Most people start with picture books, or Goodnight Moon. Not me. I kicked things off with War and Peace and finished all of Tolstoy within a few weeks. It wasn’t because I enjoyed it, I had to.

This all sounds plausible because many people represent their literary activity this way online.

Reading online has become performative1. People post photos of books mostly as a way to flex. They either feel it’s important to show they are literate or want to indicate they do something with their free time other than doomscroll.

I take issue with people sharing books they haven’t read or didn’t take the time to understand. There’s nothing wrong with abandoning a book midway or finishing it but failing to understand it. Just don’t go around claiming to have read it without proper disclaimers. This is the equivalent of photoshopping yourself into pictures from a vacation you did not take. People might believe you but trying to impress by faking is a losing game.

Longtime readers might be tempted to accuse me of hypocrisy; I’ve been sharing my annual reading list online for a decade. Do you think I gained any clout from this? I’m still writing this weekly Substack, so what do you think?

It takes more than buying a hardcover and placing it on your bookshelf to be able to claim to have read a book. Opening one is a good start, so is flipping through to the end but you aren’t reading a book unless you’re doing so with complete concentration, and actually understand what the book is about. Sometimes it might require reviewing the same pages/chapters multiple times.

Nobody understood Tenet on the first watch, even Robert Pattinson who’s in the film didn’t. It takes two watches to understand it, and three to enjoy it. Regardless of the medium, art and knowledge both work that way. Some things are easier to digest than others, but simply flipping to the end doesn’t guarantee comprehension.

When you see people boast about reading vast numbers of books in a short timespan, that doesn’t mean anything. If anything, it’s usually a negative sign. If somebody is claiming to consistently read a book every week, especially anything with depth to it and they aren’t paid to do so, they are probably just flipping to the end. That’s why it’s pitiful to see people flaunt books for clout.

Anyway, here are 10 books I read lately.

If you caught my recent article chronicling my digital detox, you know I set off to finish ten books in the remaining 10 days of August. I succeeded but it wasn’t enjoyable. Some would suggest I’m built different. I’m not. Sometimes I like to do things because they are hard and I don’t think I’ll enjoy it. Reading over 2,000 pages in 10 days certainly qualifies. (The full list is displayed at the bottom of the article)

This isn’t something you do because you enjoy it or hope to better your life in the future. I can confirm doing something like this is purely performative. I was doing it to prove a few people on Substack I could2.

The first four books were easy enough. I had plenty of time during the digital detox and I was off work. During this span I read four books (see below for full list).

Assuming you’re reading a reasonably complex book of 200-300 pages, it takes at least 5-12 hours. You aren’t doing that in a single evening after a work day. Speed reading is nonsense, if you think you are consistently reading a page in under thirty seconds, you are definitely skipping things. If anything you should try to slow down.

If I want something to stay in my memory bank, I take notes and occasionally write a Substack article about it. This is a slow, friction filled process by design. This is why I only read 10-16 books per year, although this range rises with the amount of time spent on a beach.

This is why days 6-10 were not enjoyable. What I was doing resembled flipping through to the end. I read every word, but there was no time to reflect or take notes. My work day doesn’t end at 5PM and I occasionally need to do social things which cuts into the reading and reflection time.

After finishing the remaining 300 pages I had left with the Iliad, I opted for a short fiction then decided my best move was to revisit books I had previously read. Some I didn’t get a chance to take notes on, so it was helpful to review and not a waste of time. If these were my first reads, it would have been. This is why when I see people claiming to read 50 books each year, I don’t doubt some of these people flipped 50 books through to the end but I’m skeptical they gave them the attention they deserved or derived the value they should have.

People use books read as a vanity metric, but what use is reading if you don’t recall any of the lessons or anything from the book a few months after finishing it? If somebody dedicates all of their leisure time to reading, then sure. It’s completely feasible, but that’s not happening if you’re allocating the appropriate time necessary for a successful fitness regimen, career, family and social life. There’s an optimal point where you can have balance across all of these domains; once you clear more than two books per month, your health, career or social life are going to take the hit.

I met a guy who reads 60-100 books per year, but he lives on the Scottish countryside without a TV, computer or a conventional job so we can’t use him as a typical example. He thought Blood Meridian was the worst of the last 200 books he had consumed which made everything else he said suspect.

Some people will include audiobooks in their book counts. You aren’t missing much if you are reading smut but for dense topics, your retention is going to suffer. Especially if you’re listening while driving, folding laundry or otherwise engaged in multitasking. I listen to audio at 1.5-2X speed, which is fine for entertainment, podcasts, interviews or content I’m already familiar with but if I’m serious about trying to learn something new, I’m dropping it to 1.0X and buying the book after.

Yet the presence of a hardcopy on your book shelf or nightstand doesn’t guarantee that you’ll get any value or pleasure out of it. Same thing if you’re trying to rip through it in a few short hours. Performative reading serves no purpose beyond giving people content to post about on social media.

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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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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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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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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.

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

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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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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.

Is this why you love The White Lotus? Please let me know in the Comments and don’t forget to Subscribe.

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Given this is coming out in late December, this story can be considered a holiday story, so long as you consider Die Hard to be a Christmas movie.

I hope you enjoy this story, If this is not for you, I have plenty of other articles for you to check out (see list below) and I will be returning to regularly scheduled programming next week. If you do like this and want to see more in the future, let me know and I might publish more in the future.

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

Luigi Mangione chose to be Tyler Durden

The world needs another Ben Franklin

The Power of Confidence

The Most Obvious Secret to Success

“All Pain, No Gain” by Ben Saltiel

Am I dead? I wake up with an absolutely throbbing headache.

Sunlight streams through the window—late morning or early afternoon, probably. My nightstand’s knocked over, the alarm clock’s unplugged. The room’s a wreck: clothes are scattered, drawers are out, wide open. Looks like I had quite a time last night.

I struggle to my feet and hobble over to the bathroom, in the adjoining room. That blinding light isn’t helping. I think I hear something, a faint shuffle. Probably just the neighbor through the thin walls. I open the bathroom door, then notice it’s occupied.

“Sorry about that!” I call out as I slam the door shut , then notice even my bathroom products are scattered on the floor of the bedroom next to me. I pick them up then call out “I’m just going to go brush my teeth in the kitchen, take your time!” I can’t make out the muffled response through the closed door.

As I enter the hallway, I step on a piece of broken glass. What the f#ck is that doing here? Grabbing my foot in my hand, I hop on one foot into the kitchen and settle on a stool. The glass is one solid piece, only a few centimeters in diameter. Not very deep, small enough to remove without danger. I pull it out and grab a napkin to soak up the blood that seeps out of the wound.

Looking around the kitchen, I see that my first aid kit is conveniently already open on the floor next to me. Then the rest of the room comes to and I see it’s in a similar state to the bedroom. A huge mess. Furniture toppled over, removed drawers lying in the middle of the floor. Man, what did I get up to?

