraud survives every upgrade. This is because good sober judgement cannot be automated for every scheme, hustle and play that con artists can dream up. The method and applications will change, but fraud will never disappear because the incentives are too great. It’s will only a matter of time before the next Abagnale shows up.

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Roger Federer in his Dartmouth commencement speech pointed out he only won 54% of points during his tennis career, yet that slight advantage resulted in him winning 80% of his matches. Maintaining this over a 20+ year career that includes 20 Grand Slams, is why he’s one of the greatest ever.

Pretty much every moment of his life until he retired was dedicated to the sport. This is the case for any professional or almost made it athletes. Yet from this group, only a sub-group will be remembered after they retire, and even a smaller group will continue to garner respect generations later.

What separates these groups isn’t athleticism, skills or even hard work. It’s passion. Unbridled willingness to dedicate yourself fully to being the best at your craft for decades. Many will earnestly believe they have it, but few are willing to make the sacrifices that are necessary to reach the very top. Even with this, it only matters if they win. Nobody cares about your pain and sacrifice unless it amounts to something.

If you want to be great, you need to win more than anyone else. To do this you will be propelled by two emotions: Fear and Love. Both are necessary, but the formula is delicate. The absence of one or the surplus of another will be a hindrance. You need to find the right formula, and get lucky if you hope to be great.

Nobody personifies this better than another tennis great, Andre Agassi. His autobiography Open gave incredible insights into the psychology of being a winner.

Fear gets you to the arena but love is what keeps you there.

Keep reading if you want to learn how to be great.

If this week’s article does not interest you, please check out some other recent ones:

The Role of Fear

Andre Agassi is one of the best tennis players ever but for most of his life he hated tennis. He became the number ranked player in the world and won Grand Slams despite not even enjoying the activity he dedicated every waking moment to. This was only possible because of fear. Fear is also a proxy for insecurity.

As early as 6 years old, his father made him hit over 2,000 shots every day. Not softies either, he had to return shots fired at him from a souped up ball gun. Agassi didn’t want to do it, but he was afraid of his father, Emmanuel. The senior Agassi decided Andre was going to be a professional tennis player from the moment he was born. Emmanuel was a tough man who never knew love, and he took out the shortcomings from his own life on his son. This is a consistent theme among many greats.

His rational was that if Andre trained harder, played more tennis than anybody else and had the right coaching over time he would become the best player in the world. He beat the idea of perfection into him. Andre had to win every point and every set or his dad would yell at him.

Whether Andre was on board with his plan was irrelevant. He pushed Andre very hard and served as his coach until Emmanuel sent Andre to a tennis academy noted for its strenuous training regiment. This academy produced many professionals, but Andre was the star pupil to emerge.

He didn’t want to move across the country to a tennis academy or be isolated from his friends and family which were his only oasis from the sport. It didn’t matter, his father decided he was going to do this, so he went. The training Andre did put him ahead of everyone else, who were among the best young tennis players in the country.

This dominance carried over to tournaments, where he was beating professionals as a teenage amateur. He turned professional at 15 and never looked back. Within a few years he was among the top ranked players and regularly competing for Grand Slams. Despite the success, he never felt at peace or enjoyed tennis. His entire life he played tennis because he had to, not because he wanted to. His father decided for him he would be a tennis player and once he turned pro, he had no other career opportunities as a high school dropout.

Fear of his father and failure were enough to carry him to an elite level because of the work he put in. However, he didn’t become great until he discovered love.

(The only love he had was for his hair, which was unfortunately balding. Can you blame him?)

The Role of Love

Andre had a tight circle of friends that filled the void left from his father. If not for them, Agassi likely would have flamed out early on. His older brother, childhood best friend, a former Pasteur and his trainer Gil all played critical roles in his professional and mental wellbeing. They took care of everything outside the tennis court.

As his profile grew, Agassi to deal with the pressures of the sport, needed more love that his entourage could bear. He sought romantic relationships. He briefly thought he found it with Brooke Shields, who he would eventually marry, but he quickly realized he was wrong. She didn’t understand him, nor could she help him. If anything, her celebrity profile and lack of interest in tennis made it more difficult for Agassi. Shields was trying to revive her own acting career, and was looking for a similar level of support from Agassi, who wasn't in a position to provide it. What brought them together was their mutual fear of their overbearing parents and failure. They were both lacking love and couldn’t find it in each other. This is why both became depressed and their careers suffered. Agassi persevered though.

(They look happy)

Shortly after splitting from Shields, Agassi found a new objection of his affection. The tennis star Steffi Graf. She had previously ignored his romantic advances and was in a long term relationship, but Andre with encouragement from his team pursued her any way. His pursuit was eventually rewarded and once they started dating, they immediately realized how aligned they were. Steffi was near the end of her career at this point and had nothing left to prove. Graf had been the number one ranked player, won many Grand Slams and knew she would retire as one of the best woman’s players ever, yet one of her greatest contribution to tennis was the counsel she gave Agassi.

When Andre told her how he hated tennis, her response surprised him. She said of course he hated tennis. Nobody enjoyed spending every waking second training, practicing or worrying about what they can/can’t eat, dealing with the media etc. This was a common feeling amongst the professionals. Yet she said he wasn’t acknowledging the parts he loved about tennis.

His entire career he looked at tennis as something he was forced to do and he did it. Perfectionism made him hate tennis. He hated losing points and felt little satisfaction when he won them, since he expected to (sounds like prospect theory).

His approach brought him success without joy, since it felt like an obligation. Their relationship, reinvigorated him at a time when he should have been contemplating retirement. Instead he got a second wind and in his early thirties won a few more Grand Slams and recaptured the number one ranking, ultimately played until he was 35, well past his contemporaries. By this time he had two children and a loving relationship with Graf. He finally had something to play for.

With the shift in mindset of treating his profession as an obligation, rather than a craft he has the privilege of honing, he finally had the right balance between fear and love. It was during those final years, where the fans and sports writers who long wrote him off as a punk and an underachiever, changed their tune and in turn loved Andre too. This further motivated Agassi.

Although near the end his body was barely holding together, he couldn’t let go from the sport he spent such a long time hating. Fear got him to his knees, but love got him to his feet.

Many people start with love for their craft but quickly replace this with fear. This fear can help for a time but once they reach the top of their profession, the difference between the very best and the excellent is so thin, only those that love what they do can ascend. Being able to wake up and find joy in what you do is the not so secret to success.

If you want to be better than everyone else, you need to put in more time, work harder and get very lucky. The more time and hard work you put into your craft, the more luck will be able to find you. You have to remain persistent long enough to give luck a chance. If you don’t love what you do, you will give up too early, eliminating the possibility of luck breaking your way and giving you the outcome that will make you great.

Federer and eventually Agassi both learnt they didn’t need to win every point, perfection wasn’t necessary. Just systemically showing up, giving their best effort and loving the process. This is why they are among the few we will always remember.

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In the series Westworld, visitors knowingly enter a theme park of humanoid robots so convincing that the line between performance and consciousness begins to blur. In The Matrix, humans don’t realize their consciousness is just a projection of a simulated reality from a computer program.

Both stories explore what happens when simulations stop imitating reality and start replacing it. The experience becomes so immersive that participants can’t distinguish what’s constructed from what’s real. Eventually, the simulation no longer references anything outside itself, leaving the participant to accept it as the reality.

ChatGPT, Gemini, and Claude are trained on large data sets representing our world: text, images, videos, human designed programs etc. As they become more effective, people start using them to create these same representations and their outputs become an increasing share of internet content, software code, and white-collar work. They move from mirroring reality to becoming the models the world conforms to.

Until recently we could watch The Matrix, Westworld and other sci-fi and appreciate them as fiction. As society increasingly relies on AI, we trade our reality for one that more closely resembles theirs.

This is not new. Well before LLMs or the internet, Jean Baudrillard noted that society was shifting from using models to reflect reality, to allowing models to become reality.

His book Simulacres et Simulation (Simulations) published in 1981, inspired many of the ideas embedded within The Matrix but most were too distracted by Keanu Reeves and his impressive kung fu abilities to notice.

LLMs did not start this condition, but they are the latest edition of the Matrix we are creating. This is not another article claiming we live in a simulation; that question is irrelevant. If our reality becomes indistinguishable from a simulation, does it matter?

If you’ve ever wondered why people like Elon Musk believe we live in a simulation, what Jean Baudrillard saw coming decades ago, and why LLMs bring us further from the truth, keep reading.

If this week’s article does not interest you, please check out some other recent ones:

What is Simulation Theory?

Simulation Theory is the idea that what we experience is not reality but a simulated environment created by a more advanced civilization. The support for this theory doesn’t come from The Matrix trilogy but a probabilistic argument based on assumptions about technological progress and the vastness of the universe.

If we look at how much computing power has increased in recent years, imagine what it could be in hundreds or thousands of years from now. If that trend continues long enough, it would be possible to simulate entire worlds in extraordinary detail, including conscious beings inside them. These simulations don’t need to be perfect copies of reality, just convincing enough to those experiencing them.

Given the vastness of the universe, the likelihood there isn’t at least one civilization that much more advanced than ours, is low. If they can create one simulated world, they can theoretically create infinite simulated worlds, more than what exist in the universe. These worlds would be indistinguishable from one another, so neither people living in the simulated or base reality could know which one they were in.

You can listen to Elon Musk explain it in 2016:

Since we can’t confirm which one we inhabit, taking a Bayesian approach it’s statistically more likely we live in one of these simulations than an organic base reality.

This whole line of thinking was formalized by philosopher Nick Bostrom in his 2003 paper Are You Living in a Computer Simulation?. The paper sparked serious academic debate and remains the foundation of modern Simulation Theory.

However, besides being a fun discussion topic, usually after a few drinks or semi-controlled substances, this theory lacks practical application since it makes no testable predictions and cannot be empirically proven or disproven. It’s like listening to fervent atheists and religious people argue about the existence of God, or Lebron and Jordan fans argue about who’s the GOAT. It can be entertaining but there’s no way to definitively verify which claim is accurate.

If the goal is to understand how simulations shape real behavior, power, and meaning, there’s a more useful place to look. That place is Jean Baudrillard.

A Short Introduction to Simulation by Jean Baudrillard

While Simulation Theory debates whether we live inside a literal computer simulation, Jean Baudrillard was concerned with something more immediate. He was not asking whether reality was fake, but whether the distinction between reality and its representations still mattered.

In Simulacres et Simulation, Baudrillard argues that modern societies have shifted into a new stage of abstraction. Humans used to use images, symbols, and models to represent reality. A map is meant to represent a territory. A photograph is a representation of the subject in the photo. Numbers and statistics eventually tie back to a real world phenomenon. Any meaning derived from these symbols or representations were nothing without an external reference point you can experience.

Baudrillard noted that this relationship had collapsed.

Societies became too complex, which forced us to rely on representations instead of the base entity. Our world became too large to understand so we distilled it into shortcuts: Symbols, models, narratives, heuristics etc.

Over time, these shortcuts were layered on top of one another. Models were built using other models, which were built using earlier abstractions. This resulted in representations disconnected from reality, because they only reference each other.

Instead of the model describing the world, the world was reorganized to fit the model.

Baudrillard called this condition: simulation. A simulation is not a copy of something real, it’s a self contained system of signs that work together to produce its own version of reality. Whether it aligns with the reality the base symbols were derived from is unimportant.

A video game world does not need to obey the laws of physics to feel real to its players. It just needs to be internally consistent. Once that exists, endless content can be generated inside the game without ever referencing the physical world outside it.

Baudrillard argued that modern knowledge increasingly works this way. Look at academia. Claims are often built by referencing other claims, models, and frameworks rather than direct observation. This does not mean they are necessarily wrong, they just operate inside closed systems that most people cannot independently verify. (In many cases they are wrong, for reasons covered in Most of What You Know is Wrong)

As a result, much of what we accept as reality is mediated through layers of abstraction. We can no longer easily distinguish what comes from direct observation and what comes from models interpreting other models.

Baudrillard’s warning was not that this process would happen. It was that it already had… by 1981. Now AI is only going to make this worse.

AI & LLMs Get Us Further From The Truth

LLMs are a great representation of a Baudrillard simulation. Computer programs lack sensory access to reality, so they ingest endless representations, allowing them to produce outputs that appear as if they understand it. Unlike humans, LLMs can never observe any of this “knowledge” in real life (IRL).

To compensate for this, they rely on more representations and reinforcement from humans and other machines to validate their knowledge base. Meaning doesn’t come from observations, just agreement between systems.

(If you want to learn how LLMs work, see LLMs as explained by The Big Lebowski)

LLMs are wonderful at retrieving existing representations, but that’s not how they are being used. Instead of using ChatGPT, Gemini or Claude as a research assistant, users are increasingly trusting these tools to perform the task. This output will eventually become the representation these models will train themselves on.

As AI generated content makes up a greater proportion of content, we enter a Baudrillard simulation. A human coming across this content won’t be able to discern what came from another human or from AI.

If we haven’t reached that point already, it would appear we’re nearly there. In early 2025, many outlets reported that AI produces more internet content than humans.

At the same time, humans are becoming reliant on LLMs, which we’ve established lack a direct connection to the real world. As the representations they get trained on become more abstracted, the further they move from our reality.

This will make it impossible to tell when an LLM is hallucinating or missing relevant information. Things are quite bad as it is. People make major decisions based on headlines, slogans, or short video clips.

Many who passionately voted for Brexit, shortly regretted it afterwards. Shake weight sold millions of units off hype. Both were before the launch of ChatGPT. This is because humans have always struggled with decision making, we can’t blame AI.

Young people primarily get their information from social media, which is skewed for sensationalism, even if the Chinese government isn’t actively trying to make them dumber. Who can blame them? The platform is fun and designed to be addicting but it contributes to a society that’s poorly informed and less engaged.

It’s a natural progression of delivering content faster and easier. We moved from town criers to print, from print to television, from television to the internet. Each progression should have theoretically got us closer to the truth, yet misinformation remained. Now short form video and generative AI produce a hyperreality made largely of recycled symbols, optimized for engagement rather than truth.

The scary thought is many won’t see anything wrong with this. What does it mean for something to be real? Is there such thing as the objective truth? Finding out the truth of the universe is time consuming and hard, instead people consume useless content to escape from reality. Unfortunately, the longer they stay outside of reality, the faster they lose their grip on it.

This is why the question of whether we live in a simulation or not is no longer a relevant one. We have voluntarily chosen to leave our world behind by choosing the simulation.

In many cases, people only know or interact with the representation. Money began as an exchange between real assets such as fruit for cattle. Then wealth was represented by gold and silver coins. Then paper claims on those coins. Eventually, paper backed by nothing but the faith in government. Nowadays we rarely see physical money, just numbers on a screen. The underlying referent has faded from everyday life, replaced by systems that function because everyone agrees they do.

