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

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

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

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

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

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

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

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

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

Tldr: Change is what gives time meaning.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(can skip to 30 seconds)

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

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

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Situational Awareness, run by 24 year old former OpenAI researcher Leopold Aschenbrenner was forced to liquidate its public equity portfolio to cover losses after a recent selloff in AI stocks put the fund at risk of insolvency.

The fund which was reportedly up as much as 439% by the end of June, dropped 67% within a few weeks, triggering a margin call, forcing them to sell the majority of its public equity book, to Citadel, the hedge fund led by Ken Griffin. Non-finance folk might recall the firm from the Gamestop saga of 2021.

The public hasn’t been kind to Leopold. Many called him an idiot, ignorant to financial markets, dismissing his prior success as luck etc. This is coming almost exclusively from people who never met him. It’s true he’s new to managing money but he graduated from Columbia at 19, worked at FTX (before it blew up), OpenAI (before he got fired) and is connected with many of the key figures at the AI frontier labs. I doubt his critics can boast a similar track record by the age of 25, or at all.

Leopold is the latest in a long line of fund managers that posted stunning returns for a while before their investment strategy succumbed to the wrath of Mr. Market. Whether it’s Bill Hwang, Cathie Wood, Sam Bankman-Fried or Bernie Madeoff, every few years, the financial press crowns a new Warren Buffett, only for their funds to suffer devastating losses. In some cases blowing up the fund and/or sending the manager to jail. It’s almost a guaranteed kiss of death at this point, like the Forbes 30 Under 30 list.

Nobody has accused Situational Awareness of doing anything shady or illegal but there are a few lessons that can be learned from this episode, some of which were predictable.

Margin Calls & The Situational Awareness Strategy

“Illiquidity, leverage and concentration. Each are a problem but manageable in isolation. If you have two of them, uh oh. If you have all three of them then you are whistling past the graveyard.” — Steve Cohen (sourced from Marc Rubinstein at Net Interest)

Why was the Situational Awareness blow up predictable? They were heavily concentrated into AI Infrastructure names with meaningful leverage. Beyond that, the portfolio was designed to perform well during a looser credit cycle, once money began to tighten, it was inevitable that some of the positions would be negatively impacted. The US-Iran conflict has reduced the supply of energy which has been putting upward pressure on inflation and interest rates which shifts demand for near term cashflows.

The reason Leopold needed to sell his public book as quickly as he did, was because his investment portfolio was trading on margin, which meant he borrowed to place trades. It’s not that different from taking a mortgage.

You purchase a $1 million property with a $200,000 down payment and an $800,000 mortgage. You control a $1 million asset using only $200K of your own capital. If the property rises 20%, you pay back the $800K and your equity is worth $400K. If it falls 20%, the value of your equity is worth zero because the lender is still owed $800K.

The difference is that your bank doesn’t revalue your home daily. Whereas a prime broker continuously monitors the value and volatility of an investment portfolio. When the collateral drops too far, the broker will demand additional capital, reduce the amount it’s willing to extend or begin liquidating positions.

Situational Awareness reportedly borrowed $3 to $4 for every $1 of capital. In that case, a decline of 20% to 25% would wipe out all of the fund’s equity.

Situational Awareness was running a Long-Short (LS) portfolio buying companies exposed to AI infrastructure like Micron, Sandisk and Coreweave and selling short software companies such as Adobe, Salesforce and Microsoft. This strategy was working well throughout 2026, as many piled into the AI trade. However, in July, due to a number of factors, including concerns about higher inflation resulting from the US-Iran conflict, some of these high-flying names started to give back prior gains.

Any stock that can quickly rise, can fall just as fast. It’s normal for stocks trading based on the presumption of large growth relative to current earnings to ping-pong back and forth as market sentiment changes. The AI infrastructure piece of the Situational Awareness portfolio was trading based on the belief of large growth in future earnings, making it highly volatile. Meanwhile, the short side of the portfolio, were mega cap established companies that are comparatively less volatile. They were trading down because of concerns that AI was going to be disruptive to their business models in the medium-long term.

Let that sink in. The fund was long companies whose current earnings could only justify their valuations if the future arrived quickly. At the same time, it was short companies whose current earnings would collapse if the future arrived quickly.

It’s the same bet.

When inflation expectations and interest rates rise, investors become less willing to pay for profits expected far into the future. The infrastructure stocks fell. Meanwhile, software companies continued reporting real revenue, earnings and showing no collapse in their business models. Their prices were rising against the fund as well.

Leopold could not have predicted all the developments of the Iran conflict or the precise moment investors would turn against AI stocks. Though he should have realized that a highly leveraged and correlated portfolio would eventually experience a period when several positions moved against it simultaneously.

His call about the scale of investment required to build artificial intelligence could still prove correct. Unfortunately, when leverage is involved, being right isn’t enough. You have to remain solvent long enough to collect the payoff. Leopold made several unforced errors, which threatened his staying power. Once it was too late, the sharks knew he was ripe for the picking.

Ken Griffin Plays Hardball

Ken Griffin has been a major player in the hedge fund world since before Leopold was born. One of Griffin’s favourite books is Hardball: Are You Playing to Play or Playing to Win? This is telling to the way he sees business.

Most people in tech subscribe to the Peter Thiel view on competition from his book Zero to One: Competition is for losers. Thiel isn’t anti-competition but he observes that competition benefits consumers but is often destructive to shareholder value. The most valuable businesses in history have exercised some form of monopoly therefore, founders should strive to build one ideally by creating such a strong technological and distributive advantage nobody can threaten them.

After reading Hardball, you might wonder if Thiel wrote Zero to One as his response. Hardball accepts competition as an inevitability. It doesn’t discuss monopoly businesses, instead looking at companies that successfully defeated competitors by what the authors call playing Hardball. There are a few ways a company can play Hardball, but they all require being hyper aware of what your competitors are doing, so you can figure out where you can attack them to take market share. These can be larger companies trying to shake off upstarts or smaller companies going after the market leader. Being a Hardball leader and company, means you exploit every legal advantage you have at your disposal. This means hitting the competition, usually with indirect attacks, that put them under pressure, while being ready to fend off any of their retaliations. Citadel was built for the Hardball world.

It’s not clear how personally involved Griffin was in the purchase of Situational Awareness’s equity portfolio. However, the transaction reflects the Hardball culture he created. Leopold had spent the previous two years attracting enormous attention to himself and his strategy. His returns inspired an army of professional and retail copycats to pile into the same AI infrastructure companies. The more crowded the trade became, the easier it was for Citadel and other sophisticated firms to understand what would happen if those stocks began falling.

Situational Awareness had large, highly visible positions, meaningful leverage and a relatively inexperienced manager. Citadel had the size advantage and decades of experience profiting from distressed situations. You could not design a more attractive hardball opportunity. When the margin call came, only a handful of funds could take such a big position on such short notice. In came Citadel buying the book at a 10% discount, instantly printing an easy couple of billion dollars.

This is hardly the first time Citadel has mobilized quickly during a crisis. When Enron collapsed in 2001, Griffin chartered a plane and sent executives to recruit its energy traders. Situational Awareness was merely the latest distressed competitor to discover that Griffin is rarely sentimental when markets become chaotic.

Shortly before Citadel purchased the portfolio, Citadel Securities had publicly predicted that the Federal Reserve might surprise markets with an interest-rate increase. Higher rates would have been particularly damaging to the long-duration AI stocks Situational Awareness owned. Griffin wouldn't purposefully try to hurt an exposed competitor while they were already down would he?

(If you’ve made it this far, please settle a debate for me in the comments: Is a Beef Wellington considered a sandwich? (Yes/No and Why?))

Leopold is a new investor, he might be smart and right in the long term about his AI thesis but he structured his fund in such a way that it didn’t need a Black Swan event for him to get margin called. They claim to have hedges in place but the problem with hedging, is you can almost never perfectly hedge against every risk, if you do, it will come at the expense of returns. You can’t be doing 400% returns in 6 months while being perfectly hedged.

Trading on margin is commonplace, it’s done by most hedge funds and many retail investors, so is getting margin called. Over a million South Koreans got margin called in July alone. What’s notable is Leo flirted with liquidation while the S&P 500 is just off its all-time high. This wasn’t a market panic, this was sloppy fund management.

Situational Awareness was concentrated, leveraged and reliant on loose credit conditions to succeed. A bad month was inevitable. Leopold also overlooked that when you are trying to beat the market, you aren’t just going up against a passive index, you are competing with every other fund manager out there. Situational Awareness was exposed, and a Hardball competitor would not let that slide. The hedge fund world is full of Hardball players.

Despite an embarrassing episode, Leopold Aschenbrenner isn’t finished. While he had to sell off his public book, Situational Awareness still has a $5B stake in Anthropic. Leopold remains connected to many of the key players from the AI labs. Silicon Valley and he’s still at the very start of his career. Ray Dalio and countless other investing legends had trades go south on them early in their career and they were only the better for it.

He might have lost some of the boy wonder aura but people have short memories. Masayoshi Son has lost his fortunate and rebuilt it multiple times. Aschenbrenner might have prematurely claimed to have been gifted with situational awareness, but that does not mean he can’t eventually become one of the best investors of his generation. It just takes more than a coronation from CNBC for it to be true.

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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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I found myself in the middle of a padel game with a few longtime Substack subscribers. Nick had been playing for a while and served as our rules official. Phil had played a few times before and, after a quick refresher, was back up to speed. For Tim and me, it was our first time, but we had both played other racquet sports before.

We were all fine sportsmen, but experience made a difference. I’m more accustomed to tennis, which usually doesn’t have a wall a few feet behind the baseline. The first time I tried to play a ball off the glass, I was lucky it didn’t careen directly into my face.

After a few games, I started to figure it out. Plenty of my attempts to use the wall still failed, but enough worked that it was worth to keep trying without being a complete liability to my team. We played a few matches with different pairings, and the games were all close. Until Tim and I were paired together. Then things went less well. Fortunately, our reservation expired saving us from further embarrassment.

Our booking ended at 8:30PM but there was a long line of people waiting to take the court. The place was packed on a Wednesday in the middle of summer. Although padel is nowhere near as popular as tennis, it has surged in recent years. When I first heard about it in 2009, I assumed it was a niche Spanish sport. Today, more than 30 million people play, mostly across Europe and South America.

(None of Nick, Phil or Tim are featured in this photo)

In North America, few people are playing padel, choosing to embrace pickleball instead, another more accessible variation of tennis.

Since most of my readers probably do not know how these sports differ, this week’s article is intended to explain the distinctions.

Keep reading to learn which racket sport is best suited for you!

Book I’m Currently Reading:

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

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

Tennis: Ever Heard of it?

Tennis originated from jeu de paume, a game played by French monks between 11th and 12th century. French speakers can guess it involved striking the ball with their hands. It gradually shifted to gloves, bats and eventually racquets. The game caught on and spread to European royals and Aristocrats. Those with a lot of free time.

Modern tennis only emerged in the late 19th century. Credited to a British army officer, Walter Clopton Wingfield, who started selling boxed lawn-tennis sets in 1873. The scoring system and the some of the other rules were revised shortly after but it wasn't until the All England Club held the first Wimbledon tournament in 1877 that there was an official unified set of rules.

Tennis can be played in singles or teams of two (doubles), using a strung racquet to hit a felt-covered “tennis” ball across a net. The ball can bounce once before it must be returned. The player serving stands behind the baseline and has two attempts to get the ball diagonally into the designated service box. A player wins the point if their opponent can’t return the ball in bounds. This is more or less the same premise of all racket spots, including padel and Pickleball.

A tennis match is best of 3 or 5 sets, of at least 6 games. A player needs to win 6 games, by at least a margin of two to take the set. A set can go to a maximum 13 games. To win a game, you need at least 4 points with a margin of victory of 2. Instead of counting to 4, for some reason points are counted as 15, 30 and 40. If both players reach 40 points, the score becomes deuce, and the players go back and fourth until somebody wins two consecutive points.

More than 100 million people play tennis every year. Roughly one-third live in the US, UK and Canada, while another third are in Asia. Most of the remaining players are concentrated in Europe and Latin America. For much of the 21st century, tennis participation grew roughly in line with the global population. That changed since the pandemic, with the worldwide player base increasing by approximately 25% between 2019 and 2024.

Beyond participation, people love to watch; professional tennis generates more than $3B per year, with over a billion spectators. Well below Football (European and American), Baseball, Basketball and Hockey, in line with F1 and more than MMA.

Tennis is an exciting game but it’s not seen as accessible given the athletic demands. Once the ball is served, you are pretty much sprinting, stopping and starting until the point is over. Anyone I know who plays regularly over the age of 30 is constantly nursing some sort of injury. The disparity in skill makes it difficult for beginners to play with more experienced players. There isn’t a handicap equivalent such as in golf. I suppose you can force the better player to wear a blindfold or consume a few alcoholic beverages, but even that might not be enough. Karsten Braasch beat Serena and Venus Williams easily after a few beers and cigarettes. Other racket sport derivatives are more accessible.