As I apply a bandage to my foot, I try to retrace my steps. It was my work’s holiday party, which started early, around 7pm. I don’t think I had much to drink; maybe one glass of wine? I never get drunk at work functions. Did I go somewhere after?

Glancing around the room, I search for clues that could help. What the hell, did I seriously forget to hang up my favorite Loro Piana suit? It’s so wrinkled, I’m going to need to steam it. My Ferragamo shoes, not too far away, are toppled over with the soles facing one another. Glancing around, I see a few of my other expensive suits, shoes, and watches in a pile on the couch. As usual I probably couldn’t decide what to wear. Can’t believe I didn’t at least hang them back up after, I must have really been bombed out.

I limp to the kitchen, grab a cracked mug, and fire up the coffee machine. The first sip hits hard, but it helps. I immediately make another.

After the holiday party I remember meeting up with some people. We went to that cocktail bar, the one with the bathtub in the middle and no sign. We didn’t stay out that late though, did we? I quickly brush my teeth in the sink, looking at the time on the stove I see it’s 11:24 AM. Thank God I don’t need to work today.

I head to my office in the next room. Great, now where’s my laptop? I don’t see my bag either. I must have left it at work before dinner. I guess I’ll need to get that later. Limping back to the bedroom, I see my phone on the ground poking out from under one of my sweaters. Picking it up, I see 20 notifications. I sit down on my bed, covered in my clothes and other personal affects. I really hope the maid is coming today, I should still tidy up a bit before she arrives. Otherwise it won’t be cleaning up, it will be hurricane relief.

These notifications were mostly people tagging Instagram stories from the work dinner or a few group chat text messages I didn’t open from last night. Going through the conversations, it seemed like we left the bar fairly early. I checked the AMEX app, and there are no big charges. Why am I in such rough shape this morning? I don’t think my head has ever hurt this much from drinking before. Reaching up to my temple, I feel a huge bump. Well, that would explain it. Using the camera on my phone, I see a huge bruise and red mark just over my left eye. How did I get this?

Seeing the bathroom door closed. I guess it’s still occupied. They’re certainly taking their time. I sit back down on the bed. To avoid the bright light, I face the corner with my back to the window and bathroom door. I go back to scrolling aimlessly on my phone, checking out what’s happening on Instagram. Nothing interesting. Flipping over to ESPN.com. All my teams lost last night, that sucks. My landlord texted me, asking if everything was alright? Some neighbors said they had heard some loud noises. That’s embarrassing, I apologize and promise that we’ll keep it down.

Suddenly it hits me. I don’t have a roommate. I snap to my feet, my spine starts to tingle. Who is that in the bathroom? Just as I turn to face the bathroom door, I hear the sound of it creaking open. A masked stranger dressed in black steps out and grunts “Toss your phone over right now, or I’ll slug you again!”

****The End****

I hope you enjoyed today’s article, I publish weekly on topics related to finance, books, self improvement or anything worth exploring. Please subscribe so you don’t miss anything.

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For this year, I read a total of 10 books. This is below what I have done for the past few years but the weekly posting cadence on Substack has eaten into my reading time. Nonetheless I am pleased with quality of the writing I was exposed to this year, since I would recommend all of these books. Some are of niche topics, so if you are not into that genre, don’t force yourself on my suggestion.

Some of these books inspired their own Substack articles, therefore I shared the relevant links to those along with a quick summary and my review of each book below. I hope these can inspire you to read something new and interesting in 2025.

***Correction after releasing the article I realized I didn’t include The Count of Monte Cristo by Alexandre Dumas, which I also read this year. I did the abridged version but I suggest doing the unabridged even if the length is substantial.

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

Luigi Mangione chose to be Tyler Durden

The world needs another Ben Franklin

The Power of Confidence

The Most Obvious Secret to Success

The 2024 Ben Book List

1. Books# 1-3: The Talented Mr. Ripley, Ripley Under Ground and Ripley’s Game all by Patricia Highsmith. ~1,000 pages all together or 300-350 pages per book.

Rating: 90/100 (I would gift/actively recommend)

Related Substack Article: Mimetic Theory as Explained by The Talented Mr. Ripley

Tom Ripley is one of the iconic characters of modern American fiction. His journey from obscurity to high status, is quick but alarming. Most have heard of The Talented Mr. Ripley from book lists, the 1998 film with Matt Damon & Jude Law or the recent Netflix Series but few realize that it’s only the first installment of a 5 book series. I read The Talented Mr. Ripley long ago but didn’t realize there were more in the series until Ripley Under Ground and Ripley’s Game appeared on my Amazon recommendations more recently.

We are first introduced to Tom Ripley as a young twenty something, living in New York pulling small scams and cons. A wealthy industrialist, under the impression that Ripley is good friends with his son Dickie, hires Tom to go to Italy and convince Dicky to return home. Tom takes him up on his offer but instead of getting Dickie home, befriends him and they hang out in Italy instead. I won’t go through any spoilers but the first book covers this initial period of Tom in Italy in his early twenties, while the sequel, Ripley Under Ground and trilogy Ripley’s Game take place a few years later.

All three books are really great and worth reading together, but the Talented Mr. Ripley is definitely the best. I didn’t continue with the 4th and 5th installments because they received universally bad reviews and the author herself admitted she wrote them for financial motivations.

2. Henry Kissinger by Walter Isaacson ~750 pages

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

Related Substack Article: Kissinger: War Criminal, A$$hole or Great Diplomat?

Within 5 minutes of picking up this book, I already had somebody screaming at me. They called Kissinger a War Criminal and an a$$hole. After quickly realizing that this person hated him, but didn’t know why, I decided that I had better learn more for myself.

I didn’t know much about him but he’s an important historical figure and I loved many of Isaacson’s previous biographies. Isaacson did a great job covering his early life, time as an Academic and role within the Nixon and Ford administrations. He did not gloss over Kissinger’s role in Vietnam, but he provided useful context for the many conflicts that were ongoing while he was in office. It came out in the nineties, so it couldn’t comment as much on his later life

Although the book is lengthy and the topic is not light, I am glad that I read it. It’s certainly not a topic or a subject that I would recommend to anyone, unless you are something of a history or international diplomacy buff.

3. The Qualified Sales Leader by John McMahon ~300 pages & $100M Leads by Alex Hormozi ~300 pages

Rating: 90/100 (I would gift/actively recommend)

Related Substack Article: How to not Suck at Sales

I spent a decent part of this year focused on evaluating the performance of my companies sales team. Earlier this year we hired a successful sales leader with experience managing large teams selling into some of the world's largest companies. During our sessions he shared numerous insights. One key recommendation he made was to read The Qualified Sales Leader.

McMahon has held executive sales roles at several successful technology companies, including PTC, BladeLogic, BMC Software, and others. His expertise lies in building scalable sales processes, developing sales talent, and driving significant revenue growth, so he knows how to sell.

Another book I came across was $100M Leads by Alex Hormozi. Hormozi was a gym bro that successfully scaled his and many of his clients businesses to six-nine figures in annual revenue. From his videos you would think he is another internet scammer but when you read $100M Leads, you quickly realize that he has a great understanding of sales and marketing, and knows how to explain it, in a simple and direct manner.