How much longer will it be until it’s our reality that’s been reduced to a simulation filled with representations with only faint echoes of what used to be the real world.

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By popular request, I’m releasing it earlier this year to give people a chance to buy some of these books before the holidays. Whether you know me from Substack, LinkedIn, or don’t, it should be apparent I enjoy reading on a variety of subjects, but they usually fall under one of these categories: finance/economics, history, productivity, health, and psychology, with some fiction thrown in. The same subjects I discuss on Serviceable Insights, funny how that happens.

Instead of combing through 8 years worth of posts, I created a Notion page with a Running List of Books From Previous Years. Check it out if you haven’t already.

If you want a bit of a description of each, I have a consolidated list in a Substack post for 2017-2023 (my apologies for the length & formatting).

For this year’s edition, I’ll include a short description of each book, along with my views and any associated articles I published related to them.

Keep reading if you want to inspiration for books to read in the upcoming year!

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If this week’s article does not interest you, please check out some other recent ones:

2025 Reading List

I’ve read 12 books so far and expect to finish another two or three before year-end. This is in line with other years and excludes books I started but didn’t finish.

The list contains a bit more fiction but otherwise is pretty consistent with other years with the exception of the absence of health/fitness titles this year; I got my fix doing research for my article on creatine. I haven’t come across any interesting ones lately but perhaps that will change in 2025 (send recommendations if you have them).

Without further ado, here is the list.

1. The Mezzanine by Nicholson Baker

   Rating: 70/100 (I would neither recommend no dissuade)

   Baker manages to make a journey up and down an escalator last over 100 pages, incredible from a stylistic standpoint. Fairly niche as a book, Baker isn’t the first to attempt this, but you need to be in the right mindset to get through a novel where nothing really happens. I enjoyed it, but if you’re looking for a page-turner, this isn’t it. I wouldn’t rate it higher because I don’t expect I’ll read it again, and I’d only suggest it for very avid readers, English-major types, or people who read James Joyce by choice.

2. The Castle by Franz Kafka

   Rating: 80/100 (I would recommend if asked)

   After thoroughly enjoying The Trial and The Metamorphosis, this one didn’t disappoint either. The Castle tells the story of a land surveyor’s efforts to reach the Castle in the town he was hired to survey. As you’d expect, in true Kafkaesque fashion, the task is anything but straightforward.

   It’s slightly more difficult to read than the other two mentioned above but nonetheless an all-time classic. Anyone who has ever had to navigate bureaucracy will relate to it.

   Not specifically about The Castle but my most relevant article from 2025 was How Society Uses Bureaucracy to Keep You Safe but Miserable)

3. How To Make A Few Billion Dollars by Brad Jacobs

   Rating: 75/100 (Would recommend but not insist)

   After listening to Jacobs appearance on the Knowledge Podcast, and hearing great things about his fireside chat with Paul Desmarais III, I decided to buy his book. If you don’t know who Brad Jacobs is, you should. He’s scaled several businesses in different industries to multi-billion dollar market caps. Few outside of Elon Musk can make that claim.

   The book itself is decent, though he performs better in podcasts discussing it. His charisma gets slightly lost in translation. I like Jacobs, so let’s blame his editors. If you don’t want to get the book, at least check out a few of his discussions. If you’re too lazy or time-pressed even for that, here’s an ultra-reductionist formula for making a few billion dollars: as a CEO or business owner, you need to

   (1) identify, attract, and retain the absolute most talented people you can; and

   (2) aggressively leverage technology, ideally in industries where others are not.

4. Chaos Kings: How Wall Street Traders Make Billions in the New Age of Crisis by Scott Patterson

   Rating: 80/100 (I would recommend if asked)

   Many are familiar with Nassim Taleb because of the success of his books The Black Swan, Fooled by Randomness, and Antifragile, among others. Before his writing days, he was a trader, a successful one. As his interests shifted to writing and teaching, he did less trading but co-founded a hedge fund with Mark Spitznagel called Universa.

   While Taleb eventually reduced his day-to-day involvement, Universa’s trading strategies maintained many of the principles he’s written about, producing spectacular returns uncorrelated with other top strategies. The audience for this book is fairly narrow: likely someone who has read Taleb’s other work, has a solid understanding of finance, and wants to read about internal politics at major pension funds. That probably leaves just me. I enjoyed it, but I can’t promise the same experience for everyone.

5. Clear Thinking: Turning Ordinary Moments Into Extraordinary Results by Shane Parrish* (Re-Read)

   Rating: 90/100 (I would actively recommend)

   With my bookshelves overflowing with unread options, if I choose to re-read something, it’s a pretty strong endorsement. In this case, I recommended Clear Thinking for a book club at my company. As the moderator, I needed to prepare for the discussions, I summarized my notes in two articles which you can check out here (Articles 1 and 2).

   Parrish is the founder of the popular website Farnham Street and the Youtube Channel The Knowledge Project.His subscribers number in the millions, and for good reason. He’s been sharing insights on mental models, decision-making, and learning for over a decade. Clear Thinking doesn’t disappoint if you want to deepen your understanding of those topics.

   

6. The Caesars Palace Coup: How a Billionaire Brawl Over the Famous Casino Exposed the Corruption of the Private Equity Industry by Sujeet Indap and Max Frumes

   Rating: 90/100 (I would actively recommend)

   I wrote about this just the other week (check that out here). This is a great book for people interested in the behind-the-scenes world of private equity, debt capital markets, and bankruptcy court. Think of it as a modern Barbarians at the Gate without the hype.

   For those unfamiliar with finance, it might feel dense at times, but that’s secondary. The drama between the finance heavyweights is as interesting as Apollo’s financial engineering.

7. Less Than Zero by Bret Easton Elis

   Rating: 80/100 (I would recommend if asked)

   Ellis, the author of American Psycho, published Less Than Zero at just 21 years old. While not an uplifting story, his ability to capture and subtly satirize wealthy LA teenagers in the 1980s is brilliant. Much of the criticism seems to come from readers who missed that Ellis was mocking this lifestyle. I’d consider it an accessible fiction pick for those who don’t typically enjoy novels, but if you’re looking for a feel-good story or lots of action, I’d look elsewhere.

8. The Price of Time: The Real Story of Interest by Edward Chancellor

   Rating: 90/100 (I would actively recommend)

   This was the best book I read this year. Chancellor’s deep dive into the history and economic ramifications of interest rates does a better job of explaining monetary theory than many economics degrees. His rigorous work shows how prolonged, artificially low interest rates are a key factor in economic bubbles.

   The first 100 pages serve as a great history of monetary systems and financial collapses. You don’t need an economics background to enjoy it. The later sections are more technical, but if you’re vaguely familiar with economic principles or willing to spend some time with Chat or Claude, it’s worth the investment.

   (My Article Nobody Understands Interest Rates summarizing some of the concepts)

   

9. The Technological Republic: Hard Power, Soft Belief, and the Future of the West by Alex Karp

   Rating: 70/100 (Would not actively recommend or dissuade)

   Karp is the Founder and Active CEO of Palantir. After operating in relative obscurity in the early years, Palantir has gradually risen in prominence as they’ve become an increasingly important part of the national security apparatus in many major countries. Their stock has been a meme stock with monstrous returns, that continues to trade at sky high multiples.

   As Palantir’s prominence grew, Karp became more outspoken. The Technological Republic recaps many of his public remarks, mainly that Silicon Valley’s reluctance to produce technology for the military weakens the West. He argues technologists have a moral imperative to work with the military.

   Realistically, his views could have been summarized in a few pages. The anecdotes are interesting, but the book drags; his charisma comes across better in interviews (many are on YouTube). You’ll get 80 to 90 percent of the takeaways from one of those.

   (See my article Is Alex Karp a Kafka or Dostoevsky Character?)

10. May Contain Lies: How Stories, Statistics, and Studies Exploit Our Biases—And What We Can Do about It by Alex Edmans

    Rating: 85/100 (I would actively recommend)

    This is next week’s article, so I will hold off on the summary for now but it’s worth checking out. Very good discussion how to separate fact from fiction. The best book on the subject since Thinking Fast & Slow, The Signal and The Noise or Thinking in Bets.

    Edmans, a finance professor at London Business School, examines how statistics, academic research, and media narratives can be manipulated, showing readers how to identify misleading claims and think more critically about data.

    Link to article will go here.

11. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott

    Rating: 70/100 (Would not actively recommend or dissuade)

    I have a half finished draft on this to be released at a later point.

    Scott, formerly of Google and Apple, outlines a framework for giving feedback that balances personal care with direct honesty, aimed at helping leaders build more open and effective workplace cultures.

12. Pnin by Vladimir Nabokov

    Rating: 75/100 (Would not actively recommend or dissuade)

    What’s considered to be Nabokov’s most approachable work, the semi-autobiographical tale follows Professor Timofey Pnin, an exiled academic teaching at a small American college, whose social awkwardness and nostalgia for his homeland create both humor and quiet tragedy.

Books in The Reading Queue

1. Simulacra and Simulation by Jean Baudrillard

   A philosophical treatise exploring how modern society has replaced reality with symbols and models, leading to a world of “simulacra” where representation becomes more real than the real thing. Famously, this book inspired The Matrix franchise.

2. My Uncle Oswald by Ronald Dahl

   A comic, risqué novel about the adventures of Oswald Hendryks Cornelius, a wealthy and scheming bon vivant who sets out to build a fortune by exploiting the libidos of famous men. It’s Dahl’s most adult and mischievous work.

3. Naked Lunch by William S. Burroughs

   A surreal, nonlinear novel that blends drug hallucinations, social satire, and grotesque imagery as it follows addict William Lee through a series of disturbing vignettes. It became a defining work of the Beat Generation and a landmark in experimental literature.

4. The 38 Letters from J.D. Rockefeller to His Son by John D. Rockefeller

   A collection of personal letters written by the oil magnate to his son, offering guidance on business ethics, philanthropy, and personal conduct. The correspondence reveals Rockefeller’s views on success, discipline, and moral responsibility.

   

5. House of Cards: A Tale of Hubris and Wretched Excess On Wall Street by William D. Cohan

   A detailed chronicle of the 2008 collapse of Bear Stearns, examining how arrogance, greed, and mismanagement brought down one of Wall Street’s most storied investment banks. Cohan draws on insider accounts to capture the drama and dysfunction of the era.

6. The Long Tail: Why the Future of Business Is Selling Less of More by Chris Anderson

   Explains how digital marketplaces and distribution networks have shifted business models from mass hits to niche products, showing that profitability now lies in catering to the “long tail” of specialized consumer demand. A foundational text in internet-era economics.

7. Conspiracy of Fools by Kurt Eichenwald

   A fast-paced narrative recounting the rise and spectacular fall of Enron, tracing the hubris, deception, and accounting fraud that led to one of the largest corporate scandals in history. Reads like a thriller but remains meticulously sourced.

I hope you find some inspiration from all of these titles, I look forward to checking in with you next year with the books I read in 2026 and other titles I’m looking at for 2027. Happy reading!

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Paulson, Geithner, Bernanke, and others stepped in with bailouts and money printing. I don’t need to explain that story. You’ve probably seen The Big Short or Too Big to Fail.

What if I told you that between 2005 and 2007, a similar wave of reckless risk-taking was happening elsewhere, in the beloved private equity (PE) industry?

Today, most people have heard of private equity. They are the ones who buy your favorite brands, load them with debt, cut costs, send the quality to sh!t and somehow still end up in bankruptcy court. Twenty years ago, PE was still fairly obscure.

The industry first rose to prominence in the 1980s, fueled by the junk bonds of Michael Milken and Drexel Burnham Lambert. The battle to take RJR Nabisco private was immortalized in the classic Barbarians At the Gates. After Milken’s arrest in 1989 (documented in Den of Thieves), activity slowed, but by the early 2000s, funds were larger than ever. With debt markets chasing yield, PE firms could once again take some of the biggest public companies private.

That period saw a wave of megadeals involving well-known brands such as Toys “R” Us, Hilton Hotels, and Harrah’s Entertainment (later Caesars Palace).

I picked up The Caesars Palace Coup on a transatlantic flight and could not put it down. The investigative work by Max Frumes and Sujeet Indap outlines the leveraged buyout of Caesars by Apollo and TPG, the internal turmoil that followed the 2008 crisis, the financial engineering used to avoid breaching debt covenants, and the years-long legal battles among creditors, Caesars, and the private equity sponsors.

The book perfectly captures what happens when private equity overpays and overleverages. It also explains why debt covenant contracts today run thousands of pages long, earning law firms substantial fees.

In this piece, I will summarize the key lessons from The Caesars Palace Coup and explore what it reveals about private equity, debt, and how great businesses can be destroyed by financial engineering.

Keep reading if you want to learn about the private equity industry, debt, business management and bankruptcy courts!

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Basic Primer on Private Equity

Private equity firms raise funds that pool capital from investors known as Limited Partners (LPs). The private equity firm itself acts as the General Partner (GP). These funds are structured as partnerships for tax reasons. This is the whole carried interest tax loophole libs are always clamoring about.

The GP takes the committed capital from LPs and uses it to identify and acquire businesses it believes are undervalued. Once under their ownership, they usually make changes to the company’s management team, operations, and capital structure (more on that later) to increase the value of their stake before selling it.

A typical private equity fund targets between 6 and 15 investments. Unlike venture capital firms, which make dozens of bets expecting only a few to drive returns, private equity funds rely on more consistent outcomes across their portfolio. Their investments usually have a lower upside but less binary risk, so each deal must generate a meaningful return. (Click here for a long winded explanation of VC)

The LP commitments represent the equity that the private equity fund invests in its portfolio companies. The rest is financed with debt. In most cases, buyouts are funded with 60 to 80 percent debt, depending on credit conditions and the risk tolerance of lenders. This is why they are called Leveraged Buyouts (LBOs).

Covenants are restrictions placed on a company until its debt is repaid. They typically include financial ratio requirements such as EBITDA or operating cash flow needing to exceed interest payments by a certain multiple (anywhere from 2-6X). Covenants can also limit asset sales, dividend payments, or additional borrowing. They exist to protect lenders and ensure that equity holders don’t plunder the business and get reckless with borrowed money.

Debt is often issued in multiple tranches, each with a different level of seniority and repayment priority. Senior debt sits at the top of the capital structure and is often secured by specific assets or the company as a whole. Junior or subordinated debt sits below it, is often unsecured, and carries a higher interest rate to compensate for the greater risk of non-payment in the event of default or bankruptcy.

If everything goes according to plan, the private equity firm acquires the company, raises the necessary debt, makes operational changes (cost reductions or asset sales), and uses the company’s cash flow to service the interest and gradually pay down principal. When the firm exits the investment, the lower debt balance means the equity value has increased, similar to how a homeowner builds equity by paying off a mortgage.

