Warren Buffett

Buffett's approach is simple to describe and almost impossible to copy. He buys great businesses at fair prices and then just...

holds them. Forever.

He calls it "buy and hold" but that undersells it — he means hold until the sun burns out. He looks for companies with a real unfair advantage over competitors.

Something that protects them from being wiped out. He calls it a "moat" — like the water around a castle.

Think Coca-Cola. Everyone knows it.

Nobody can replicate it. He puts a LOT of money into a small number of bets — usually his top five holdings make up over 70% of everything.

Most fund managers would have a panic attack at that level of concentration. Buffett calls it being convicted.

His old mentor Graham taught him to hunt for cheap, beaten-down companies and flip them fast. Charlie Munger, his business partner for 45+ years, talked him out of that.

Munger said: just buy the best businesses you can find and never sell. Buffett admits that shift made him hundreds of billions of dollars.

Ray Dalio

Dalio thinks in cycles — economic cycles, debt cycles, historical cycles that repeat over decades and centuries. His core belief: everything in markets has happened before.

Study history deeply enough and you can anticipate what comes next. He called the long-term decline of US dollar dominance a slow, inevitable process — not a crisis tomorrow, but not permanent either.

His All Weather approach is built for radical uncertainty. Instead of predicting what will happen, build a portfolio that does okay no matter what.

Stocks, bonds, gold, and commodities tend to move in different directions across different economic environments. Own a smart mix and you're never completely wrong.

Warren Buffett

Rule No. 1: Never lose money.

Rule No. 2: Never forget Rule No.

1. Buy businesses, not stocks — the distinction matters more than most investors realize.

Let compounding do the heavy lifting and get out of its way. Never use debt to invest.

Be fearful when others are greedy, greedy when others are fearful. Time in the market destroys timing the market in every long enough data set.

For most people, a low-cost S&P 500 index fund will outperform almost any active strategy, including most professional money managers — including, he's said, what most of his estate will go into after he's gone.

Ray Dalio

His most important principle: pain plus reflection equals progress. He applied this to investing, management, and life.

Most people's biggest problem is they avoid pain instead of learning from it. His second idea: diversification is the holy grail of investing.

Not 15 correlated stocks — real diversification across asset classes, geographies, and economic environments that actually move differently. Third: everything is a machine.

Markets, economies, relationships — they all operate by rules that can be understood if you study them. He documented all his rules in a book called Principles.

Whether or not you agree with him, very few investors have been this explicit about writing everything down.

Warren Buffett

Buffett's whole thing is: do so much homework that the risk basically disappears. He doesn't diversify across 500 stocks to protect himself — he researches 10 companies so deeply that he's more confident about those 10 than most people are about anything.

He never borrows money to invest. Ever.

He keeps a mountain of cash at Berkshire — over $100 billion sitting around doing nothing — specifically so he can swoop in when everyone else is panicking and selling cheap. He once called derivatives "financial weapons of mass destruction" back in 2002.

Wall Street laughed. Then 2008 happened and Wall Street stopped laughing.

He doesn't predict where the stock market is going. He predicts whether a business will still be dominant in 20 years.

That's it.

Ray Dalio

He hates overconfidence in any single bet. The 1982 disaster cured him of that.

His solution: systematically stress-test every idea. Hire people to argue against you.

Find the best counterargument to your own position, then decide. He called this "believability-weighted decision making" — the person who has been right more often on a specific topic gets more weight in any disagreement.

At Bridgewater, this became formalized into actual systems and algorithms. His personal risk profile is moderate.

He doesn't use excessive leverage, and All Weather is explicitly designed to reduce volatility rather than maximize return.

Warren Buffett

Despite a $120B net worth, Buffett still lives in the same gray stucco house in Omaha he bought in 1958 for $31,500. He drives himself to work.

Breakfast is McDonald's — he orders based on his mood: $2.61, $2.95, or $3.17. He plays bridge obsessively, often online with Bill Gates.

He drinks multiple Cokes a day (Berkshire owns a large stake in Coca-Cola; coincidence is left as an exercise to the reader). He has pledged to give away more than 99% of his wealth, primarily to the Bill & Melinda Gates Foundation and his children's foundations.

He takes a $100,000 annual salary from Berkshire. He does not own a smartphone.

Ray Dalio

He lives in Westport, Connecticut. He practices transcendental meditation daily and says it's one of the most important habits in his life.

He runs and practices yoga. He and his wife Barbara pledged to give away more than half their wealth through the Dalio Philanthropies, focusing on ocean conservation, education reform in Connecticut, and mental health research.

He posts long essays on LinkedIn about global macro trends — which is either a public service or unsolicited geopolitical commentary, depending on how you feel about him.

Warren Buffett

Apple. Berkshire started buying Apple in 2016 — late by any tech investor's standard, from a man who spent decades insisting he didn't understand technology.

By 2023, the position had grown to over $170 billion, returning more than 800%. Buffett called it the best business he'd ever seen and admitted he should have bought it earlier.

Honorable mention: American Express in 1963 during the Great Salad Oil Scandal, when he put 40% of the Buffett Partnership into AmEx at distressed prices while the rest of Wall Street was running away.