I would expect most people seeing this do not work in sales, but much of life revolves around your ability to sell yourself. Knowing the basics of why people buy, or would be interested in what you are trying to sell, will give you a great in advance in any endeavor that you attempt.

4. Player Piano by Kurt Vonnegut 300-350 pages

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

Related Substack Article: A 1952 Satire Book Predicted Chat GPT

Kurt Vonnegut Jr., one of the great satire writers of his time, quickly established his prowess in his debut novel Player Piano (1952). Written shortly after WWII, Vonnegut created a world almost completely automated by machines, leading to societal changes once considered unthinkable.

In 1952, Player Piano was clearly a satire. In 2024, you might confuse some of its lines with quotes from technology or media companies. Vonnegut was eerily prescient with many of his predictions of the future; not only have we achieved many of the innovations that seemed like science fiction at the time, we continue to approach a society mirroring the one shown in Player Piano.

Good book and as everything from Vonnegut, quite funny at times.

5. Benjamin Franklin by Walter Isaacson ~600 pages

Rating: 85/100 (Niche topic, I would recommend if asked)

Related Substack Article: The world needs another Ben Franklin

Benjamin Franklin was successful as a newspaper editor, tradesmen, entrepreneur, politician, diplomat, scientist, inventor and author. Oh and he also played a major role in the American revolution and drafting the Declaration of Independence and US constitution. Not only did he accomplish all of this, he managed to have more fun than anybody else.

Walter Isaacson as usual, does an incredible job bringing readers back to the early establishment of the United States, why Benjamin Franklin, all of the Founding Fathers best embodies the spirit of America, and how his personality was entrenched in the constitution and the spirit of America.

Franklin was a very successful polymath that managed to impress people across America, Europe and many domains. If you are interested in learning about the early history of the United States or just want to know more about a legend, this is a great book to check out.

6. The Trial by Franz Kafka ~300 pages

Rating: 85/100 (I would recommend if asked)

Related Substack Article: Millei+DOGE: Austerity is cool again?

The Trial, regarded as Kafka’s most famous works, masterfully portrays the dangers of oppressive and absurd bureaucracy. Kafka is an excellent writer, that can make great points while being very funny. Although it was written over 100 years ago, the novel’s surreal and nightmarish exploration of justice and power, should still concern us today since individual liberties versus the role of government remain an ever pressing matter.

Seemingly citizens of each country has accepted that some level of bloated government bureaucracy is a necessity of life. This angers some more than others. The recent mandates of Javier Millei in Argentina, and Elon & Vivek with DOGE, appear to be trying to reverse this trend although they face substantial opposition.

7. How to Make Friends and Influence People by Dale Carnegie ~350 pages

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

Related Substack Article: How to not suck in 2025

The timeless guide to building strong relationships, winning people over, and influencing others effectively while staying genuine. Through practical advice and real-life examples, Carnegie teaches skills like remembering names, being a good listener, and making others feel valued. He outlines strategies for persuading people by appealing to their interests rather than through argument or manipulation.

The book also highlights the importance of encouragement, recognition, and constructive feedback in leadership and collaboration. Structured into clear sections with actionable takeaways, it remains a relevant resource for navigating personal and professional relationships with confidence and grace, offering readers tools to foster authentic connections and inspire cooperation.

It’s still worth reading in 2024 or 2025.

See also:

Zero to One by Peter Thiel

Rating: 90/100 (I would actively recommend/gift)

Related Substack Article: Revisiting Peter Thiel's Zero to One: 10 Years Later Part I

Neither a new book or something I read for the first time, but it has now been 10 years since Thiel released Zero to One. In 2014, Thiel was largely unknown outside of technology circles. Few would have guessed in the years after its release, Thiel would silently become one of the more influential members of the Republican party. Many former employees or colleagues such as JD Vance, Elon Musk & David Sacks now hold heavily influential roles in the Trump White House.

Even with this political influence, he remains focused on business and technology. Palantir, which he co-founded, is one of the most highly valued technology stocks and his many funds continue to back the most iconic startups. One of my early Substack article was to look back at some of the predictions he claimed in 2014 to evaluate if we would agree with him in 2024.

Despite his politics, he is one of the most interesting people alive today. His insights on businesses and the future should not be ignored, as he has exhibited many times his ability to see where the puck is going, before anyone else has even shown up to the arena.

Have a great holiday season to all my readers!

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Satire points out flaws within society by using humor. Classic works of fiction such as Animal Farm, Catch-22, Don’t Look Up and Wag The Dog take aim at political regimes, institutions or even human nature.

Satire is a powerful technique but far too often, lines that appear as comical exaggerations contain more truth than we realize.

Kurt Vonnegut Jr., one of the great satire writers of his time, accomplished exactly that in his debut novel Player Piano (1952). Written shortly after WWII, Vonnegut created a world almost completely automated by machines, leading to societal changes once considered unthinkable.

In 1952, Player Piano was clearly a satire. In 2024, you might confuse some of its lines with quotes from technology or media companies. In today’s article I am going to discuss the implications of a fully automated society, how Gen AI and the proposed regulations are bringing us closer to the world created by Vonnegut 70 years ago.

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

Why I’m Quitting Coffee

Stoicism Explained by Star Wars

How To Make Better Predictions

Sorry Jocko, Discipline is Overrated

Technology, The Luddites & Techno Optimists

Long before the internet and fancy algorithms, humanity relied on technology to expand. The discovery of fire1, invention of better farming tools and creation of aqueducts made it possible for civilization to sustain increasingly greater population sizes. With some exceptions, despite this rapid population growth, there was a persistent labor shortage, since activities always relied on human labor2.

Up until the late 18th century, most people lived on the country side and if they were not conscripted in some noble persons military conflict, they were likely a farmer (no Costco’s in those days). It was the Industrial Revolution that saw inventions leading to the disappearance of entire lines of work and the creation of what now resembles the modern career (M-F 9-5 work week, coffee breaks, Peggy’s disgusting muffins you are forced to try etc.).

This created many new kinds of jobs, but they were not available to everyone, leading to unemployment and then anger against this new technology. This led to the rise of the Luddites, a group of English workers in the early 19th century who rebelled against this technology by actively sabotaging machinery. The movement lasted less than a decade but hundreds of years later, people opposed to technological progress are still called Luddites.

On the other end of the spectrum, there were countless Techno-Optimists, this group would contain most noted scientists, economists, inventors & entrepreneurs. Their goal was to keep pushing society to adopt new technologies that would make life better. If you are reading this from your computer or mobile device, you can probably guess which group ultimately won. Nonetheless, despite great achievements from technology, many new problems arose. In response to these issues, Luddites will say stop or slow down, while Techno-Optimists will say:

ChatGPT, AGI & The Automated Society

Sam Altman, clearly inspired by Jeff Goldblum in Independence Day and Jurassic Park, along with the team at OpenAI have forced the world to notice the promise and potential pitfalls of Generative AI and Large Language Models (LLMs). Their flagship product, ChatGPT is believed to have passed the famous Turing Test3.