Unfortunately, just like with mortgages, companies can fall behind on their payments or even default. When that happens, they must negotiate with creditors or file for bankruptcy. This is when the real fun begins. Creditors, management, and the private equity sponsors all fight to protect their claims, and if no settlement is reached, the battle moves to bankruptcy court, where lawyers argue over who is entitled to what.

Normally it doesn’t come to that, but when it does chaos can ensue. Just like it did in the case of Caesars Palace.

A Short Overview of The Caesars Palace Coup

I will now try to summarize a 300 page book in a few short paragraphs, if you find this remotely interesting, check out The Caesars Palace Coup.

Harrah’s Entertainment had been operating regional casinos for decades until a Harvard professor named Gary Loveman came along and realized there was a massive opportunity to use data and analytics to improve the customer experience. Other casino operators focused on real estate and spectacle, building ever-larger resorts, while Loveman focused on understanding customer behavior. He launched a loyalty rewards program that proved to be a gold mine for Harrah’s. Instead of returning to academia, Loveman stayed on and eventually became CEO.

Under Loveman, Harrah’s revenue grew consistently across all locations and business segments. Yet Loveman could never understand why the market wasn’t rewarding the stock with a higher valuation multiple. The stock seemed perpetually cheap. He wasn’t alone in thinking that.

Private equity giants TPG and Apollo group shared Loveman’s view. Harrah’s had all the qualities of a perfect private equity target. Strong management team, low debt in it’s capital structure, consistent cashflow and the casino business was believed to be recession proof.

In 2006, Harrah’s had at a market cap of ~$15B and $10B of outstanding debt giving it a total enterprise value (TEV) north of $20B. Acquiring a company of this size would have previously been unthinkable but in the early 2000’s PE firms had taken several large companies private such as Hilton Hotels ($26B), Toy-R-US ($6.6B) and Texas Instruments ($44B). PE funds were raising larger funds and there were many interested lenders willing to fund these large LBOs.

TPG and Apollo paid a total of $28B to acquire Harrah’s, which they later renamed Caesars Entertainment, after their most visible asset. From that purchase price, about $4B of that was equity with the rest coming from debt financing (85% debt). Some of the existing lenders rolled over their debt but TPG and Apollo had to raise ~$20B from the market. They had to do this during 2007 as banks and lenders were starting to become skittish about lending. Nonetheless, they got it done and the deal closed in January 2008. Just months before the financial crisis.

The debt carried pretty much no covenants. The only one was they needed to maintain an Interest Coverage Ratio (EBITDA / Interest Expense) greater than 2.0X. That’s not asking for much. Sign of the times. Probably why the financial system nearly collapsed a year later. As such, TPG and Apollo’s thesis of the Casino business being recession proof was put to the test.

Turns out, during a crisis, people don’t have money to go to Vegas and gamble. After years of steady growth, suddenly Caesars revenue was getting wrecked. This is after loading up with $20B of debt, much of it high yield. It wasn’t long before they started to flirt with the 2.0X Interest Coverage Ratio Covenant. TPG and Apollo needed to reach deep into their bag to stem the tide.

TPG tried to help streamline operations by reducing costs anywhere they can; not easy in a heavily unionized environment. The net result, Caesars stopped investing in hotel upkeep and they started to look shabby. Guest and employee satisfaction took a hit. Meanwhile Apollo took care of financial engineering. They created a maze of subsidiaries and special-purpose entities, transferring assets among them to raise cash and to protect certain properties from creditors.

These maneuvers were meant to buy Caesars time to weather the storm and get back on track but it didn’t happen as quickly as they had hoped. Caesars revenue continued to slump, underinvesting in maintenance wasn’t helping things. The debt burden kept growing and it eventually became clear Caesars was going to default.

Apollo’s use of these entities was not exclusively benefit of the Caesars parent company, they were trying to keep some of the better assets out of the reach of creditors in the event of bankruptcy proceedings. When creditors found out about this, they were pissed. These creditors they were upsetting were some of the largest and sophisticated firms in the financial world, such as Oak Tree Capital (led by Howard Marks), Appaloosa (David Tepper), Elliot Management (Paul Singer), GSO and many others.

In the years long legal battle that followed, Apollo and TPG lost badly. In 2017, the creditors were made whole and the partners working the deal for Apollo and TPG were lucky they weren’t personally held liable. Despite the stumble, neither firm really suffered. They continued to raise larger funds, their efforts to avoid bankruptcy was well received by LPs. Caesars Palace still exists today and they did eventually grow into the valuation Apollo and TPG expected it to, it’s just that the excess value went to the debt holders and none went to the investors, employees or other shareholders. Loveman lost his job but at least a bunch of law firms earned millions in fees from all their litigation efforts.

How Private Equity Impaired a Healthy Business

Harrah’s Entertainment was thriving under Gary Loveman’s leadership. The company was steadily growing revenue each year, customers were loyal, and employees were motivated.

Unfortunately, Loveman’s frustration with the company’s stagnant share price led him to fall prey to the same siren song that lured F. Ross Johnson into the ill-fated RJR Nabisco buyout. He was not only enticed by the financial upside of the deal but also believed that the expertise of Apollo and TPG would help take Harrah’s to the next level.

Harrah’s was performing well, it was not a distressed asset. That meant the private equity firms had to pay a high price to acquire it. The timing, however, could not have been worse. Revenues began to decline almost immediately after the deal closed. Apollo and TPG had contributed only a small amount of equity, relying on extreme leverage to create value.

As growth slowed, valuation multiples compressed and profitability fell. The company could no longer service its massive debt load. It was a perfect storm of everything that private equity investors fear: falling revenue, tightening credit conditions, and debt levels too high to sustain.

Their cost-cutting measures provided short-term relief but did little to address the deeper issues created by excessive leverage and a collapsing economy. The absence of strong corporate governance allowed the private equity sponsors to run Caesars with minimal regard for other stakeholders, treating it more like a balance-sheet experiment than a living business.

If not for the intervention of Oaktree, Appaloosa, Elliott, and the court system, Apollo and TPG might have escaped accountability. Instead, they were forced to confront the consequences of their own financial engineering and the value destruction it caused.

Still, both firms were large enough to move on. Within a few years they had raised billions more and were back to buying new companies. For them, Caesars was a lesson, not a scar. For everyone else, it was a warning.

Private equity can work when executed with discipline, patience, and aligned incentives. The asset class has produced genuine success stories. This was not one of them.

The Caesars Palace Coup highlights its dark side: when greed, leverage, and misplaced confidence combine, even great companies can be hollowed out from within.

The next time you see a beloved brand “go private,” remember that it might not be for its own good.

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Aligning with Clear Thinking, the first part covers why *actually thinking is important. Sounds obvious but we often do things without thinking because of various barriers and default behaviors which impede our progress. Between Lord of the Rings, The Godfather, and every other pop culture at my arsenal, you likely thought I was tapped out. The cupboard was bare.

Well guess again.

Buckle up buckaroos! Sequels are often disappointing but that is not the case this day. Building on what we covered in Part I, this article will focus on building mental strength. What are the skills and traits needed for you to overcome default cognitive biases and put you on the path to success?

How else do you plan on hosting the Catalina wine mixer and driving a Range Rover? Luck? Brute force? Creatine? Good luck with that.

Continue reading if you want to learn how to think good!

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Part Two: Building Strength

To defeat the enemies of clear thinking you need more than willpower.

You are fighting against biology and decades of existing behavior. You can’t willpower or white knuckle yourself to success. We need equally powerful forces on our side:

Last week we discussed why inertia can hurt, but it can help us as well. Once you start building positive habits, the longer you stick with them, the harder they become to break. Do you brush your teeth everyday? Is this a decision you struggle with? I hope not. You’ve been doing it for so long, it’s no longer a difficult habit to maintain.

Similarly, the longer you eat healthy, the easier it is to continue. A good diet becomes the new default and harder to break. Comedian Tom Segura recounts his experience eating fast food after a long streak of clean eating, suddenly one bite made him feel awful, discouraging him from reverting back to his previous unhealthy eating habits.

There are some tools you can use, such as rituals. Rituals focus the mind on something other than the moment. It creates a pause, enough time for the rational part of your brain to weigh in, before you act.

Beyond rituals there are four types of strengths you need to develop if you want to fight against the enemies of clear thinking:

2.1 Strength #1 — Self-Accountability

Self-Accountability is taking responsibility for your abilities and limitations. Without this you won’t be able to move forward.

Part of being an adult is the ability to hold yourself in check without needing parents, teachers or mentors to do this for you.

This is part of the danger of defining success or failure based on external rewards. Whether that’s trophies, praise or acknowledgement. To be successful you generally need to be willing to commit to things for extended stretches where you won’t get external feedback. They don’t conduct competitions or give out medals each day.

Only you can gauge if you are improving or on the path to success. You need to be able to accept responsibility when you screw up, or else you are feeding into your ego’s desire to shield you from blame.

You are the master of your fate, you are the commander of your own soul.

People who lack self-accountability are running on auto-pilot and will never be in charge.

Parrish gives the example of his inability to deliver the software update on time and despite his myriad of excuses, his colleague didn’t care. If he couldn’t deliver his work on time, they would need to delay an important mission. Parrish defended his ego with all the reasons it wasn’t possible. His colleague didn’t care. It was on Parrish to manage his workload based on the deadline, neither of them could control.

Parrish uses this to contrast the difference between kind and nice people.

Kind people will tell you things a nice person will not. A kind person will discreetly tell you when you have spinach on your teeth at a social event whereas a nice person won’t say anything because it’s uncomfortable. A kind person will share hard truths, even if it might be uncomfortable for them and the receiver of the message. A nice person will avoid giving critical feedback because they are concerned with hurting somebody’s feelings.

Nobody cares as much about your excuses as you do. At the end of the day, it comes down to if the outcome was reached or not. In the NBA, players acknowledge it’s a make or miss league. If you make the shot, you’re the hero. If you miss, nobody cares about how much you practice or how pretty your jumper is.

Self-serving bias will always come up with reasons or excuses why there was nothing you could have done to change the outcome. Whether it’s your fault or not, it’s still your responsibility. Sometimes the circumstances are not in your favor. You might have been dealt a bad hand but all you can do is your best given the circumstances. Poker players know even if they play a hand perfectly, they can still lose.

As a personal trainer, too often I could see clients refuse to accept accountability for their actions. They would show up to all you can eat buffets before a training session and blame external factors on this. Clients that only came because their wife/husband wanted them to be there, were almost never successful. I would only spend a few hours with my clients each week and couldn’t control what they did the second they left. To achieve their goals they would need to take accountability and ownership.

When I started as a fitness professional, I was nice. As I got more experienced, I became kind. I would start to tell them the reason they weren’t seeing results was because they weren’t holding themselves accountable. They could drive to McDonalds right after the gym and guzzle down 3 milkshakes. If they wouldn’t take accountability for their health, they could never be successful.

How you respond can make things better or worse

You can’t control everything but you can control how you react to things. This is a lesson from stoicism. If somebody cuts you off in traffic, you can’t control their car but you can control how you respond to the situation.

Parrish suggests asking yourself “Will this action make the future easier or harder?”.

If you find yourself in a hole, stop digging.

“You’re refusing to accept something that already happened, and that’s crazy.”

Complaining is not a solution. You are not a victim. The most important story is the one you tell yourself. No successful person wants to be around a chronic victim, a passive person. Self-accountability is the strength of realizing that even though you don’t control everything, you control how you respond to everything.

2.2 Strength #2 — Self-Knowledge

Know thyself

If you never utter the phrase “I don’t know” you are aren’t trying to understand. You are probably dismissing things that surprise you. Otherwise you are just trying to rationalize outcomes instead of figuring out how it worked or why that happened.

Accurately being able to assess what you know and don’t know is the key to playing games you can win. Smart people get into trouble when they try to step outside their domain of expertise. Believing because you are successful in one arena, this will automatically translate to success elsewhere is simply hubris. We touched on the Dunning-Kruger effect last time, proving a little knowledge about a topic is a dangerous thing. Understanding how much you know compared to the average participant is essential to figure out your chances at outperforming. Otherwise you are playing a game of chance, with bad odds.

Parrish uses the example of smart real estate investor declining to invest in a business outside of his area of expertise. Too often, our egos will lead us to overstate our chances of winning in activities we aren’t experts in. Charlie Munger shared a similar sentiment, figure out where you have the edge and stick with that.

In some cases, skill doesn’t play a large role in the outcome. The probability difference for winning between a professional and an amateur is relatively small, such as a single hand of poker or Bingo. In these cases, it’s not irrational to think you can win in these kinds of games. However, in other activities where luck plays a relatively small role, such as sprinting or swimming, talent is nearly directly proportional to your chances of winning. If you are going to try your hand at something you aren’t an expert in, you should first evaluate to what extent can a less skilled participant win. (I covered this in greater detail in How To Make Better Predictions).

2.3 Strength #3 — Self-Control

Without the ability to control impulses, you aren’t any different than wild animals in the forest. You can’t eliminate physiological reactions or the conditions that trigger them but you can manage how you respond to them. Often creating space by pausing or slowing down, gives a chance for your rationality to catch up to your default instincts or behavior.

Channeling intensity from short bursts into prolonged motivation is what separates winners from losers. This is why Odysseus can survive the entire Odyssey, whereas Ajax can’t even get past the first battle against Hector (film only reference. They nerfed Ajax like crazy in Troy (2004) but Brian Cox as Agamemnon was phenomenal).

If you can’t control your impulses, you are sabotaging yourself, making it harder to reach your long term objectives. It’s as if you’re in a canoe with one person occasionally paddling in the wrong direction. You might not always make the right choice but at least make sure you aren’t fighting dissent within your own camp (mind).

2.4 Strength #4 — Self-Confidence

Self-confidence is sticking the right balance between your earned competence and your aspiration (belief) of where it can be.

The story of Icarus flying too close to the sun, shared another, often overlooked lesson. If Icarus flew too low, he would have also perished. Many focus on hubris, and overconfidence leading to the fall but many ignore that most dreams are killed not by a lack of competence but people’s lack of confidence to even attempt a daring feat. (More about that in The Power of Confidence).

Dunning-Kruger effect is so powerful because it shows how a little knowledge coupled with excess confidence creates a dangerous cocktail. Being able to discern what you know, versus what you strongly believe is very important, otherwise you fall into dangerous thought patterns you won’t be able to break free from.

The people who fail the most are those more focused on proving they are right instead of being right. Outcome over ego.

2.6 Setting the Standards

You are the average of the 5 people you spend the most time with.