Padel: Tennis inside a glass case of emotion

A wealthy Mexican businessman wanted to build a tennis court, but didn’t have space so he needed to settle for a smaller one, with walls probably to prevent the ball landing into his neighbours yard. Eventually instead of playing around the walls, he decided to incorporate them into the game to compensate for the smaller court, giving the game an added element of strategy. It was a niche game he would play with friends until one of those pals brought the game to Spain in the early 1970s. The game spread to Argentina which saw a surge in popularity in the 80s and 90s, making it the main hub for padle outside of Spain.

Padel is played in doubles on an enclosed court measuring 20 metres long and 10 metres wide, instead of 24x11 on a tennis court. Players use a short, solid racquet with holes cut into the face instead of strings. The ball looks almost identical to a tennis ball but with less pressure causing it to travel more slowly. The serve works the same as in tennis with the only difference that the server first bounces the ball, then strikes it underhand below waist height, instead of overhead.

Beyond that the key difference is how the walls come into the play. The ball must first bounce on the opponent’s side of the court, but it can then strike the surrounding glass or fencing and remain in play. A player can allow the ball to rebound off the wall behind them before returning it, or deliberately hit the ball against their own glass to send it over the net. This changes how you hit the ball.

In tennis you are generally try to hit shots with top spin to put the ball out of your opponent's reach. In padel, those kinds of shots take harder ricochet's off the wall making them easier to return. Instead you would rather use backspin, so the ball falls into the corner eliminating any chance to play it. This subtle change along with the underhand serve reduces the advantage stronger/powerful players have in tennis.

Although it’s not as popular as tennis, the sport is growing at a staggering rate. In 2018, there were only 8 million players, by 2025, this jumped to 35 million and has plenty of room to grow. 80% of the players are in Europe and South America, with North America and Asia still largely untapped.

It’s not a surprise, the format makes it more accessible and social. The doubles format on the smaller court allows for more communication between points, and reduces the amount of running, since each player only covers half of their side of the court. The carryover from tennis, and other racket sports, make it easier for new players to quickly pickup the game without the same risk of injury. There is clearly a huge demand for this, as evidenced by similar emerging racket sports.

Pickleball: Ping-Pong for Claustrophobics

If padel is a mix of tennis and squash, pickleball is tennis mixed with ping-pong.

Pickleball was invented around the same time as padel, but in the US. It’s played on a much smaller court measuring 6 by 13 metres. The rackets are similar to paddle but the ball is made of plastic reducing the speed even further.

Like padel, the ball is served underhand, except the server does not need to bounce it first. The serve and the return must each bounce once before either team is allowed to volley. Beyond that, the basic objective is similar to tennis, padel or ping-pong: get the ball over the net and hope the other person misses.

Another key difference is that players can’t volley in the first seven feet before the net. This area is known as the kitchen. Players can enter it to return a ball after it bounces, but can’t wait inside to smash the ball out of the air. No cooking happens there.

Pickleball also has a more simple scoring system. Games are played to 11 points, and a player or team must win by two. Only the serving side can score. In doubles, both partners serve before possession passes to the opposition.

The smaller court and slower ball reduce the athletic demands even further than padel, let alone tennis. This makes pickleball ideal for older, less athletic players, or anyone looking for something more physically demanding than ping-pong without risking an injury from tennis. This is why some dismiss it as a sport for retirees, but it’s increasingly enjoyed by every age group. Former pro tennis players such as Jack Sock, Genie Bouchard and Sam Querrey have transitioned to professional Pickleball. Not to mention, former greats like Andre Agassi, Andy Roddick and others who occasionally pop in for celebrity games. They don’t help dispel the stereotypes though.

This accessibility explains why the sport’s growth has been extraordinary. In 2020, slightly more than 4 million people played pickleball across North America. By 2025, that figure reached 26 million. This is where the majority of players reside, as Pickleball isn’t as international as tennis or padel yet.

Nonetheless, each sport is surging these past few years, as people are looking to spend more time with friends hitting a ball around. The size of the court, type of racket and material of the ball are less important.

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

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

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

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

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

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

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

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

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

Book I’m Currently Reading:

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

Related Reading:

1. The Odyssey by Homer

2. The Illiad by Homer

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The Odyssey is The Greatest Story Ever Told

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

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

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

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

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

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

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

Christopher Nolan is the right person to capture that feeling.

Christopher Nolan is The Greatest Director of The 21st Century

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

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

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

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

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

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

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

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

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

This Is One of the Best Casts Ever Assembled

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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If it were to exist, why couldn’t it be in Budva, Montenegro? The town has a population of 17,000 inhabitants but a seemingly endless supply of coastline and delectable seafood. This seems like the correct ratios for the celestial realm.

Peak season in Budva felt far less crowded compared to San Sebastien, Dubrovnik, the Cyclades or the Amalfi coast. It’s not surprising, flight routes make it arduous to get to Montenegro. I needed 2 connections to travel 1,000 KM.

There were, inevitably, a few loud Italian and French tourists. Those are unavoidable. Fortunately, they were spread across different sections of the beach. This is preferable. When these two groups come into contact, dangerous chemical reactions can occur.

The relative lack of distraction allowed me to advance in my reading, which happened to be about the history of speculation and financial bubbles. I couldn’t help but notice the similarities between the way people overcrowd investments and vacation spots. Both offer value at the start, but as more people partake, it quickly erodes.

Tulips are nice if you buy them for a few dollars and plant them in your garden. At thousands of dollars per bulb, nobody is putting them in the ground. The same logic applies to crowded tourist destinations. Santorini and Capri are beautiful. That is unfortunately why everyone is trying to get there.

If you want to find great investments or vacation spots, you can’t look where everyone else is. Consistently making good investments takes time, effort, and a willingness to look slightly off the beaten path. Finding beautiful, affordable places that have not yet been completely ruined by crowds requires the same thing.

Keep reading to learn the link between vacationing well and beating the market.

The Book I was Reading on the Beach:

1. Devil Takes The Hindmost by Edward Chancellor

Cool Book You Probably Haven’t Read:

1. The Gray Lady Winked by Ashley Rindsberg

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Montenegro is a beautiful Country

Despite being the size of Connecticut, Montenegro is seemingly a non-stop collection of beautiful views. Whether you’re into beach, mountains or forest, they have all in great supply. I was in Budva, along the beach, just a short boat ride away from Dubrovnik. Budva feels like a mini version of Dubrovnik, with some similarities to Santorini. Just many more clubs, casinos and shirtless bald men smoking cigarettes at 9AM. No, they did not actually film Casino Royale in Montenegro, although they certainly could have.

Montenegro is the living embodiment of a place benefitting from the end of The Golden Era of Travel. While cruise ships can dock in Kotor, the port of Budva doesn’t have room for them, which limits how busy the town can get. This coupled with difficulty to reach the country via plane, adds enough friction keeping the worst kind of tourists away. The lazy travellers who want everything pre-packaged and booked by their travel agent/LLM before they arrive. God forbid they encounter anything unfamiliar or a language other than English.

In the case of Montenegro, pretty much everyone I encountered spoke English. Although it helps curry favour with the locals if you can speak Montenegrin or another West Balkan language. I suspect locals charge western tourists higher prices.

At the beach, the waiter quoted me 20 euros for a chair, after I sat down his colleague told me it was 30. The group of young local women nearby were charged 15 while the middle aged British couple were charged 40. They said it was 20 yesterday and 10 the previous day.

Initially I didn't like getting overcharged but it confirmed my hypothesis that Pretty (Male) Privilege does exist. It’s just less effective than being a young local girl.

Beyond widespread English and getting charged tourist price for beach chairs, Montenegro is pretty accessible as a travel destination, the difficult part is getting there. Seemingly few people are willing to deal with this inconvenience. Montenegro gets around 2.5 Million visitors each year, which is 5-10% of what Croatia, Portugal, Italy, Greece or France get.

This is consistent with my experience; even amongst regular travellers, I know few people that have been to Montenegro. Or Albania, Bulgaria, pretty much any country that doesn’t have regular direct routes from major Western European capitals.

This doesn’t mean they can’t enjoy their vacation. It’s just that it will be difficult to have a much better experience compared to the average traveler at these common destinations because of tourists traps, high prices, endless crowds and loud noises. This is not unlike the stock market.

It’s Never Different This Time

“The four most dangerous words in investing are: This time it's different.” — Sir John Templeton

There is nothing wrong with investing but when too many people decide they can get rich by trading instead of building something productive, markets become susceptible to bubbles.

What is a bubble? It’s when the asset you didn’t buy grows rapidly over a short time frame. When something you own experiences similar growth, that’s just the wisdom of the market working its magic.

The more asset prices are driven by the belief that some greater fool will pay more than you did, the more markets behave like a casino.

People are lazy and don’t like uncertainty. Finding good stocks, businesses, or assets with the potential to outperform is hard. It requires work, patience, and the humility to accept you could be wrong. There is no shortage of people seeking above-market returns but few willing to do what it takes.

Instead, people gravitate to assets that have already performed well. If something has gone up recently, it becomes easier to believe it will keep going up. These are momentum trades. They are psychologically comforting not requiring much imagination. Investors can outsource their conviction to the crowd. Everyone else believes in it, so maybe they should too.

(^ The average investor during a bull market)

In Thinking Fast and Slow, Daniel Kahneman describes how our brains are constantly searching for patterns, even when they don’t exist. Once something happens, it becomes easier to imagine it happening again. He gives the example of being less surprised the second time he bumps into a friend in a random place. Even if the chances aren’t any greater than seeing anyone else he knows. His brain has decided that friend has become the guy Kahneman sees in unexpected places.

Investors are no exception. SpaceX’s valuation isn’t based on the companies performance but rather the belief that there will be a lot of demand to buy SpaceX shares. It has gone up a lot recently, therefore it will continue so you should get in before you miss the upside. This self perpetuating belief can be reduced to some other fool will pay a higher price than you did, but of course you’re not the fool.

If you want outsized investment returns, you need to be willing to take a chance on something that isn’t already universally accepted as a sure thing yet. The more certain an investment feels, the more competition there will be to own it. This buying pressure increases the entry price and reduces future returns. The best opportunities are usually found in assets that are priced less certain than they actually are. The market expects X, but you strongly belief it will do Y. This is why by knowing an industry or asset better than most people, you will have an advantage.

The not so big secret in investing is that if you want to beat the market, you need to tolerate more boredom, pain, and uncertainty than the average investor. Warren Buffett when asked by a group of students how to become a better investor responded to read 500 pages of annual reports each day. He knew none would follow his advice.

You need to look where other people are not. Anyone can harvest oil if it’s sitting at ground level. To make real money, you need to drill deeper. So I’m told. The closest I’ve been to an oil field was an olive farm.

Investing and finding great vacation places work the same way. The further you get from the herd, the more potential there is for alpha. This does not mean every decision will be a winner. Some obscure stocks are ignored for good reasons. Some off-the-beaten-path destinations are cheap because they are inconvenient, boring, or mildly cursed. That’s okay. The goal is not to look smart every single time. The goal is to win over the long run.

Would you rather visit 20 different countries/cities or return to the same safe tourist destination each year? Some will disappoint but every so often, you end up sitting in an only midly overpriced beach chair in Montenegro, eating fresh seafood, staring at the Adriatic, glad you aren’t fighting for a reservation in Cannes.

If you want interesting vacations, don’t build your itinerary from Instagram influencers, cruise ship routes, or the first page of a travel guide. By the time a place becomes obvious to everyone, the things that made it worth visiting are overbooked and overcrowded.

The stock market is no different. Any stock tips you hear at the hair salon or auto shop, aren’t worth pursuing. By the time an investment feels obvious, safe, and socially validated, much of the return has already been captured by someone else. Like most things in life, the best returns come before the crowd arrives.

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This is by far the biggest IPO in history, and prices SpaceX comfortably within the 10 largest public companies by market capitalization. Higher than Tesla ( $1.6T) META ( $1.5 T), and Berkshire Hathaway ( $BRK-B $1.1T) or JP Morgan ( $1T).

Looking at financials alone, this doesn’t make much sense. SpaceX generates ~$20B in annualized revenue, but has a ~$5B operating loss and -$20B free cash flow. Other trillion dollar companies generate >$100B revenue while being highly profitable.

Investors know this yet still the stock price soared because in the short term the stock market is a voting machine. There are more people wanting to buy than sell shares. There are many reasons why people would want to be a SpaceX shareholder.

Regardless of what you think of his politics or whether billionaires/trillionaires should exist, you are a delusional hater if you don’t think Elon Musk is one of the greatest entrepreneurs ever. Up there with Jobs, Vanderbilt, Edison, Ford and other titans.

For nearly three decades Musk has made doubters look foolish. Whether it’s online payments, electric cars, or rockets, Musk finds a way to win. This inspires a level of patience and devotion amongst employees, investors and customers that few big company CEOs can enjoy. While this is part of what makes SpaceX and his other companies great, it’s also why it makes his companies terrible stocks to buy today.

If your goal is to generate alpha, buying great companies alone won’t do it. You need great stocks. Right now SpaceX trades at an outrageous multiple, with a limited float and buying shares around the time of the IPO is usually an easy way to get rugged.

Keep reading to find out why you should not buy SpaceX right now.