If you don’t feel like watching the clip, Peter Thiel, believes this might be more important than the achievement of AGI and it will have dramatic changes society. He did not go into much detail but we can surmise that he’s referring to the high number of jobs estimated to be changed, displaced or eliminated because of AI automation.

The range of proposed solutions have been to:

• Don’t interfere but trust new jobs will be created

• Slow down progress by increasing regulation or to take a pause

• Impose taxes on the companies benefitting from AI

• Create new government programs such as Universal Basic Income (UBI)

• Make major investments in re-educating the workforce

• Federal job guarantees (create government jobs)

There are many others but most rely on increased central planning of the economy. Whether you are a Capitalist or Socialist, this should concern you. Why?

Player Piano’s Automated Society

"Without regard for the wishes of men, any machines or techniques or forms of organization that can economically replace men (will). Replacement is not necessarily bad, but to do it without regard for the wishes of men is lawlessness.” Player Piano

Player Piano takes place in Ilium, New York, a city divided into three parts. The northwest for the engineers, managers & civil servants, the northeast for the machines and the south (called Homestead) for the remaining citizens (or slaves depending on your perspective)4.

A third World War left the US with a labor shortage, which prompted the engineers and managers to design factories that required few workers. Within 10 years of the conclusion to the war, all manufacturing and physical labor jobs are performed by machines. High school graduates with top percentile test scores end up in the northwest as engineers or managers, everybody else goes to the army or public works.

To avoid the natural boom and bust cycle, consumption and production, like most things, are decided by machines. Instead of a free market, Homesteaders receive an income from the government to afford a standardized home, food, home appliances and a little pocket pocket money that goes to drinking, cigarettes & entertainment. Their basic needs are met and they enjoy a lot of leisure time, since their household chores are also automated. Yet these Homesteaders lack purpose. Especially those old enough to remember life before the war are deeply unhappy. They have nothing to aspire to and have no chance for upward mobility. Even for the younger generation, save the very fortunate few that score highly enough to become a northwester, know that their fate is decided for them by the time they are 18.

Engineers and managers, have much higher disposal incomes and enjoy higher status compared to the Homesteaders. Despite these advantages, they don’t have much more freedom. They are cogs part of a much larger system; even most senior managers and engineers lack autonomy to make any consequential decisions. To maintain their position, they need to follow strict protocols and sets of behavior imparted by their organizations, as well as the law. This maintains order long enough, but eventually turns into a power keg filled with a population ready to rebel.

Lessons

Player Piano is a satire, yet in 2024 politicians and thought leaders in response to the anticipated job losses from AI, are going to recreate this society. Preventing technological progress is at best a short term solution, that even the most ardent advocates acknowledge. Other proposed ideas center around the government taking a more active role in managing the economy, whether it comes from UBI, taxation or creating valueless jobs; all policies present in the story.

If the best ideas our elected officials can muster are to pay people not to work or give them meaningless jobs, we are in trouble. While some might be happy with a guaranteed living stipend from the government, I like Vonnegut, expect many more would be deeply unsatisfied. Ironically, Vonnegut was a self proclaimed Luddite and in favor of Socialism. Yet through Player Piano, he expresses his own skepticism of how Socialism or Communism would work in a society where humans lack autonomy and everything is centrally decided top down aided by technology5.

UBI and federal job guarantees would prevent physical starvation however humans need more than that to feel fulfilled. Instead of this doom and gloom over the inevitability that AI will come and take our jobs, government should take a leading role in giving its citizens a sense of optimism for the future by helping support new and exciting projects that will create opportunities.

Despite all the technological progress present in Player Piano, things were not that different compared to how humans actually lived in the 1950s. Where were the Jetson style flying cars or sonic airplanes travelling at the speed of light? Even the wealthiest Northwesters were still driving cars and living in normal houses. Instead of the government trying to control technology and the economy, another solution not depicted in Player Piano, would be making major investments to help with advancements not directly related to AI.

This is not to say, there should not be some sort of regulations around the usage of AI and technology, there should be, and I’m confident it will come. The goal of these regulations should not be to simply slow down or stop AI progress, as this is more likely to benefit incumbents, making them more powerful. By incentivizing entrepreneurs and smaller companies, new jobs and industries can spring up, creating new opportunities for workers displaced by technology or new graduates looking for their first role.

Governments are trying this with investments into Cleantech and semi-conductor chips, but surely there are many more difficult problems facing the world in need of capital and labor to try to solve? If you take away one lesson from today’s article, it is that UBI and federal job guarantees might prevent people from starving but would leave large parts of the population without autonomy or hope; this would recreate the society of Player Piano and this should have you very concerned.

I will leave you with his great quote from Albert Camus:

“The only way to deal with an unfree world is to become so absolutely free that your very existence is an act of rebellion.”

I hope you enjoyed today’s article. Please Subscribe, I am only a few away from 300 Subscribers! If you did not enjoy today’s article, please feel free to let me know in the comments below or by replying to this email. I appreciate any and all feedback.

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Based on the Lindy Effect, it is no surprise that The Richest Man in Babylon, published by George S. Clason in 1926, continues to be among the most consumed personal finance books. Babylon fell into ruins and largely disappeared 1,300 years ago, yet the lessons of building and maintaining wealth remain as timeless and relevant as ever. With endless content and personal finance gurus trying to convince people to forget everything they know about budgeting, investing, etc., it can be easy to overlook enduring basic first principles. Let this review serve as that reminder.

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The book begins around the year 2000 BCE, when Babylon was at its peak of civilization. A bunch of broke Babylonians sit around whining about their lack of wealth, until they decide to simply ask the richest person in Babylon, Arkad, how he became so rich. They were roughly the same age and started off with equal footing, so why were they constantly cash insecure while Arkad was swimming in it? Arkad, being generous with his wisdom and time, told them exactly what he had learned from another wealthy man, Algamish.

This sounds complex but what this really means is save your money. There it is, why bother with the remaining 100 pages of the books? But wait, there’s more!

Algamish specifically suggested starting by simply saving 10% of Arkad’s earnings each month for the next year. Arkad did this, then promptly invested it poorly. The brickmaker offered to take his savings to buy some precious stones from the Phoenicians, then sell these back in Babylon at a much higher profit. What could go wrong? Well, those sneaky Phoenicians sold the brickmaker some useless glass, which of course the brickmaker could not identify, resulting in Arkad losing his entire investment. He repeated the process the next year, this time investing it more wisely. However, instead of letting his winner ride, he took the profits and spent it all on wine (to drink) and fancy clothes.

Algamish pointed out to Arkad that he was sacrificing long-term wealth for short-term splurges. It was not until the next time they saw each other two years later that Arkad put it all together. He was saving, investing, and reinvesting and watching his wealth climb. Algamish, not impressed with his son’s abilities to follow these lessons, decided to bequeath part of his empire to Arkad.