I discussed this in The Most Obvious Secret to Success. Set high standards for yourself, and this should hopefully raise standards for everyone. If you are in a losing environment, eventually you will become a loser. Any good coach, general manager or HR team’s job is to make sure they hire people that will contribute to a winning atmosphere that raises standards, and get rid of people that detract from this.

Champions don’t create standards of excellence, standards of excellence create champions. Parrish shares an anecdote about Henry Kissinger during his time in the State department. Known for exceptionally high standards, when a staffer came with a draft of a memo, Kissinger asked him if it was his best work? The staffer took it back and worked on it more. When he returned to Kissinger, he got the same question again. He returned to polish it further. Only after his third attempt did Kissinger agree to read it.

He didn’t want to waste time looking at unpolished, incomplete drafts. Parrish doesn’t want to either. If you create a culture where presenting incomplete drafts is acceptable, then that’s what you will get.

I do think it’s important to caveat that in some cases speed is better than perfection. Having spent endless hours working on internal documents that never got read or used for anything useful, I eventually opted for sharing drafts very quickly to solicit feedback before investing more time into it. When you are busy and you receive unclear, open ended instructions, it’s likely your efforts will be wasted.

This should not be an excuse to do work badly, when you receive a clear and precise request, it should be done well, the first time. Low standards often come because we don’t care. We lack pride. You shouldn’t accept shipping out low quality products or else you will eventually forget what good and great looks like.

At the same time, you need to exercise judgement when you don’t want to make the perfect the enemy of the good. If you can do something well in 1 hour but it would require 5 hours to make it perfect, you need to decide if the additional investment is worth it. In the case of airplane safety, I would say yes. For an internal memo nobody is going to read anyway, good is likely sufficient.

2.7 Exemplars + Practice

Choose the right exemplars, models to follow. Show me your role model and I’ll show you your future. A better boss will make you better. A strong colleague makes you stronger (check out this article by Giacomo Falcone (no not of the Falcone crime family you Batman nerds) about how your desk mate might be sabotaging your career.

The concept of Mimetic theory from Rene Girard, popularized in Silicon Valley from Peter Thiel and others, believes that desire is driven imitation of our models. We see somebody we aspire to be like, which guides our actions and behaviors to imitate them. If you have high quality A players, managers and mentors around you, there’s a pretty good chance you will mimic their behavior increasing the likelihood of you being an A player in your own right.

Your exemplars or models don’t need to be alive or somebody you know personally. If you believe mimetic theory, it’s preferable to be somebody you don’t know or can possibly compete with. Otherwise this will eventually invite rivalry.

Conclusion

Clear thinking doesn’t just happen, it’s a skill you cultivate. The strengths of accountability, knowledge, control, confidence, and high standards aren’t abstract ideals, they’re muscles you can train every day. Habits turn into defaults, rituals give you pause, and the right role models show you what’s possible. If you commit to practicing these strengths, you stop running on autopilot and start designing your outcomes.

In the end, clear thinking is less about avoiding mistakes and more about consistently stacking small, better choices that compound over time. The future will always test you, but if you’ve built strength, you’ll be ready to meet it head on. No excuses, no shortcuts, and without needing luck or brute force to carry you through.

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They are often an excuse for self-proclaimed intellectuals to convey status. A venue where they can embarrass so-called friends and acquaintances with their superior insights. Others might just be there for the snacks or excuse to socialize without having read the assigned book.

I have been part of several of such groups; good times were had and most ended without violence or death. This is why when my company was brainstorming ways to get employees engaged with the new core operating principles we were rolling out, I suggested we start a book club.

As the principle for the month of August was to "Be fact-driven and purposeful.” the first person that came to mind was Shane Parrish. Parrish worked in a Canadian intelligence agency before founding the popular website Farnham Street. Farnham Street is dedicated helping people “Think better. Make smarter. progress in () life and career. Find your focus.” Between Farnham Street, his newsletter Brain Food and his YouTube channel, Parrish has an audience of millions, including yours truly.

This is why for the inaugural book club meeting, I suggested Shane’s book, Clear Thinking. If you are serious about making better decisions and putting yourself in the best position to achieve your goals, Clear Thinking is a must read. In today’s article I give an overview of some of the principles and ideas from the first part of the book, with the hope this inspires you to read this for your own.

Check here for Part II.

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Section One: Enemies of Clear Thinking

1.1 Think Badly or not at all?

Intelligent people regularly do stupid things. A stupid action isn’t when you get an undesirable result, but from following a process that obviously wasn’t going to work. Stupid actions usually arise not because we lack intelligence but because we weren’t thinking clearly.

Think back to the last time you did something you immediately regretted. Did you spend minutes to hours on the decision or did you just react?

Rationality is wasted if you don’t use it. Too often logic gets crowded out by other factors: our default actions or behaviors. Sometimes we are quick to anger or fast to assume intent. When we rely on our defaults, instead of our rational thought, we are more likely to do stupid things, or actions we will later regret.

Being aware of these barriers to clear thinking is the first step to try to prevent them from crowding out rational thought. Think of these barriers as little Gríma Wormtongues from Lord of the Rings whispering into Théoden King of Rohan’s ear. Only once they removed Gríma from his side could he think clearly again.

Here are some of the barriers to clear thinking:

1.2 The Emotion Default

Parrish uses the example of Michael & Sonny Corleone. One doesn’t allow emotions to cloud their judgement, the other succumbs to them. Predictably one dies much sooner than the other. Sonny’s inability to manage his emotions while making decisions causes him to make many unforced errors. This reckless behavior creates a huge mess for the Corleone family, forcing Michael to clean up the mess.

There is a Sonny Corleone in all of us.

When we are reacting out of anger, sadness or another emotion, we aren’t in an optimal headspace for decision making. Whether this is how we comport ourselves in our personal lives or make big decision for our careers, our emotions at the time of the decision should not be the loudest voice.

(Not a fan of The Godfather? you can also check out Stoicism Explained by Star Wars)

1.3 The Ego Default

What matters more, appearing successful or being successful?

The answer might seem obvious but hubris has been the ruin of many. Not only is it enough to win, people want the praise and trappings that come with it. Before long, people get more satisfaction from the latter, than the former and that’s when trouble arises. This is why victorious Roman generals would have a slave (servus publicus) stand in the chariot with them whispering reminders their mortality (“Memento mori”).

It’s also true that without confidence, you won’t accomplish much. What’s important is that your confidence needs to come from competence or it’s simply hubris. Being aware of your abilities and limitations is important when making decisions. Overestimating your talents or worth can get you into dicey situations.

It might seem obvious but this happens all the time. There’s a reason why one of my most viewed articles to date is titled “Should I Go into Debt for a Rolex”. People want to hack their way to status, which they wouldn’t need to do, if they had it.

Parrish reminds readers of the Dunning-Kruger effect; a little knowledge can give you unjustified confidence which begins to decline as you get a bit more.

1.4 The Social Default

How often are our choices our own? Are we doing things because we believe they are right or because that’s what everyone else is doing. Have you ever started clapping because other people around are? Sure you have. It’s hard to fight the urge. Social pressure is a powerful thing.

It’s not fun to feel part of the “outsider group” we want to be accepted. We don’t want to stand out, so we would rather do the same as others even if we don’t agree. We are effectively outsourcing our thoughts to others. Sometimes there’s strength in numbers and you can benefit from the wisdom of the crowd, other times that wisdom is madness.

As we increasingly outsource our thinking to LLMs or our investment decisions to ETFs, we are not really thinking, we are operating on auto-pilot and letting the universe decide our fate. If you’re an economist that believes that humans are rational decision makers, perhaps this is a good thing. For those of us living in the real world, we are just as likely to be listening to people that have also yet to abandon their defaults. Which is why groups can hold wrong views for a long time.

Parrish gives the examples of virtue signaling. Many people suddenly adopt the same set of professed beliefs because it costs them nothing to be wrong since they are sticking with the herd. He uses the example of a Princeton Professor that asked his students what their position on slavery would have been if they were white living in the south prior to abolition. Guess what? Everyone in the class believed they would have been abolitionists, that would have spoken out against slavery and worked tirelessly against it. That’s easy to say in 2025 but we know people rarely want to go against common convention.

Even if they felt like it was wrong, they probably wouldn’t have spoken out against it. They wouldn’t want to have risked the backlash by straying from the consensus. How often do you see somebody decidedly right-wing or left-wing politically speak out against their parties orthodoxy?

Ironically it’s those that go against convectional beliefs that often make history. We only know or care about artists who dared challenge convention or take risks. You might underperform but you also might change things for the better. This is also why best practices aren’t always the best. By definition they are average (I wrote about this in Benchmarking is Lazy).

Contrary to what people think, being right or wrong isn’t based on if people agree with you or not. You will be correct if your facts and reasoning are correct. Unfortunately in a corporate environment, risk taking or trying things outside convention is often discouraged. Managers or execs would rather stick with the crowd so if things don’t go their way, they can minimize their own involvement in the outcome. Buffett talks about the agency-principal problem. Personal gain/loss ratio is too obvious, most people just don’t want get fired so trying something new and risky isn’t worth it. If it works out the company benefits more than they do, if it doesn’t work out, they get fired but the company persists.

1.5 The Inertia Default

The reluctance to act or change is very powerful.

How often do you change toothpaste brands? Experiment with new hairstyles or take a different route to work? One of my favorite tv shows Westworld shows humanoid robots following different loops, yet upon reflection, we humans follow very similar loops since we rarely stray from pre-determined behaviors. We stick to decisions we made long ago, regardless of how our environment has changed or what new information has come to light. How open minded can we be if we don’t change?

Shane shared an experience many investors can relate to. He invested in a promising restaurant chain with a CEO, Shane highly trusted. In the years following the investment, the CEO made many small transgressions which were easy to rationalize at the time. Eventually the CEO’s attitude impaired the investment. Only when Shane zoomed out, did he realize the signs were there but he was too slow to change his mind. If he were quicker to react, he might have been able to salvage his investment.

Objects never change if left alone. They don’t start moving on their own if not touched. Once minds are set in a direction they will continue in that direction until an outside force forces a reconsideration of that view. This is why it’s not a coincidence conspiracy theorists often live alone in a cabin in the woods. There’s nobody to talk sense to them. This further gets into problems with LLMs re-enforcing problematic beliefs or when people create echo chambers by not seeking out contrary viewpoints or ideas.

There are many reasons why people don’t want to change. Anybody working in sales & marketing pros understand this well; since their job is generally trying to convince somebody to change or adopt a new behavior. People are afraid the change will lead to worse results. People will prefer discomfort over uncertainty. Assuming you clear the uncertainty hurdle, you next must contend with another: the resistance to new effort. Especially if they aren’t convinced this new effort won’t lead to a worse outcome.

Good salespeople or marketers can give their target audience the confidence that adopting their product/service will not require a lot of new effort and will lead to a better outcome. You need to be the best sales person for clear thinking.

How often do you double down when you are wrong instead of stepping back, re-evaluating and admitting you stuck with the wrong choice for too long? Don’t let your reluctance to change prevent you from making a better decision.

1.6 Default to Clarity

We can’t eliminate our defaults. We can re-program them.

Shane Parrish advocates for the same advice I offered in my most popular Substack article to date, Sorry Jocko, Discipline is Overrated (12K+ views). Instead of repeating what I covered in the article, I’ll summarize by saying we both posit the reason we fail to reach our goals is because relying on discipline alone will guarantee failure. Instead build systems which put you on the path to success. Re-program your defaults. If your goal is weight loss, remove sugar filled beverages from your house and replace them with healthy alternatives.

Conclusion:

Clear thinking isn’t about eliminating mistakes, it’s about stacking the odds in your favor by refusing to operate on autopilot. Parrish begins Clear Thinking by discussing barriers for a good reason. When you become aware of your defaults, you give yourself the chance to override them. That’s how better decisions are made. Not by luck, but by design. Part II will dive deeper into how to reprogram those defaults, but for now, the challenge is clear: start noticing when you’re about to act like Sonny Corleone, follow the herd, or cling to inertia. Awareness is the first step to clarity.

See here for Part II

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1. Hooded guy blasting Linkin Park through his headphones whilst fighting demons

2. Fitness influencer only training the gluteus maximus in front of their tripod

3. Loud, broccoli haired teenagers taking up space but not doing much exercise

4. Creatine

Creatine has been a gym staple since Jane Fonda’s workout tapes and for good reason. Unlike most gym supplements, it actually works. Results may vary but taking creatine will lead to an increase in muscle mass and strength. This has been known for decades. While there has been some debate around dosage, studies are aligned. If you don’t believe sissy scientists, ask a bodybuilder and they’ll tell you the same.

Yet suddenly creatine is appearing in places you would never expect. No longer relegated to workout sites, it’s now showing up in prominent podcasts, newsletters, and dinner party conversations. The Economist wrote about it last week and recently PGA tour golfer Ben Griffin blamed overdosing on creatine for his poor round.

This is thanks to the army of health gurus with microphones and dimmed out green screens. People like Andrew Huberman, Rhonda Patrick, and Peter Attia have elevated it from a strength-and-conditioning staple to a must-try bio-hack offering cognitive benefits and even the ability to offset sleep deprivation. Their audience, which numbers in the tens of millions hang on their every word.

As a mere mortal I wasn’t immune to the hype. I had tinkered with creatine early in my fitness days but never stuck with it. I was satisfied with my results without it, and stopped taking supplements after a bad experience with pre-workout (Jack3d should never have been legal).

After investigating some of the claims made by health influencers, I tried it for myself and the results were unexpected (to put it mildly). As I’ve previously documented by experience giving up coffee & alcohol, today’s article will discuss what the research says about creatine and what happened when I took it for 5 months.

Keep reading if you are interested if creatine might be right for you!

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What The Research Says

Muscle and Strength Gains

How Creatine Works

Your muscles and brain run on adenosine triphosphate (ATP). Creatine increases phosphocreatine, which enables faster ATP regeneration permitting your muscles to squeeze out an extra rep or sustain effort for longer. Over time, this translates into more training volume and growth. On top of that, creatine pulls water into muscle cells, making them fuller and triggering anabolic signals. So creatine lets you train more, which results in more muscle mass and greater strength.

A common question is how is this different from steroids? For one thing, creatine is a legal nutrient supplement, simply enhancing what you get from animal proteins. This helps accelerate ATP regeneration. Steroids on the other hand, are synthetic hormones that directly change your body’s physiology in order to boost muscle protein synthesis and recovery. This is why it can produce such rapid and dramatic increases in size and power. You are effectively turbocharging your hormones.

TLDR: Creatine tops up energy stores, steroids change your biology. Don’t do steroids. No matter how cool Sean Austin made it look in 51st Dates.

The Science Behind Creatine for Strength & Muscle Gains

The effectiveness of creatine isn’t just theoretical, creatine has gone through over 500 peer reviewed studies and 250+ controlled trials and held up to the scrutiny. Meta-analyses covering dozens of studies confirms creatine supplementation increases strength, power output, and lean body mass compared to placebo.

