Taylor Pearson

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Taylor Pearson

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Essays

Greatest Hits (Sorted by Theme)

Learn how to...

  • Risk Management - Apply Antifragility to make Entrepreneurship the Safest 21st Century Career and Surround yourself with a community that will foster success
  • Writing and Reading - Read 60 Books a Year and 67 Recommendations on Where to Start
  • Habits and Rituals - Build Daily Habits and a Weekly Review to Enable Doing Your Best Work
  • Focus - Decide What to Focus on and Why It's Essential That You Do
  • Systems - Leverage Systems to Be 10x More Effective, and Discover Frameworks that Yield Disproportionately Large Results
  • Marketing - Grow your business 527% in 18 Months and sell 5000 Books in Four Weeks As a First Time Author
 

Want more? Browse the full archives below

Subtractive Productivity: How Doing Less Can Achieve More

October 22, 2021 By

There are two ways of looking at your work. One is as a subtractive process, the other is as an additive process. Understanding the difference between these two points of view is one of the highest leverage ways to improve your and your team’s effectiveness. Failing to understand it is probably one of the largest sources of waste and frustration in most companies. So what's the … [Read more...]

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The Bullwhip Effect and Supply Chain Inflation

July 30, 2021 By

Talk about inflation and supply chain is all the rage these days. How do these two factors interact? How exactly does supply chain disruption cause inflation? Fortunately, there’s a game for that: The Beer Game. For a game with the word "beer" in its name, The Beer Game is not very fun. I would say it comes in a pretty distant second to beer pong. For a game about supply chains, The Beer … [Read more...]

Filed Under: Uncategorized

Terminator Mode

July 16, 2021 By

Have you ever brought home an exercise bike and let it gather dust in the basement? Ever started and quit a diet? Do you have a project 80% of the way done that is sitting on your hard drive not doing you any favors? If you are, I welcome you to the club. I have done all of these things (multiple times)! This is as near a universal human phenomenon as I can imagine. The Hero’s Journey is … [Read more...]

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Risk is Not Getting What You Want

June 18, 2021 By

One of the most important concepts in finance and investing is risk-adjusted returns: how much return you got per unit of risk that you took. If I go bet everything I have on 23 in Roulette at Caesar’s Palace and I win, that doesn’t make it a good bet with a good risk-adjusted return, it just means I got lucky. Any game where the house has a guaranteed edge such as roulette has a negative … [Read more...]

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Static vs. Dynamic Games

June 11, 2021 By

You can broadly categorize all games into two types: dynamic and static. I use "games" in the broader/more general sense that includes things like business, investing, school, etc. Static games are games where the actions and outcomes of one player do not affect the actions and impact of another player. Schooling is generally a static game. Just because someone else got an A on a test, … [Read more...]

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Festina Lente: Why Slow is Smooth and Smooth is Fast

June 4, 2021 By

  Occasionally, there is a saying that hits you in just the right way and just the right moment and you keep coming back to it over and over. One of those for me is: Slow is Smooth and Smooth is Fast. I’m not sure of the original source, but the saying is widely attributed to the Navy SEALs. The origin of the idea is probably much older though likely still military in … [Read more...]

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Taylor’s Machete

May 28, 2021 By

Most of us have a knee-jerk reaction that when something bad happens to assume that someone or something is "out to get us." My personal favorite example is that every time I lose my wallet, my first thought is "someone stole my wallet." I have, in fact, never had my wallet stolen but have been sufficiently careless to misplace it many times (usually somewhere I can find it, … [Read more...]

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The Systems Bible

May 14, 2021 By

… [Read more...]

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Illegible Inefficiencies

April 23, 2021 By

I’ve been (rental) house hunting for the last couple of months. I don’t really know anything about real estate investing, but I’ve been trying to read up (John T. Reed’s Best Practices for the Intelligent Real Estate Investor is my favorite so far). It’s been interesting seeing what aspects of a home (rental or for sale) that I care about are priced in and which aren't. Factors which I care … [Read more...]

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Do The Thing You Want To Do

April 16, 2021 By

One of the recurring themes of this newsletter is that reality has a surprising amount of detail. We have a tendency to oversimplify a complex reality to be able to deal with it. That’s fine, as long as you realize what you’re doing. One of the corollaries to reality has a surprising amount of detail is this: Do the Thing You Want To Do. This seems so obvious, but people often don’t do … [Read more...]