The poor Babylonians listening to these lessons then simply dismissed Arkad’s accomplishments, saying that he only really developed his wealth because he cozied up to Algamish or because he had more willpower than the rest of them. Arkad, like any other personal finance guru would, disagreed with these claims. Effectively saying, he put himself in the position to be successful because he truly wanted it to happen. If any person really wanted to be wealthy, they could easily follow those same steps and accomplish similar results.

Those poor whiny Babylonians, were not the only people trying to solicit advice from Arkad. The King of Babylon, realizing that if Babylon were to remain competitive for years to come, they needed more wealthy citizens. If they did not have a new generation of investors willing to participate in pre-seed funding rounds in pre-revenue & pre-product startups launching Crypto AI wrappers, Babylon would be downgraded to a tier 3 city. He too called on Arkad to share his knowledge. Arkad assembled a classroom of students for him to teach

The 7 Cures for a Lean Purse:

1. Start thy purse for fattening - Save 10% of your income

2. Control thy expenditures - Scrutinize your budget and ensure every dollar spent is either 100% necessary or 100% valued until you arrive at a 10% savings rate

3. Make thy gold multiply - Invest your savings, keep it invested (compound your interest)

4. Guard thy treasure from losses - Avoid get rich schemes, only take investment advice from relevant experts

5. Make of thy dwelling a profitable investment - Own your home

6. Insure a future income - Factor in growing future expenses, plan accordingly

7. Increase thy ability to earn - Become so skilled at your profession, you will increasingly grow your wages

The rest of the book is largely redundant repeating many of the lessons Arkad shared above. The remaining pages provide endless examples of people wasting their money, missing out on potential big investment opportunities or putting themselves in a position to benefit from good fortune when it comes. These lessons are stunningly obvious, yet followed by so few.

Arkad became the richest man in Babylon by adhering to very simple but uncomfortable advice. It takes discipline and consciousness, to avoid splurging money on fancy things and ensuring that 10% each month gets set aside for investment. Some personal finance guru’s push for higher savings but Arkad acknowledged, that he still wanted to enjoy his life while his wealth grew. Wealth building does not need to be especially painful or complex. By following the simple lessons from The Richest Man in Babylon, I have no doubt that you could one day achieve similar wealth. If you choose to ignore these lessons and fall short of your goal, don’t blame it on ignorance.

Thank you for reading this weeks article. Please let me know your thoughts by commenting below or messaging me back. For you many new subscribers, please check out some of my older articles here.

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Zero to One is regularly listed as one of the best books ever written on Startups, business and technology. It was well received upon its release and ten years later, it remains as relevant and prescient. Not only do most of the lessons remain true, Thiel’s own prominence has dramatically risen. When Zero to One came out in 2014, beyond a thinly veiled caricature on the TV Show Silicon Valley³, few people knew him outside of technology circles. Two years later, he spoke at the Republican National Convention. Never afraid of being contrarian or controversial, regardless of how people feel about his political views, most would agree that he is among the most influential people to emerge from the Valley in the past 20 years.

Welcome to Part Two of my series revisiting Thiel’s Zero to One.

In Part One, I investigated Thiel’s claims around Technology vs Globalization, Boldness over Triviality and Competition.

This post focused on Chapters 4-6, specifically competition & long term value and how repeat successful entrepreneurs negate arguments reducing success with luck.

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Chapter 4: THE IDEOLOGY OF THE COMPETITION

“Rivalry causes us to overemphasize old opportunities and slavishly copy what has worked in the past.”

Thiel believed that companies engaged in competition did not have the luxury of innovating; this was something reserved for Monopoly businesses. This runs contrary to conventional Economic theory, that teaches that Monopoly companies stop innovating, while competitive companies need to innovate to survive.

In Part One, I went through the product releases from Apple, Alphabet, Amazon and META since 2014 and demonstrated that almost all of their successful products actually came from acquisitions. Even when they do launch new innovative products, they have a difficult time effectively commercializing them.

What Thiel might have missed in 2014, was that these companies would balloon in size after rapid hiring sprees and become the subject of increased government attention, in part because of several scandals. In the aftermath of the Great Financial Crises, regulators were largely focused on the banking sector allowing technology companies to operate mostly unencumbered. There was a noticeable shift in sentiment at around the time President Trump was elected, that invited scrutiny from both sides of the article. While Social Media platforms such as Facebook and Twitter drew the initial ire, it eventually permeated to the other Tech companies as well.

This new distrust stifled at least a few product launches. Facebook’s crypto play Diem, which seemed promising technologically, could not take off because of a lack of trust amongst the public and Facebook in the wake of Cambridge Analytica. Similarly, Google was working on a Smart City project “Sidewalk Labs” with the city of Toronto. They faced severe criticism for the handling of personal data, which was among the reasons they eventually cancelled the project. These are among many examples of the public and regulators reluctance to trust big tech companies which inhibited their efforts to launch new innovative products.

Gemini Struggles

I believe this contributed to the increased involvement of additional stakeholder groups that made shipping products an increasingly slow and difficult process. Google’s Gemini is a perfect example of this. Despite having what many believed was a massive advantage when it came to Artificial Intelligence, Open AI beat Google to market with the public release of Chat GPT. After capturing the initial hype and praise, Google released their competitor with far less fanfare. Google had been playing catch up the entire time, this was only further exasperated when users started noticing some odd issues with their image generation application.

This image generation difficulties, were largely linked to the involvement of Diversity Equity and Inclusion (DEI) initiatives at the company. Big Tech in general has had to contend with increased political activism from their workforce, which critics point to as a sign that innovation may no longer be there primary driving force. Even when politics are not involved, it appears that the Big Tech Monopolies have struggled launching new product lines. After many years working on Autonomous Vehicles, Apple announced layoffs in this division and wanted to pivot the existing employees to focus on other AI opportunities. Considering, Apple had the opportunity to acquire Tesla only a few years ago, this is a big blow to their reputation as innovators.

As Big Tech has matured, their new model appears to have adapted to allowing smaller companies to take the initial technology or business risk, then rapidly acquire or copy them. Only a few years ago, people joked that Evan Spiegel, CEO of Snapchat, was the Product Manager for the rest of the Social Media companies because of the rate that Instagram, Twitter and Linkedin were copying his Snapchat features. Meanwhile META can monetize their audience at a rate 10X that of Snapchat, so what incentive do they have to beat Snapchat to test these new features1? 

On the other end of the spectrum, Tesla while the leader in the electric vehicles, has seen far more entrants join their market over the past 10 years compared to any of the other big tech companies yet they continue to innovate at an incredible rate. They have released the Model X (2015), Model 3 (2017), Model Y (2020) and announced the Cybertruck, not to mention many other software and battery improvements. They went from being the only Electric Vehicle Manufacturer, now every major auto company has one, not to mention many other upstart new entrants. If anything, the competition has inspired Tesla to continually push the envelope and not “slavishly copy what has worked in the past”. All of Elon’s companies are engaged in serious competition yet manage to find ways to innovate. 