A highly cited example is a 2003 analysis of 22 trials published in the Journal of Strength and Conditioning Research, which concluded that creatine can increase strength gains by roughly 8% more than training alone. Another 2005 study from McMaster University, showed older men significantly increased muscle mass and bone density by taking creatine. Aging is associated with reductions in muscle mass and strength so if creatine is effective in helping older men gain or preserve muscle, then your gym bro should pass the shaker.

That’s not to say these results don’t apply to other demographic groups too. Plenty of studies looked at college aged, trained, untrained, women (pre and post menopause) and others. Basically it’s pretty universally accepted creatine works well for muscle gain and strength. With as little as 5g daily, you should expect to see an improvement of 5-10% after a few weeks. If you were to stop taking it, eventually your stores would go back to baseline levels but you won’t lose all the muscle and strength you gained.

Cognitive Benefits

Does Creatine Make you Smarter?

Like your muscles, your brain also runs on ATP. Expending mental effort burns energy. Creatine increases phosphocreatine in the brain, giving neurons a quicker way to regenerate ATP and keep firing under stress. Creatine doesn’t make you smarter but it can help you can handle a higher work capacity before tiring out, just like with your muscles.

I’m sorry to the people looking for a Bradley Cooper Limitless pill, creatine won’t increase your intelligence. The only confirmed way to boost your IQ is to Subscribe to Serviceable Insights.

Unfortunately, the science behind the cognitive benefits of creatine isn’t as solid as for muscle & strength gains and requires a bit more scrutiny. There are a few dozen studies and trials with positive results, but it’s far from a slam dunk.

For one thing, there are far fewer studies and many were on specific populations with a problem. This includes: sleep-deprived individuals, patients with neurological disease or vegetarians. You might wonder what’s the problem with the vegetarians? Well, they don’t eat meat.

This leaves them with lower creatine stores since meat and fish are the main dietary source of creatine. The next time a self righteous vegetarian/vegan tries to lecture you about how useless animal proteins are, just remember they are deficient from creatine and not thinking straight. So be nice to them.

Large Doses & Sleep Deprivation

In all seriousness, creatine seems to help these groups but results were less clear for young healthy omnivores. Some studies show promise, others lacked measurable effects. It appears the benefits of taking creatine for healthy adults already consuming animal proteins are largely muscular and not cognitive. Some studies tested larger doses (10 - 20 g daily) on healthy adults, yet were still inconclusive. Many health influencers such as Joe Rogan, Andrew Huberman or Rhoda Patrick advocated for creatine for cognitive benefits and even recommend larger doses because of studies such as the 2018 study Avgerinos et al. showed improvements in short term memory and reasoning but other studies failed to replicate this.

In their defense, an interesting insight came from pairing sleep deprived individuals with high creatine doses. The 2024 study by Gordji‑Nejad et al. gave a single large dose of creatine (0.35 g/kg translating to 25 g for a 150 lbs person) during 21 hours of sleep deprivation. It produced marked benefits for the subjects: processing speed improved by 16–29%, memory improved by ~10% and lower subjective fatigue by ~8%.

So according to the research, there might be some cognitive benefits in taking creatine if you are naturally deficient from your normal diet or after a bad night sleep. Beyond that, it’s too early to declare decisively there are meaningful cognitive benefits to taking creatine. However, individual experiences may differ…

My Experience With Creatine for 5 Months

The Three Horse People of Fitness Nutrition Advice

I’ve been following Dr. Rhoda Patrick’s Youtube Channel Found My Fitness for over a decade. I haven’t taken all of her advice but I’ve appreciated her scientific approach and willingness to experiment with new protocols herself. She has many videos, reviewing scientific literature related to exercise or nutrition science. She’s also had authors of highly cited studies on her channel to discuss their findings as well as other studies. Dr. Patrick has been promoting the use of creatine for years, but she has recently been emphasizing higher dosages and its use for cognitive benefits. She claimed to take high doses on days where she’s sleep impaired, usually when jet lagged due to her travel schedule.

She’s not alone in promoting creatine to her loyal audience. Stanford researcher and professor Dr. Andrew Huberman, has more than 7M Youtube subscribers and has quickly emerged as a leading internet personality on anything related to health. Like Dr. Patrick, he’s recommended creatine on his channel several times, at times referencing studies highlighting cognitive benefits. He’s another internet personality I’ve been following dating back to before the global pandemic. While some people have questioned his advice, like Patrick, his suggestions are generally grounded in scientific research, even if they aren’t always the consensus.

Finally you have Tim Ferris, famous for authoring best sellers such as The 4 Hour Work Week, The 4 Hour Chef or Tools for Titans. Ferris has been successful in many domains and has shown his willingness to treat himself like a human guinea pig. He might lack the scientific credentials of Patrick or Huberman, but he’s been early on many health & fitness trends and even ran a sports nutrition company before becoming an author. If you don’t know him, you can think of him as a master of efficiency/optimization. He too had been advocating for large dose creatine usage.

With these three strongly advocating for its use, and a bit of Googling, there didn’t appear to be a large risk in trying creatine so I thought it was worth giving it a shot.

What Happened?

Strength & Muscle

The last week of March, I ordered a small case of creatine along with bottle of Omega-3 pills. While some suggest doubling up the creatine dosage for the first few days, which they call the loading phase, I just stuck with the 5g daily dose first thing in the morning mixed in a glass of water. People will say bloating is normal during the loading phase, but this normally dissipates after 5-10 days. In my case, I gained 20 lbs during my first week of creatine use.

This was only with the 5g daily dose. This gain can’t be fully credited to the creatine; I temporarily upped my calorie consumption after realizing I was operating at a daily calorie deficit of 500 - 800 calories. I workout every day and don’t eat breakfast, so my under consumption of calories was definitely impacting my muscle gain. Even with this concerted effort to eat more, I was still operating at a deficit closer to 300-500 calories, so this weight gain was definitely not isolated to that.

After a few weeks I went back to my regular eating schedule and with my creatine stores saturated, my weight dropped by 5lbs. I was still 15lbs heavier than when I started, however my body composition had not materially changed. This was noticeable in the gym.

I’ve been training regularly for 16 years, which categorizes me as an experienced lifter. At this point, progress should come more slowly, unless I’m attempting new exercises or ones I haven’t tried in a while. This was not the case with creatine.

For a handful of exercises such as the incline bench press, flat bench press or the barbell front squat, within a few months of taking creatine, I was able to lift at least 10% more. Not only could I lift heavier weights and for more reps, I was no longer experiencing as great of a drop off between my third and fourth set of an exercise. This drop off is fairly common for lifters with a higher proportion of Type II (fast twitch) muscle fibers. This was something I had grown accustomed to and dramatically lowered my training volume during my workouts. With creatine, my training volume could climb considerably allowing for great strength and muscle gains which, were consistent with what the studies and fitness influencers claimed.

Now some of you might point out, the increased power output could have come from gaining weight. This could partially explain it but since I maintained or increased my output for exercises where body weight is a disadvantage such as for chin ups, TRX rows or box jumps, I still consider this valid. At the same time, my cardiovascular fitness improved despite carrying more weight.

TLDR: The Strength & Muscle Gain Research is Legit

Cognitive Benefits & Large Doses

When it came to cognitive benefits, I didn’t notice anything new from the adoption of creatine or Omega-3. I felt pretty good as a baseline, and since I regularly consume meat or fish to begin with, the additional creatine didn’t do much for me. Still consistent with the research.

Some of the fitness influencers said to get the cognitive benefits, you would need to do at least 15-20g, to break the blood brain barrier or whatever. So to test the claims by Rogan and Patrick, for a few weeks, I tried upping the dosage to 10g per day or 20g on days when I didn’t sleep well. Well this protocol did have a noticeable effect. It might not have sharpened my focus or improved my memory but it did a terrific job of disturbing my stomach; especially on the 20g days. As I attempted the higher dose four months into the experiment, my creatine stores were already saturated so adding the higher dose seemed like overkill. Even when I was sleep deprived, I didn’t feel any shaper with the higher dosage. One possible explanation could be for my bodyweight, 20g is insufficient, but that dose was already pretty difficult to consume and I wasn’t tempted to add even more.

My conclusion is the people telling you to consume large dosages are probably just trying to get you to go through your creatine supply faster to sell you more. Shampoo companies try the same strategy. Speaking of shampoo, on major concern people have with taking creatine is the link to hair loss. This came from a 2009 study on Rugby players that saw a 56% spike in DHT levels after a high-dose creatine loading (25 g/day). This appeared to be a one off that didn’t appear in other studies. In 2025, a randomized controlled trial specifically tested for this for 5g of daily creatine and it found no significant difference in DHT, DHT-to-testosterone ratio, or any hair growth metrics between the creatine and placebo groups.

If you are afraid to take creatine because of hair loss concerns, you shouldn’t be. In my case, my hair’s fine. If you really are concerned, don’t just take my word for it, I’m not a medical professional or scientist, just a guy writing on the internet. I shared a few studies, but there are plenty more, which might be more appropriate and applicable depending on your specific situation. Speaking only for my experience, I can say creatine delivered what I was hoping for with the strength and muscle gain but fell short when it came to the cognitive benefits. Is this conclusive? No, but just another data point for you to consider when you decide if creatine is right for you.

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Between the publications of Antifragile (2012) and Skin in The Game (2017), Taleb co-authored a paper, “The Precautionary Principle (with Application to GMOs)” (2014) which generated a considerable amount of controversy upon it’s release. The scientific community were aghast because the Taleb and his co-authors had concerns with genetically modified organisms (GMOs).

Being publicly against GMOs then and still today is the easiest way to get looped in with Conspiracy Theorists, Pseudoscientific Fitness Influencers or Hysterical Hypochondriacs (this group also represents my key Subscriber base).

Jokes aside, regardless of your views on GMOs, Taleb’s discussion of the Precautionary Principle is worth re-examining, as it’s helpful to understand the different types of risks, and why most risk models fail. At the same time, let’s take this time to re-visit some of Taleb’s key ideas when it comes to risk.

Keep reading to find out why you should use the Precautionary Principle to ensure your own survival.

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Principle Origins & The Philosophy of Nassim Taleb

“The Precautionary Principle” originated in the 1970s in Europe. First appearing in German environmental law, showing a shift in how regulators wanting to acting on risk instead of waiting for harm. This perspective gained momentum in the proceeding decades and has extended to other sectors. Yet when it comes to managing risk, there’s the academic view and the practitioners perspective.

Nobody understands the practitioners perspective better than Nassim Taleb. He’s been successful in finance and as an author because of his reflections on risk; he credits his experience as a trader since traders and hedge funds’ livelihoods are tied to their ability to manage risk. If they can’t manage their risk properly, they blow up, creating a natural evolutionary cycle. Academics on the other hand, can be wrong for decades without consequence since they are tenured salaried employees at publicly subsidized institutions. This is why when it comes to risk, Taleb suggests learning from people exposed to the impact of bad decisions; people with skin in the game.

Black & Gray Swans

Wall Street traders equipped with sophisticated academic models blow up by understating rare but extreme outcomes. In the stock market, most days are characterized by small gains or losses, which in aggregate trend up over time. From the perspective of an investor, this seems great. Investors portfolios are worth a bit more each year on paper and investment professionals get to charge fees based on these higher asset values. Individual stocks might rise or fall dramatically but market wide, volatility remains low and everybody is happy. However, this can create a false sense of safety. Taleb often gives the turkey example: A turkey is fed every day for 1,000 days, growing ever more certain the farmer cares for it—until day 1,001, when it’s killed for Thanksgiving.

Since the overwhelming majority of trading days are low volatility, when you plug market data into a risk model, it makes extreme high volatility days seem so unlikely, it’s as if they aren’t there. However, they do eventually happen and can wipe out years or decades worth of gains overnight, suddenly popping the illusion of safety. Just like the turkey on Thanksgiving. Each time this happens, investment professionals will say it was unforeseeable, unimaginable but most importantly: not their fault.

They will call it a Black Swan event. However, by saying that, they will only prove they don’t know what it is. A real Black Swan event would be an extreme event, falling outside any believed range of outcomes. Think Aliens arriving on earth or a horse winning a professional golf tournament. Neither a market collapse nor a pandemic qualify. Historically, the US enters a recession territory every decade with market sell offs happening more frequently. Major, deadly pandemics are known risks that happen infrequently. Most of us are just too young to remember the bubonic plague or the Spanish flu. These extremely rare but known risks are Gray Swans.

Understanding the difference between unprecedented and very rare events is an important step for risk management. Former US Secretary of Defense Donald Rumsfeld popularized the notion of different forms of military intelligence into:

1. Known-Knowns: Risks you are aware of and have insight into

2. Known-Unknowns: Risks you are aware of but lack knowledge or verifiable data

3. Unknown-Unknowns: Risks you don’t even know exist

This is important for military planning but apply to any type of risk activity. On Rumsfeld’s matrix, Black Swans are generally Unknown-Unknowns. Most military commanders or hedge fund traders, have an idea how to handle the first two types of risks, but it’s in the third type, which are the most consequential, that often carry the greatest potential for danger.

Ruin Dynamics and Systemic vs Self-Contained Risk

If somebody handed you a glass of water and said there was 4% chance of dying immediately, would you drink it? What if they instead said the entire planet would explode. Would that change your decision making process? Should we as a society treat these type of scenarios differently?

Nassim Taleb believes we should. Risks that only impact the principal actor or small amounts of people, should not be treated the same as events carrying systemic wide risk. If the ultimate goal is to ensure the continuation of the human race, we should do our best to eliminate or minimize risks that put this in jeopardy.

When negative risks are contained only to the person performing the action or a small number of people, these are considered localized harms. An example of this is driving. More than one million people die in car crashes each year, but it’s impossible for one single driving accident to kill more than a handful of people at a time. A fender-bender in Athens can’t physically harm somebody in London. Therefore Brits shouldn’t have a say in banning driving in Greece. When harms are localized, each person can take risk decisions on their own behalf. This is why despite the high death counts, banning driving isn’t necessary. Requiring insurance serves as an adequate system since repeat offenders would eventually be uninsurable.

However, some events have the potential to cause irreversible catastrophic damage. This is ruin risk. In these cases, more stakeholders should weigh in. Especially when all it takes is a single single instance (Ex: A major flood, pandemic or nuclear explosion) . This is why an individual shouldn’t have the right to risk blowing up the planet to quench their thirst. One problem with the scenario I provided, was it presented the question as if the probability was known to be 4%. It’s one thing to make decisions when the probability is well understood and a completely different thing when the model has little to no predictability. This goes back to the Known-Knowns versus Unknown-Unknowns.

