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.

Scott Galloway

Galloway's personal investing style is relatively conservative given how loud he is. He keeps a heavy allocation in index funds and real estate.

He does make concentrated bets on individual stocks when he has conviction — he famously held Amazon for years. He angel invests occasionally but is not prolific.

His real wealth comes from business exits and media income, not portfolio management.

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.

Scott Galloway

Diversify, own assets, and do not confuse being smart with being lucky. Galloway preaches that the most reliable path to wealth is boring — buy index funds, own property in growing cities, and let time do the work.

He is deeply skeptical of anyone who claims they can consistently beat the market.

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 — north of $300 billion sitting in Treasury bills — 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.

Scott Galloway

Moderate. Galloway has experienced the full spectrum — he had a company go public and then go bankrupt (Red Envelope), which taught him that financial ruin is always closer than you think.

Post-L2 sale, he became much more conservative. Heavy real estate holdings in New York and Florida.

He preaches diversification publicly and mostly follows his own advice, with occasional concentrated stock positions.

Warren Buffett

Despite a $149B 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 carried a $20 Samsung flip phone until 2020, when he finally switched to an iPhone. He mostly uses it as a phone.

Scott Galloway

Galloway owns significant real estate in New York and Florida. He talks openly about his wealth and spending — nice apartments, good restaurants, private school for his kids.

He is not frugal and does not pretend to be. But he is very intentional about where money goes.

He has said his biggest financial luxury is "buying back his time" — paying for convenience so he can focus on what matters.

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.

Scott Galloway

Selling L2 to Gartner for an estimated $134 million in 2017. He built L2 into the go-to benchmarking firm for digital competence of luxury and consumer brands.

The exit, combined with his media career taking off simultaneously, catapulted him from "NYU professor" to "famous rich guy who yells about tech on the internet."

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.

Scott Galloway

Red Envelope. Full stop.

Galloway has been brutally honest about this — he took a gift e-commerce company public, it was valued at hundreds of millions, and then it went bankrupt. He has called it the most painful experience of his career and has said it took years to emotionally recover.

He lost a significant amount of personal wealth in the collapse.

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.

He graduated in 1951, worked for Graham in New York, and in 1956 started his own investment partnership in Omaha with $105,100 from family and friends. He turned that into something much bigger, compounding at around 30% per year for over a decade.

Along the way he bought into a dying Massachusetts textile company partly out of spite, taking control in 1965. In 1969 he shut the partnership down and kept the mill.

That company was Berkshire Hathaway. What happened next is the greatest investing run in history — and it started with a grudge.

Scott Galloway

Scott Galloway is a serial entrepreneur and NYU Stern School of Business professor who became famous for his brutally honest takes on Big Tech. He founded nine companies over his career, including L2 (a business intelligence firm sold to Gartner in 2017), Red Envelope (an e-commerce company that went public then bankrupt), and Prophet (a brand strategy firm).

His 2017 book The Four, about Amazon, Apple, Facebook, and Google, became a bestseller. His YouTube channel and Prof G podcast reach millions.

He called Amazon buying Whole Foods before it happened. He also co-hosts Pivot with Kara Swisher, one of the most popular tech podcasts in the world.

He teaches brand strategy at NYU and is known for his profanity-laced, data-heavy lectures that go viral every semester.

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.

Scott Galloway

L2 Inc (founder, sold to Gartner), Red Envelope (founder, IPO then bankruptcy), Prophet (co-founder), Section4 (founder, online education), Prof G Media (founder)

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.

Scott Galloway

UCLA (BA), UC Berkeley Haas School of Business (MBA).