Therefore Thiel’s perspective on Rivalry forcing companies to fall back on what worked and stopped innovating, should be adjusted to reflect that the lack of competition, can also prevent new products from getting to market, because these companies do not have any direct competitors that pressures their delivery timelines.  

Chapter 5: LAST MOVER ADVANTAGE

“If you’re the first entrant into a market, you can capture significant market share while competitors scramble to get started. Moving first is a tactic, not a goal. Being the first mover doesn’t do you any good if someone else comes along and unseats. It’s much better to be the last mover, make a last great development in a specific market to enjoy years or decades of monopoly profits. The way to do that is to dominate a small niche and scale up from there, toward your ambitious long-term vision.”

When Thiel wrote this, he had several recent examples to draw upon. Facebook was not the first digital social network but at the time had completely dominated the landscape, eradicating the incumbents, Myspace and Friendster from relevance2 . Similarly, Google was not the first search company, but within only a few years were rendering >90% of search revenue.

Thiel once again, posits something that runs contrary to what economic theory and business school has taught for the past decades. Instead of trying to build a Monopoly by being first to market, then constantly staying ahead of the competition, all you really need is a defensible innovation that cannot easily be replicated. This does not need to be purely technological, Airbnb and other marketplace businesses have shown incredible staying power by harnessing such a demand and supply advantage over alternatives. VRBO (launched in 1995) and Couchsurfing (2004) were both early to market but were quickly supplanted only a few years after Airbnb’s launch. While not a Monopoly within the context of the entire vacation rental market, Airbnb is the dominant platform when it comes to short term home rentals3.

NVIDIA was far from being the first semi-conductor chip company, yet their creation of the Graphics Processing Units (GPUs), helped them reach a valuation north of 2 Trillion in 2024, worth more than the next several largest Semi-conductor chip companies combined. NVIDIA quickly went from frontrunner to Monopoly status in a remarkably short span, unless another competitor can quickly match their capabilities, they could own this for a foreseeable future.

The examples of Airbnb and NVIDIA would be evidence that Thiel is still correct that last mover advantage, defined by releasing a game changer feature is more important to achieve a Monopoly than First Mover Advantage.

Chapter 6: YOU ARE NOT A LOTTERY TICKET

“If success were a matter of luck, these kinds of serial entrepreneurs (Founders who have started multiple Billion dollar companies such as Steve Jobs, Elon Musk and Jack Dorsey).  probably wouldn’t exist”.

This quote is in response to people like Malcolm Gladwell and others who attribute the success associated with launching a Billion dollar company more with luck than the individual itself. To summarize his arguments and others, people like Gates, Jobs, Musk etc. were only able to accomplish such incredible things because they came around at the right moment in history and the circumstances were such that made it possible for them to realize their ambitions. If it had not been them, likely it would have been somebody else. This is a direct contradiction to The Great Man theory which states that a few key individuals drive civilization forward.

Playing the undoing game, if Gates, Jobs or Musk had been born a century earlier, it is fair to suggest they likely would not have been tech entrepreneurs. The enabling technology did not yet exist, these men likely would have been enlisted in some military conflict and even if they managed to avoid it, they likely would have died of some disease that has since been cured my modern medicine. On the other hand, suggesting that these individuals were merely fortunate opportunists, (lottery tickets) would lead one down the path of believing that there is no point in trying to change the outcome of the future, since the future is already determined and we should simply resign ourselves to fate.

Following this line of thinking can get dark pretty quickly. Fortunately, Thiel along with the names that he mentioned, clearly did not believe this and launched multiple category defining Billion dollar businesses. Thiel posits that if luck is the key determining factor, than how could there be multiple individuals to have created multiple category defining businesses? For a company to be considered category defining, let’s assume that as of this writing, they are valued at least over $1 Billion dollars. Since the book came out, are there more examples of these kinds of entrepreneurs?

There could be more but off the top of my head, 6 people come to mind:

1. Parker Conrad (Zenefits & Rippling)

2. Max Levchin (PayPal & Affirm)

3. Palmer Lucky (Oculus & Anduril Industries)

4. Sam Altman (Hydrazine Capital* & Open AI)

5. Adam Neumann (WeWork & Flow*)

6. Travis Kalanick (Uber & CloudKitchens*)

7. Adam D’angelo (Facebook* & Quora*)

8. Brad Jacobs (multiple but most recently GXO)

It is hard to dispute that Parker Conrad, Max Levchin and Palmer Lucky achieved this status. Their companies may not be category defining at the same scale as Musk or Jobs but their sequel efforts are leaders within their respective verticals (Conrad in HR Software, Levchin in Fintech & Lucky in Modern Defense Tech). 

Sam Altman is best known as the CEO of Open AI, which is undoubtedly a category defining company. Prior to his involvement with Open AI, after selling his startup Loopt, Altman founded Hydrazine Capital. According to reports, the returns generated by Hydrazine Capital, have given Altman a net worth in excess of $2B. He has regularly stated that he does not own equity in Open AI, therefore being able to amass such a net worth must mean his fund performances must be among the best performing Venture funds. If we count Hydrazine Capital as a category defining company, his brother & co-founder would also qualify for this list. Jack founded performance management company Lattice, which was recently valued at $3B.

Interestingly, the 4 first names on this list have links to Thiel. Conrad and Lucky received funding through one of Thiel’s VC funds, Levchin co-founded PayPal with Thiel. Altman and Thiel overlapped as partners at Y Combinator and Thiel was among the early backers of Open AI.

Adam Neumann definitely got WeWork to a valuation well over a billion dollars and was able to raise a substantial amount of money at a high valuation for his sequel effort, Flow but it is still premature to call it successful. 

Similarly, Kalanick undoubtedly built one of the best known Web2.0 consumer companies in Uber. Not enough is known about CloudKitchens to be able to declare it a success but like Neumann, they technically are both valued over a billion dollars. It should be noted that both of these sequel ventures raised during the peak Post-Covid Venture funding bubble.

D’angelo was not technically a founder of Facebook but he was one of the first hires so I would count him in this group with an asterisk. Quora is still private, but achieved a peak valuation of $2B before a downround cut the valuation below Unicorn status. With an asterisk on both, he would be the easiest to dislodge from this list.   

Brad Jacobs is not as well known as the other names on this list but he has founded seven companies—all billion-dollar plus corporations (some are spinoffs)4.

While not a founder, Frank Slootman5 managed to incredibly scale up 3 companies by more than 10X.

1. Data Domain was acquired for $2.4 Billion, when he joined it was doing low millions in revenue.

2. ServiceNow grew from $110M to $1.9B in annual revenue under his leadership

3. Snowflake went from $4 Billion to a peak valuation of $70 Billion during his tenure. 

If you believe that the existence of founders with multiple category defining companies disproves the Lottery Ticket theory, then Thiel is correct. There are at least several founders that have managed to launch multiple billion dollar companies since Zero to One was released.