When there is low confidence in the model and the potential for ruin, more prudence is needed. Dealing with Known-Unknowns or Unknown-Unknown risks, means the probability for ruin could be uncomfortably high. This is why more diligence should be done to improve confidence in the model before introducing this risk. Especially when some effects are irreversible.

“If the risk is one of ruin, standard statistical inference breaks down; absence of evidence is not evidence of absence.” Taleb et al, 2014

The Ramifications & Conclusion

Taleb argues the conventional approach of putting the burden of proof on regulators or consumers to prove the danger before introducing these risks is backward. Anyone looking to introduce these type of risks should first prove there’s near zero probability of ruin first.

This is why he’s against GMOs, engineered pathogens or gain-of-function virology. These new and largely untested methods, have a lot of uncertainty coupled with the potential for ruin. Naturally, this drew the ire and criticism from the science community; taking his argument as being anti progress/science. Others say dismissing things with minimal risk of ruin but with guaranteed advancements for society is foolish. There was a lot of criticism to the article and concept at large.

Taleb failed to convince anyone to remove GMOs from the food system, and lost some clout with the science community. However, this line of thinking alerted him early to the potential risk caused by the COVID-19 pandemic in January 2020. He was among a group that warned the White House of the risks of the pandemic. They advised to close their borders to prevent the spread, implement aggressive testing, lock-downs and protecting the elderly before the pandemic could reach the US.

The White House, and pretty much every other country did not take their advice. Instead of acting quickly and decisively, they opted for a wait and see approach, to not unnecessarily cause economic harm. Well we know how things played out.

While this might not have changed anything, Taleb’s perspective on risk, could have potentially reduced the spread of the pandemic. This is because he understood the difference between localized and system risk, ruinous events and how to manage risks when the probability is not well known. Insurance, elimination or avoidance. You don’t need to be a best selling author or accomplished trader to understand the key concept: Make sure you don’t blow up!

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These I can live with. Don’t let laws of physics get in the way of a cool scene. What I absolutely cannot stand however, is any instance when you see a character break into a full on sprint while wearing a suit. Anyone who has ever worn one that’s remotely form fitting, immediately understands how absurd this is. Bringing your knee anywhere near your waist is a struggle, yet the idea Tom Cruise can take off on a full on sprint, then continue at an elite marathoner pace in a Tuxedo and dress shoes is stupid. I don’t question TC’s running speed, but not dressed like that.

Yet Ethan Hunt isn’t the only protagonist that believes they can’t compromise style while trying to save the world. I had my research assistant Chad Petey, go back and study the 100 most watched action movies ever and they’ve concluded this happens in at least 13 different films. This is just for the main character, if we include villains, henchmen and extras, this number quickly swells up. How did this get so out of hand?

In today’s article I will explore how this epidemic began, explore why and compare the performance of suit wearing protagonist versus our casually dressed hero’s.

Continue reading to learn why action movies and running in suits make no sense.

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The History/Timeline of Action Movies

Action movies began over a hundred years ago, during the silent film era. People normally consider The Great Train Robbery (1903) to be the first but it took until the 1920’s, for Douglas Fairbanks to emerge as Hollywood’s original action star. He starred in films such The Mark of Zorro (1920) and Robin Hood (1922), mixing athletic stunt work and charismatic heroism. When you can’t speak you need to make up for it somehow; some modern actors never got this memo.

The 1930s-1950s, the Golden Age of Hollywood, introduced sound and improved stunts in action films. Some memorable moving pictures included Errol Flynn’s The Adventures of Robin Hood (1938) or Wartime and Westerns from John Wayne such as Stagecoach (1939) or High Noon (1952). However, the big shift began in the 1960’s, when Sean Connery played James Bond for the first time in Dr. No (1962). This would begin one of the major film franchises, including dozens of films, spanning several actors. If you’re reading this, you know who James Bond is, don’t make me explain him to you.

It was the 1980’s when action franchises really blew up. Between Sly Stallone, doing nothing to help dispel Italian stereotypes, Arnold Schwarzenegger showing bodybuilding is at least as useful as a degree from Julliard and Bruce Willis, as the unstoppable everyman cop John McClane. Since then budgets, stunts and special effects have just gotten grander, to the point where these movies are considered a flop unless they generate $100M the opening weekend. With pressure like this, action heroes need to bring their best effort to win over demanding audiences.

This begs the question.

Why do Action Heroes Wear Suits?

Action hero’s take some variation of this formula:

Hero/Protagonist blessed with a particular set of skills, needs to

1. Prove they are worthy

2. Rescue/avenge their partner, child or pet

3. Reluctantly save the world, since they are the only one capable

4. Clear their name/survive the hunt

5. Protect or retrieve item so it doesn’t fall into the wrong hands

Mostly to save time, the hero is usually already pretty skilled at the start of the film. They might not be in their final form, but they are rarely starting from zero, otherwise it will take a lot of plot armor to convince the audience with minimal training they can start defeating supercharged baddies. Unless of course, they are “The one!”.

Heroes sprinting or fighting in suits made sense in previous eras because that was the style at the time. Men wore suits to work, to church, on airplanes and even when they were just hanging out. It stands to reason, they won’t always have time to slip into athletic gear when they needed to get somewhere in a hurry.

As men started to abandon suits for casual outings, the only times they would be worn would be for work or formal events. From what Hollywood taught us, action hero’s generally work in fields requiring many of these. Especially spies or people in law enforcement that can’t appear inconspicuous therefore it’s essential they wear custom suits walking around large metropolitan centers at all times.

This is why it’s completely normal for James Bond, Ethan Hunt and John Wick to be wearing suits; it’s part of the job and it could blow their cover if they wore something else. Although perhaps saving the world might not be their only motivation.

James Bond is great, but let’s face it. The guy’s a boozed out womanizer. Audiences used to find that cute but in 2025, neither drinking or womanizing are fashionable. You should expect much less of that whenever they cast a new Bond actor. In any case, as effective as Bond is, his suit wearing is far more for style, than function. He has shown he will happily reduce his probability of success, if that helps further his cause with his desired concubine.

While Ethan Hunt is slightly less distracted than Bond, his motivations are far from pure either. Hunt only continues to save the world because he’s been suffering through a mid-life crisis since he retired after MII. This explains the unnecessary stunts such as running around the tallest building in the world, holding his breath for 5 minutes or hanging off an airplane in flight. He just needs to feel something.

John Wick isn’t even trying to save the world. He’s trying to obliterate anyone that has remotely wronged him. I wouldn’t be surprised if the next edition is a vendetta against a barista that gets his order wrong. It makes for a good movie, but real heroes don’t have the luxury of style points.

Real Hero’s Don’t Wear Suits

Great heroes accomplish the impossible. That’s easy when you have superpowers but when you are just a motivated cop, vigilante or agent, you need to really dig deep and give everything you’ve got.

John McClane was just trying mend a shaky marriage and surprise his kids for Christmas when circumstances forced him, a regular NYPD officer to have to take on Hans Gruber’s entire crew. With just a pistol and jet lag, he had to take on European tourists armed with automatic weapons. Do you think he had time to change into a suit first? No. Despite being invited to a formal event, he had to go functional. He needed something breathable, perfect for ripping up for bandages if he gets shot. That’s the type of guy he was. Do you think McClane would wear Lululemon? Of course not. If he’s going to the gym, it’s with combat boots and the same gym shirt he’s had since high school.

John McClane, an active cop. Probably doesn’t even own a suit.

Know who else would never be caught dead in a suit? The ultimate action hero. Jason Bourne. Jason Bourne never fights in suits, because he’s actually a killing machine. He doesn’t care about style points. He will kill with his bare hands, a magazine, a pen. Whatever he has at his disposal.

He doesn’t even know who he is. What he is or why people are after him. It doesn’t matter. Send whoever you want after him, but nobody you would want back. Bourne had the entire US National Security apparatus after him, yet he came out on top. He did this with minimal equipment or support. Relying only on his training and instinct. Of all the action protagonists, none can match Bourne’s ability to stealthily blend in with a crowd, and always find a way to extract himself or his target from the situation. A suit would only get in the way.

Can Anybody Pull It Off?

With the exception of anyone starring in a period piece or a Guy Richie movie, it rarely makes sense for an action hero to be wearing a suit. If they are wearing a suit, it can only be to impress people. Take the Kingsman series for instance. It’s an organization of posh British aristocrats. Of course they need to be wearing a suit while saving the world. How else would people know they are posh aristocrats?

Otherwise wearing a suit mostly gets in the way if you’re ever dealing with a villain that’s at least slightly above replacement level. Take Ryan Gosling. In Drive he’s in a white bomber jacket and jeans. Despite the tall task in front of him, he manages to overcome his obstacles. The next time we see him in an action sequence is in Only God Forgives. He foolishly challenges Lieutenant Chang, who beats him senseless. Despite removing the jacket, the suit definitely didn’t do him any favors.

If a suit must be worn, the best example to follow is Christian Bale/Christopher Nolan’s adaptation of Bruce Wayne/ Batman. Bruce Wayne wears suits for his day to day sauntering. Attending board meetings, hosting fundraisers or bringing Russian dancers to dinner. When he is the Batman, he wears his Batsuit. Bruce Wayne isn’t trying to fight crime in $5,000 outfits. When you are going up against incredible villains such as Ra’s Al Ghul, The Joker and Bane you don’t have time to fix your lapel. You need to be locked in. Bruce Wayne is style, the dark knight is business.

Perhaps the one exception is The Matrix because apparently while inside, everybody needs to wear suits. This applies whether they are an Agent or part of the Nebuchadnezzar crew. Neo is “The One”, and can download any skill, so he must have found the package for maneuvering in sub-optimal clothing. This combined with his nemesis, Agent Smith, also wearing a suit evens the playing field. This is why Neo can get away with it. But what if we have it backwards though? Neo may not actually be “The One” or the hero of the story at all. What if Agent Smith is really “The One” and he would have defeated Neo, if not for his fashion choices? Makes you think.

After a century of action sequences, while it makes for a nice aesthetic, good style has never made saving the world any easier. When a protagonist chooses Italian tailoring over functional fabric, the filmmakers are just signaling the villain is made of cardboard and the stakes are not high enough. When you see somebody sprinting for extended stretches in Oxfords, it’s probably CGI. With no disrespect to Bond, Hunt and Wick but these are not serious heroes since they are not living up to their potential. They lack foes worthy of their full attention which is why they are the equivalent of great athletes stuck in an era of weak competition. This ultimately nerfs their legacy and leaves the audience wanting more.

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In recent weeks, I had the good fortune to see works of art that will likely be discussed and re-watched much longer than the usual TikTok cycle. Succession creator Jesse Armstrong returns with a film Mountainhead, the premise being a few tech executives on a weekend retreat as a global calamity occurs, caused by deepfakes and Artificial Intelligence. Sounds like a far fetched scenario, I know.

If you want something more realistic, what about a TV series about a comedian flying a Boeing 737 to prove a point about airline safety? Well Nathan Fielder in season 2 of The Rehearsal, takes things to another level, physically and comedically. Fielder stretches the limits of what can be allowed on network television. He has shown to be fearless; allowing him to take his comedy to depths not previously seen. The Rehearsal season 2 is must-watch TV, that is among the best seasons of television this decade (thus far).

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Mountainhead

Mountainhead is an incredible satire on the personalities of the Silicon Valley elites. It’s difficult not to see the film and immediately see it as an SNL style spoof on the All-In Podcast. Jason Schwartzman's character is clearly based on Jason Calacanis, the moderator of pod, that’s mostly famous for being friends with Elon Musk. He was also an early investor in Uber, which he reminds people about often. While’s he’s rich, he’s neither a billionaire or a centi-millionaire, making him the poor man of the group. Sacks and Chamath have ridiculed him for this on many occasions on the All-in pod. Although he’s well connected in tech circles, Calacanis lacks the pedigree of a top investor or company builder, which Chamath and Sacks are not afraid to remind him, when he’s taking a contrary position to them. They way they speak to him, sometimes borders on bullying, which is exactly the dynamic shown on Mountainhead.

While ripping on Jason is mostly good natured, some of their comments reveal the hubris from these besties. This isn’t completely unwarranted; they have played important roles in generation defining companies such as Google, Facebook, PayPal and others, while amassing large fortunes. Besides, what’s the point in having “eff you money”, if you don’t ever say eff you, every now and then?

This is all fine and good, but when you hear some of their comments and how quickly these tech executives have managed to secure access to the White House, it shows they clearly believe their powers extend far beyond the realm of tech or business. This isn’t exclusive to technology, plenty of energy or finance executives or former entertainers made forays into politics, with varied success. What’s different in this case, is the sincerity to which tech executives believe they are making the word a better place, regardless of clear negative externalities their products cause. The mantra of many tech elites appears to be, technology is not only the best solution to all human problems, it's the only one.

If regulators or governments dare get in the way, they are anti-progress. While satirical, it’s not a stretch to think that many tech elites would buy a country if they could. Not the U.S. or China, of course. But something small. Vulnerable. Maybe in the Caribbean.

The group dynamic in Mountainhead echoes what has been playing out in real time on the All-In Podcast. Chamath and Sacks are now full-on Trump whisperers. Calacanis is a devout Elon Musk loyalist, which, until recently, meant being softly pro-Trump even after years of warning how catastrophic his return would be. David Friedberg is the outlier, more intellectually honest, less partisan. Politically a libertarian, but still grounded in reality. He is the closest analogue to the film's Jeffrey "Jeff" Abredazi, a billionaire who, unlike the rest, seems aware that something has gone deeply wrong, and they might be the cause.

Then there is Venis "Ven" Parish, an amalgamation of Big Tech CEOs. He’s clearly some caricature of Zuckerberg, Bezos and Benioff, possibly others. Obsessed with biohacking, convinced he understands philosophy, and certain that his work is saving humanity. He does not just disrupt industries; he thinks he is evolving the species. Randall Garrett (Steve Carrell), isn’t exactly David Sacks. Maybe certain aspects of Peter Thiel or a Bill Gurly type. More of an old school VC, that serves as something of a mentor to the rest of the group. They give him a god complex, believing he can control his health and live forever. This is clearly referencing the longevity investments Thiel made a while ago. Perhaps also a reference to Bryan Johnson.

Regardless of the exact characters, the film will prove prescient. Misinformation and deepfakes are already distorting public perception. Open Twitter right now and scroll through footage from Israel or Iran. If you believed everything you saw, you'd assume both countries have been wiped off the map. In less than a generation, tech founders went from hoodie-wearing outsiders to front-row seats at inaugurations. Jesse Armstrong, the creator of Succession, brings the same scalpel here, eviscerating the powerful while making you laugh. If you loved Succession, you will love this. If you hate Big Tech, you will love this. If you work in tech, you will probably call it "mid."