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The Frontier Thesis

April 2, 2021 By

One of the things that stand out in Alexis de Tocqueville's Democracy in America is the impact of the frontier on early American society. Tocqueville observes that the stability of all governments, and especially democratic governments (Tocqueville was writing in the early 1800s so democratic governments were still a pretty new phenomenon) require the people to be happy (or at least not too … [Read more...]

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Chesterton’s Fences and Gordian Knots

March 5, 2021 By

When you encounter a difficult and complex problem, what’s the best way to approach it? There are, broadly, two ways of doing so: as a knot or as a fence. The knot approach is encapsulated in a legend of Alexander the Great. According to legend, Alexander marched his army into the then-Phrygian capital in modern-day Turkey. Upon arriving in the city, he encountered an ancient wagon. Its … [Read more...]

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On 4 Minute Songs

February 19, 2021 By

Musician John Mayer gave a talk at Berklee College of Music where he asked students a simple question: "Do you want people to listen to your music?" "If you do," he went on, "that means there are certain rules, like no song is longer than 4 minutes. You can write 10-minute songs and talk about how people don’t understand you, but you can’t complain that no one listens to your songs. Of course … [Read more...]

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My Remote Work Best Practices

February 5, 2021 By

I got my first job with a distributed company in 2012. We had about a 25 person team across three continents. It was the first time I had worked for a company where everyone wasn’t in the same office. Overall, it was a great experience, I had a lot more flexibility with how I used my time - no more worrying about asking to come in late because of a dentist appointment and it was easy to pop off … [Read more...]

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How to Win at Business

January 15, 2021 By

How do you win at business? One can go into the philosophical questions of what does "winning" mean anyway or is that even the point? But, let's take the question at face value: how does one company outcompete others to succeed in the marketplace? The seemingly abstract nature of this framing is important. Most business books tend to start off much more tactically, at a lower level of … [Read more...]

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Trees are the Root of all Evil

December 18, 2020 By

Suppose I ask you to remember the following four objects: an orange, a watermelon, an American football, and a tennis ball. How will you keep them in your mind's eye? You will do it by grouping them. Some of you will group them by the type of object they are: Two pieces of fruit: the orange and the watermelon.Two sports balls: the football and the tennis ball. Those of you who tend to … [Read more...]

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My Favorite Stone Soup Recipe

December 4, 2020 By

Some travelers come to a village, carrying nothing more than an empty cooking pot. Upon their arrival, the villagers are unwilling to share any of their food stores with the hungry travelers. The travelers go to a stream and fill the pot with water, drop a large stone in it, and place it over a fire. They go out and scrounge up a few roots and tubers around the village to add to the pot, but … [Read more...]

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Pull the Andon Cord

November 27, 2020 By

Toyota for the last 20 or 30 years has been the benchmark car maker for reliability. This seems normal now, but it's important to know that Toyota used to make really, really terrible cars. In the 1960s, the heyday of the American automotive industry, Toyota’s reputation was about as bad as it could have been. Then, by the early 80s, they were the best cars in the world and parents across America … [Read more...]

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Goodhart’s Law: How to not lose $4.6 billion

November 20, 2020 By

  Goodhart's Law states: When a measure becomes a target, it ceases to be a good measure. Take evaluating real estate as an example. When most people buying/renting a house or a condo, the internet search order goes something like: Pick the location Pick the price range Pick the square footage (or number of bedrooms) Finally, bring in other parameters, such as … [Read more...]

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Take the Turkey Out of the Oven

November 13, 2020 By

As we approach Thanksgiving, it’s time to talk turkey (that's the only terrible pun here, I promise). Every year, millions of Americans cook a turkey on the same day. Most people only cook a whole turkey once a year so you don’t get a lot of repetitions in your lifetime which makes it kind of stressful. It takes a long time to cook so if you mess it up, you usually don’t have time to cook … [Read more...]

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9 Questions to Ask Before You Start Something New

November 6, 2020 By

One of the subjects which I have written and thought the most about is what I like to call priority management. Ultimately the goal of priority management is to spend your time and energy in a way that aligns with your priorities (which themselves are derived from your values). I think there’s a lot to be said on the nuances of the subject (and I’ll link to further reading below), but, … [Read more...]

