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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

My Best Essays

This page shares my best articles. Not sure where to begin? Below are what many consider to be my “greatest hits” – the essays and articles that have been the most popular or had the greatest effect on readers’ lives.

Marketing and Business

Browse all Marketing and Business Operations essays

  • Jesus Marketing (Or How I Sold 5000 Books in Four Weeks As a First Time Author)
  • The Business Production Function: A Framework for Growing Early Stage Ventures
  • How to Get Lucky: Focus On The Fat Tails

Investing & Decision Making

Browse all Investing & Decision Making essays.

  • Nuclear Winterizing Your Investments? – The Cockroach Portfolio
  • A Big Little Idea Called Ergodicity (Or The Ultimate Guide to Russian Roulette)
  • The Ultimate Guide to the OODA Loop

Bitcoin 

Browse all Blockchain & Cryptocurrency essays

  • Why is Bitcoin Valuable
  • The Blockchain Man
  • Markets are Eating the World


Full Archives

2023

  • April 05 The Physics of Kaizen: Why Somebody Should Get Credit for Fixing Problems That Never Happened

  • March 08 5 Philosophies of History

  • February 01 The Collison Decision Matrix: How to Make the Right Decision

2022

  • November 18 The St. Petersburg Paradox (AKA How to Not Pull a FTX)
  • November 04 Best Operations Management Books and Resources

  • August 03 Tempo: timing, tactics and strategy in narrative-driven decision-making Summary

  • July 15 The Origin of Wealth Book Summary (Or, An Introduction to Complexity Economics)

  • May 25 Out of the Crisis Book Summary
  • May 18 Company Culture & How It Can Be Worth $150 Million

  • March 02 The Four Levels of Organization

  • February 11 How to Use the Cynefin Framework to Make Better Decisions

2021

  • December 10 The Toyota Production System: A Love Letter
  • December 03 Insurance Makes Wealth Grow Faster

  • November 19 6 Keys to Innovative Thinking: The Innovator’s Dilemma Book Summary

  • October 29 How to Predict our Economic, Political and Cultural Futures
  • October 25 Best Practices for Operational Excellence
  • October 22 Subtractive Productivity: How Doing Less Can Achieve More

  • July 30 The Bullwhip Effect and Supply Chain Inflation
  • July 16 The War of Art Summary and Notes
  • July 16 Terminator Mode
  • July 02 The Smartest Guys in the Room – Bethany McLean

  • June 18 Risk is Not Getting What You Want
  • June 11 Static vs. Dynamic Games
  • June 04 Festina Lente: Why Slow is Smooth and Smooth is Fast

  • May 28 Taylor’s Machete
  • May 20 Metaphors We Live By – George Lakoff
  • May 14 The Systems Bible
  • May 07 The Maginot Line Problem
  • May 06 Systemantics by John Gall

  • April 28 Fail-Safe Investing by Harry Browne
  • April 23 Illegible Inefficiencies
  • April 16 Do The Thing You Want To Do
  • April 02 The Frontier Thesis

  • March 05 Chesterton’s Fences and Gordian Knots

  • February 19 On 4 Minute Songs
  • February 05 My Remote Work Best Practices

  • January 27 The Effective Executive Summary
  • January 15 How to Win at Business
  • January 13 Certain to Win: The Strategy of John Boyd, Applied to Business by Chet Richards

2020

  • December 18 Trees are the Root of all Evil
  • December 04 My Favorite Stone Soup Recipe

  • November 27 Pull the Andon Cord
  • November 20 Goodhart’s Law: How to not lose $4.6 billion
  • November 13 Take the Turkey Out of the Oven
  • November 06 9 Questions to Ask Before You Start Something New

  • October 30 Metaphorical Proof of Work
  • October 23 History has a History too
  • October 16 The Farthest Down the Chain Principle
  • October 09 Invisible Absorbing Barriers
  • October 02 In Praise of 2/3rd-ism and Messy Compromises

  • September 25 The Explore/Exploit Tradeoff: When should I Leap?
  • September 18 We Are All Journalists Now
  • September 04 The Mental Model that Explains Political Revolutions and Financial Crises

  • August 28 RETO: The Robustness Efficiency Tradeoff
  • August 21 The Origins of Political Order Review and Summary
  • August 14 Nietzsche and Ergodicity