The Rehearsal

Nathan Fielder is the new king of comedy

With all due respect to Severance and White Lotus, Nathan Fielder just created the standout season of television this decade. He also just snatched the crown from Sacha Baron Cohen (SBA), Eric Andre, and even the late Andy Kaufman to become the reigning king of method comedy.

Method acting, popularized by Marlon Brando and employed by modern legends like Daniel Day-Lewis and Jeremy Strong, requires the actor to stay in character throughout the shoot. Nathan has adopted a similar commitment, except his stage is the real world, and his character is just a strange, obsessive version of himself. This is in contrast to SBA or Kaufman that played characters with no similarities to their own personalities. The difference from the character Fielder plays on his shows and how he is in real life, is subtle. To the point that when he’s doing interviews, whether he’s promoting a show or not, it’s difficult to decipher if he’s still show Nathan.

This is likely because for most of his career, he performed under his own name. Fielder began his television career nearly twenty years ago doing short segments on This Hour Has 22 Minutes, a CBC comedy show. He was far from a main player but he did enough to convince execs at Comedy Central to let him launch his own show, Nathan for You. The premise was simple: Nathan, a supposed business genius, offers absurd marketing advice to small businesses. The execution was anything but. He started with simple premises such as having an ice cream store temporarily offer a poop-flavored ice cream. Convince a a realtor to guarantee any homes she sold were certified "ghost-free." He then took it to another level when he realized using parody law, he could rip off Starbucks. He created Dumb Starbucks. That last one went viral globally. People thought it was a Banksy installation. The stunt made international news before being shut down by health inspectors. Nathan had arrived.

The show wasn’t just about laughs, though it was consistently hilarious. It captured the quiet desperation of small business owners struggling under regulation, competition, and modernity. It revealed how easily Nathan could convince people to do outrageous things. And it hinted at the deeper commitment and ambition lurking beneath the surface.

(In 2014, I saw him at a show at the Just For Laughs Festival and got to ask him a question on stage)

By season three, Fielder had declared war on Uber with a sleeper cell of rogue taxi drivers. The logistics were insane. The laughs were real. But as his fame grew, and as smartphones made him more recognizable, the show became harder to produce. So he stepped back. He helped Sacha Baron Cohen on Who Is America?, consulted off-screen on other projects, and disappeared from the spotlight.

The Rehearsal

(Some Spoilers Alert)

The show begins with an odd but compelling premise: what if people could rehearse difficult moments in their lives before they happen? It quickly evolves into something surreal. In one storyline, Nathan helps someone rehearse becoming a parent by simulating an entire life with a child actor. Eventually, Nathan inserts himself into the simulation, raising the child himself, until it becomes impossible to tell where the show ends and Nathan begins.

Season one is weird, brilliant, and not for everyone. It is far from mass-audience sitcom territory. But if it clicks with you, it really clicks. Season two, is where he takes things further than you would expect from any network television show can go.

It starts with a genuine safety concern: many plane crashes are caused by miscommunication between pilots. Nathan investigates. He meets with the former head of the FAA, who agrees it's a problem. So Nathan does what any sane person would: he decides to stage a rehearsal for pilot communication. But not just that. He spends two years learning to fly starting on small planes working his way up until he is trained to pilot a commercial Boeing 737. Legally. He goes through the same training as a commercial pilot, finds a plan and flies 100 people, logging airtime under obscure FAA rules. The scene is astonishing. He actually lands the plane. It is not a joke. It is not CGI. He did it. Why? Because that is what the show required. Because that is who Nathan is.

Along the way, The Rehearsal explores real issues: the mental health of pilots, the pressure they face, the impossibility of disclosing conditions without risking their careers. It also remains funny, darkly, awkwardly, relentlessly funny. Nathan finds bizarre people and lets them talk. He recreates Sully’s Hudson River landing just to understand it better. He lives as Sully. He creates an alternate history where Sully isn’t actually a hero, he was just a dude distracted by Evanescence.

He takes on one of the largest film and television studios in the word: Paramount+. Fielder learnt they removed an old episode of Nathan for You , that as part of the episode, included the creation of a brand that raised money for Holocaust awareness. Paramount+ claimed it did not want to "take sides" in the Israel-Palestine conflict, so it pulled any content related to Judaism. Despite pointing out to them that they still host plenty of content related to N@zis and other potentially sensitive content, the studio did not reverse their position. His response is scathing.

At the time, The Curse, his other show with Emma Stone and the Safdie brothers, was waiting on a season two renewal with Paramount+. He wasn’t just risking a professional relationship. He was risking his career. That HBO let the episode air is nothing short of astonishing. This goes to show, not only the lengths Nathan will go, but the extend to which the network, will allow him to spend endless money and go after anything he sees fit. HBO or Max, whatever they call themselves these days, is not a small network. This isn’t Adultswim or some small network. They have shareholders and eliminate even decent shows at the drop of a hat. They allow Fielder to do this because they acknowledge that he’s special. He might not drive the most views, but for the people who get him, they will subscribe to HBO just to watch anything he does.

He’s built a fiercely loyal fanbase because Nathan Fielder is fearless. He commits harder than anyone. He never breaks. And somehow, always lands the plane.

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Franz Kafka became a legend creating surrealist worlds filled with human life size insects and inscrutable bureaucracies. For a century, his works such as The Metamorphosis, The Trial and The Castle, inspired generations and made us contemplate the absurd nature of corporate life.

With attention spans shrinking faster than my Subscriber count; many millennials and Gen Z’s can’t be bothered to attempt reading hundred year old books. Instead, the geniuses at Apple realized, they can lure in these generations with Adam Scott and corporate office dance montages included in their Apple TV membership. This is because, not much has changed in the last hundreds years when it comes to how corporations view their workers.

The emergence of new technologies broadens the reach of these same entities, allowing them to interact with workers in new ways. Unfortunately, in 2025, we don’t have Franz Kafka but we have the genius behind classics such as Heavyweights, Zoolander and Tropic Thunder. Ben Stiller has shown to be a master at capturing the human condition, fortunately for us, he decided to investigate the role corporations can play in our life coupled with the emergency of new technologies.

It took 30+ years, but Severance represents the culmination of Ben Stiller’s artistic progression, making him the perfect person to create one of the most fascinating series of the 2020s. This article will explore why everyone is fascinated and loves Severance, his masterpiece.

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Is Ben Stiller this generations Kafka?

“Youth is wasted on the young. I’d go further: life is wasted on... people.” Roger Greenberg (Ben Stiller), Greenberg (2010)

An advantages of being born in the nineties, was a front row seat to the golden age of comedy films1. During the 2000’s, multiple classics were released each year from the likes of Judd Apatow, Will Ferrell, Adam McKay and of course, Ben Stiller.

Stiller was born into comedy. His father, Jerry Stiller (Frank Costanza on Seinfeld), and mother, Anne Meara, were a major comedy duo in the ’60s and ’70s. As a kid, Ben was always making characters and shooting short films, often in a mockumentary style. His early talent stood out, even landing him a spot on Saturday Night Live. He left after four episodes since SNL wouldn’t let him make the short films he actually cared about.

He did fine anyway. He got his own sketch show, scored roles in big films, and began directing studio features. Through the ’90s, his box office success was uneven, but a clear creative voice emerged. In Heavyweights and The Cable Guy, Stiller explored taboo topics with a kind of dark satire that didn’t land with mainstream audiences at the time, but would later earn cult status.

His breakout came with a streak of hits: There’s Something About Mary (1998), Meet The Parents (2000), and Zoolander (2001). These films proved he could balance wide appeal with genuinely funny, off-kilter humor. After these successes, as well as the growing profiles of frequent collaborators Owen Wilson, Will Ferrell, Judd Apatow and others, Stiller was given increasingly more freedom from film studios to make the movies he wanted.

He used it by making the movie nobody else would attempt. A brazen, critique of Hollywood, the film industry and everyone in it. I am of course talking about the comedy masterpiece Tropic Thunder (2008). The film is a satire that skewers Hollywood’s obsession with prestige, method acting, and box office glory. It mocks self-important war films, actors chasing Oscars by playing disabilities or other races, and studio execs who care more about profits than art. Each character parodies a real industry archetype: washed-up action stars to drugged-out comedians. It shows how far Hollywood will go to sell "authenticity." Kirk Lazarus (Robert Downey Jr.) summarizes it best:

In spite of the critical meta-comedy (or perhaps because of it), Tropic Thunder was smashing success at the box office and the film was well received critically. Yet some people failed to understand Stiller’s satire and took offense to some of the depictions in the film. As the culture shifted towards a higher emphasis on politically correct humor, making films such as Tropic Thunder were no longer feasible.

Stiller seemed to play it safe after that, reverting to sequels of his previous films, re-makes or drama comedies with more emphasis on the drama. This is why Tropic Thunder was probably the last honest thing Stiller made… until Severance.

Severance

If Tropic Thunder was Stiller’s bombastic takedown of Hollywood excess, Severance is his cold, clinical dissection of corporate life. It’s slower, dark and pretty strange but the satire cuts just as deep. Severance tells the story of workers who agree to surgically divide their consciousness into two parts, one that only exists at work (the innie) and another that only exists outside of it (the outtie). Both are unaware of what happens while the other consciousness is “awake”. It’s a sci-fi metaphor turned brutally literal: the most extreme version of “leave your personal life at the door.”

The concept is surreal, funny in a bleak way, and deeply sad. It feels Kafkaesque not just in tone, but in how it reflects our real lives back at us through a distorted, corporate lens. A person becomes two people. Neither is free. Both are trapped.

Severance is unfortunately perfectly suited for the time. Trust in big tech has plummeted, public sentiment toward corporate power is at a generational low, and the promises of meaningful work have never felt more hollow. Younger generations, already spending more of their social time in work settings than any cohort before them, are growing wary of companies that refer to themselves as families but behave more like cults. I’m not sure what kind of families they grew up in, but most don’t fire children after a poor performing quarter or two. It’s no wonder a show about slicing your soul in half just to survive the workday feels more like documentary than fiction.

Stiller’s previous work gave him the perfect source material to make Severance funny while also feeling too real. In The Cable Guy, we met a man addicted to television and desperate for connection. In Greenberg, a man disconnected from the world and paralyzed by meaninglessness. In Tropic Thunder, actors trapped inside roles they no longer understood. Severance is the natural extension of this through-line: people playing roles so deeply they forget who they are.

Stiller learnt his lesson from Tropic Thunder; if he was right, funny and obvious, people would feel alienated. If he wants to point out hypocrisy without upsetting his audience, he had to return to the darker, more subtle approach. Stiller easily could have made a film like The Office Space (1999), that shows the absurdity of bad management and the gradual descent towards apathy. Instead, Stiller replaced this apathy with pessimism. This is why now, Severance strikes such a nerve, with generations burned out by corporate life and craving a different relationship with work. Everyone is so miserable in their home and work lives, the idea of disconnecting from either or both is not such an implausible prospect in 2025.

Conclusion

If Kafka were alive in 2005, and hired to create The Office instead of Greg Daniels, we likely would have ended up with something closer to Severance2. Since he wasn’t, we had to wait a bit longer for Ben Stiller to get a few bad cash grabs out of his system, to instead go back to what he had caught onto to, nearly 20 years earlier in The Cable Guy. Another story about somebody obsessed with their job, disconnected from reality and grasping for connection.

So while it may have taken decades, Severance feels like the project Stiller was always building toward. It’s funny in a way that’s not funny at all, just like modern life. As one of Stiller’s earlier characters White Goodman once said, “I'm not okay, you're not okay, but that's okay!”.

If you liked this and are a fan of The White Lotus, check out last week’s article, Why does everyone love The White Lotus?

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Tanya McQuoid (Jennifer Coolridge), dashing across the deck of a yacht in the beautiful waters of Sicily, shrieks her now iconic line during the second season of The White Lotus. It’s absurd, but also deeply tragic, which represents what the show is about.

The White Lotus is managing to dominate public discourse, proving that long-form storytelling can still command attention in the age of algorithm-driven content. Their success is no accident, like all good art, they tap into something deeply relevant about the world we live in today and make people reflect, between laughs (maybe cries).

This article will break down why The White Lotus isn’t just great TV, but how it reveals as much about the viewer, as the characters on the show.

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The Premise: Luxury, Entitlement, and Chaos

“What do you think is gonna happen? You’re gonna travel the world and suddenly, like, gain some perspective?” Olivia Mossbacher (Sydney Sweeny) —White Lotus Season 1

The White Lotus is named after a fictional luxury hotel chain with locations around the world. The premise is simple: each season takes place at a different resort, following a new cast of ultra-high-net-worth (UHNW) guests and the hotel staff who serve them. The dynamic remains the same: entitled, high-maintenance guests indulge in an extravagant vacation while finding endless reasons to be dissatisfied with the hotel, their travel companions, locals or themselves.

The show masterfully parodies the concept of first-world problems. The characters are so rich that basic survival is not a concern. Their problems are, for the most part, unrelatable to the average viewer. The White Lotus creator, Mike White, masterfully exaggerates their grievances, highlighting their detachment from real-world struggles. They can’t sit back, relax and enjoy their vacation, because any inconvenience or perceived injustice is an assault on their sense of self. They can't let that stand.

This alone isn’t what makes the show good. There’s too much content out there making commentary on rich people being bad. What keeps fans hooked is the intoxicating blend of exotic locations (Hawaii, Sicily, & Thailand aka Taiwan), hypnotic music, a bombshell cast, and a dark undercurrent exposing the complex moral decay of society, extending beyond the ultra-wealthy.

Giving The People What they Want

The subtlety is key, because for a film/tv series to go truly mainstream, they have to avoid alienating large parts of their audience. If The White Lotus went overboard, it would descend to anti-rich people propaganda, that only appeals to people looking for that sort of thing. It’s not impossible to have success by catering to a niche group, but it will be hard to reach the same cultural relevance if most of the population feels like the show isn’t for them. You can’t accuse The Sopranos, Breaking Bad or Game of Thrones of trying to repel certain audience types. Well perhaps, some vegans were triggered by all those deli meats and prosciutto sandwiches (sorry!).

Most people aren’t looking for explicit political declarations when watching premium television. The White Lotus is a good show because it threads the needle of bringing up charged topics without bludgeoning viewers with their own ideology. This allows for various viewing motivations. For those that want to see beautiful rich people making funny quips in exotic locations, great. If you want a more intelligent show, you can get lost in the thrill of a murder mystery with overly self important nouveau riche people. Regardless of who you are sitting with everyone can find a way to enjoy the show. Anyone can find a character to root for, regardless of their beliefs.

This is because of the subtle Rorschach test embedded into the writing.