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Metaphorical Proof of Work

October 30, 2020 By

New technological paradigms have an unintended side effect that is sometimes just as influential as the new technology itself: new metaphors. Computers have been an impactful technology, but the idea of computing as a metaphor has also been impactful. In neuroscience, to take one example, the idea of looking at the brain as a type of computer has probably made a pretty big difference to the … [Read more...]

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History has a History too

October 23, 2020 By

There’s a tendency when you read about history to see it as the capital-T Truth. History books we read in school tend to portray themselves as an objective account of past events. They are anything but. The history of any subject has a history (meta, right?), typically called its historiography. American historians writing in the 1960's tended to have views colored by the Cold War and Civil … [Read more...]

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The Farthest Down the Chain Principle

October 16, 2020 By

What do theories of guerilla warfare, college football, and running a company have to do with the development of modernism and postmodernist philosophy? Kind of surprisingly, I think the answer is a lot. Let’s start with football (of the American variety). Generally, the way that the game is played is that there is a head coach along with an offensive and defensive coordinator. Generally, … [Read more...]

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Invisible Absorbing Barriers

October 9, 2020 By

Eugene Wei, an early employee at Amazon, has an excellent blog post on invisible asymptotes. It is worth reading in full, but to briefly summarize, the idea is that as a company grows, it will approach invisible asymptotes where its growth slows in certain areas. This idea is captured in the technological S-Curve: An otherwise ignored technology or company suddenly gains major traction, … [Read more...]

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In Praise of 2/3rd-ism and Messy Compromises

October 2, 2020 By

One of my most shared Tweets ever said: I have no idea how to test this but I suspect that there is a strong correlation between the number of history books someone has read and how moderate their opinions are. History is a list of simplistic ideologies failing to work as promised over and over again. That’s a big claim to pack into a tweet, but it’s one version of an evolving line of … [Read more...]

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The Explore/Exploit Tradeoff: When should I Leap?

September 25, 2020 By

I recently got a question from a reader asking about if and when they should move from working on their current business to a new venture. I’ve gotten a bunch of versions of this question over the years (often from myself): when should I leave this job for another job? When should I leave this job to do my own thing? When should I leave my business to take a job or start another … [Read more...]

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We Are All Journalists Now

September 18, 2020 By

I tweetstormed a popular (and apparently still controversial) opinion that the investment management business is turning into the media business. I am, as usual, far from the first person to make this observation. This is a natural result of aggregation theory applying itself to the investment management business. Aggregation theory says, quite simply that the internet had two big … [Read more...]

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The Mental Model that Explains Political Revolutions and Financial Crises

September 4, 2020 By

When asked how he went bankrupt, Ernest Hemingway replied “gradually, then suddenly”. It’s a great phrase because it seems to apply to so many things. Often times, things seem “stuck” until they change all of a sudden. An industry that has seen no innovation or change is suddenly upended by a new entrant (E.g. Payment processing before Stripe, Cabs before Uber/Lyft). A peaceful movement … [Read more...]

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RETO: The Robustness Efficiency Tradeoff

August 28, 2020 By

The Robustness-Efficiency Trade-Off (RETO) states that systems (systems used herein the very general sense meaning it could be a project, company, country, society, etc.) must trade-off between being Robust and being Efficient. This is one of the most important tradeoff spaces and gaining a better understanding of it will make you a better entrepreneur, investor, ecologist, or … [Read more...]

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Nietzsche and Ergodicity

August 14, 2020 By

One of the main ideas associated with German philosopher Friedrich Nietzsche was the notion of the "eternal recurrence of the same". The idea being that over an infinite period of time, everything recurs infinitely. He relates this to the notion of Amor Fati, often translated as "love of one’s fate", and associated with Marcus Aurelius and Stoic philosophy (though Aurelius never used the phrase … [Read more...]

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Becoming an Intergalactic Gazillionaire is Harder Than it Looks

July 31, 2020 By

In last week’s edition, we looked at how two farmers, Bill and Ann, can cooperate to improve the overall productivity of their farms. This lesson is generalizable well beyond farming - cooperation, be it between investment strategies or basketball teammates, can produce a “whole is greater than the sum of its parts” effect. Some interesting research is being done on this topic by Ole Peters and … [Read more...]

