Warren Buffett Made 7 Real Decisions That Changed History. Would You Have Made the Same?

Note: To make this real-world story interactive for my 16-year-old son, I designed the logic and used AI to code and generate this text-adventure simulator. You are about to play a system built by an ordinary dad and an AI. Let’s see if you can beat the odds.

Most biographies tell you what Warren Buffett decided. They don’t make you decide first.

I built an interactive simulator that does exactly that. But before you play it, here’s what you’re actually being tested on.

Seven real decisions. Seven moments where the greatest investor alive did something that most people would not have done. The question is whether you would have.

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Decision 1: He Rejected Harvard

In 1950, Buffett applied to Harvard Business School. He was rejected.

What he did next: he enrolled at Columbia Business School, where Benjamin Graham taught.

Benjamin Graham would become his mentor, give him his first job, and teach him the entire intellectual framework he still uses today.

If Harvard had accepted him, none of the rest follows in the same way.

The question the simulator asks: when you’re rejected by your first choice and offered a less prestigious alternative, do you take the second option seriously — or spend your energy trying to get into the first one?

Buffett took Columbia seriously. It changed everything.

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Decision 2: He Moved to Omaha

After working for Graham in New York, Buffett could have stayed. New York is where finance happens. Wall Street is where the information flows, where the deals get made, where the smartest investors congregate.

He moved back to Omaha, Nebraska.

His reasoning: he thought better without the noise. In Omaha, he could read without distraction, think without the crowd’s opinion constantly interrupting.

This is harder than it sounds. Most people who move away from the center of their industry feel like they’re falling behind. The information asymmetry seems to work against you. You’re not in the room where things happen.

Buffett’s bet was that calm thinking beats noisy information. He was right. He has been right about this for 70 years.

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Decision 3: He Didn’t Buy Technology Stocks in 1999

This is the one that gets written about as if it’s obvious. It is not obvious.

In 1999, Buffett was being called obsolete. His funds were underperforming the market. The Nasdaq was up over 80% for the year. Smart people — serious, credentialed investors — were saying he had lost his edge. That value investing was dead. That this time was different.

He didn’t buy a single dot-com stock.

The simulator asks: when you have massive underperformance relative to the market, when the most respected voices in finance say your framework is broken, when your investors are pulling money out — do you hold or do you adapt?

He held. The dot-com bubble collapsed in 2000. His framework was intact.

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Decision 4: He Invested in Coca-Cola When Everyone Said It Was Too Expensive

1988. Coca-Cola was trading at what looked like a high valuation relative to its earnings. A value investor was supposed to buy cheap. This didn’t look cheap.

Buffett invested $1 billion — roughly 35% of his portfolio at the time.

His logic: the brand was a moat. The global distribution was a moat. The pricing power was a moat. You pay more for a great business than a mediocre one.

The Coca-Cola position has returned roughly 20x. It’s still in his portfolio 36 years later.

The simulator tests whether you’ll pay a fair price for a great business or keep waiting for the cheap price that never comes.

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Decision 5: He Gave Away 99% of His Wealth

In 2006, Buffett announced he would give away 99% of his wealth, mostly to the Bill & Melinda Gates Foundation.

At the time, this was the largest charitable pledge in history.

The decision isn’t just about money. It’s about what you believe your wealth is for, and what legacy means. Buffett had always maintained that growing up in a wealthy family gives you an unfair head start — and that his children’s advantage should be their education and capability, not his fortune.

Most people would not make this decision.

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Decision 6: He Held Berkshire Hathaway Through the 1987 Crash

The 1987 stock market crash erased 22% of market value in a single day. It was the largest one-day drop in history.

Buffett didn’t sell.

Not a single share.

His reasoning: nothing had changed about the underlying businesses he owned. The market’s panic didn’t reflect any change in reality. Selling in response to market conditions, rather than business conditions, would mean he was making decisions based on the wrong information.

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Decision 7: He Bet Against the Hedge Fund Industry

In 2007, Buffett made a $1 million bet that a simple S&P 500 index fund would outperform a portfolio of hedge funds over 10 years.

A hedge fund manager took the bet. The hedge funds lost.

The bet was a statement: most active management doesn’t beat passive investing after fees. The financial industry sells complexity as value. Most of the time, it isn’t.

Buffett won the bet in 2017 and donated the $1 million to charity.

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Would You Have Made the Same Calls?

These are the seven decisions in the simulator. You won’t see the options before you commit. You get the situation, the stakes, and what you knew at the time. Then you decide.

Most people don’t match Buffett on all seven. Some decisions feel obvious in hindsight and were genuinely contrarian at the time. Others look hard even knowing the outcome.

The simulator is free, runs in your browser, and takes about 8 minutes:

[→ Play the Warren Buffett Life Simulator](https://ordinarymantrying.com/tools/buffett-simulator.html)

If you want to compare yourself to other legendary decision-makers, there are 9 more simulators — Steve Jobs, Elon Musk, Nelson Mandela, Marie Curie, Walt Disney, Soichiro Honda, J.K. Rowling, Oprah Winfrey, and one more:

[→ See all 10 life simulators](https://ordinarymantrying.com/tools/)

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I’m an ordinary Chinese person who built these simulators with AI as part of a 5-year public experiment. If you’re curious about how this blog was built — from zero, in a week — I’m documenting everything live here: [Building in Public](https://ordinarymantrying.com/building-in-public-experiment/).

## Related Reading

– [10 Legends, 10 Real Decisions: Free Interactive Simulators](https://ordinarymantrying.com/life-simulator-legendary-decisions/)
– [How I Analyze Stocks Using AI (Free Tools)](https://ordinarymantrying.com/tools/)
– [Building in Public: Week 1](https://ordinarymantrying.com/building-in-public-experiment/)