  • July 31 Becoming an Intergalactic Gazillionaire is Harder Than it Looks
  • July 24 The Farmer’s Fable: Free as in Lunch
  • July 17 Reality Has a Surprising Amount of Detail:
    Business Edition
  • July 14 Reality Has a Surprising Amount of Detail
  • July 14 The Art of War Summary (and Quotes) by Sun Tzu
  • July 10 Become Like Water My Friend

  • June 23 Book Notes – Breakthrough Advertising
  • June 15 Tit for Tat Strategy and The Evolution of Cooperation
  • June 12 Fire Two Shots, But Never Fire First
  • June 05 The Sand Pile Effect: Why are there weeks in which decades happen?

  • May 08 Being More Entrepreneurial
  • May 01 My Most Important Decision Principle

  • April 17 Wile E. Coyote Systems
  • April 08 A COVID-19 Crisis Management Plan for Startups and Small Businesses

  • March 13 Corona, Attractor Landscapes & Dinosaur Markets
  • March 07 Coronavirus Primer for Reasonably Rational People

  • February 28 COVID-19, Vladimir Lenin, and Portfolio Protection
  • February 21 Mortgages
  • February 16 The True Believer Summary (and Quotes) by Eric Hoffer

2019

  • October 10 A Big Little Idea Called Ergodicity (Or, The Ultimate Guide to Russian Roulette)

  • August 28 The Best Finance Books, Blogs, Podcasts, and Other Resources

  • July 17 Priority Management: How to Prioritize Tasks and Keep Your Life in Balance

  • May 15 A Blockchain Explanation Your Parents Could Understand

  • April 17 The Paint Drop Method for Figuring Out What To Do with Your Life (and Becoming the Best in the World At It)
  • April 03 The 3 Laws of Marketing: Why Nobody Buys Your Sh*t

  • March 27 Platform Power Summary
  • March 27 Influence by Robert Cialdini Book Notes

  • February 28 Markets Are Eating The World
  • February 06 The Best Intermediate-ish Crypto Resources

  • January 31 The Business Production Function: A Framework for Growing Early Stage Ventures
  • January 16 The Best Books I Read in 2018

2018

  • December 31 Finite and Infinite Games Summary and Quotes
  • December 31 Seneca’s On the Shortness of Life Summary and Quotes
  • December 31 Man’s Search for Meaning Summary and Quotes
  • December 26 How to Unlock Your Creative Potential
  • December 20 What is Mimetic Theory? A Summary of Things Hidden Since The Foundation of the World by Rene Girard
  • December 07 Three Focus Failures and How to Avoid Them
  • December 04 How to Get Focused for 2025

  • November 07 Will Smart Contracts Eat the World?

  • October 10 Best Psychology Books
  • October 09 What is a Security Token? A Comprehensive Guide to How They Work and Their Impact
  • October 01 The Best Biographies of All Time

  • September 28 Best Self Help Books
  • September 26 Best Motivational Books of all Time
  • September 19 The Best History Books
  • September 05 State of Bitcoin (Fall 2018)

  • August 22 Cryptocurency and the Turkey Problem
  • August 19 Impro: Improvisation and Theatre Summary and Notes
  • August 13 The Bitcoin Standard Book Summary and Notes
  • August 01 When Will Crypto Crash (Again?)

  • July 23 Blockchain Explained: How Does Blockchain Technology Work?

  • June 16 The Black Swan Book Synopsis, Quotes and Notes
  • June 16 The Essays of Warren Buffett Summary and Quotes
  • June 16 Market Mind Games by Denise Shull Summary and Quotes
  • June 16 The 80/20 Investor by David Schneider
  • June 16 The Most Important Thing Illuminated by Howard Marks Notes and Quotes
  • June 05 The Ultimate Guide to Apprenticeships (Or How To Find Your First Remote Job)

  • May 01 What Gives Bitcoin Value? Or The Most Important Idea In Cryptocurrency

  • April 10 How to Stop Procrastinating Using the 70% Rule

  • March 27 Complexity Science: A Basic Explanation (with examples and resources)
  • March 13 Why the ‘Worst’ Crypto Networks Will be the Biggest
  • March 04 Why Apprenticeships Matter

  • February 25 Misbehavior of Markets Summary and Quotes
  • February 20 12 Books That Make You Think
  • February 05 Blockchain Supply Chain Use Cases: A Multi-Trillion Dollar Opportunity?