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The Farmer’s Fable: Free as in Lunch

July 24, 2020 By

Today, I’d like to tell you a little story about a farmer named Bill. If you're not into farming, it just so happens that Bill discovers one of the most important principles in investing and decision-making in this story, so there's also that. Anyway, back to Bill. Bill grows crops. In a good season, Bill harvests 150 seeds for every 100 seeds that he plants. That’s a 50% growth … [Read more...]

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Reality Has a Surprising Amount of Detail:
Business Edition

July 17, 2020 By

This week I published an essay on why Reality Has a Surprising Amount of Detail. It looks at common causes of overconfidence bias and how individuals can counteract them to make better decisions. One of the most common places where I see this show up is in business decisions. Entrepreneurs, executives, and managers often fall prey to overconfidence. I’d like to tell a … [Read more...]

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Become Like Water My Friend

July 10, 2020 By

Sun Tzu's The Art of War is a book nominally about, well, war. It’s kind of deceptively titled though. A more accurate title would be “The Art of Not Going to War Unless You Really Can’t Avoid It And Then Still Avoiding Fighting as Much as Possible.” That’s a bit of a mouthful, so probably best to stick the original, but you get the point. The Art of … [Read more...]

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Fire Two Shots, But Never Fire First

June 12, 2020 By

On the Western Front of WWI, the French soldiers had a very simple rule for engaging with the Germans: fire two shots, but never fire first. It was the French practice to “let sleeping dogs lie” when in a quiet sector and never be the first to attack, but to respond with two bullets for everyone that came over. This simple rule was very effective for preventing casualties and is an example of … [Read more...]

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The Sand Pile Effect: Why are there weeks in which decades happen?

June 5, 2020 By

  Russian revolutionary cum dictator Vladimir Lenin once remarked that: There are decades where nothing happens; and there are weeks where decades happen."   I tweeted this phrase in early March 2020 as the COVID-19 virus arrived in Europe and North America. It seemed at the time that February was more like a century in the past than a few … [Read more...]

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Being More Entrepreneurial

May 8, 2020 By

Last week, I wrote about Jospeph Campbell's idea of the Hero's Journey. There are three major stages of the hero’s journey: The Departure Act: the Hero leaves the Ordinary World.The Initiation Act: the Hero ventures into unknown territory (the "Special World") and is birthed into a true champion through various trials and challenges.The Return Act: the Hero returns in triumph. From the … [Read more...]

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My Most Important Decision Principle

May 1, 2020 By

There was a bluegrass band I used to go see when I lived in Birmingham, Alabama. The only thing I remember from the concerts is the fiddle player. She just looked like she was doing exactly what she was supposed to be doing with her life. You could feel it and it was really beautiful and amazing to watch. We tend to notice and admire people that have accepted their own calling, whatever it may … [Read more...]

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Wile E. Coyote Systems

April 17, 2020 By

Airplanes tend to have redundant subsystems and other design features that let them keep working even after a certain amount of abuse. The first dozen rivets falling out might never be missed. But, the thirteenth rivet popping out may cause the wing to fall off. Perhaps no one knows this better than our friend Wile E. Coyote. Perpetually chasing his nemesis, the roadrunner, he often finds … [Read more...]

Filed Under: Uncategorized

Corona, Attractor Landscapes & Dinosaur Markets

March 13, 2020 By

Only the Paranoid Survive" -Andy Grove Perhaps in no other week will the name of this newsletter be more apt. I started following the coronavirus situation in January and mentioned it in this newsletter two weeks ago. I lead that newsletter with a line from Vladimir Lenin: "There are decades where nothing happens, and there are weeks where decades happen." As it turned out, I was at … [Read more...]

Filed Under: Uncategorized

COVID-19, Vladimir Lenin, and Portfolio Protection

February 28, 2020 By

There are decades where nothing happens, and there are weeks where decades happen.” - Vladimir Lenin To borrow a turn of phrase from a Russian dictator, “There are decades where nothing happens, and there are weeks where decades happen.” We may be living through a week in which decades are happening. COVID-19 … [Read more...]

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Mortgages

February 21, 2020 By

The task is not so much to see what no one yet has seen, but to think what nobody yet has thought about that which everybody sees." - Arthur Schopenhauer I read an article last week on why The 30-Year Mortgage is an Intrinsically Toxic Product. While the 30 Year Mortgage is primarily an American phenomenon, it made me think of something more broadly applicable.Most individuals … [Read more...]

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