Zero to One is regularly listed as one of the best books ever written on Startups, business and technology. It was well received upon its release and ten years later, it remains as relevant and prescient. Not only do most of the lessons remain true, Thiel’s own prominence has dramatically risen. When Zero to One came out in 2014, beyond a thinly veiled caricature on the TV Show Silicon Valley3, few people knew him outside of technology circles. Two years later, he spoke at the Republican National Convention. Never afraid of being contrarian or controversial, regardless of how people feel about his political views, most would agree that he is among the most influential people to emerge from the Valley in the past 20 years.

With the benefit of a decade of hindsight, I decided to revisit the book to evaluate how much of Thiel’s views and predictions would be considered true in 2024. For this series, I go through each chapter to determine if I think he is still right today.

Today I will be evaluating Chapters 1-3 and will cover the remaining chapters in subsequent posts.

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If this article interests you, here are some others you might enjoy:

Chapter 1: The Challenge of the Future

“This age of globalization has made it easy to imagine that the decades ahead will bring more convergence and more sameness… the division of the world into the so-called developed and developing nations implies that the “developed” world has already achieved the achievable, and that poorer nations just need to catch up.  But I don’t think that’s true. My own answer to the contrarian question¹ is that most people think the future of the world will be defined by globalization, but the truth is that technology matters more. Spreading old ways to create wealth around the world will result in devastation not riches. In a world of scarce resources, globalization without new technology is unsustainable.” 

¹ The contrarian question is “What important truth do very few people agree with you on?”

Let me ask ChatGPT. Did technology or globalization have a bigger economic impact since 2014? Shockingly, Open AI’s Large Language Model seems to think it was technology. This might seem obvious today but at the time Zero to One was published, it was less clear.  

In 1998, Nobel Peace Prize Winning Economist Paul Krugman was skeptical of the promise that technology would represent for the economy. Famously writing "By 2005 or so, it will become clear that the Internet's impact on the economy has been no greater than the fax machine's." Even by 2012, when Thiel was lecturing at Stanford, technology's impact was already heavily noticeable although not to the same extent.

Globalization measures the increasing free flow of goods and services, which would include technology. To isolate technology from globalization, let’s evaluate its impact based on the growth in IT relative to other sectors in addition to its increasing relevance within the US and global economies. At the time, global IT spending made up 5% of global GDP and Apple, Microsoft and Google were consistently among the 10 most valuable companies in the world. 

Since 2012, while IT spending has grown, it still makes up about the same percentage of Global GDP4 but tech companies comprise 7 out of the 10 most valuable firms5.    

There is conflicting data when it comes to international trade but at least by Global Trade to GDP ratio, it has actually declined since its 2011 peak. Even though global trade has increased, it makes up a smaller percentage of GDP. Meanwhile, relations between countries have certainly frayed and this is negatively impacting primary beneficiaries of globalization, such as China. 

(This Chart shows Global Trade as a % of GDP as per the World Bank )

Ray Dalio in his March post on China had two passages that more or less make Thiel’s case, that technology is more impactful than globalization: 

1) “The Chinese economic model is based on gaining an increasing share of world manufacturing output, which has a good chance of not happening because countries that in the past have imported Chinese goods are more likely to prevent them with rising tariffs.” 

This passage is not consistent with increased globalization. Dalio in his piece mentioned that the US-China Trade war was one of the main factors setting China up for a 100 year storm. Although Trump gained most of the headlines for his bold actions during his Presidential term, both major American parties have embraced protectionist measures against China over the past decade. 

2) “While technology development has always been a critical defining force and while it is well known that whoever wins the technology war wins the economic, geopolitical, and military wars, this has never been truer than now, and China and the US are the leaders and big adversaries.”

In 2024, the main headlines concerning the US and China are no longer about cheap goods, but ByteDance, a Chinese Social Media platform and Semiconductor chips in Taiwan. Semiconductor chips could put the US and China on a potential collision course for increased hostilities and maybe even armed conflict over the next decade.   

During the Global Pandemic, the importance of technology was on display. If not for Videoconferencing, Cloud Storage and other innovations, we could only imagine how hazardous it would have been for the Global economy. The Pandemic also exposed the fragility of supply chains and some of the downsides concerning Globalization while technology proved to be antifragile.  

Conclusion: Thiel so far has been right, that Technology is more relevant than Globalization.  

Chapter 2: Party Like IT’S 1999

“The entrepreneurs who stuck with Silicon Valley learned four 2 big lessons from the dot-com crash that still guide business thinking today”: 

1. Make incremental advances

   1. Anyone who claims to be able to do something great is suspect, (be more humble). Small incremental steps are the only safe path forward.

2. Improve on the competition

   1. Don’t try to create a new market prematurely. The only way to know if you have a real business is to start with an already existing customer, so you should build by improving on recognizable products already offered by more successful competitors. 

These lessons have become dogma in the startup world and yet the opposite principles are probably more correct. 

1. It is better to risk boldness than triviality 

2. Competitive markets destroy profits (See Chapter 3)

Is it better to risk boldness than triviality?

If your goal is to own a small share of a massive market, incremental advances might be fine. However if you are choosing to merely improve upon something that already exists, you are by definition setting yourself up for competition. This competition will at best slow down your growth, assuming you are able to maintain this advantage. You can benefit from first mover advantage but if you want to capture maximal value, you are ideally not directly competing with anybody. Some recent examples come to mind: 

Deel became one of the fastest growing companies in recent memory when they enabled companies to quickly hire remote, global talent as if they were full time equivalents (FTEs)6.  If they set out with the goal of building a better Workday, they would not have been able to hit $100M in just over one year and $400M in ARR, 4 years after launch. Deel recognized that there was a clear void in the market for hiring international talent and set out to build something unique. This is not something that was being attempted by anyone else and although there appears to be questions about the legality of some of their maneuvers, what Deel did was certainly bold and made hiring international talent much easier. As a point of comparison, it took Rippling 8 years to reach $300M in ARR. Rippling is a great business, but it is definitely more of an improvement over existing vendors such as Workday, which is why their growth is much more consistent with a top performing SaaS company, and not the astronomical vertical X growth of Deel7. 

Open AI has quickly become the most hyped AI company in the world. While not the only Large Language Model, the public launch of Chat GPT certainly kicked off the most recent AI hype wave. Open AI reached the $2B in revenue figure just a few months ago and expects to be able to more than double this in 2025. For a company that only began to sell a few years ago, that is astronomical growth. If Open AI had released a slightly enhanced version of Alpha Fold or Boston Dynamics, they wouldn’t be the household name they are today. All of the other AI models trying to chase them, are going to face the tall task of trying to compete for relevance as normally the first mover will command most of the attention.

Until a competitor can emerge that demonstrates their technology is such a massive improvement over the incumbent, that there is no reason to consider the alternatives. Open AI has this massive advantage. While Open AI & Deel have first mover advantage, it is merely an advantage. To capture long term value from their respective markets, they need to prove that they can be the last company in their category (See Chapter 5). Based on the examples provided, we can evaluate Thiel’s claim as True, since small incremental improvements are not the only safe path forward.