Book I’m Currently Reading:

1. Devil Take the Hindmost: A History of Financial Speculation by Edward Chancellor

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1. Confessions of an Advertising Man by David Ogilvy

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Stocks Go Up Because People Want to Buy and Hold Them

Imagine two identical companies. Company A announces they intend to wind down operations at the end of the year. They will honour any existing performance obligations, but not make any new sales. They will sell off all assets, settle any liabilities and distribute the difference to their shareholders at the end of the year. Meanwhile Company B will continue operations for the foreseeable future.

Would you pay more for a one time $250 payout in 6 months or $100 annually for the next 20 years? What if that $100 increased by 10% each year?

If an investor thinks a company will have more earnings to distribute to them in the future, they will pay a higher price to own it. If many investors share this opinion, the market clearing price, where demand meets supply, will rise.

When you see a stock price oscillating, this is a reflection of buying versus selling pressure. The market can be willing to pay up for a stock one day, then shun it the next. This can be driven by investors changing their outlook on the business, shifting preferences between near vs long term cashflows, available liquidity in the financial system etc.

Great companies can perform poorly in the stock market over extended stretches because it doesn’t fit with what investors are looking for. High growth tech companies with negative earnings were in great demand during the Dotcom Boom and ZIRP eras, but out of favour during high interest rate, low liquidity regimes. The time and price you choose to buy a stock along with your holding horizon will have as much if not more of an influence on your investment return than the companies performance.

This is why being a great company doesn’t on its own guarantee a high share price. Does SpaceX qualify as a great company?

SpaceX Is Not a Rocket Company. It’s an Elon Musk Conglomerate.

SpaceX started as a rocket launch/space company 20 years ago, but today you can think of it as three separate but related businesses:

1. Space - Rockets (Falcon, Starship, Dragon etc.)

2. Connectivity - Starlink

3. AI - Compute Business (Grok, Cursor)

The Space division is responsible for decreasing the launch cost by about 85% down to $2,700 per KG (down from $18,500 historical average). This cost reduction has saved US government agencies such as NASA, DoD, NRO along with commercial satellite operators billions of dollars. Beyond the immediate cost savings, it makes it economically feasible to do new things in space, from building data centres and colonies to enabling low-earth orbit broadband and mobile satellites. This segment does about $4B in revenue and has grown 8% year over year (YoY).

The Connectivity division sells secure and high speed internet connections to consumers, enterprises and governments. Starlink is ideal for underserved rural and remote areas, or areas with compromised internet access like Ukraine or Iran. Starlink began in 2020 and generates >$11B in annual revenue, growing 50% YoY.

The AI division (previously xAI) merged with SpaceX in the past year. xAI was the merger of Grok and Twitter and as of March 31st were doing $3B annually growing 22% YoY. They have since secured >$15B in annualized revenue from deals with Anthropic, Google and others. They recently acquired the right to purchase Cursor.

The Space division is launching more rockets per month than every other player combined. Their competitor Blue Origin doesn’t even have a launch pad right now. Starlink has been in business 6 years but generates nearly as much revenue as Canadian telecom giants Bell Canada and Telus. The AI division is getting paid billions per month from competitors, because they have capacity at a time when people are desperately seeking it.

SpaceX is a great company. That doesn’t mean it’s a good stock.

SpaceX’s Greatest Asset Is Also Its Greatest Risk

Greece’s conquest died with Alexander.

Great-man companies inherit the same problem. When the founder is responsible for a disproportionate share of the vision, talent recruitment and investor confidence, succession is not a normal management transition. It’s an existential valuation event.

This is the biggest risk to SpaceX shareholders today. What happens on the day Elon isn’t there? There is no way to justify the IPO valuation without an unwavering belief in its founder.

Based on Friday’s performance, a lot of people believe in Musk to the tune of 100X revenue. This is great for anyone who owned shares pre-IPO but very expensive for somebody buying the stock today.

Compared to other companies at this scale, SpaceX would need at least $100B in annualized revenue to justify a $2T valuation. That’s 10X where they were 3 months ago. Not only would they need to quickly scale their revenue, they would need to show a path to get operating margins in the 30-40% range. None of the trillion market cap companies with >10X revenue have operating margins below 40%. The only exception to this is Tesla, another Musk company.

Most expect SpaceX and Tesla will merge. Taking Friday’s share prices, the entity would have a combined market cap >$3.5T with ~$110B in annualized revenue and operating profits of -$1B (assuming they can’t find any synergies). That’s a more manageable 35X revenue, but still well above any of the other companies.

Until then, investing in SpaceX at 100X revenue, is effectively taking early stage venture capital uncertainty but paying mega cap IPO prices. You need to believe the company can double revenue for the next 3 years just to catch up to where their peers trade today. That leaves no margin for error, which seems like an unnecessary risk.

SpaceX definitely isn’t the first company to go public at a rich premium, but when you look at short term stock performance from recent IPOs, its rarely beneficial to buy within the first day or even week of trading. It’s common to see a stock drop 50% below its IPO price within its first year of trading.

Last year Figma ( ) reached a peak share price of $122 on its first day of trading (3X the initial offering price) but can be bought for below $20 right now. Figma has grown revenue nearly 50% YoY and beat its latest earnings estimates in a major way, but only trades at 10X revenue for a $10B market cap.

Figma and SpaceX aren’t comparable companies but they are part of the recent wave of IPOs that feature a limited float, which makes the price susceptible to large short term pumps. The float is the number of shares that are available to be bought in the open market. Every company has a certain number of shares held by insiders or part of the company’s treasury, that are restricted from being sold. The higher this ratio, the easier it is to distort the share price.

Assume a company has a million shares, but nine hundred thousand are held by the CEO who won’t sell, it doesn’t take much to pump the stock. One whale can make it surge with the purchase of 10,000 shares. The buying pressure wins, which sends the stock to the moon. This is a common feature in crypto coin offerings, most of which are nothing more than orchestrated rug pulls. If you timed it correctly, you could make anywhere from 50-1,000X your money in an hour. Most participants were unfortunately bag holders. In the case of SpaceX, it’s hard not to feel like one.

Only 4-5% of SpaceX shares are part of the public float. Most mature public companies float 60-90% of their shares. SpaceX’s float is slightly more aggressive than recent tech IPOs between 10-15% (such as Circle, Uber, SoFi) but not unprecedented. Figma, Robinhood, and others were between 5-10%. Robinhood’s trading debut wasn’t as explosive as Figma’s but it opened at $38 and reached a peak of $55 after a few weeks before dropping below $10 per share within its first year.

These limited floats aren’t necessarily designed to fleece public share investors. It’s common for founders at VC backed companies to own more shares in their companies compared to most public company CEOs. In the case of SpaceX, Elon Musk owns ~40% . For reference, Jensen Huang from NVIDIA has less than 4% and Mark Zuckerberg has ~14%. Both companies have been public for a while now.

It’s also normal for pre-IPO shareholders to be subject to an 180 day lockup before they can sell their shares. This temporarily suppresses the float. Once it expires, the share price usually takes a hit as early investors and employees look to cash in.

In the case of SpaceX, the lockup is structured differently. Musk and some early investors are subject to a 366 day lockup, whereas other pre-IPO shareholders are locked up for a maximum of 180 days. Some can be released earlier based on certain milestones. In 6 months, the shares that would be eligible to be sold that could contribute to the float could reach up to 60% (if all these investors choose to sell).

Certainly not all of these shareholders will sell, but a 30-60% post-lockup float is pretty normal for new IPOs. With Musk owning such a large number of shares, it places a ceiling on how big the float will get, but the point remains, the way the stock trades during the early days or weeks post-IPO is not really reflective of where the stock will be in a year.

The way the stock trades before the lockup starts to expire, isn’t really reflective of how the broader market views SpaceX stock. Musk successfully convinced NASDAQ to relax their policies around float percentages which means by default many index funds need to buy SpaceX. Since an increasing portion of the market is held in these passive funds, billions of dollars will be directed towards SpaceX shares, and there won’t be any selling pressure for at least the next few months.

This sets the table for SpaceX’s price to support the current valuation, and potentially climb in the short term, but in the long term, the market is a weighing machine. I suspect people will look at META, Microsoft and Alphabet at 10X revenue and 30-40% operating margins, and wonder if it’s worth paying 100X for a moonshot, no matter how much they believe in Elon Musk. SpaceX might very well one day start space colonies and become the most profitable company ever, but in the short term investors are asked to buy into a completed story, that’s only just begun.

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(Check out this great breakdown on the SpaceX S1, from )

No. I was in an abandoned airport hangar on the outskirts of Berlin about to run 8 kilometers with eight exercise stations mixed in. I was doing this alongside my buddy with whom I could split the stations as we wanted but we both had to run the full distance.

We were about to compete in what’s called HYROX. Some people claim it’s short for Hybrid Rockstar, but thankfully that’s not been sanctioned by the organizers.

The confusion is natural. HYROX is geared towards hybrid athletes, people who can run and lift weights. The type that go to run clubs/Barry’s Bootcamp but also have a gym membership. You can usually spot a HYROX athlete from a distance. They are wearing unnecessarily expensive gear and spend as much time documenting or tracking the workout as they do completing it.

Although to an outsider this might appear cringe, you need to do some combination of this or you’re going to struggle. Although I’m skeptical of the HYROX crowd’s belief that colour coordinated sports bras and short cut 10% off their time.

In any case, there we were: a leading venture capitalist and a burgeoning Substack writer preparing to suffer for the next hour.

This is the story of how our race unfolded, what I learned from the experience, and how HYROX went from relative obscurity to a global fitness phenomenon.

Keep reading to find out.

Book I’m Currently Reading:

1. Devil Take the Hindmost: A History of Financial Speculation by Edward Chancellor

Book Worth Re-Reading:

1. So Good They Can’t Ignore You by Calvin Newport

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

How The Race Went

It took us 70 minutes to complete the race, which placed us ~100th out of 300 teams that participated in the Open Doubles Race that day in Berlin. For a first time effort that’s considered good. Experience helps in races like these. We got two time penalties of one minute each, registering our official time at 1:12. The winning team did it in ~53 minutes, another 19 did it in under an hour. The difference between 50th and 100th place was a couple of minutes. Most teams did it somewhere between 1:15-1:20. A bunch couldn’t finish, due to injury or cramping.

We spent 34 minutes on the runs which put is in the middle of the field. We started off strong but I started cramping up after the 3rd station, which slowed us down considerably. My partner was finishing almost a minute faster than me on some runs, but since he had to wait it didn't matter. Our two penalties came because he crossed the run exit sign too far ahead of me. He was waiting for me in front of the entrance to the station, so we didn’t get any advantage. HYROX is full of little rules like these that we weren’t aware of.

Our 34 minutes of run time, only measures the time spent in the run zone. These aren’t actually a kilometer long, but closer to 750-800M. This is the distance between the entrance and exit signs you see as you enter or exit the Roxzone. The Roxzone is considered its own area, between the runs and the stations. The total Roxzone distance is somewhere between 250-350M. We spent 13 minutes there, which is also middle of the pack. Mostly because we stopped for water and walked for parts of it. This is a race so every second adds up fast.

We started strong on the stations. We did the 1000M Ski ERG in 3:51, the 65th best time. 1:44 for the 50M Sled Push (83rd place). Once the cramping started, we began moving slower to the stations which count towards your time. My teammate had to pick up more slack for me from the 4th station onwards, so we fell from the top quartile to closer to an average time. For most stations, the difference between top quartile and the mean is about ten seconds. Far less consequential compared to the runs and Roxzone.

This is why as much as it’s a hybrid athlete race, the key determinant of the finishing time comes down to running.

In my case I didn’t do enough of it. The three week trip to Japan 6 weeks before, was a setback, but it could have been negated. I was running at the pace I wanted on the treadmill with relative ease, but at a HYROX you aren’t just running 1KM then doing a station, before running another KM. You have to sprint an extra 100-200M before the station, then again before starting the next run. This quickly adds up and over the course of the race, you do closer to 9.5KM.

This wasn’t a case of gassing out, I spent almost the entire race in Zone 4 and barely entered Zone 5. This was a different feeling. I was never breathing super hard, this was simply my body refusing to push faster. It was smart enough to slow down to prevent cramping. Not everyone was so lucky. There were several teams collapsed along the track, with medics or teammates trying to rub out hamstring or calf cramps. Fortunately, I was able to avoid those until the very second the race ended.

If I could redo it, I would train to run for an hour straight at a slightly faster pace than what I would want to run for the HYROX. When you factor in the fatigue from the stations, you are going to run a bit slower. If the goal is to do the runs + Roxzone at an average pace of 4 mins per KM, I would train to run for an hour at 3:50.

I’m confident without cramping and better preparation, we could easily shave at least 5 minutes off our time. I’m certain we will do one again, because the HYROX environment is set up in such a way that the second you finish, you can’t wait until your next one. That’s why HYROX has achieved the scale it has so quickly.

A Brief History of HYROX

HYROX was founded in Germany by Christian Toetzke and Moritz Fürste in 2017. Toetzke had experience organizing sporting events such as running, cycling and triathlon races. Fürste was a former German field hockey star who won two Olympic gold medals.

They identified a gap in the fitness market. Millions of people go to the gym as their primary form of exercise, but they didn’t have a good event to compete in. Runners have marathons, cyclists had road races, weightlifters have power lifting competitions. The closest thing to a holistic fitness competition was CrossFit.

