The Psychology of Money

The Psychology of Money
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DATE: Wed, Oct 14, 2026
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20 SSH IC 

15 Grady Corn IC
16 Imperial Walker

10 Arm Circles forward and back

The Thang

 

8 Minnesota Mike Tyson’s Financial Success Is Behavioral (Not Pure Intelligence) Key Story Ronald James Read

  • Janitor and gas station attendant
  • Died with $8 million in investments.
  • Richard Fuscone Harvard MBA
  • Retired in his 40s Mansion cost $90,000/month to maintain Eventually declared bankruptcy

Insight 

  • Financial success depends more on behavior, discipline, and patience than intelligence or status.

Key principle

  • Finance is a soft skill about behavior.

32 Plank Jacks  Experience Shapes Risk Tolerance

People’s investment behavior is shaped by when they grew up and what they experienced.

Examples: People who lived through the Great Depression preferred bonds. Investors in the 2000s prefer equities. Example of experience:

Someone who started investing in 2008 (financial crisis) will likely be more risk-averse. Someone who started in 2012 (bull market) may take more risk.

Key Insight

  • Risk tolerance is influenced by life experience, not intelligence.

36 Gas Pumps Luck and Risk Play Huge Roles

Example: Bill Gates Only about 300 students attended Lakeside School where he had access to a computer.

Roughly 1 in a million students had that opportunity.

Another example: Kent Evans Brilliant student from the same school Died in a mountaineering accident

About 36 high school students per year die in similar accidents (~1 in a million risk)

  • Insight Success requires: Hard work, Skill Luck But risk and luck are inseparable.

 

17 Burpees  When Is Enough Enough?

Examples of excessive greed: Bernie Madoff

Ran massive investment firm Still risked everything in fraud. Example: A McKinsey CEO with $100M+ net worth committed insider trading for $17M more. Insight

Capitalism creates: Wealth Envy

  • The danger: never feeling satisfied.
  • Key question: When is enough enough?

38 Flutters IC Getting Rich vs Staying Rich

Example: Jesse Livermore

Made fortunes in the 1929 crash

Eventually lost everything and Suicide in 1934.

Key Principle Getting rich requires Risk, Optimism , Aggressiveness Staying rich requires Humility, Frugality, Fear of losing everything

14 General Grant Merkins  Compounding Requires Survival

Example: Warren Buffett

Began investing at age 8 99%+ of his wealth came after age 50 Invested through 14 recessions

  • Key idea: Compounding works over decades, not years.
  • Important principle: Avoid catastrophic risk.

8 Pull-ups  Margin of Safety & Room for Error

Examples: Bill Gates kept 1 year of payroll in cash.

Buffett always keeps large cash reserves.

  • Concept: Room for error Example: Plan works at 8% returns But still survives at 4% returns This flexibility protects you.

30 Stone Crabs IC  “Tails” Drive Outcomes

Most results come from a small number of huge successes. Examples: Venture capital Stock market

Tech companies Acceptance rates: Google Apple

Facebook Each hires <1% of applicants.

  • Key principle: A few big winners drive most results.

50 Deep Lungs (L/R2) Wealth vs Rich

Rich: High income, Visible spending

Wealth Assets not spent

Example: Someone driving a $100,000 car only proves they used to have $100,000.

  • True wealth is: The car not bought, The upgrade declined , The watch not purchased

15 AppleJack Merkins  The Value of Money

The real value of money: Control over your time.

Highest form of wealth: Independence, Freedom

Ability to choose what you do daily.

11 Dead Bugs (l/r1) The “Valet Fallacy”

People buy luxury items for status signaling.

But observers rarely admire the owner.

Instead they think: “I wish I had that car.”

Respect and admiration come from:

Character Relationships Time freedom

Not material goods.

50 Freddies (IC) Be Reasonable, Not Perfectly Rational

Example: Harry Markowitz Nobel Prize winner

Created optimal portfolio theory

Personally invested 50% stocks / 50% bonds

  • Reason: He wanted to sleep well at night.
  • Lesson: The best financial strategy is the one you can stick with long term.

Expect the Unexpected

Example: Fukushima Daiichi Nuclear Disaster (2011)

Built to withstand the largest recorded tsunami. Larger wave occurred anyway.

  • Lesson: Unprecedented events always happen.
  • History is: ~80% reliable ~20% wrong

14 Squat Jumps  The Russian Roulette Fallacy

Risk with catastrophic downside is unacceptable.

Example: Russian roulette odds may be good

But the potential outcome is fatal In finance: 

  • Avoid risks that could wipe you out completely.

18 Penning Pickers (L/R2)  Volatility Is the Cost of Investing

Think of volatility as: A fee — not a fine

Example: A fee = ticket to Walt Disney World

A fine = punishment from the Internal Revenue Service

Market volatility is simply the price of long-term returns.

12 Ranger Merkins  The Dangers of Confirmation Bias

Example: If someone expects a recession:

They only read negative news.

  • Lesson: Avoid extreme narratives.

138 SSH Optimism vs Pessimism

Pessimism sounds smarter because:

It focuses on risks, It feels analytical

But long-term progress favors optimism.

Example: Oil prices: $20 per barrel in 2000

$138 per barrel in 2008

High prices created new innovation and supply.

Index Investing Simplicity

Most investors underperform markets.

Example: Average investor underperforms index by ~0.5% per year due to bad timing.

Simple strategy: Buy low-cost index funds

Save consistently Stay invested.

Social & Behavioral Observations

Example Low-income households spend $412/year on lottery tickets.

Wealthy households spend $103/year.

Reason: Lottery tickets sell hope, not rational math.

Also: 40% of Americans cannot cover a $400 emergency.

 

Core Lessons -boil down to 10 core principles:

  1. Behavior > intelligence in finance
  2. Experience shapes risk tolerance
  3. Luck and risk influence outcomes
  4. Know when enough is enough
  5. Getting rich ≠ staying rich
  6. Compounding requires survival
  7. Always build margin of safety
  8. A few big wins (tails) drive success
  9. Wealth is what you don’t see
  10. Money’s ultimate value is freedom and time

COT

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