Chapter 3: ALL HAPPY COMPANIES ARE DIFFERENT

“All happy companies are different: each one earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.”

&

“Only Monopolies have the luxury of long term thinking because of their excess profits. This does allow them to launch new and exciting business lines.”. 

One of the key ideas from Zero to One, is the notion that companies should aim for a monopoly. He cited basic economics, contending that the more competitive the market, the less profits there will be available, since more entrants will join and compete those excess profits away. This was explained famously by Jeff Bezos “Your margin is my opportunity”. Do the 5 largest public companies have a monopoly? Let’s define a Monopoly as owning >50% market share in at least one vertical. 

Top 5 Companies

1. Microsoft - Above 50% market share in a few key segments (operating system (PC), Microsoft Office) definitely a Monopoly. 

2. Apple - Above 50% market share in the US smartphone market (a monopoly) and a few other key segments such as their App store. Monopoly.

3. NVIDIA - For the time being, very hard to argue they do not have a Monopoly over the GPU market.

4. Saudi Aramco - Not a Monopoly but 10% of global oil supply is still massive.

5. Alphabet - They have a Monopoly on Search, and own market share in a few other key segments. 

This would confirm Thiel’s claim in Zero to One; the most valuable companies (the happiest) solve a unique problem.

We can also include a few other companies in this category such as Facebook (Social Media) and Amazon (not a Monopoly but dominant share in a few key categories). To maintain a long term technology monopoly, companies must constantly innovate and demonstrate to consumers that they have the strongest offering. In the last 10 years, Big Tech has certainly launched new products to the consumers benefit, however when we look at each of the big tech monopoly businesses, we see that many of these innovations look more like product enhancements to existing products instead of new innovations and when they do innovate, it appears to come from copying the competition or from M&A activity. Don’t believe me? Let’s go company by company:

Microsoft:

How has Microsoft’s product suite changed since 2014? 

Beyond improvements to Microsoft Office Suite, Azure and PC operating system, they have further enhanced their video game portfolio, the most prominent move coming with the Minecraft acquisition & the Activision deal. They acquired Github in 2018, which represents a powerful business product extension targeted for developers, especially now that they can enable Auto-pilot capabilities.  

This is likely why they made the genius decision to quasi acquire Open AI. With this one move, they leapfrogged Google and can now reap the benefits of the most recent AI revolution. Beyond these great acquisitions, I can’t think of any examples of an internally developed new technology representing a meaningful new innovation for Microsoft since 2014 (sorry Balmer).

Apple:

Apple, one of the most innovative companies in the history of the world and the house that Steve Jobs built. What have they brought us since 2014?

Outside improvements to their iPhones, Macbooks and iPads, they launched the Apple Watch in 2015, the AirPods in 2016, Apple TV+ in 2019 and the Vision Pros in 2024. While all of these products contribute Billions in revenue to Apple each year, none have represented the paradigm shifts that Apple were known for under Steve Jobs. Apple has done the best at commercializing their new innovations out of this group, but their new products are pretty closely related to what they were offering 10 years ago. Their attempts at a driverless car, went nowhere. Apple TV+ is engaged in intense competition, and not even in the top 5 amongst streaming platforms. Right now the Vision Pros are the most likely product that could prove me wrong. 

Amazon:

Amazon pioneered e-commerce and Cloud Hosting, launched Kindle readers, and forced retailers into guaranteeing 2 day delivery through Amazon prime. However since 2014, it is harder to point to new product launches that have thus far created a similar effect. They made a great acquisition of Twitch but otherwise, Amazon Music, Prime Video and Echo/Alexa represent improvements or copies from existing businesses. In the case of Alexa, it just did not live up to the hype. If I was writing this, 4 years ago, it would seem that Amazon was poised to take over. They were firing on all cylinders, looking to move into Gaming, Healthcare and more verticals. Outside of the continued AWS dominance, Bezos transitioned to Chairman to compete with Elon on Space full time, they shut down Amazon Care and Smart Home initiatives, they are walking back their no touch checkout and their Lord of the Rings TV series fucking sucked. At least over that span Bezos did get jacked and embrace his villain arc.  (They also made a smart investment in Anthropic)

Alphabet:

The last Search company, owners of Android and Youtube, not to mention one of the most influential mafias rivaling Thiel’s PayPal disciples. They have made major improvements to all their products since 2014, and they are not afraid to take big swings. From their post 2014 products, Waymo (autonomous vehicles) has not lived up to their commercial aspirations but is unquestionably an innovative product. Google Suite has emerged as a viable threat to Microsoft Office Suite8 and their acquisition of DeepMind scared the rest of Silicon Valley into creating Open AI.

While Alphabet gets a lot of praise for their willingness to experiment and work on innovation, few of these cool things that Alphabet has worked on over the past decade, have turned into meaningful revenue generators.  In 2014 Search represented 90% of their revenue, they have successfully diversified so that it only represents closer to 50%, but that growth came from Youtube, G-Suite and Cloud. These are all great product lines but they acquired Youtube nearly two decades ago, and while the product has improved substantially, it is still roughly the same model. G-Suite and Cloud were Google’s responses to Microsoft Office and AWS. Everybody expected Google to dominate AI but Bard ended up being a huge flop, which pierced Google’s mystic image. Google is definitely an innovator but their ability to commercialize these new innovations needs to be reaffirmed. 

Facebook:

Since 2014, Facebook’s Corporate Development team have successfully acquired and integrated Instagram, WhatsApp & Oculus to the extent that some would argue they are more valuable than the original product. If not for Google’s acquisition of Youtube, I would be prepared to call the Facebook acquisition of Instagram, the greatest of the Consumer Web 2.0 generation. The dominance of these acquisitions is evidenced by the many attempts of politicians to undo them, years after the fact. While they have naturally made major enhancements to all of these platforms since acquiring them, with the size, scale and talent available at Facebook, if Thiel’s contention is correct, why did they have to acquire these much smaller startups for Billions, instead of developing it internally? 

If you look at Facebook today, they have made Instagram, What’sApp and Oculus core to their product roadmap, with most of their new developments coming through these platforms. Many of Facebook’s other initiatives such as Diem/Libra (Crypto platform) & Lasso (Tik Tok Competitor) never took off. Their latest new platform release, Threads (Twitter Competitor), was the fastest app to reach 100M users (5 days), yet growth quickly stalled after a few months, and with it being less than one year since it’s launch, it’s still too early to call if it can reach a similar scale to the other Facebook platforms or if it only exist to be a temporary heel to X (formerly Twitter). Outside of their Metaverse initiatives, their social strategy for the past few years has appeared to be a watch and copy approach9. 

This appears to be consistent with what the rest of the Big Tech Monopolists have reverted to10. Thiel was right that all happy companies are different because they earn a Monopoly. These companies were all Monopolies when he wrote Zero to One and they are still Monopolies today. However, despite these excess profits, their innovation efforts have all somewhat underwhelmed over the past 5 years. I will discuss why I think that is the case in Chapters 4 & 5 summaries in the next post. 

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