CrossFit got pretty big in the early 2010s but as a competition, it’s not accessible for most gym goers. Outside of professionals, few can master all the techniques required for the Olympic lifts and gymnastics to qualify for a CrossFit competition. Even if you are in good shape, if you draw a workout with exercises you aren’t good at, you’ll have a tough time being competitive.

HYROX eliminates the variance and luck of the draw by designing each race in the same format. The movements are comparatively less technical. There are optimizations, but anyone can push a sled or use a rowing machine with minimal instruction. Handstand pushups and backflips are harder to learn.

700 people competed in the first HYROX event in Hamburg 2018. The vision was to create something resembling a marathon. Where elite athletes or first-time amateurs can do the same workout, just in different times. Since the race format is standardized, participants across cities and seasons can compare their times.

The company’s expansion accelerated after a sports marketing group Infront made an initial investment in 2019. They would later become the majority owner in 2022. Infront is owned by China’s Wanda Group, but HYROX’s founders continue to own a stake and operate the business.

Since the ownership change, HYROX’s growth has been spectacular. They had 90K athletes compete during its 22–23 season. In 2024, this grew to 325K across 60 events. There are 100+ events and >1.5 million athletes expected for the current 25-26 season. They offer the race in several formats. You can compete as an individual or as a team, in the Pro or Open format. The difference comes down to the weight on the sled, lunges and farmer carries (we did the Open).

There is no reason to expect this growth will slow down any time soon. No matter how many HYROX events they add, most sell out months in advance. The number of HYROX specific gyms have doubled in the past year but seemingly most people still haven’t heard about it.

At its 2018 peak, somewhere between 2-5 million people participated in CrossFit, across 15,000 affiliated gyms although only ~400,000 registered for the CrossFit Open Championship. There are only around 5,000 HYROX affiliated gyms right now, but unlike CrossFit, most HYROX participants don’t train at one of these affiliates.

We are nowhere near peak HYROX. A greater percentage of participants can compete in HYROX compared to CrossFit and HYROX hasn’t come close to reaching the same culture awareness that Peak CrossFit did.

Final Observations

The fitness and fashion industries have a lot in common. New concepts can come and go quickly, and there is a lot of competition for mindshare. Both industries are massive but there’s plenty of competition. Some brands or sporting events can endure decades to centuries, whether that’s Ralph Lauren, Rolex or running a Marathon.

HYROX has been on a great run these past years, but many fitness concepts got big then ran out of steam. Do you know anyone that has done a Spartan Race or Tough Mudder lately? I’m sure a decent number of readers don’t even know what those are.

HYROX has a lot of momentum but if they want to become a mainstream sporting event staple like a Marathon or Triathlon and not a passing fad, they need to strike the right balance between accessibility and difficulty. Is HYROX trying to cater to everyone or just elite Hybrid athletes?

From a business sense, these are different customer profiles. Professional marathon runners will do multiple every year and probably get sponsored, whereas the majority of participants are amateurs who will only do one or two in their lifetime.

HYROX is appealing to both groups right now but most amateurs will eventually move on to something else. Like most direct to consumer brands, churn rates are high. The number of people fit enough to run 8KM and do 8 stations in under 90 minutes is generously only in the tens of millions. Perhaps GLP-1s and Peptides will increase these numbers.

As they eventually start to saturate their core user base, they will need to decide between providing easier, watered down versions or keeping it as something intense. Many Marathon organizers offer shorter events. Half marathons, 5 or 10KM races. You can do the half Ironman as an alternative to the full, but that still requires months of preparation.

HYROX is cool right now and its participants are pretty fit. It will be fascinating to see 5-10 years from now, if this sport will remain a staple or if it will fizzle out like many concepts before them.

In the meantime, I know I’ll definitely do at least another one, and I hope you consider doing one too.

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Last week I had two interactions with strangers that convinced me humanity was more civilized when the threat of death or violence was more present.

People feel too safe, enabling dishonorable behavior without consequences.

A driver became irate because I did not allow him to make his turn exiting a parking lot. He believed he had the right of way, and decided to drive his car next to mine, blocking the incoming lane to let me know. He threw a few insults my way then told me he hoped that I would kill myself. I told him his reaction was out of proportion for the perceived slight, but he kept going. Finally I asked what he wanted to do about it? I didn’t mean it as a threat, but I later realized it could have been perceived that way. The man was two decades my senior, I was comfortable with my chances against him in hand to hand combat.

Naturally he didn’t actually want to fight. He just wanted to dump any pent up frustration he had against the world on me, while seated securely in his truck. He drove away, which was the end of the exchange. I’m not somebody looking to get into a fight. We’ve all been taught violence is not the answer, and I liked the shirt I was wearing. Getting his blood off of it would be a nuisance. I was at peace with how the exchange ended. Then a similar incident occurred at the golf course.

I was playing a Saturday golf round at public course, which was playing very slow. It took 2.5 hours to get through the front 9. The rest of my group left and I was debating whether to keep playing or stop. I noticed at the turn there was nobody on the hole in front of me so I decided to continue. I quickly caught up to the group in front of me, which consisted of a man, his wife and young child. It was a Par 3, they weren't on the green yet and the group on the next hole had already teed off. I figured I would skip the hole and play through. I indicated this to the man as I was driving by, he didn’t react initially. Once I got up the tee box, I saw the group ahead was still in range of where I could hit my drive. I had to wait for them and they were taking their sweet time. So long that the group behind me finished their hole. The man from the group started yelling at me that he wasn’t going to wait for me to play. I hit my drive, well beyond the range where his wife or son could hit but he was still upset. He hit a ball into me and kept yelling. Now it’s common etiquette to let a single player play through and I wasn’t delaying them. His reaction was once again over the top.

He was with his wife and kid. I wasn't going to hit a ball back at them or fight the guy in front of them. Perhaps I could teach his son a valuable lesson but I play at this course regularly, it’s not worth a potential ban/getting arrested. This guy clearly only behaved this way because he didn't think he would face repercussions.

If only there was a socially acceptable way we could settle disputes such as these without societal repercussions.

Dueling. For centuries this kept gentlemen in line. Protected honor and helped settle disputes in an amicable fashion. It’s time to bring it back. Keep reading to learn why.

Book I’m Currently Reading:

1. Novelist as a Vocation by Haruki Murakami

Current Nightstand Book:

1. Debrett’s Guide To Etiquette & Modern Manners by John Morgan

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

Necessary Disclaimer

I want to reiterate I am not a violent person. Yet there is only so much disrespect one can handle before needing to defend their honor. Although the longer the first stranger kept whining, the more willing I was to risk a few punches to the face to get him to stop. If any professional associates are reading this, I am not actually calling for violence.

In 2026 there is no rational reason to fight a stranger unless your life is at risk. The risk to reward ratio doesn’t make any sense. Any satisfaction you might get from winning a fight does not outweigh the legal and reputational consequences that come with it. It hasn’t always been this way though.

The History of Dueling

Dueling was created as an attempt to formalize violence.

The earliest traced sources go back to medieval Europe where nobles would occasionally settle legal disputes with Trials by Combat. Similar to what we saw in Game of Thrones. Instead of a Judge and Jury, they put it in Gods hand to decide. If the losing combatant died, it’s because God wanted him to, therefore he was guilty.

The modern gentleman duel started during the Renaissance in France and Italy (of course). The aristocratic culture was obsessed with personal honor and reputation. A public insult could not stand unaddressed therefore noblemen began settling private disputes through arranged combat.

By the sixteenth and seventeenth centuries, dueling was common among European elites. It was usually associated with swords, Zorro style. Allowing somebody to insult your honor was a challenge to your masculinity.

Despite the authorities attempts to ban it, France became the great center of dueling culture. The Crown and the church agreed that it was destabilizing and wasteful but they couldn’t stop the elites from doing it. Refusing a duel made someone look cowardly, and for an aristocrat the social penalty was worse than the legal risk.

By the eighteenth century, dueling had spread as far as the American colonies. The weapon of choice gradually shifted from swords to pistols. This also changed the nature of the game. Sword duels required skill and training, whereas pistol duels were more a question of luck. Who could get the shot off first without the gun jamming. The weapon quality wasn’t very reliable back in those days.

This leveled the playing field and had the advantage of shortening the duel time. Just like on the golf course, people had limits on their patience to watch grown men wave swords at each other.

The duel was not supposed to be a chaotic brawl. It was seen as a gentlemen act with rules, seconds, formal challenges, apologies, negotiated settlements and rituals designed to make the violence seem civilized. As demonstrated by the esteemed gentlemen Sir Larry David.

Dueling was so common, it was almost a right of passage for prominent statesmen. Alexander Hamilton, Andrew Jackson, Abraham Lincoln, Lord Byron, Otto von Bismarck and most great Russian writers of the 19th century were all involved in a duel at some point.

It wasn’t all fun and games. Thousands of people died from these duels, some of whom were fairly consequential. Aaron Burr, Évariste Galois and Alexander Pushkin all died from duels. They certainly would have made more contributions to politics, mathematics and literature had they survived.

The Decline and Consequences of a Duel Free Society

Dueling began to fall out of favor in the nineteenth century. As the government became more powerful, they were able to crack down on private violence. Instead of risking potential death, aggrieved parties had alternatives to deal with reputational harm. Courts, newspapers and mediation etc.

As dueling spread from an Aristocratic activity down to the Middle-class it transitioned from gentlemanly to reckless, archaic and ridiculous. A bit like what happened to Soho House.

As societies became more bureaucratic, commercial and legalistic, defending your reputation via violence became unnecessary. Refusing to fight somebody looked more civilized then cowardly.

By the late nineteenth and early twentieth centuries, dueling had mostly disappeared in Britain and North America, though it lingered in other parts of Europe. It really ended after WWI. Enough people died that, the idea of two men arranging a private honor contest seemed less cool.

While the effectiveness of dueling as a way to contain violence is debated, its removal has not helped foster a more respectful society. My experiences with the two strangers shows, that the impetuous to avoid violence relies on the insulted party accepting besmirchment. The legal system does a bad job of punishing medium-aggressions. To sue them for damages, they would have to tangibly damage me. This seems unfair.

They would not have behaved that way if they knew I was carrying a sword.

“Trigger fingers turn to Twitter fingers” — Drake

This is not a new phenomenon. People like to talk tough on the internet or when they feel protected either by physical distance or the legal system. Few of these people actually want to fight, they just want to insult people consequence free. This isn’t an internet thing either. Without trying to spoil School Ties (1996), the premise is that Brendan Fraser, a student at an expensive prep school, is poor and Jewish. Predictably some of the rich WASP kids engage in antisemitic behavior. When Brendan Fraser challenges the people responsible to fight him, of course none of them step up. He called them cowards and that was the end of that. How embarrassed their aristocratic ancestors must have been.

Now these are high school aged boys in the 1950s. Antisemitism was rampant and there was a certain safety in numbers dynamic picking on the only Jewish kid as a way to try to gain social acceptance. I’m not sure where on the spectrum of genius to madness of crowds, did people decide insulting people’s honor should come without bearing consequences.

Open Twitter and you’ll see endless angry hateful people out there without a proper outlet. You can extend that across social media, phone calls or even Op-Eds in your local newspapers. The further people get from the consequences of their actions the more emboldened they become. When people argue about free speech versus censorship, they seem to misunderstand the right to say anything does not mean you don’t face consequences.

Free Speech does not equal Consequence Free Speech. The government should not prevent somebody from posting things on the internet, but if they post something that is against the law, the government is well within their rights to punish them accordingly. A privately held social media company is free to decide what content they allow on their platform, but the more they play this role of arbiter, the closer they get to an editorial position, making them responsible for the content they do not censor.

There needs to be some rectifying force that keeps people in line, some societies do a better job than others. While in Japan, I noted that the legal system does not need to keep people in line because societal values are already engrained. Fighting serves an important role in hockey as a release valve, to allow teams to continue playing after they feel justice has been served. In leagues without fighting, you witness all kinds of cheap, underhanded and at times dangerous behavior, that referees are not able to rectify.

A few years ago it looked like dueling was making a comeback. Mark Zuckerberg was going to fight Elon Musk at the Coliseum. It would have been a monumental moment of the 21st century, but unfortunately the fight never happened. The stakes were too high, and I’m sure both men had teams of lawyers, PR people and other professionals trying to talk them out of it. Zuck and Musk don’t even hate each other. They were in a temporary spat, that they felt they could be settled the old fashioned way.

Violence is not the answer, but the more society tries to erase it, the more permissive it becomes of disrespectful actions that fall short of illegality. The more often this behavior occurs, the more it becomes normalized and that’s how we lose our civility.

We do not need more violence but we need better substitutes for it. Honor, shame, manners, reputation and social consequence all existed because law alone cannot govern every interaction between human beings. A society where nobody is ever afraid to be rude is not a peaceful society. It’s one where the decent are expected to absorb the indecency of everyone else.

We probably should not bring back dueling but people should twice before acting like they deserved to be challenged to one.

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It didn’t matter which sport but inevitably anyone who played with me would have witnessed a tantrum at some point.

After a loss, I would throw my hockey stick across the locker room upon entering. Probably blaming the refs or some external factor for the outcome.

A backgammon game could end with the board and pieces scattered across the room.

