Think Like an Investor

Probabilistic thinking, Michael Burry, and how to make smarter decisions under uncertainty

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This Week at a Glance:

  • đź’ˇ Mental Model: Probabilistic Thinking – Why the best investors think in odds, not absolutes

  • 📚 Book Rec: Thinking, Fast and Slow – Mental traps costing you clarity

  • 📉 Case Study: 2008 Market Crash – How Michael Burry made $100M by being early, hated, and right

Probabilistic Thinking

Stop Chasing Certainty. Start Playing the Odds.

This is why the House always wins.

Most people crave certainty: “Is this a good investment?” “Will this work?”

But successful investors, founders, and strategists don’t ask if something will work — they ask how likely it is to work, how big the upside is, and what the downside looks like if they’re wrong.

That’s probabilistic thinking — evaluating outcomes in terms of odds, not absolutes.

Key Takeaways:

  • You can make a smart decision and still lose.

  • You can make a dumb decision and still win.

  • What matters is not a single outcome, but whether your decision-making process consistently puts the odds in your favor.

The world is noisy. Probabilistic thinkers stay calm by anchoring their decisions to logic, not emotion.

Helpful mindset shift:

“I don’t need to be right every time. I just need to make high-expected-value bets consistently.”

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How to Outsmart Your Own Brain

Kahneman’s timeless framework for making clearer, calmer, more rational decisions—especially under pressure.

I read this in 2018 and still rank it as the most transformational book I ever read.

If you’ve ever made a decision you knew was emotional — and regretted it later — this book will change how you think.

Kahneman breaks down the two systems that drive your mind:

  • System 1 – fast, instinctive, emotional

  • System 2 – slow, rational, deliberate

Most people default to System 1 — especially under pressure. But the most successful investors, leaders, and decision-makers learn how to slow down and let System 2 take over.

You’ll learn how to:

  • Catch yourself before emotional decisions ruin long-term outcomes

  • Think more clearly under pressure

  • Use base rates and data to guide better decisions

  • Separate signal from noise — especially in a chaotic world

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We can be blind to the obvious, and we are also blind to our blindness.

Daniel Kahneman

This isn’t a quick read — but it’s one you’ll reference for life. I recommend every serious thinker and investor read it at least once.

How Michael Burry Saw the Crash No One Else Would

A masterclass in probabilistic thinking, emotional detachment, and holding your ground when everyone thinks you’re wrong.

A solid movie that breaks down a complex topic in a fun way.

In the early 2000s, the U.S. housing market looked unstoppable. Prices kept rising. Banks handed out mortgages like candy. Wall Street packaged them into complex products and sold them as "safe."

But beneath the surface, the system was cracking.

Enter Michael Burry.

A former neurologist turned hedge fund manager with no big-name backing or Wall Street pedigree—just a deep understanding of data and a willingness to follow the numbers wherever they led.

What Burry saw terrified him:

  • Mortgage defaults were inevitable

  • Risk was being wildly mispriced

  • The entire financial system was built on a house of cards

So he made a bet no one else dared: He shorted the housing market.

The media mocked him. His investors threatened to sue him. People called him crazy.

But Burry wasn’t guessing. He was thinking in probabilities.

His models showed that the odds were in his favor—even if the timing was uncertain.

He didn’t need to be right immediately. He just needed to be right eventually.

And he was.

When the housing market did collapse in 2007-2008, Burry's foresight paid off. His hedge fund, Scion Capital, earned approximately $700 million for its investors, and Burry personally profited by about $100 million.

The lesson?

You don’t need to be right every time. You just need the odds, the structure, and the patience.

That’s how you win when the world is on fire.