  • January 23 The Best Longform Articles I Read In 2017
  • January 15 Why Is Bitcoin Valuable?
  • January 10 Debt: The First 5000 Years by David Graeber Summary and Quotes
  • January 10 The Best Books I Read In 2017
  • January 09 Reasons and Persons Summary
  • January 02 Will Cryptocurrency Protocols Be Fat or Thin?

2017

  • December 20 The State of Cryptocurrency Investing: End of 2017 Edition

  • November 23 Bug Out Bag Essentials for Reasonably Rational People
  • November 16 You Want Democracy? Try A Hard Fork

  • October 25 How to Change Your Life using Punctuated Equilibrium
  • October 11 Denial of Death Summary and Quotes
  • October 10 The Blockchain Man
  • October 03 The Dark Side of Growth

  • September 26 Four Books To Better Understand How Cryptocurrency Works
  • September 12 Kaleidoscope Thinking: How to Think Faster and More Clearly
  • September 05 Everything You’ve Been Taught About How To Read a Book Is Wrong

  • August 20 How to Prioritize like a Billionaire
  • August 16 The State of Cryptocurrency: 2017 Edition
  • August 10 The Best Philosophy Books
  • August 02 The Ultimate Guide to the OODA Loop

  • July 27 How to Get Into Cryptocurrency: The Best Cryptocurrency Resources
  • July 17 Why History’s Greatest Innovators Optimized for Interesting
  • July 12 The Truth about How Creativity Really Works

  • June 17 The Organization Man Quotes and Summary
  • June 14 How to Discover Your Core Values List (and Use Them to Make Better Decisions)

  • May 31 Lessons on How to Amass Power, Get Things Done, and Be Eaten Alive

  • April 05 7 Essays That Will Help You Succeed In Internet Business

  • February 28 A Brief History of Existential Terror
  • February 15 The Safety And Sanity Of Entrepreneurship [TEDx Talk]
  • February 01 The Illegible Margin: Seeing Like a State Book Summary

  • January 18 Learning How to See
  • January 04 Go West: How The Frontier Makes All The Difference (A 5 Year Retrospective)

2016

  • November 30: A Simple Marketing Campaign Checklist
  • November 09: The Overton Window and How Creative Business Ideas Arise
  • November 02: My Favorite Morning Routine

  • October 19: Speed of Implementation and The Law of Shitty Click Throughs
  • October 05: The 70% Rule: How to Move Fast and Break Things (and why you should)

  • August 31: Fingerspitzengefühl: What Elite Tank Commanders, Chess Grandmasters, and Entrepreneurs Have in Common
  • August 17: The Unlikely True Story of Ingeborg Francesca Jurkutat
  • August 03: Strengths, Weaknesses, and the Math of Mastery

  • July 20: How to Get Lucky: Focus On The Fat Tails
  • July 06: How (And Why) To Find An Online Mastermind Group

  • June 22: 6 Essential Insights on The Future from Warren Buffett and Charlie Munger
  • June 08: How to Overcome Your Fear of Failure with The Bucky Method

  • May 18: How To Plan Your Ideal Day
  • May 04: The Real Truth About How to Work Smarter, not Harder

  • April 20: How to Improve Your Mindset
  • April 06: The Work: What a Philosophy Professor and Strength Coach Can Teach Us About Our Careers

  • March 17: Effectual Reasoning: The Little Known Method Entrepreneurs Use to Figure Out What They Want
  • March 08: Why Product Market Fit is Overrated (and what to focus on instead)

  • February 23: Disintermediation and Selectorate Theory

  • January 12: Hunt Your Sacred Cows: trend recognition for fun and profit

2015

  • December 30 My Ten Most Influential Reads of 2015
  • December 17 Antifragile Planning: Optimizing for Optionality (Without Chasing Shiny Objects)
  • December 02 8 Ways to Read 60 Books A Year

  • November 17 Jesus Marketing: How I Sold 5000 Books in Four Weeks As a First Time Author (With Less Than 700 Email Subscribers)
  • November 07 The First Job Dilemma (Or Welcome to The Hyper-Meritocracy)

  • October 21 The Margin Matrix: Why successful people are usually wrong

  • September 30 Get on the Plane: You Become What You Do at the Margins
  • September 09 The Retirement Catch-22: Why Those Who Want to Retire Most, Can’t