After a bad shot, I would throw my tennis racket on the ground. I saw Andy Roddick and other Pros do it and thought it was normal. I didn’t realize they got paid to use those rackets whereas my parents had to buy mine.

These types of freak-outs were regular occurrences, then I turned ten years old and realized it was just a game.

This profound realization didn’t come from meditation, a therapy session or even a find myself trip to India. I realized these outbursts weren’t helping me, so I stopped.

At ten years old I understood I was allocating energy in a way that didn’t help me or make my life better. I was not a kid genius, but considering most adults could never figure out this basic lesson, I must have been less stupid than I thought.

People have a difficult time stopping behaviour that makes their life worse. Many won’t even accept or acknowledge they have an issue. Among those that do, many will decide it’s too difficult to change or even impossible based on their circumstances.

This thinking is common but not rational; it’s the ego whispering sweet nothings instead of facing harsh reality. If you are serious about improving without coming off as one of those annoying influencer types. Keep reading.

Book I’m Currently Reading:

1. Hardball: Are You Playing to Play or Playing to Win? by Stalk, Lachennaur & Butman

Book I most recently received as a gift:

1. The Fourth Turning Is Here: What the Seasons of History Tell Us about How and When This Crisis Will End by Neil Howe

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

Falling into a groove limits your growth

At some point, most people decide to settle.

Even if they aren’t satisfied with their career, fitness abilities, dating options or daily routine, they aren’t willing to do anything about it. Then that’s who they become.

Sometimes this happens consciously, but usually it comes from a handful of early experiences that harden into identity. You are the shy one. The funny one. The bad student. The lazy one. The person who isn’t athletic. The person who doesn’t read. The person who has a temper. The person who is simply “not good” at certain things.

Once that image settles in, life becomes easier in one sense. You can protect yourself from potential disappointment and have a convenient excuse for when things don’t go your way. It’s like a script you can use to dismiss opportunities when they appear.

“I’m just not that kind of person.” or “I do not have that type of canine in me!”

These sentences do more to limit human potential than any lack of talent. Many of these identities are formed when we are too young or inexperienced to know anything. This is dumb because with a few exceptions, your talent at a certain activity when you are 10 years old has little bearing on your long term potential.

If you regularly play youth sports, you can develop enough athleticism to play in most adult intramural leagues. If you eschew sports or fitness your entire childhood and only decide to get in shape in your forties, you are going to have a much tougher time. Deciding you aren’t sporty or athletic becomes a self-fulfilling prophecy. The longer you avoid exercise, the harder it will be to get in shape.

If you want to be competent, avoid these kinds of limiting beliefs. Too many people decide they aren’t math people because they struggle with high school math. In reality, your mental horsepower only becomes a limiting factor once you reach Master or Doctorate level mathematics. Virtually anyone able to get into University has the intellectual capacity to get through bachelor level mathematics. The reason they don’t has more to do with their mindset. They fail before showing up to the class.

These stories you tell yourself do more damage than good. Just because you are told things by others as a child doesn’t mean you need to be shackeled by these labels for the rest of your life. Once you realize this, you are free to do anything.

Free will only exists for people who exercise it

If you believe the Universe is preordained there is no reason to do anything. The cards will fall as they do and you couldn't change the outcome if you wanted.

Nobody who achieved anything great accepted the universe as this immutable entity, they decided they wanted to do something and they were going to make it happen regardless of what obstacle got in their way.

Whether or not free will exists in some grand philosophical sense is irrelevant. Your life feels predetermined if you act like a passive observer. You become a slave to the whims of the free market, the government or other people around you. Fortune favours the bold, if bold is another way of saying people who try to change the universe in the way they want.

The universe doesn’t bend easily. Just wanting something doesn’t guarantee an outcome. The bigger the ask you make, the greater the input. Talent, timing and luck all matter. Unfortunately most people surrender long before reality has the chance to reject them. People fail to understand that the difference between a 0% chance and a small chance is massive.

A big reason for this is the fear of being judged. People worry that if they suddenly take something seriously, others will notice. If the unserious person starts writing, the out-of-shape person starts training, the quiet person starts speaking up, it might look forced. Someone might find it cringe.

The only people who care about something being cringe, are cringe people. Cool or successful people don’t care about that sort of thing. They are busy doing cool/successful person stuff to judge.

People are cringe until they aren’t. Look at Arnold Schwarzenegger. He went from Austrian immigrant with a thick accent, to the biggest bodybuilder in the world. Then he became a movie star, governor of California and then he married a Kennedy. He didn’t care about making a fool of himself. He worked out or improved his craft almost constantly. Willing to look foolish in the near term to look brilliant in the long term.

Nobody cares about what you are doing as much as you. People going around calling things cringe, is an inevitable reaction to their own discomfort when they see something that doesn’t conform with their mental model. If you study any highly successful person, you will find plenty of cringe. Things that don’t align with how the average person lives, or how most people think they should.

They will over allocate time and attention to things others won’t. They will put in more hours and obsess about things, in pursuit of their goal. They don’t care if other people think it’s excessive or not.

You don’t need permission from the people who knew an older version of you. You don’t need to preserve their comfort by remaining familiar. Put your will on the universe. Make the change. Let everyone else adjust. You just need to decide it’s important to become the best version of yourself, and you’re willing to ruin the mental image you’ve built for yourself.

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

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

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

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

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

Book I’m Currently Reading:

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

Book I most Recently Gifted:

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

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

What is Risk?

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

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

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

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

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

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

Bad Investors Avoid Risk, Good Investors Consider It

(Not Investment Advice)

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

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

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

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

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

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

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

Upside vs Downside Risk

(Not Military Advice)

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

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

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

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

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

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

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

How Does The Barbell Work

(Still Not Investment Advice)

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

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

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

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

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

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

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

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

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

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

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

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The average couple will spend ~$35,000 to throw a wedding, while guests will spend around $600 to attend. Few will get married more than once per year, but there’s no limit on the number of wedding invitations you might receive. Once you reach your late twenties, you quickly discover you know more people than you realized. You hit thirty and start to view engagement announcements as early hurricane alarm systems.

Everything around the special day has gotten out of control. Women are expected to find a new outfit for every wedding, plus additional looks for the cocktail, rehearsal dinner, or whatever pre-wedding event now requires its own dress code. Men can usually get by with one or two decent suits, but remembering to pick them up from the dry cleaner remains one of civilization’s great administrative burdens.

If the wedding requires travel, the commitment escalates. For casual acquaintances, this can serve as a convenient excuse to opt out. Close friends, direct family members, groomsmen, and bridesmaids do not enjoy this luxury. No matter how obscene the groom/bridezilla gets, they are expected to smile and be supportive.

The decision criteria on whether to attend somebody’s wedding and associated etiquette is well documented but not enough attention is focused on the people that really matter. The poor souls that are obliged to organize and attend bachelor and bachelorette parties.

There lacks a clear consensus on the proper rules and etiquette surrounding stag and stagette parties, as a veteran of six bachelor parties, in this article I share my knowledge to help fill this void. Keep reading to learn the history behind stag parties and to ensure you aren’t responsible for any Faux Pas this wedding season.

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

The History of Stag Parties

You might be surprised to learn this, but the concept of the bachelor party originates none other than from Ancient Greece, specifically Sparta.

The night before a solider would get married, he and his co-soldiers would share a succulent meal and get really drunk. There were not many women in attendance. Feel free to draw your own conclusions.

By the early 19th century, Western Stag parties would turn into classy black tie affairs, often hosted by the groom or his father. Some drinks would be shared, but festivities were usually contained to one evening. In the late 19th and early 20th century, these type of festivities became more rowdy affairs but the acceleration really happened during the Post-War period. This is when the stag parties ditched the black tie soirees for nightlight, pranks, destination trips etc.

Bachelorette parties are relatively new, having only become widespread in the 1960s and 70s. Eventually men ran out of convincing response when asked why they were permitted to have a wild send-off but the women were not?

Globalization, couples getting married later and easy access to credit cards have made these type of celebrations get increasingly out of hand. Nowadays, it’s rare if nobody in the friend group isn’t dead set on a multi-day excursion to Vegas, Nashville, Ibiza, Barcelona, Tulum or some other version of adult Disney world.

The invite is inevitable. Proper organization and expectation setting is needed to ensure friend groups don’t want to disband after the stag party.

Organizing a Bachelor/Bachelorette Party

These days the organization of a Bachelor/Bachelorette party takes similar project management to a Salesforce or SAP implementation. The complexity for both grow exponentially as more people are involved.

The Bride or Grooms responsibility as it pertains to their stag party is simple:

1. Elect the organizer(s)

2. Give them the preferred guest list of attendees

3. Tell the organizer(s) what type of party they are hoping for (Bonus points for anticipated budget)

They should not be involved in the process, but they need to assign clear ownership. Someone has to be accountable for the planning, budgeting, deposits, reservations, reminders, and managing the collective anxiety of the attendees. This usually falls on the best man or maid of honour. The “honour” is meant to compensate for the fact that they have just been assigned an unpaid operations role.

The organizer can share responsibilities with another person, but if somebody is expected to help, it needs to be made explicit by the bride or groom. Everyone should know what they are responsible for. Ambiguity is where chaos begins. If everyone thinks someone else is booking the Airbnb, you will be sleeping on the street.

The bride or groom needs to be clear about what they want. It reduces the risk of disappointment, and gives the organizer political cover. The organizer can explain to the group that these are the wishes of the person getting married, not the deranged personal vision of the best man, maid of honour or some other outspoken attendee.

If the groom wants everyone to spend $10,000 on a two-week trip to Mongolia, everyone should understand that’s his dream. If the bride wants six matching outfits, three separate themes, and one dinner where everyone dresses like a mermaid, don’t blame the maid of honour. Their job is hard enough. They need to thread the needle between the stag’s wishes and reality. These do not always align. When they don’t, compromise becomes necessary.

If the bride or groom wants something extravagant but the desired guest list is not on board, someone is going to have a bad time. The organizer then has to answer the central planning question: does the stag care more about maximizing attendance, or having the party they imagined?

When the bride or groom is being unreasonable, the organizer needs to temper expectations. When the attendees are being difficult, the organizer may have to cajole them or accept lower participation. This is the delicate art of stag-party diplomacy: protecting the bride or groom’s vision while preventing an all out mutiny.

As much as possible, the bride or groom should be spared the uglier details of the planning process. They do not need to know who complained about the hotel, who ignored five payment reminders, who objected to the itinerary after voting for it, or who tried to create a breakaway faction.

This unfortunately falls on the organizer. It’s a not a fun position, but hopefully they take delight in ensuring one of their closest friends gets a proper sendoff. This does not mean, attendees have free rein to make it more difficult for the organizers.

How to Attend a Stag Party

If you are invited to a bachelor or bachelorette party, your job is simple: help the stag have a good time. If you can’t commit to that, don’t go.

Regardless of the time, money, and logistics required, once you decide to attend, you need to let go of your grievances. If the event is too expensive, too far, too long, or too inconvenient, tell the organizer you’re out as early as possible. It’s better than agreeing to go but sabotaging the event by acting like a hostage.

Unless you are a groomsman or bridesmaid, you are not obligated to attend the stag party. If the bride or groom did not explicitly name you as one of their 5-10 closest friends, your attendance at any pre-wedding event is discretionary. Honestly, even the wedding itself is optional. Especially if this is somebody’s second or third time at the altar; you've already put in your time. Just keep in mind, your pal and their spouse might take your absence personally. That being said, if the stag attended your bachelor/bachelorette party, you should return the favour. If you can’t make it, the classy thing to do would be to send some money to the organizer to at least cover a round of drinks. Again not necessary.

Not every stag party will be accessible to everyone the bride or groom would like to invite, and that’s fine. The point of the event is to give the person getting married a proper send-off. It’s not a friendship lifetime achievement ceremony.

Some people will move mountains to be there. Others wouldn’t inconvenience themselves even if the organizer arranged everything perfectly, subsidized the trip, and had a helicopter pick them up from their front lawn. Don’t design the event around the lowest common denominator in the group.

A good compromise is when everyone feels a little upset. However, in the case of a stag party, the stag matters more. This does not mean everyone should be financially abused, but it also does not make sense to optimize the entire event around the cheapest, easiest, least disruptive option for every guest.

Just like at a wedding, your comfort is not the priority. It’s not about you. If you don’t think you will enjoy yourself, do everyone a favour and decline. Showing up as a martyr benefits nobody. Not everybody is built for a wild Stag party and that’s fine. Just wait for your own bachelor party to insist on a Settlers of Catan marathon.

Every stag party also has a small group of people who treat the event like General Custer’s last stand. They will go way too hard, too early while forgetting their real age. If this group is limited to regular attendees, they can usually be contained. If it includes the stag or the organizer, all you can do is prepare yourself emotionally.

You also need to be mindful of the two most dangerous budget personalities. The first is the “treat yourself” person. They will casually try to upgrade every aspect of the trip, quickly doubling the cost of the trip before anyone can protest. You can identify people with phrases such as:

1. “It’s only an extra $300 per night per person.”

2. “I found a better restaurant. It’s just a $300 tasting menu.”

3. “I got us a better table. We only need to commit to ten bottles.”

