Investor Profiles
Profiles of the investors whose thinking shapes my own. Not hero worship -- critical examination. What worked, what didn't, and what survives translation to a retail investor's reality.
Jack Bogle
Founder, Vanguard Group · 1929 – 2019 · Listen · 10 min
Born the year the market collapsed and his family's savings went with it. Wrote a Princeton thesis at twenty-two arguing mutual funds were a bad deal. Got fired at forty-five and used it. Built Vanguard with an ownership structure that made his personal enrichment impossible -- on purpose. The industry called his first fund "Bogle's Folly." It now manages $1.5 trillion. He never became a billionaire from any of it.
"Don't forget the little guy you serve." -- His last public warning to the industry.
Milton Friedman
Economist, University of Chicago · 1912 – 2006 · Listen · 16 min
Not an investor, and he never managed anyone's money. He is here because nearly every idea that governs how money works in your life came through him first. He helped build income tax withholding at twenty-eight and spent the next sixty years wishing it away. He argued for forty years that the Federal Reserve turned an ordinary recession into the Great Depression, and in 2002 a Fed governor stood up at his ninetieth birthday and apologized for it. Then the monetary rule he spent his life advocating was adopted, and abandoned inside three years.
"The use of quantity of money as a target has not been a success." – Friedman in 2003, on his own rule.
Cathie Wood
Founder & CIO, ARK Investment Management · b. 1955 · Listen · 12 min
Left AllianceBernstein at fifty-eight after they rejected her vision for disruptive innovation ETFs. Founded ARK with her own money. Published all research for free. Called Tesla to $4,000 pre-split when the consensus was fraud. ARKK returned 152% in 2020. Then lost 80% peak to trough. Sold Nvidia before the AI boom. Still buying.
Conviction and stubbornness share a border. Wood lives directly on the line.
Ryan Cohen
Chairman, GameStop · Co-founder, Chewy · b. 1985 · Listen · 7 min
Built Chewy into a $3.35 billion PetSmart acquisition -- the largest e-commerce deal on record at the time -- by arguing that Pets.com had failed on logistics, not on the idea. Then bought 13% of GameStop when the consensus was that it was going to zero, and filed the 13D that turned a shareholder into an activist.
Conviction matters more than consensus. But conviction without operational knowledge is just gambling.
Carl Icahn
Founder, Icahn Enterprises · b. 1936 · Listen · 28 min
The original corporate raider. Built a fortune by identifying companies trading below breakup value and applying enough pressure to surface it. Sixty years of hostile takeovers, proxy fights, and greenmail -- from TWA to Apple. The philosopher-king of Queens who made a career out of proving management wrong.
"Some people get rich studying artificial intelligence. Me, I make money studying natural stupidity."
Ray Dalio
Founder, Bridgewater Associates · b. 1949
Built the largest hedge fund in the world from a two-bedroom apartment after losing everything in 1982. Pure Alpha has generated more net gains for investors than any hedge fund in history. Gave away the operating system -- Principles, All Weather, "How the Economic Machine Works" -- for free. The man who turned catastrophic failure into a $150 billion machine.
"Pain + Reflection = Progress." He meant it literally.
Chuck Feeney
Co-founder, Duty Free Shoppers · 1931 -- 2023
Co-founded Duty Free Shoppers, built a multi-billion-dollar fortune, then secretly gave away $8 billion through Atlantic Philanthropies without telling anyone for thirteen years. Wore a $15 Casio watch. Flew coach. Carried his papers in a plastic bag. Died in a rented apartment in San Francisco with $2 million to his name. On purpose.
"I want the last check I write to bounce."
Kanye West
Founder, Yeezy · b. 1977 · Listen · 17 min
The first celebrity to negotiate full brand ownership in a major partnership deal. Built Yeezy from a sneaker collaboration into a $1.7B annual revenue brand -- owning the trademark outright while Adidas manufactured. Proved that cultural capital could convert to financial equity at scale. Then lost it all through his own words.
Own the brand, license the infrastructure. Everyone else was doing it backward.
Hetty Green
Financier · 1834 – 1916 · Listen · 8 min
The richest woman in the world, and the only buyer left in New York when the city ran out of money in 1907. She sold property and held cash through years that made her look foolish, then lent the city $1.1 million at 6% during the panic and said publicly she could have charged forty. Made her husband sign away every claim to her fortune before the wedding, in 1867. Worked from a desk in a bank lobby because a lobby is free.
The value of cash is not what it earns. It is what it can buy in the year nobody else has any.
Ferdinand Pecora
Chief Counsel, Senate Banking Committee · 1882 – 1971 · Listen · 8 min
An immigrant prosecutor the Senate hired at $255 a month because it had run out of other options. In sixteen months he put the chairman of the largest bank in the country under oath, established that the House of Morgan had paid no income tax, and produced the Securities Act of 1933, Glass-Steagall, the Securities Exchange Act of 1934, and the SEC.
Every rule is a scar. There is always a name, a date, and a transcript.
Ivar Kreuger
Financier · 1880 – 1932 · Listen · 7 min
Controlled two-thirds of world match production by lending money to broke governments in exchange for national monopolies. Paid 20% dividends out of new investors' money across 400 interlocking companies, invented the low-vote share class still used in technology listings today, and forged Italian treasury bills in his own hand.
Frauds that look like frauds get caught early. The ones that last are attached to a business that actually works.
Charles Schwab
Founder, The Charles Schwab Corporation · b. 1937 · Listen · 6 min
On May 1, 1975, fixed commissions ended and most of Wall Street raised prices. Schwab cut them that morning, put his brokers on salary so they earned nothing extra when you traded, and spent the next forty-four years removing costs until the commission reached zero in 2019.
Every time the industry competes on a price the customer can see, that price falls. The money reappears somewhere harder to see.
Jesse Livermore
Speculator · 1877 – 1940 · Listen · 5 min
Shorted the Panic of 1907 until J.P. Morgan personally sent word asking him to stop, then shorted the Crash of 1929. Went bankrupt four times. Wrote down the rules that would have saved him and did not follow them.
Leverage does not scale with skill. It converts being wrong from a setback into an ending.
Muriel Siebert
First woman member, New York Stock Exchange · 1928 – 2013 · Listen · 5 min
Nine men refused to sponsor her application to the New York Stock Exchange. The tenth agreed. The exchange required $300,000 of the seat price to come from a bank; no bank would lend until she was a member, and she could not be a member without the loan. It took two years. She was the only woman on that floor for the next decade.
The outsider is the one who cuts the price. Insiders have something to protect.
Anne Scheiber
Auditor, Bureau of Internal Revenue · 1893 – 1995 · Listen · 9 min
Twenty-three years reading other people's tax returns for the government, and not one promotion. She retired in 1944 having never earned more than $4,000 in a year, bought the brand-name companies whose returns she had audited, reinvested every dividend, and almost never sold. She died at 101 with $22 million and left it to Yeshiva University to fund scholarships for Jewish women.
She did not beat the market. She stayed in it for 51 years and paid it almost nothing in tax on the way.
Paper Trail: Elon Musk
Audio series · Ten episodes · b. 1971 · Episode one is live · 11 min
He landed in Montreal at seventeen with about $2,000, cleaned a boiler room for $18 an hour, and took a bank internship at a pay cut to see how money worked from the inside. This series follows that money for thirty years, one surviving document per episode: a Brady bond, a term sheet, an SEC filing, a stack of no-confidence letters, an S-1, a Christmas Eve financing, an index inclusion notice.
The machine is the subject. He is the tour.