Ray Dalio

2008. While most hedge funds were losing 20 to 30 percent, Bridgewater's Pure Alpha fund returned +9.5% and the All Weather fund was roughly flat.

This wasn't luck. Dalio had been warning about the debt bubble for years.

Clients who followed his framework avoided the worst of it. By 2010, Bridgewater managed $80 billion.

The win wasn't a single trade — it was being structurally right about the entire environment when almost everyone else was wrong.

Warren Buffett

Buying Berkshire Hathaway. He bought it in 1962 as a cigar butt — a cheap, dying textile company — and then kept it instead of winding it down into a clean insurance holding company.

The C-corp structure meant decades of tax drag. He has estimated this single mistake — triggered partly by spite after the owner tried to lowball him on a buyout — cost Berkshire and its shareholders roughly $200 billion over 50 years.

He also admits missing Google and Amazon, both of which he understood well enough to buy and simply didn't.

Ray Dalio

1982. He predicted a depression caused by Mexico's debt default.

He was wrong. He lost his own money, had to lay off all his staff, and borrowed $4,000 from his father.

He's talked about it publicly as the most formative experience of his life. The lesson he drew: strong conviction without aggressive stress-testing is just expensive confidence.

He also admitted later that his radical transparency culture at Bridgewater went too far in some ways. Recording every conversation and requiring every decision to be challenged in real time worked as a philosophy.

As a daily workplace experience, multiple lawsuits and employee complaints suggested it could become oppressive rather than honest.

Warren Buffett

Warren Buffett was born in Omaha, Nebraska in 1930. He bought his first stock at age 11 — three shares of a company called Cities Service.

He paid $114. He was eleven.

By 14, he owned a 40-acre farm and had filed his first tax return. He applied to Harvard Business School and got rejected.

Best thing that ever happened to him, honestly. He ended up at Columbia instead, where he met Benjamin Graham — the guy who basically invented the idea of buying undervalued stocks.

After graduating in 1951, Buffett started his own investment partnership in Omaha with $105,000 from family and friends. He turned that into something much bigger, compounding at around 30% per year for over a decade.

Then in 1969, he shut it down and quietly took over a dying Massachusetts textile company he had bought partly out of spite. That company was Berkshire Hathaway.

What happened next is the greatest investing run in history — and it started with a grudge.

Ray Dalio

Ray Dalio grew up in a middle-class family in Jackson Heights, Queens. At 12, he bought shares in Northeast Airlines for $300 using money earned caddying.

The airline was taken over shortly after and his shares tripled. That was the moment.

He studied finance at Long Island University, got an MBA from Harvard Business School in 1973, then worked at Merrill Lynch and a commodities firm. In 1975 he started Bridgewater Associates out of a two-bedroom New York apartment.

Just him and a phone. By the late 1980s Bridgewater was advising pension funds, sovereign wealth funds, and central banks.

By 2012 it was the largest hedge fund in the world.

The 1982 disaster shaped everything. Dalio publicly predicted a depression triggered by Mexico's debt default.

He was wrong. He lost so much that he laid off his entire staff and borrowed $4,000 from his father to cover expenses.

He rebuilt completely from that near-failure. The experience taught him that strong conviction without aggressive stress-testing is just expensive confidence.

Warren Buffett

His main vehicle is Berkshire Hathaway — a company he took over in 1965 when it was a dying textile mill. He basically gutted the textile business and turned the whole thing into a giant money machine that owns other businesses.

Today it's one of the most valuable companies on earth. On the stock side, his biggest bet is Apple — worth over $175 billion at its peak.

He also owns huge chunks of Bank of America, Coca-Cola (since 1988 — he really doesn't sell), American Express, and Chevron. Then there are the companies Berkshire owns outright.

GEICO, one of the biggest car insurers in America. Burlington Northern Santa Fe, a massive railroad.

Dairy Queen, See's Candies, Duracell. Basically a random collection of boring, cash-generating businesses that he loves precisely because they're boring.

His first fund — Buffett Partnership Ltd. — ran from 1956 to 1969.

He returned around 30% per year while the market did 8.6%. Then he shut it down, said he couldn't find enough cheap stocks, and walked away at the top.

Ray Dalio

Bridgewater Associates is the whole story. He founded it in 1975, built it to $150 billion in assets under management, and stepped back from day-to-day management in 2017 before stepping down as co-CEO in 2022.

The fund runs two main strategies. Pure Alpha seeks to outperform markets through active macro bets.

All Weather is designed to perform adequately in any economic environment — regardless of whether growth is rising or falling, inflation is high or low. The All Weather approach has been widely copied under the name "risk parity." He has also invested personally in various companies and become a prominent voice on global debt cycles and geopolitics.

Warren Buffett

University of Nebraska–Lincoln (B.S. in Business Administration, 1950).

Columbia Business School (M.S. in Economics, 1951) — the only school that mattered, where he studied under Benjamin Graham and got his only A+.

He also spent two years at the Wharton School before transferring. Harvard Business School rejected him.

He's described that rejection as one of the luckiest things that ever happened to him.

Ray Dalio

BA from C.W. Post College (now Long Island University), 1971.

MBA from Harvard Business School, 1973. He's talked about not being a great student — he got into Harvard on determination and test scores rather than academic polish.