This person is impervious to financial pain. Other attendees are not.

The second is the extreme cost-cutter. This person is equally dangerous, just to the other extreme. At dinners they will order only a side dish and raid the bread basket. They will go too hard at the pregame because they refuse to buy drinks at the bar. They will try to convince everyone to walk 10 kilometres home late at night to avoid a $20 Uber. If given free rein, they will quickly ruin everybody else’s good time.

With luck, everybody in attendance will be on the same financial page but if not, the organizer needs to set expectations early so neither type ruins the event. It doesn’t need to be expensive for it to be a good time, the goal is to create a memorable event that the stag actually enjoys, at a cost the group can reasonably tolerate.

If you want to reduce costs, one way to do it is by avoiding merch. Nobody needs a custom T-shirt, hat, fanny pack, shot glass, or tote bag commemorating Ashleigh’s Last Ride. Nobody will wear it again. It will appear in three Instagram stories, spend eight months in a drawer, and eventually end up at Salvation Army or in a landfill.

The point of a Bachelor/Bachelorette party is to have an amazing time, nobody forgets but will never bring up ever again. Whether you are organizing or attending the event, the best thing you can do is give your friend a proper send off as they end their life as an unmarried person and begin their life as somebody’s husband or wife.

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Was I about to lose to an inanimate object?

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

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

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

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

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

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

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

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

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

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Longevity Matters

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

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

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

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

Pain Tolerance

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

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

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

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

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

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

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

Morale

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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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The few Japanese people I knew were great, beyond that, outside of restaurants and anime my other exposure to the fine folks of Japan was minimal. Mostly being stuck behind crowds of them on vacation as they took thousands of photos; an activity they certainly don’t have a monopoly on.

As I’ve travelled across Japan these past few weeks, I have come to realize that the Japanese as a group are superior. The criteria being how they treat guests in their country.

For a country that receives more than 40 million tourists per year, Japanese residents know how to make you feel like you are their first. Whether you are in a big city or a tiny town, shop keepers/restaurant owners will walk you to the door, morning commuters will go out of their way to bring you to the correct train platform. These are just a few examples of gestures that are engrained in the culture.

The contrast between how kind and thoughtful Japanese are versus tourists are stark. Enter any train station, there can be 50,000 Japanese and you won’t hear a thing. The only noise will be from the 10-20 tourists, running around looking for directions and dragging their rolling suitcases along the pavement.

If you haven’t been to Japan yet, here is a short primer on what you should know and why during the waning days of the golden era of travel, it is still one of the best countries to visit, in spite of the waves of tourists.

Japan is not just cleaner, quieter, and more orderly than the West. It has a deep food culture, a vintage luxury market so good it makes shopping feel like value investing. Even Richard Gere is rumoured to be running around the country these days. Keep reading to learn what makes the country exceptional.

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The Role of Zen Buddhism in Japanese Culture

An explanation for why the Japanese are so kind to tourists is because they are Zen.

If you are unfamiliar with Zen, it’s a branch of Buddhism that instead of focusing on an abstract doctrine, emphasizes direct experience, discipline, simplicity, and the presence of mind. I experienced this personally.

It was exactly a week into my trip to Japan when I was overcome with an overwhelming sense of calm. Nothing could bother me.

This happened as my wife whisked me from one matcha and ceramic shop after another, an activity that would try any mere mortals patience. Yet I remained unperturbed.

Although I didn’t care for tea or overpriced bowls, I was neither happy, sad, upset, bored or rushed. I simply was.

As I fought boredom and waves of slow moving tourists, I realized I had ascended to a level of Zen I had never previously encountered. My travels throughout Japan had brought me here. How was this possible?

In Japan, Zen Buddhism’s influence runs beyond the religion. It has shaped the country’s taste for minimalism, quiet beauty, ritual, self-control, and respect for practice. You can see this in things like tea ceremonies, gardens, martial arts, calligraphy, architecture, and everyday etiquette.

There is a strong emphasis on process over outcome. The Japanese are deeply conscious of how things are done, not just whether they get done. You see it in the tea ceremony, where every motion matters, in stone gardens where emptiness is part of the composition, in the meticulous wrapping of ordinary purchases, and in the quiet order of train platforms and public spaces.

Beneath all of it is a heightened awareness of the space one occupies, and of the burden one’s noise, movement, or disorder can place on others. Attention is paid not only to function, but to form, rhythm, restraint, and consideration. Even small things are treated as worthy of care.

Tourists not trained in the ways of Zen stick out like a sore thumb. They are focused on achieving their outcome without considering the space, noise or smell they are giving off. This makes the non Zen masters among us, appreciate the locals even more.

The Food Scene: More Than Just Sushi

When Westerners think of Japanese food, they generally focus on Sushi and high quality cuts of beef. Both are exceptional but you can go a full week eating neither and consistently come away impressed. There are plenty of tourist traps, especially in the bigger cities, but when you stumble on legit places, they aren’t just good, they’re memorable. This can come at any price point too. You can drop hundreds of thousands of yen (hundreds of US dollars) at Kobe Beef or high end Omakase restaurants but be as impressed by hole in the wall ramen, donburi or okonomiyak places.

I’ve had friends go who hate fish/seafood, vegetarians, meat heads, picky eaters and everything in between but they all found something they enjoyed. If you don’t like the food in Japan, you are the problem.

Something you’ll commonly see are tiny bars/restaurants with seating for up to 6 people, and only one or two staff working there. It’s an intimate setting, where before you know it you’ll be chatting with the other patrons whether they are Japanese or from other countries all over the world. This might just be a me thing. Apparently I bear a resemblance to Richard Gere, even if he’s more than 40 years older than me.

Part of this can be explained by the limited space in big cities, but also the comfort Japanese have in smaller settings. They don’t need a large foot print, or even a big staff. It’s pretty normal for the chef to also serve you and ring up your bill. It’s not uncommon to see a small dude crammed into a metallic structure barely large enough for him to stand in serving up takoyaki. Of course he will have a line out the door and the octopus balls are going to be incredible.

Something you should know, Japan is still a very cash oriented culture. Outside of big cities, a lot of places don’t accept credit cards, especially if you are going to temples and other sight seeing attractions. Those certainly cost money.

You can always withdraw from ATMs in the 7-Eleven, which are not at all like the ones you see in the US. I hate to say it, but the food quality there is on par with mid-tier American restaurants. Of course these are usually things you can eat on the go, like sushi, onigiri, maybe a Bento box. I would never otherwise eat food from a convenience store but the Japanese 7-Eleven is on a different level.

The Vintage is Better Than Buying New

During the late 1980s, Japan’s economy was ripping. It was the world’s great manufacturing powerhouse, producing everything from cars to consumer electronics, while a population known for high savings also had money to spend. Chanel bags, Rolex watches, and high-end European fashion became fixtures of Japanese consumption.

Then the bubble burst in the early 1990s, and Japan never fully recovered its old economic momentum. The country endured decades of weak growth, recurring deflation, and near-zero interest rates, yet wage gains remained stubbornly limited. The result is striking: many Japanese workers still earn roughly what they did 30 years ago.

One consequence of that era is visible all over the country today. Vintage shops are overflowing with luxury goods. There are plenty of modern pieces too, but it’s not a coincidence that so much of the supply dates back to the 1980s and early 1990s. The Japanese are known for taking excellent care of their belongings, and there is far less stigma around buying second-hand goods than in many Western countries. As a result, locals and tourists alike participate in a lively resale market for designer items, creating an unusually deep supply of high-quality used luxury.

You can walk into a vintage store and find piles of Louis Vuitton bags stacked the way corner stores used to toss bad DVDs into a bargain bin by the door. Japan has strict anti-counterfeit enforcement, shoppers have more confidence that what they are looking at is authentic. That does not mean everything is cheap. In many cases the prices are no better than what you would find online or even buying new. You still need to hunt. Normally I don’t like to spend much time shopping but the value investor in me does appreciate trying to find arbitrage opportunities.

Concluding Thoughts

What makes Japan special is not just the food, the cleanliness, or the shopping. It’s the social ethic beneath all of it.

The Japanese have built a culture that places unusual weight on restraint, order, and consideration for others. You see it in the silence of train stations, the care given to ordinary purchases, and the constant awareness of the burden one’s noise or disorder can place on everyone else.

That is what makes Japan so refreshing, and also slightly humiliating for the average tourist. In a country receiving more than 40 million visitors a year, the locals still manage to treat guests with patience and generosity, while many visitors repay them by being loud, messy, and oblivious.

Japan is worth visiting for many reasons, but the most valuable thing it offers may be the reminder that civilization is built out of small daily acts of discipline and respect.

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

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

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

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

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

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

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

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The Role of Fear

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

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

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

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

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

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

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

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

The Role of Love

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

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

(They look happy)

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

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

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

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

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

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

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

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

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

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This pattern persisted until I came across a few insights:

1. 90% of podcasts don’t make it past 3 episodes. Releasing 21 episodes means you will put out more content than 99% of other podcasters

2. Mr. Beast, Alex Hormozi and countless creators put content out daily or weekly for years before cracking 1,000 subscribers/followers

3. Most content is bad. Even before LLMs, the internet was drowning in slop. There are so many unremarkable books, movies and shows that generate plenty of views

With that Serviceable Insights launched March 15 2024 with one goal:

Publish 100 articles in 100 weeks, offering readers at least one useful thing each post.

As of March 2026, SI has ~1,200 subscribers, and generates100,000 views per year.

I don’t know what these numbers will look like two years from now, but Serviceable Insights is just getting started and remains a Day 0 newsletter.

Whether you are a long time reader or discovering me for the first time, my objective remains the same. Inform and entertain. This will not change. Why? Because that’s what I would want to read, and if I don’t want to read this, why should you?

This week’s article will share some of the lessons I’ve learnt along the journey to 100 articles with the hope of inspiring current and aspiring content creators alike.

Keep reading to find out!

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Pre-Launch

Lesson# 1 —“Victory is secured by choosing battles on your own terms, exploiting terrain, and forcing the enemy to fight where you have the advantage.” Sun Tzu

Lesson # 2 — “Be So Good They Can’t Ignore you.” Calvin Newport via Steve Martin

It takes anywhere from weeks to months to establish a habit. If you stick with something long enough, it becomes second nature, like brushing your teeth or engaging in petty thefts.

Don’t write to maximize Subscriber, Likes or Comments. Write great articles on topics you enjoy. If you are going to commit to producing content on a regular basis, you are signing up for a marathon. Even successful creators regularly burn out.

I knew I couldn’t write 100 articles on one topic, which is why I decided to run a generalist account. This goes against conventional advice. Most people will tell you to specialize in one niche, where you get known as the best writer for that vertical. Subscribers know what to expect each week and you are more likely to get discovered by people looking for that that topic.

Despite knowing this, I decided my interests are too varied. I came up with the title Serviceable Insights because it was sufficiently broad enough that as long as readers learnt something, I would have achieved my mandate.

In terms of cadence, I went with weekly to get into a consistent groove. It also works out nicely to ~50 articles per year. More than that is excessive for an employed person earning zero income from this.

To make it as easy as possible to turn this into a habit, I wrote 6 articles before I released my first post. Four of those articles were a series related to startup equity, one an article explaining Mimetic Theory, and another a look back at of Peter Thiel’s book Zero to One. Sufficiently varied but with some consistent themes.

I schedule sent them and Serviceable Insights began.

Early Days

My early articles sucked.

There were some interesting premises but the writings were too long and not optimized for an email inbox. I was writing novels without having built nearly enough credibility with my audience to expect that much patience.

There was good information in there but it was overwhelming. Even if people opened the article few would read to the end. It took me a while to appreciate this.

In the first two months I only gained about 50 Subscribers and none of my articles made it to 200 views. I was only being read by people who knew me. Friends, family members, work colleagues, Linkedin connections, stalkers etc.

I started getting regular comments and interactions from fellow Substackers, who were nice enough to occasionally promote their work as would I with theirs.

I started to see a steady climb by month three. After a 5,000 word article on Henry Kissinger surprisingly bombed, I knew I needed a different approach. I worked on that article for 3 weeks and nobody cared. Seeing this, my next few articles were shorter, and on more universal topics. Business and life lessons from Game of Thrones, Succession, a summary of The Richest Man in Babylon. These articles only took a few hours to write and resonated much better with my audience.

I followed this up with my first relative big success at the time with an article explaining how to sell. This was my first article to reach 1,000 views within the same week and it generated me almost as many subscribers as all my previous articles combined. This was a more dense article compared to the last few weeks. This told me, I could write longer articles, if the writing was good enough.

Considering I wrote this from a generalist blog, expert sales people coming across the article were willing to afford me more tolerance compared to if it came from a sales blog. People who normally wouldn’t be interested in sales, were willing to give it a chance and then were happily realized this knowledge could help them.

My Subscriber count was trending towards 200, and 50% were opening my newsletter each week. I was starting to assemble a loyal following. My next few articles didn’t do as well but they were still getting more views than the prior month. In late July, I got hit with inspiration, cranked out an article in 3 hours. I didn’t think much of it at the time, but what came next was unexpected.

