George Soros

Soros doesn't use a fixed strategy. He uses a theory.

He calls it reflexivity — the idea that market participants don't just react to fundamentals, they influence them. House prices going up makes people confident.

Confident people borrow more. Borrowing pushes prices higher.

Until it doesn't. Markets create self-reinforcing loops that diverge from reality for a long time before snapping back.

In practice, this meant making very large macro bets — currencies, interest rates, commodities, whole stock markets — when he believed a loop had gone too far. He didn't diversify to reduce risk.

He concentrated into high-conviction positions and used leverage. He famously said: "It's not whether you're right or wrong, but how much money you make when you're right and how much you lose when you're wrong."

Bill Gates

Gates invests through Cascade Investment LLC in established, cash-generative businesses — railroads, waste management, agricultural equipment, farmland. His biggest single Cascade holding for years was Canadian National Railway.

He has sold most of his Microsoft stock over time. His investment philosophy outside Microsoft mirrors Buffett's: durable businesses with pricing power, bought at reasonable prices.

George Soros

He believes in fallibility — specifically, that every market participant is operating on imperfect information, including himself. His approach: form a hypothesis, bet on it, watch for signals that the hypothesis is wrong, and change course decisively when those signals arrive.

He is explicitly anti-certainty. He thinks the most dangerous investor is the one who mistakes confidence for competence.

His philosophy of the open society — the political version — applies equally to markets: no position is so right that it can't be challenged.

Bill Gates

His core framework: read obsessively, think long-term, and separate emotion from analysis. He takes annual Think Weeks — solo retreats to a lake cottage in the Pacific Northwest where he reads papers and books for two weeks with no interruptions.

He publishes a reading list twice a year at gatesnotes.com. He has said that the best investment he ever made was paying $100,000 to take Warren Buffett to dinner every year.

George Soros

He had an unusual relationship with physical discomfort as a risk signal. He's talked about trusting his back pain — when a position was going wrong, he'd feel it before he saw it in the numbers.

That's either profound intuition or a good story. Either way, he wasn't a systematic rule-follower.

He made enormous bets and reversed course on short notice when the thesis broke. His risk management wasn't "don't lose money." It was "don't lose so much that you can't play again."

Bill Gates

Gates's risk tolerance is intellectual and deliberate rather than impulsive. He takes genuinely large bets — TerraPower on nuclear fission, billions into climate technology, the Gates Foundation's campaigns to eradicate diseases that kill millions — but only after intense research.

His Think Weeks exist to force slow, rigorous thinking on big decisions. At Microsoft, he kept enough cash on hand to run the company for a full year with zero revenue because he never wanted short-term survival pressure to force a bad long-term decision.

That discipline carries into his personal finances.

George Soros

He lives in New York and his estate in the Hamptons. He donated over $32 billion — more than 80% of his peak wealth — to the Open Society Foundations.

He's been married three times; his third wife Tamiko Bolton is 42 years younger than him. He plays tennis.

He's in his mid-90s and still occasionally publishes essays on markets and geopolitics. He handed chairmanship of the Open Society Foundations to his son Alexander in 2023.

Bill Gates

He wakes up early, exercises on a treadmill while watching documentaries, and reportedly does the dishes every night. He has said dishes are meditative.

For a man worth $130 billion, the emphasis on routine is either deeply grounded or very good PR. He drove himself to work at Microsoft for years and lived in a normal house long after he could afford otherwise.

George Soros

September 16, 1992. Black Wednesday.

Soros had been building a short position against the British pound for months. Britain was in the Exchange Rate Mechanism — a system that required it to keep the pound within a fixed band against other European currencies.

He believed the pound was overvalued and Britain couldn't sustain the interest rates needed to defend it. He was right.

The Bank of England spent billions trying to hold the peg. It failed.

Britain withdrew from the ERM. Soros made approximately $1 billion that day.

Total profits in the surrounding weeks were closer to $2 billion. He became known as the man who broke the Bank of England.

Bill Gates

Microsoft Windows. The decision to license MS-DOS to IBM for the PC while retaining the right to sell it to other manufacturers was arguably the most lucrative business decision in tech history.

Every PC manufacturer then licensed Windows. Gates captured the entire PC market without building the hardware.

By 1999, Microsoft's market cap hit $616 billion.

George Soros

2000. Soros had been warning about the dot-com bubble for years.

He was right about it being a bubble. But he kept buying tech stocks because he thought the momentum would continue a little longer.

It didn't. The Quantum Fund lost $3 billion in a matter of months.

He later said: "I was too early and then I panicked." That's a remarkable thing for someone of his stature to say. The lesson: being right about the direction of a trade doesn't mean you're right about the timing.

Bill Gates

Missing the internet. Microsoft was late and initially dismissive of the internet as a platform.

Gates eventually course-corrected and wrote the Internet Tidal Wave memo in 1995, redirecting the entire company toward internet strategy. But the delay allowed Netscape to establish footholds, and Microsoft's browser monopoly tactics led to the landmark antitrust case United States v.

Microsoft in 2000, which threatened to break up the company.

George Soros

George Soros was born György Schwartz in Budapest in 1930. His family survived the Nazi occupation by obtaining forged papers and hiding.

He saw up close what happens when governments go bad. He fled Hungary after the war, worked as a railway porter and waiter in London, and studied philosophy at the London School of Economics — where he became a student of Karl Popper, whose big idea was that open societies are better than closed ones.

That stuck.

He moved to New York in 1956 and spent the next decade working at brokerages and learning the markets. In 1973 he co-founded the Quantum Fund with Jim Rogers.

From 1970 to 2000, the fund averaged roughly 30% annual returns. That's the second-best sustained hedge fund record in history, behind only Jim Simons.

He stepped back from active management gradually through the 2000s and has spent most of his time on philanthropy ever since.

Bill Gates

Bill Gates was born in Seattle in 1955. He taught himself to program on a PDP-10 at age 13.

He enrolled at Harvard in 1973, dropped out in 1975, and moved to Albuquerque with Paul Allen to found Microsoft. Their break came when they licensed an operating system to IBM for the original PC — and crucially, retained the rights to sell it to anyone else.

That decision made Microsoft. Windows became the standard operating system for the world.

Gates became the world's richest person in 1995 and held that title for much of the next 15 years. He transitioned out of Microsoft's day-to-day around 2000 and fully moved into philanthropy via the Gates Foundation.

George Soros

Soros Fund Management is the vehicle. The Quantum Fund, which ran under it, returned roughly 30% annually for three decades.

The 1992 trade — shorting £10 billion of British sterling — was the most famous single day in hedge fund history, but the 30-year sustained record is the real story.

He stepped down from managing outside money in 2011 and converted to a family office. He's donated over $32 billion to the Open Society Foundations, which funds democracy and civil society programs in over 120 countries.

That's more money than he kept for himself.

Bill Gates

Microsoft (co-founder, former CEO and chairman). Cascade Investment LLC (his personal investment vehicle).

Bill & Melinda Gates Foundation (co-chair). Major holdings through Cascade include Canadian National Railway, Deere & Company, and significant farmland.

Early Microsoft equity remains a massive portion of his net worth.

George Soros

London School of Economics, BSc and MSc in Philosophy, 1952. Student of Karl Popper.

He's credited Popper's concept of the open society as the foundation of both his philanthropic work and his investment theory.

Bill Gates

Harvard University — studied mathematics and computer science. Dropped out in 1975 after his sophomore year to found Microsoft.