  • August 11 The End of Jobs Book Summary (Audio and Video Included)

  • July 22 My General Operating Principles: 37 Principles for Making Hard Decisions
  • July 03 The Work and The People
  • July 01 We’ve Reached The End of Jobs

  • June 16 An Entrepreneur’s Library: Business Books I Find Repeatedly Useful
  • June 02 A Single Word Summary of 188 Books on Entrepreneurship

  • May 19 Crafting Marketing Meta Narratives (Or Why I’m Giving Away 339 Hours of Work For Free)
  • May 02 Illegible Currency Arbitrage: How to Optimize for What Matters, Not What You Can Measure

  • April 19 The Taboo Productivity Trap: On Dealing with Blah-ness
  • April 04 4 Strategies To Find The Work Only You Can Do (And Why It’s More Profitable Than Ever)

  • March 23 Blink: The Power of Thinking Without Thinking Book Review
  • March 23 Be Slightly Evil: A Playbook for Sociopaths Book Review
  • March 23 Anything You Want Book Review
  • March 21 Adapt: Why Success Always Starts with Failure Book Review
  • March 21 Nine 80/20 Principles for Entrepreneurs Learned From Writing a Book
  • March 07 The Commoditization of Credentialism: Why MBAs and JDs Can’t Get Jobs

  • February 14 To You Who Wants More Freedom
  • February 07 Welcome to Extremistan. Don’t Be a Turkey.

  • January 31 Asset Thinking: How Do You Invest In Entrepreneurship?
  • January 24 How To Start Writing A Nonfiction Book: The Exact Process for Writing a Bestseller
  • January 10 Ever Think, “I Feel Stuck?” Escape From Hintergedanken Purgatory
  • January 03 3 Steps to Prioritizing Your Reading

2014

  • December 27 The Annual Review: How I Get Clarity, Confidence and Conviction In My Life and Business
  • December 20 Identity Based Decision Making: How Your Identity Makes You Wealthy
  • December 09 How I Found Freedom in an Unfree World Book Review
  • December 06 Going All In: The Ignorance of Diversification in Life and Entrepreneurship
  • December 01 The ONE Thing Book Review

  • November 29 Thinking in Limits: Two Simple Questions for Becoming a Better Entrepreneur
  • November 28 Platform Power Summary
  • November 22 Mountain Top Blogging: A Framework for Life Changing Blog Posts
  • November 15 The Entrepreneur’s Weekly Review
  • November 08 Location Leverage: 10X Your Location Independence
  • November 01 The Fourth Economy and The Future of Work

  • October 05 The Rise of the Practitioner-Publisher

  • September 20 The Path to Wealth and Power is Paved by Definition

  • August 25 Case Study: Growing a B2B eCommerce Business 527% in 18 Months
  • August 16 What is Optionality? How Can Optionality Improve My Performance?
  • August 02 The Entrepreneur’s Daily Ritual

  • July 12 The Joys of Missing Out (JOMO)

  • June 14 9 Frameworks To Add a Few Hundred Thousand to Your Bottomline in 18 Months
  • June 01 Business Education is an Oxymoron

  • May 24 How To Read 60 Books a Year
  • May 18 Listen to What’s Being Whispered, not What’s Being Said

  • April 27 My Favorite Heuristic for Evaluating Relationships: The Antifragile Person
  • April 12 What to Do When You Don’t Know What You Want

  • February 23 5 Mental Models To Create Dramatically More Leverage
  • February 16 Existential Terror is Just Another Term for Happiness
  • February 09 Why Cash is Worth Less Than You Think

  • January 19 Scaling
  • January 06 Rip, Pivot, Jam – How to Work at the Limits without Dying

2013

  • December 23 Change Your Location. Change Your Life.

  • October 29 Table Selection – When to Hold ’em vs. When to Fold ’em?
  • October 12 The Black Box System

  • August 18 Influence by Robert Cialdini Book Notes

  • July 20 The Cat Furniture Problem

  • May 19 A Purpose-Driven, Productive, Detouristified Life
  • May 12 Antifragile Summary and Book Notes

2012

  • October 28 Career Learning: Be The Dumbest Guy in the Room

  • July 09 Change Your Attitude Change Your Life (how to develop a positive attitude)

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