Going Viral

Lesson # 3 — “What is an expert anyway? Just some guy from out of town?” Mark Twain

Lesson # 4 — ‘The greatest victory is that which requires no battle.” Sun Tzu

The best creations flow easily. Mark Twain, Cormac McCarthey and Rick Rubin all expressed this. It’s difficult to predict what will resonate with an audience but pain on your part does not guarantee enjoyment on theirs.

When Mark Twain wrote The Celebrated Jumping Frog of Calaveras County, he didn’t think much about it. He was shocked to see how much readers across the country resonated with his story.

I don’t deserve to be mentioned in the same breath as Mark Twain, but I had a similar experience with Sorry Jocko, Discipline Is Overrated. In response to an unintentionally funny Youtube video from 5+ years prior, I wrote down some quick thoughts outlining my perspective on discipline versus building systems to achieve goals. I didn't say anything new but for whatever reason, the article was a hit.

The day it came out it, it generated 400 views. This was slightly better than my previous best but nothing shocking. To that point, my articles would usually generate most of its views within the first 24 hours, then gradually taper off by the end of the week. Instead of view counts dropping off, they started accelerating. By the fifth day, I had already gotten more views and likes than my previous 4 articles combined. People were sharing, re-stacking and commenting. I was even getting hate messages. Within a month, it had amassed 6,000 views and generated 100 subscriptions.

This doesn't sound like a lot but keep in mind, I only had 200 Subscribers at this point and most articles were getting around 200 views. The article also directed traffic to other articles, generating me additional subs and engagement.

Every few months, some decent size Substack account would share it, and I would get another engagement boost. This is still paying dividends nearly two years later. As of this writing, it’s been viewed 12,500 times, has 200+ likes, 45 comments and 30 re-stacks. That’s rare for an account with 1,000 subscribers, let alone 200.

This came after only 4 months and 20 articles. To this day, I still don’t think it’s one of my best but it doesn’t matter. Enough people on the internet thought there were enough useful learnings and it was worth the time to read, comment and share.

When you have a strike of inspiration, jump on it. Ride the wave and see where it takes you. Not every article needs to be perfect. There is so much bad content out there on the internet, you would be surprised what rises to the level of good or useful. Content you consider mediocre might be a revelation to others.

The Slog

Lesson# 5 — “Stay in the game long enough to get lucky.” Naval Ravikant

A lot of success in life comes from sticking with things long enough to bear the fruits of your persistence. This is true in finance, business, politics and content creation. Giving up guarantees your failure. The ability to keep going even when the evidence of success isn’t there, is what separates eventual winners from current losers.

After the viral article, I didn’t have another article crack 1,000 views for 6 months.

Subscriber counts continued to grow but article views were flat. Some of my best work, such as Robbing Banks is a Rich Man’s Sport came out during this stretch, but the data was uninspiring.

It’s frustrating to feel like you are putting out better content without anything to show for it.

Nonetheless, I kept at it. I knew it was going to be a grind before I started, here it was. It had only been a few months; the Discipline article gave me a false sense of the work that was required to break through on the internet. So I kept at.

Putting something out each week can feel daunting. You get busy with other things, you get tired but you still need to find a way to get 1,000-2,000 words out. Instead of approaching it as 2,000 words each week, break the work into manageable chunks. If the intro and each section is ~150-300 words, look at it as writing 300 words, 4-6 times. Anyone can write that much and you can squeeze those out in 30 min blocks.

If you are stuck, start writing ideas down. They don’t need to be connected or even coherent. By putting them on a page, your brain will try to make sense of it. It can’t help it. If the words aren’t flowing, just keep throwing down more ideas until the floodgates open. Before you know it, you’ll have too many words and you might need to divide them into several sections or even multiple articles.

Start earlier in the week so you don’t find yourself the night before your weekly release cadence with nothing written. 2,000 words in one evening can be difficult, especially when you don’t have the spark of inspiration. I do my best thinking in the sauna. I can normally connect all the ideas and the articles before I sit down to write. If not, sometimes writing one section or the introduction is enough for me to fill in the blanks throughout the rest of the week.

The Hot Streak

Lesson # 6 — “Luck is what happens when preparation meets opportunity.”

As I continued putting out articles, I would pick up things and incorporate it into my writing. 2024 might have finished with a whimper but 2025 started with a bang.

My cold streak of articles without 1,000 views ended with Should I go into Debt for a Rolex? It didn’t reach the heights of Sorry Jocko, but it performed really well on Substack, reaching 3,000 within the first week. Huge accounts were commenting and re-stacking it, eventually getting it to 5,000 views.

Why did it do so well? I hit the trifecta.

1. Great title: It needs to make people want to click on it. Whether their goal is to tell me how stupid I am or if it’s something they are actively contemplating, it did a good job of peaking people’s curiosity. If the title was less provocative like “Luxury watches are expensive”, it wouldn’t have performed as well.

2. Thumbnail: Visuals catch the eye more than a title will. By having Zuck sporting his oversized gold chain and expensive watch, it stood out compared to other articles on Substack. There’s a reason you see a lot of thirst traps on social and print media, it catches the eye. Anytime I’ve posted Margo Robbie, Sydney Sweeney, a cute girl or dog in the thumbnail, the article has reached at least 1,000 views. Photos of Rick Rubin or overly niche memes haven’t done as well.

3. Strong Introduction: If you’ve managed to get somebody to open the article, you only have a few seconds to capture their attention before they click off. Long time readers might afford you more leeway, but you have no goodwill with readers discovering you for the first time. If you can’t hook them in the first few lines, you’ll lose them. This extends to the entire article, but the deeper somebody gets into it, the more willing they will be to finish it. You need to get them far enough long they will want to read to the end. To do this, eliminate fluff.

Beyond this, the Rolex article did well because I didn’t hedge. I took a position and I stuck with it. If you want somebody to read your writing, you need to be credible. Don’t kill your own credibility with words like perhaps, sometimes, potentially etc. Get the facts and information then make your claims.

You aren’t writing a Phd thesis defence, you can make some bold statements that aren’t immutable laws of physics. The benefit of writing is you can follow your line of thinking. If you have good sources and your arguments are logical, it doesn’t really matter if you are wrong. Plenty of great writers, authors, academics and investors have made many wrong calls without losing face or respect.

If your goal is build an audience you need to take positions. Readers will respect this more than offering no opinion. Just don’t take dumb takes with the goal to get dunked on. You’ll get views, without respect. Just look at Taylor Lorenz. My articles started popping off because I took strong positions and backed them up.

Should I go into Debt for a Rolex?, Is Skiing a dying sport?, American Tourism is Getting Wrecked, and Is Pretty (Male) Privilege a Thing? are some of my best performing articles to date and they are all examples of that. They all came out within the first half of 2025 about a year after I started.

Since then, most of my articles reach 1,000 views. Not always within the first week or even from Substack. Now I get up to >1,000 monthly views from Google and other search engines, some on articles written two years ago. Between Substack, my subscribers and reader sharing, I get anywhere from 5,000-20,000 views per month.

The Future

It’s already been 2 years and 100 articles, but I feel like I haven’t even started yet. Looking back at old articles, I’m shocked anybody was willing to tolerate such awful writing. If you don’t look back at work you did 6 months ago and think it sucks, you aren’t improving quickly enough.

Nonetheless, I love my articles. All of them. Even the bad ones. They aren’t all gems and that’s fine. 100 articles in 100 weeks will do that. I learnt something writing each one and as a result, I’ve improved immeasurably in the past two years. I’ve only distilled a tiny portion of those lessons in this article with the hope this will help current or aspiring readers.

I want to thank my 1,210 subscribers, everyone from those that have been with me from the beginning and those who subscribed recently. This includes friends, family members, professional acquaintance and complete strangers on the internet. A special shout out to and many other Substackers regularly engaging and sharing my work as well as publishing great content themselves.

Here’s looking forward to another 100 articles, that will only get better. In the meantime heed these lessons

Lesson # 1 —“Victory is secured by choosing battles on your own terms, exploiting terrain, and forcing the enemy to fight where you have the advantage.” Sun Tzu

Lesson # 2 — “Be So Good They Can’t Ignore you.” Calvin Newport via Steve Martin

Lesson # 3 — “What is an expert anyway? Just some guy from out of town?” Mark Twain

Lesson # 4 — ‘The greatest victory is that which requires no battle.” Sun Tzu

Lesson # 5 — “Stay in the game long enough to get lucky.” Naval Ravikant

Lesson # 6 — “Luck is what happens when preparation meets opportunity.”

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Business books focus on product, strategy, sales yet none can succeed without money. If the CEO bankrupts the company because they spend all the funds on parties, pet llamas or other unproductive items, none of those other departments matter.

Individuals hire financial planners to serve a similar function. One could question their utility since most just charge 1% of AUM to tell them to spend less money and put their investments into ETFs. I’m sure some are probably fine, just not the ones advising Nick Cage or Wesley Snipes.

Hard transition + trigger warning*

Readers might be shocked to learn there is something more valuable and important than money. Time.

Not everyone agrees but let’s compromise and say they are at least equivalent. This begs the question. Why is everyone so obsessed with watching their finances but afraid to audit how they spend their time?

If time is money, why are there armies of bean counters but no clock watchers?

There is endless content on managing finances but very little on how to effectively audit how you spend your time.

A companies financial health is depicted in the 3 financial statements: The Profit & Loss Statement, The Balance Sheet and The Cashflow statement.

What if we were to apply this framework to time management?

Do you have a busted time balance sheet? Are you incurring crazy losses? Are you bleeding cash?

Keep reading to find out!

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

The Time P&L Statement

How did you spend your time between X-Y Date

The P&L statement shows what happened between certain dates. Usually shown quarterly or annually, but it can be any frequency. Monthly, weekly, daily whatever.

In a financial sense you’ll normally see what revenue has been generated, expenses incurred during that time, the taxes paid, if you believe in that sort of thing and what’s left after you net these out. The profits and/or the losses.

From a time standpoint, you can allocate every second to see how it’s used. People generally spend around a third of their time sleeping, another third working and activities around work such as commuting or going to your companies awkward picnic. That remaining 6-9 hours during the week is where we are supposed to squeeze in everything else. Important things like getting dressed, exercising, personal hygiene, reading Serviceable Insights, crying to The Ride of The Rhohirrim.

People will whine that there isn’t enough time in a day but spend 5 hours a day on their phone. Mostly doom scrolling Instagram. Not to mention wasting time watching crappy Reality TV or other bad shows. Except for Succession, Succession is great (if you are a fan check this and this out).

The way you spend your time will determine your mood and general satisfaction with your life. I am not Sigmund Freud but if you aren’t happy, you should spend more time on things that will make you happy.

To be happy you need some combination of safety, security, companionship and the sense of a great mission/purpose. For some that’s religion, worshiping the God or sports team of their choice. Others will fill that void by going into politics, starting a company or dedicating their life to research. Some research such as the cure for cancer benefits society, other research only exists so people don’t need to admit they are unemployed. Whatever floats your boat, I’m not one to judge.

If on balance you find yourself waking each up morning happy, energized and excited for what’s to come, you are spending your time well. You’re running a profitable life.

This doesn’t mean you need to love every second of your life. Sometimes like an early stage startup, you need to run losses in the short term to be very profitable in the long term. In fact, if you never find yourself doing something you aren’t naturally inclined to do, you will never achieve anything of consequence let alone your life purpose.

The more you can learn to take pleasure in the activities you don’t naturally want to do, the easier it will be to achieve your great purpose. Sisyphus was condemned to roll a stone uphill each day only to watch it fall back down each night. With no way to escape this fate, the only way for Sisyphus to defeat the Gods who condemned him, was to enjoy their punishment.

Kobe Bryant was cursed with the desire to be the greatest basketball player ever. Better than Michael Jordan. Kobe Bryant didn’t enjoy waking up at 4AM and training four times per day, but he loved the separation he was creating between him and his competitors. These were long term investments in his future, creating assets that paid him dividends for decades. These are the things you would see on the balance sheet.

The Time Balance Sheet

A Snapshot of Your Assets and Liabilities At A Point In Time

Unlike the P&L and Cashflow statement, the Balance Sheet only shows an exact moment in time. It shows the assets, liabilities and shareholders equity of an organization or individual. Assets will generate positive cash flow in the future, whereas liabilities will eventually reduce cash.

It’s an oversimplification, but all things equal you want more assets than liabilities. If you care about the future, you want to see more money or time flowing your way. Not all assets are created equal. Some are short term, others are longer term. The only way to create long term assets is through investing time and money. For companies this is machinery, GPUs, intellectual property etc. For people these are skills and experience.

Since assets have finite lifespans, companies and individuals need to constantly invest or their balance sheets will eventually shrink. One good workout won’t make you fit but if you’ve invested thousands of hours exercising across your life, it takes a much longer period of inactivity before you would be weak and frail (we discussed this in Biohacking That Works (and Doesn’t).

To get good at something, you need to invest your time with dedicated practice. The more time you invest, the better you will be and the more separation you will get from everybody else. If you are building this advantage in areas that are economically valuable, you can feel secure financially, as long as you can sustain this edge. You don’t need to exclusively build skills that are financially motivated. If you get really good at activities and hobbies that you enjoy, you can satisfy other necessary conditions of happiness. Making close friends are great assets that will make you happy for years to come. Accomplishments that boost your self esteem and confidence are assets. Spending a high portion of your time doing something you love might be an intagible but there are worse things.