The Rorschach test, (also known as the inkblot test) is a psychological test where individuals describe what they see in a series of inkblots. Their responses are analyzed to assess personality, emotional functioning, and potentially screen for certain mental conditions. It exemplifies how people can come up with many different interpretations despite seeing the same image.

The White Lotus, is a rare example of a show that can address charged topics without alienating potential audiences. During this era of hyper polarization, it’s increasingly rare. The clever writing permits people to watch whatever show they want to see. If certain viewers are looking for a show depicting out of touch rich people, they have plenty examples of this. If others want a show depicting the irony of people whining about injustice while staying in a $10,000 per night resort, this is served to them as well. Regardless of your politics or bias, The White Lotus is here to welcome you.

A perfect example of this was on display during the first season, when Nicole Mossbacher (Connie Britton), a successful CEO of a big tech company, shared her views on diversity equity inclusion (DEI). As a female in an industry overrepresented by men, many would expect her to be supportive of such measures but she wasn’t. During a dinner discussion, she says DEI makes it impossible to hire young straight white men, therefore they are the ones that deserve sympathy. Naturally her college aged daughter Olivia and her friend Paula, disagreed, thinking she was out of touch. This depicts a conflict between different generations of women, that can have conflicting views of what equality means.

Some younger women feel the more senior women at their firms are not doing enough to support their growth; that they see other women as competition instead of allies. Nicole would represent this perspective. She exhibits this behavior when Rachel Patton (Alexandra Daddario) tells Nicole that she was an inspiration. Nicole at first seems touched, then quickly turns sour then accuses Rachel of writing an unflattering article about her, implying she didn’t deserve her position. This scene demonstrates the clash between the second and third generation feminist movements, the tension around DEI and other topics in a nuanced but not cringe or over the top way. This brings thoughtful discussion to the topic without making the audience feel bludgeoned politically.

This is done by acknowledging different perspectives, thus performing the Rorschach test. Those that agree with Nicole’s point of view, can dismiss Olivia and Paula’s perspectives as self interested or the ignorance associated with their lack of life experience. Those sympathetic to Olivia and Paula, can equally dismiss Nicole as being old and out of touch, or that this confirms their view on women whom view other women as competition. The same scene can be shown to a diverse range of views but they will come away believing that Mike White shared their perspective.

To left leaning fans of the show, The White Lotus is a satire of the moral decay of the wealthy. It reinforces their belief that we need to eat the rich. To those on the opposite end of the spectrum, it shows how out of touch global elites are, and why these aren’t the people we should trust to run our institutions. The White Lotus can pull off this delicate balance because of great writing, and terrific acting.

Casting Brilliance

The White Lotus team has mastered the art of casting. They are great at selecting actors that perfectly embody charcutiers of people we know or can imagine knowing in real life. Since The White Lotus is a dramedy (Drama-Comedy), which is an added difficulty for the actors to balance. If they are too realistic, we will simply detest their characters and the show won’t be funny. If they aren’t authentic enough, it feels more like a sitcom, lacking any real stakes or tension.

Take Tanya McQuoid. If she was played by anyone other than Jennifer Coolridge, we probably would have hated her; which would have a significant impact on our enjoyment of the show. Her silly exclamations and one liners make her impossible not to love, even if she occasionally does objectively bad things. Portrayed differently, Tanya can easily come off looking as a villain.

Great art can challenge us and enhance our understanding of the world. When we are confronted with characters we are meant to dislike, but find ourselves loving, we should reconsider our beliefs. Many from the woke crowd will hate on rich people all day but the second Jennifer Coolridge comes on, they can’t help but laugh and smile. They won’t admit this, but maybe they don’t hate the rich as much as they claim.

What is equally impressive and adds to the difficulty, is that the cast and location change every season, effectively depriving the audience of the emotional connection they forged with the previous characters. Few shows have been able to successfully pull this off. True Detective season one with Matthew McConaughey and Woody Harrelson, was among the best seasons of television ever. Unfortunately the show runners could not repeat this success in subsequent seasons.

The fact that The White Lotus has managed to do this for multiple seasons now, puts them in unchartered territories. They have done good job of mixing in new personalities such as the Spillers (Audrey Plaza & Will Sharpe) in season 2 or Chelsea (Aimee Lou Wood) in season 3 while also trying new takes on similar characters such as with Cameron Sullivan (Theo James) and Saxon Ratliff (Patrick Schwarzenegger). Although the basic format can get stale very fast, these great characters quickly win viewers over, making us forget about previous seasons.

So Why Does Everyone Love The White Lotus?

Most people think of The White Lotus as a show that skewers the excesses of the ultra-wealthy, but the reason it’s so enjoyed, is because viewers can see the show they want based on their own biases and sympathies. The White Lotus is a dramedy, but the extent it’s a drama or a comedy, depends how you view the world.

Each characters has plenty to like or hate, so what Mike White has done, has given each of us a canvas to build our own adventure around. This stands in stark contrast to many contemporary shows that attempt to take a clear stance on morality, but fail to sway anyone or make a watchable show. The White Lotus thrives in the murky in-between in its gorgeous settings while beautiful people, do ugly things.

As we approach the Season 3 finale, the question isn’t whether Mike White and his team will deliver but what we’ll see in the inkblot of its story. The more we watch, the more we learn about ourselves. And if there’s one thing people are truly obsessed with, it’s themselves, which is why everyone loves The White Lotus.

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Upon reflection, I saw a strange parallel. The Trial depicts a society where individual liberties have been replaced with an ever-growing bureaucracy, designed to further perpetuate itself, at the expense of everyone else. The Technological Republic, on the other hand, argues that this is what our society will become if we do not stand up for individual liberties, which are among the hallmarks of Western civilization. The way we defend these liberties, is technological and military superiority.

Translation: He wants you to buy more Palantir stock. If you are a short seller, he especially wants you to put down the coc@a!ne and reverse your position. Karp is a colorful character. Since Palantir has become a stock market darling, he has become increasingly outspoken. One of the topics he has regularly discussed in public is his belief that Silicon Valley companies should focus more on solving problems related to national security instead of launching another photo-sharing app.

(not AI, he did this during a live interview)

This article will give a short primer on The Trial and what Kafkaesque means. Discuss what Alex Karp wrote about in The Technological Republic, and contemplate whether his views and actions would be consistent with a Kafka protagonist or other great characters of literature. If you haven’t already clicked off, buckle up, buckaroo!

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The Trial & A short intro to Kafka

Franz Kafka’s The Trial is one of the most unsettling novels you’ll ever read. Josef K., is arrested and prosecuted without ever being told what crime he committed. He becomes the latest victim of a nightmarish legal system, where guilt is assumed and justice is just an abstract concept without a functional reality. While it’s a darkly funny, it lingers with you as the weight of the implications settles in mostly because of how prophetic it turned out to be.

The Trial was published in 1925, shortly before the rise of the National Socialist (Nazi) party in Germany. Soon, Kafka’s absurd bureaucracy would be mirrored in real-world horrors, where Jews, like Kafka would be arrested without accusation, due process, or access to a legitimate court. The legal machinery that devoured Josef K. in fiction became horrifyingly real, ultimately culminating in the Holocaust, where millions of Jews and other targeted groups were systematically exterminated. Kafka, who died in 1924 from tuberculosis, would not live to see these events unfold or he likely would have perished in a concentration camp, like most of his family.

The Trial is not about hateful political ideologies but rather the crushing weight of excessive bureaucracy. A system that no longer serves people but instead perpetuates itself for its own sake. I wrote about this earlier this year in How Society Uses Bureaucracy to Keep You Safe but Miserable, before I started The Trial. I took a different approach but the bottom line’s the same: if bureaucracy is not actively kept in check, it will become overgrown and eventually erode everyone’s freedom.

Beyond bureaucracy, Kafka’s novels discuss themes such as dehumanization, authority and existential isolation. His work is so iconic, that people refer to things as Kafkaesque when a situation is surreal, oppressive, and/or absurd. The term is often used to describe when individuals are caught in nightmarish bureaucratic loops, against nameless/faceless illogical agents acting on behalf of an uncaring system. In Kafka’s novels, the protagonists are generally the victims of these bureaucracy, yet still choose to fight or reason against their oppressors. These characters often exhibit alienation, guilt, and deep self-doubt, making them appear depressed or overly self-critical, as though they are fundamentally flawed.

If you contrast this with another great fiction writer of the 20th century, Fyodor Dostoevsky, his characters often go through major moral and psychological turmoil, and encounter existential questions. They differ from Kafka protagonists in that they often perceive themselves as more enlightened, morally superior, or "better" than the people around them. Therefore depending on how people perceive themselves, we can decide if they are a Dostoevsky or Kafka character.

We can all find ourselves in Kafkaesque scenarios; anyone that has ever gone to renew their drivers license or apply for a permit, will attest to this. Yet when faced with this scenario, do you accept your fate or try to be like Josef K? Alex Karp sees the West approaching this.

Alex Karp & Palantir

Before co-founding Palantir 20 years ago, Alex Karp did not fit the bill of the typical Silicon Valley Founder at the time. Instead of coding late into the night on side projects, he was busy earning his law degree from Stanford and a PhD from Goethe University. Karp started his career at the Sigmund Freud Institute, an institute focused on psychoanalysis, as per its namesake. He ran a hedge fund for a couple of years before joining Palantir with his former Stanford classmate, Peter Thiel in 2004.

Palantir Technologies is a software company that specializes in data analytics. They work with many large companies but they are primarily known for partnering with governments and military organizations. They first rose to prominence when reports suggested their work aided the operation that led to the death of Osama bin Laden. Shortly after, documents leaked by Edward Snowden indicated that Palantir played a role in supporting the National Security Agency's (NSA) surveillance programs, which were designed to monitor and analyze global internet traffic. Despite questions about these programs, nothing hindered Palantir’s growth.

In 2024, Palantir generated ~$3B of revenue, while growing at a rate of around 30%; they currently have a market cap of around $200B, which is in line with Salesforce and Adobe that generate around 10 times more revenue. The market is currently rewarding Palantir with a very high multiple, which means investors expect sustained future growth.

This can be partially explained by the many ongoing military conflicts providing a boon for military and defense stocks. The United States alone spends nearly a Trillion dollars per year on military and defense, meaning there is plenty of money up for grabs for those that can secure those sweet government contracts. Possibly inspired by the success of Palantir, there has been an emergence of newer startups entering the space. VCs are suddenly very interested in funding defense-tech companies, investing $3B in 20241. This contrasts sharply with when Palantir started; Karp said no VCs were interested in the sector, forcing them to raise funds from the CIA and Thiel’s Founders Fund. This is why, two decades later Karp can confidently take a victory lap, since those investments paid off handsomely and Palantir is well positioned as a leader in a space that is suddenly the hot thing.

The Technological Republic: Hard Power, Soft Belief, and the Future of the West

Alex Karp through The Technological Republic posits the West's technological leadership is endangered by a culture of complacency and misaligned priorities. He believes Silicon Valley has deviated from its historical collaboration with the government on significant technological advancements, such as the internet. Instead founders have been focusing on photo sharing apps and other trivial products. This is consistent with Thiel’s famous quote:

Karp sees this shift as part of a broader societal trend where intellectual fragility and a lack of ambition have infected academia, politics, and business, making this generation weak and less equipped to address, real pressing challenges. He’s certainly not the only person to lodge similar complaints about Silicon Valley innovations failing to address more important issues. For Karp, ensuring Western Democracies, remain the most technologically advanced is the most critical issue of the day. This is needed to maintain hard power, and soft belief.

If the US does not win the emerging artificial intelligence race, it will cede its superiority to rivals such as China, which has a different set of values. This might sound obvious, but as Karp sees it, many people in Silicon Valley and major institutions, are unwilling to say the quiet part out loud, America/the West needs to win. They are afraid of alienating anyone, so they choose not to say or stand for anything.

When Karp sees employees at big tech firms such as Google and Microsoft unwilling to work with the US military, but having no qualms working with the Communist Party of China (CCP), he sees this as an example of people wishing to benefit from the comforts of Western civilization without doing anything to protect it. Karp does not believe you can fence sit. You either support a cause, or you support its opposition. If you don’t support America and its allies, then you are for their enemies. Most people try to pretend these dilemmas do not exist, but in a competitive situation, opting out, is tacit support for somebody. This is effectively the trolley problem.

Many in positions of power feel unable to express their perspectives on issues of consequence, without potentially damaging their institution. However, not offering an opinion, is sometimes worse than taking a position. Karp highlights how this led to the ousting of former Ivy League Presidents Claudine Gay and Liz Magill; when they failed to denounce on-campus antisemitism. Karp doubts they are antisemitic or supported what they saw, but chose not to do anything because they felt unable to exercise their personal judgement, without in some way alienating a stakeholder of their university. In essence, they found themselves on the trolley and instead of choosing a track, they stepped out of the control room, hoping they would not be held responsible for the outcome. This approach failed them.

Karp on the other hand is not afraid. He has risked alienating customers and employees by taking public stances supporting Israel after the attacks of October 7th. He and Palantir were among the first Western companies to visit Ukraine after the invasion by Russia. Karp sees the situation as absurd. The West is in a great competition, yet many of its brightest technologists don’t want to help them win, which aids the competition. As CEO, Karp does not believe his job is to be a soulless agent serving only the system and shareholders. Therefore this begs the question, is Karp a Kafka or Dostoevsky character?

Conclusion: Who is Alex Karp?

Undoubtedly, Karp in his public appearances is giving off Dostoevsky main character energy. He does not follow the generic strait laced, publicly traded tech company CEO playbook. He’s brash, loud and unapologetically outspoken when sharing his views. On the spectrum he’s much closer to believing he’s the smartest person alive instead of being fundamentally flawed. While right now Palantir’s share price is on an incredible run, and he’s flying high, markets can be unpredictable and this can change almost overnight, just look at Zoom shares over the past 5 years.

Yet, you cannot overlook some absurd contradictions in Alex Karp’s rhetoric. He criticizes Silicon Valley for prioritizing trivial consumer apps over serious technological innovation, yet his co-founder, Peter Thiel, helped bankroll the very social media revolution that led to that shift. He argues that American tech companies have a moral duty to strengthen the West’s technological superiority, yet Palantir’s involvement in NSA surveillance raises questions about whether all "Western values" are being upheld equally. If Palantir and other American big tech companies win, how certain are we, we can still enjoy all of these freedoms2?

This paradox makes it difficult to place him cleanly in the Dostoevsky or Kafka archetype. If the West maintains its technological dominance, Karp will be seen as a visionary that saw what others didn’t and prevented the decay. If the West loses the AI arms race and America cedes control to adversaries, then Karp was a Kafka protagonist, that saw this happening but lost because too many in our society were afraid to standup for something. Perhaps it doesn’t matter whether we win this technological war or not, because one way or another, we will all be Josef K.

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