Beyond investing to give yourself economic and spiritual assets, another type of investment you can make is to give yourself more time. Some measures are short term others create more time for yourself indefinitely. If you spent a Sunday meal prepping for the week, that would create a time asset but it would only last until the end of the week. If you trained your dog or built a robotic chef that could prepare and clean your meals for you, that would be a longer term asset.

The more time you can create for yourself to go after your life mission/purpose, or on activities that will give you fulfilment (security, safety, companionship) the better your life will be.

Creating time assets are good but the way you spend your time matters more. Spending all of your time automating tasks just to create more free time for yourself is pointless if that free time doesn’t translate to something that will improve your life.

Imagine an 18 year old with Billions of dollars and no responsibilities but chooses to spend their next 70 years watching trashy reality TV and eating hot pockets instead of doing anything worthwhile. Would they have a better life or be happier than somebody with many friends, a loving family and plenty of fulfilling life experiences?

Money matters, but only if it’s used to help you accomplish your goals. Create long term assets that let you live a good life.

Time Cashflow Statement

It costs money to live. Seemingly every time we step outside (or not) we have expenses flying at us. There are no shortages of ways to spend our money. We’ve previously explored the merits of going into debt to buy a Rolex.

Not all spending creates assets. Nothing wrong splurging on a nice meal or a fancy outfit from time to time if you can afford it, but if this where most of your money is going, your balance sheet is going to look bad and your P&L will eventually suffer.

Just like in a corporate setting, some spending and investments offer a higher return on investment. A $60 Uber Eats order to give your Burrito a private car ride, saves you 20 minutes once. Spending an equal amount on a house keeper or gardener, can save you hours. Spending a bit more money for something that saves you hours on a recurring basis can be a great investment but only if you use this time productively.

Taking on debt only makes sense if it helps finance assets that will at least eventually pay for the debt and associated interest. In the context of time, it only makes sense to take on liabilities if these savings will offset the future commitment. Skipping the gym saves you time in the short term, but the longer you push it off, the harder it will be to get back on track. Not sleeping works the same way. Pulling an all nighter hurts your health and performance, so if you are doing it, you better be getting something worthwhile in exchange. Staying up all night watching re-runs doesn't qualify.

If you are spending money, it better be investments that create long term, high quality assets that will save you time and/or bring in more money. This allows you to make bigger and better re-investments in your time, happiness and financial wellbeing.

Spending money on hobbies is fine, if you get real enjoyment out of these hobbies and it brings you long term happiness. If you’re chasing a new activity every week, and you have equipment gathering dust, these are impaired investments.

You need to strike the right balance between having enough cash saved so you feel financially secure, but be able to invest in things that help you achieve your objectives so you feel fulfilled. Hoarding cash just for the sake of hoarding won’t make you happy. Having no cash is also problematic.

A good time cashflow statement, shows positive cashflows that turns into cash and investments that will get you closer to your goals of feeling safe, secure, with adequate companionship and your great mission/purpose.

When was the last time you properly audited the way you spend your time?

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The problem is simple. Men like this cast enormous shadows. Their children are not just competing with one another, they are competing with the force of the founder himself. He advises presidents, knows every major tech leader personally, and owns media assets that can be used to advance both personal and business interests.

That description fits Logan Roy, the patriarch of Succession, one of the most iconic characters in modern television.

The Roys were widely understood to be modeled on the Murdochs, the family behind Fox and News Corp, who controlled major parts of the media landscape for decades while publicly fighting over the future of the empire.

The creators and cast have said as much.

But what if the real person closest to Logan Roy is not Rupert Murdoch? What if there is another living billionaire who fits the role even better?

A man who has been divorced many times, owns major media assets, recently fought a proxy battle, and is now trying to hand parts of his empire to his children.

That man is Larry Ellison.

Ellison, the co-founder of Oracle and the self-styled samurai of Silicon Valley, was close with Steve Jobs, has spent years operating like a kingmaker in tech and media, helped finance Elon Musk’s takeover of Twitter, recently acquire a stake in Bytedance US (TikTok) and has recently backed his son David Ellison’s bid to help take control of Paramount through Skydance.

Even some of the public commentary around him feels like it belongs in Succession.

The similarities do not stop at the surface level. In temperament, ego, family dynamics, and the instinct to treat business, media, and power as one seamless game, Ellison may be the closest thing America has to a real Logan Roy.

Don’t believe me? Keep reading.

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

Early life/ Upbringing

Logan Roy was born in Dundee, Scotland, (where Brian Cox is actually from), sometime around 1939. Due to the war, he and his siblings were sent to Quebec to be raised by their aunt and uncle. Logan lost his sister to tuberculosis, which his uncle blamed him for. That same uncle beat him, and the scars were still visible when Logan was in his eighties in Succession. He had a strained relationship with his brother Ewan, and his own children seem to have few happy memories of him.

Larry Ellison was born in New York in 1944. At nine months old, he was given up for adoption to his aunt and uncle, who raised him in Chicago. He did not learn they were not his biological parents until he was a teenager. His adoptive father may not have been physically abusive like Logan’s uncle, but he once told Larry he would never amount to anything. That became fuel Ellison would burn for much of his life.

Like many founders and industrialists, both men seem to have drawn energy from the need to prove a father figure wrong.

Both built vast empires, but neither followed a conventional path. It is unclear whether Roy attended university, but his rise began with an advertising business that he scaled into a conglomerate. By the start of Succession, Waystar Royco spans cable news, newspapers, film studios, theme parks, cruises, and more.

Ellison was a strong student, but dropped out of pre-med and headed to Silicon Valley to work in tech. After stints at several companies, he started a venture with former colleagues selling consulting services. He then came across a relatively obscure IBM research paper on relational databases, which became the basis for what would later become Oracle. Ellison realized IBM did not fully appreciate what it had and was too large and bureaucratic to move quickly. A smaller, leaner company could build the future faster.

IBM had made this mistake before. A few years earlier, it had let a handful of engineers walk away with another software idea it did not care much about. That company became SAP.

It is never entirely clear what motivated Logan when he started Royco. Ellison, by contrast, initially thought he might one day build a company with about $10 million in revenue and 50 employees. He overshot that pretty quickly. Then the ambition changed. The goal was no longer to build a good company. The goal became being number one. Not the number one database company, but the number one technology company in the world.

Competitive Fervor

One of the central themes in Succession is that to succeed at the highest level, you need to be a killer. Logan clearly believes this and tries to hammer the lesson into his children.

In the first episode, while explaining to Kendall why he is delaying retirement, Logan tells him: “I know that you’ve read a lot of books about business management and this and that. But sometimes it is a big dick competition.”

He makes the point even more explicitly in the season two finale. When Kendall asks whether Logan ever thought he could do the job, Logan replies: “You're smart, you're good, but you’re not a killer. You have to be a killer!” It is one of the defining lines of the series and helps set up one of the best season finales in television history.

We only meet Logan after the empire is already built, but by every account, he took no prisoners getting there. He is estranged from his older brother. His rivals fear him as much as they hate him. Even the President of the United States is wary of crossing him. He threatens to grind people’s bones into his soup. He is willing to sacrifice loyal employees when it serves his purposes. There is never much doubt that, once Logan wants something, he does not believe anything should stand in his way.

“I see him as a driving force. He gets what he wants. And when he focuses on something, he gets it.”

That’s not a line from Succession, that’s Marc Benioff talking about Larry Ellison.

“Larry has his foot on the accelerator to the floor trying to drive 150 MPH leaving his competition behind him. He knew eventually he would shoot the car over the cliff but like James Bond, the car will break into 10,000 pieces but he will still be on the other side.”

Ellison was not always like this. One of the things that initially attracted him to technology was that it gave him time to hike and left room for leisure. That changed after Oracle. By his own telling, his first wife left him because he was not ambitious enough. His second wife left him because he was too ambitious. Some would call that growth.

One turning point Ellison often cites was a trip to Japan, where an executive told him Americans were too comfortable with second place. For many of the Japanese businesspeople he met, you were either first or last. Wait, no, that is Ricky Bobby. Still, somewhere along the way, Ellison became obsessed with crushing the competition. It was never really about hitting a revenue target. He wanted Oracle to be number one.

What began as a mission to build the top pure software company, at a time when most firms bundled hardware and software together, evolved into something even bigger. Ellison wanted Oracle to become the largest technology company in the world. Bigger than IBM or Microsoft.

He would openly taunt competitors, put up billboards outside their offices, and run ads that depicted Oracle as superior fighter jets. Ellison had no problem taking direct shots at Bill Gates at the height of his powers. This was the antitrust-era Bill Gates, not the softened, philanthropic version most millennials and Gen Z know.

While Ellison was more of a sprinter Gates was a marathon runner type of psycho. He removed the radio from his car so he wouldn’t be distracted during his commute to and from work. Ellison would sail yachts and stay busy with hobbies outside of work.

Oracle never quite became the number one technology company, but for a long time it was one of the most formidable players in the industry. That is a remarkable achievement for a business-to-business software company competing across decades against Bill Gates, Steve Jobs, Larry and Sergey, Zuckerberg, and pretty much every other titan of modern tech. Despite this, with Ellison’s reluctance to sell Oracle stock, in 2025 he briefly surpassed Elon Musk to become the world's richest man.

Contrarian

Before Peter Thiel, Ellison was Silicon Valley’s contrarian.

Oracle succeeded in large part because Ellison repeatedly saw something others did not and was willing to bet the company on being right. Few people initially believed relational databases would become a major category. Later, Oracle moved aggressively away from client-server applications and toward internet-based systems in the 1990s, before most people thought the internet would matter much for enterprise software.

Ellison’s logic was simple. This was the only path to number one. If Oracle stayed in client-server, SAP would remain ahead. If the internet reshaped enterprise computing the way Ellison thought it would, Oracle would be best positioned to ride the wave. There were many other examples like this. Ellison was rarely afraid to act on his own view of where technology was going, even when the rest of the industry and most analysts disagreed.

Logan made similarly bold calls in media. When others thought home video would kill movie theaters, Logan invested in theaters because he believed people would still want to go to the cinema. While Kendall and others were drawn to flashy websites and trendy digital assets, Logan preferred regional newspapers and local affiliate channels. These were aging businesses, but they still held influence and had sticky audiences, much more so than websites that could come and go with the seasons.

When he faces a proxy fight, Logan entertains two very different ways out: acquiring a politically opposed legacy media rival or buying a newer, buzzier tech-media company. His preference was the legacy media rival because that’s what he understands and value. Logan appreciates technology, but he never mistakes it for power itself. In his worldview, technology can amplify influence, but it cannot replace it. Real power still comes from controlling media assets that can shape opinion and pressure politicians into submission.

Influence

While Logan’s influence on politics is explicit, Ellison’s was more bespoke until recently.

In a fairly short stretch, Ellison went from being a rich political donor with strong connections to becoming a far more direct player in the machinery of information and influence. He helped finance Elon Musk’s takeover of Twitter, Oracle became deeply embedded in TikTok’s U.S. structure, and his son David Ellison now runs Paramount Skydance, which gives the Ellison orbit meaningful control over a major Hollywood studio and a broad set of media assets.

Ellison is the elder statesman of Silicon Valley. He was close with Steve Jobs, is viewed as a mentor by figures like Elon Musk and Marc Benioff, and is probably no more than a second-degree connection away from almost any important person in tech. He has spent decades accumulating not just money, but proximity to power.

It is also quite clear that he has unusual access to President Donald Trump. Ellison hosted a fundraiser for Trump in 2020, joined a post-election call about strategies for contesting Trump’s loss, and appeared beside Trump at the White House for the Stargate AI announcement in January 2025. Oracle was also central to both the earlier TikTok negotiations and the newer TikTok U.S. joint venture. None of this proves that Ellison is writing policy himself, but it does suggest something simpler and probably more important: when Larry Ellison wants something done, he can pressure politicians into making it happen.

That feels very Logan Roy. Logan may be fictional, but one of his defining traits is that he does not need formal office to exercise power. He can call the administration, intimidate rivals, shape narratives, and make politicians behave as though he outranks them. Even decide who the next President will be. This makes him hated by many politicians and the general public alike.

Ellison is not loved by everyone, either. The Paramount-Skydance deal drew heavy scrutiny from Democrats who preferred Netflix acquire Paramount.

This sounds exactly what Gil Eavis says of Logan Roy throughout Succession. It’s quite clear the Eavis character is at least partially based on Bernie Sanders, and although Sanders was not calling out Ellison during Succession’s filming run, he now is.

So this raises the real question. Was Logan Roy always closer to Larry Ellison than Rupert Murdoch, even if the writers did not fully realize it? Was this simply a question of time catching up with the character?

Here you have two men raised by relatives rather than by their biological parents, both marked early by hard and often humiliating father figures. Both built empires through bold, contrarian bets. Both obsessed with winning and treat business as a theatre of dominance rather than a vehicle for profits. Both understood that money alone is not enough. To bend the world to your will, you need power, money and influence.

That is why I submit that Logan Roy may be less a portrait of Rupert Murdoch than an accidental prophecy of Larry Ellison.

Or maybe Ellison saw Logan Roy and decided the resemblance was an aspiration.

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