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In 2007, Fortune magazine photographed a group of former PayPal employees in pinstripe suits around a restaurant table, styled like movie gangsters. The image crowned them the PayPal Mafia. The name stuck because the facts behind it were hard to ignore: a few dozen people from one chaotic payments startup went on to found or fund YouTube, LinkedIn, Yelp, Yammer, Palantir, SpaceX, and Tesla, and to...

Until late 2000, the New York Stock Exchange priced shares in eighths of a dollar, a habit inherited from merchants who chopped Spanish silver dollars into eight pieces to make change. That detail says a lot about the institution. Behind the screens and the algorithms sits more than two centuries of tradition, panic, and improvisation, beginning in May 1792 when 24 brokers signed the Buttonwood Ag...

In the late 1920s, governments wrecked by the First World War did not always turn to banks for hard currency. Some turned to one Swedish engineer. Ivar Kreuger, born in Kalmar in 1880, lent entire nations millions of dollars, and in return they passed laws giving him the exclusive right to make and sell matches inside their borders. He was known as the Match King, and for a time he functioned as a...

In 1979 an MIT computer science student named J.P. Massar used a Lincoln Lab mainframe to test a claim his friends had brought back from a course called How to Gamble if You Must: that blackjack could be beaten. The math held. What followed was two decades of organized card counting that took millions from casinos in Atlantic City, Las Vegas, and beyond, and it looked very little like the book Bri...

Jack Whittaker was not a desperate man when he bought $100 worth of quick pick tickets at a supermarket in Hurricane, West Virginia, on Christmas Eve 2002. He had spent twelve years as president of Diversified Enterprises Construction in Putnam County and was worth more than $17 million. Then one ticket hit a $314.9 million jackpot, at the time the largest single ticket lottery payout in American...

Give 61 people $25 and a coin rigged to land heads 60 percent of the time, and let them bet freely for 30 minutes. In the study at the center of this episode, 28 percent went bust, the average payout was $91 against a cap of $250, 18 players staked everything on a single toss, and two thirds bet on tails at some point. The fix has existed since 1956, when John Larry Kelly Jr. of Bell Labs worked o...

In 2023 the Federal Reserve, the institution that controls the U.S. money supply, posted a record loss of $114.3 billion. That puzzle opens a plain-language tour of how the Fed came to exist and how it works. America's first two central banks were killed off in the 19th century, leaving a free banking era of thousands of currencies and recurring panics in 1873, 1893, and 1907. In the last of those...

In 2003, Chris Moneymaker was a comptroller in Tennessee with a master's degree in accounting and a side job at a restaurant in Spring Hill. He paid $86 to enter an online satellite tournament on PokerStars and won a seat at the World Series of Poker main event, which normally cost $10,000. It was his first live tournament. This episode follows how a man trained to eliminate variance walked into a...

Allen Pace III was paid to find weaknesses in the Dunbar Armored depot on Mateo Street in downtown Los Angeles. As a regional safety inspector, he photographed the interior, drew floor plans, memorized every camera position, and learned that the main vault was left open on busy Friday nights. Then he was fired for tampering with company vehicles. The next night, September 12, 1997, he let himself...

At the peak of Zimbabwe's hyperinflation, a banknote printed with a one and 14 zeros could not cover a one-way bus fare. This episode takes the crisis apart piece by piece, starting from a surprising place: after independence in 1980, Zimbabwe was the breadbasket of its region, and its dollar was officially valued above the U.S. dollar. The damage came later. Land reform dissolved the property tit...

Yahoo could have bought Google for $1 million in 1998. It declined. Ten years later it turned down $44.6 billion from Microsoft as too little, then sold its core business to Verizon for $4.83 billion. This episode reads the company's life as a corporate tragedy, beginning in January 1994, when Stanford graduate students Jerry Yang and David Filo built a human-edited directory called Jerry and Davi...

Wirecard sat on Germany's DAX index with a valuation of 24 billion euros, a celebrated homegrown rival to Silicon Valley. Then, on June 25, 2020, it admitted that 1.9 billion euros, a quarter of its balance sheet, was missing and had probably never existed. This episode reconstructs how the illusion was built. Founded in 1999, the company began by processing payments for pornography and online gam...

From roughly 1836 to 1865, the United States ran without a unified national currency. State-chartered banks printed their own paper notes, each a promise to pay gold or silver to whoever walked up to the counter. Wildcat banks exploited that promise by printing far more paper than they could redeem and, by one account of the name, by setting up shop in wilderness so remote that only wildcats lived...

In late 1922 a loaf of bread in Berlin cost about 160 marks. Less than a year later the same loaf cost 200 billion. This episode traces how an advanced industrial nation destroyed its own money, beginning in 1914, when Germany suspended the gold standard and chose to pay for the First World War with borrowing instead of taxes, betting that a quick victory would let it bill the losers. Defeat left...

At 14, Warren Buffett filed his first income tax return and claimed a $35 deduction for wear on his bicycle and watch, the tools of his paper route. This episode follows that habit of precise accounting through a lifetime of compounding. He sold gum and Coca-Cola door to door at seven, bought a 40 acre farm at 14, and ran pinball machines in Omaha barber shops at 15. Rejected by Harvard Business S...

In the summer of 2024, Toys R Us released a promo made with OpenAI's Sora that showed founder Charles Lazarus as a boy dreaming up a toy empire beside a cartoon giraffe. Viewers found it creepy, and the synthetic memory suits a brand that now lives on as licensed intellectual property. This episode tells the full story, starting in April 1948, when Lazarus opened a baby furniture store called Chil...

John Slack died in 1896 as a coffin maker in White Oaks, New Mexico, keeping quiet about one of the boldest swindles in American history. In the early 1870s he and his cousin Philip Arnold walked into San Francisco banking offices with a handful of garnets and flawed diamonds, played the part of ignorant country prospectors, and let the financiers believe they were the ones taking advantage. With...

The last survivor pact from old mystery novels and sitcoms is a real financial instrument with a long record. In a tontine, investors pay a lump sum into a trust that pays annual interest to the group. When a member dies, that share is divided among the living, so payouts climb for each survivor until the last one dies and the trust dissolves. The idea takes its name from Lorenzo de Tonti, a Neapo...

On January 26, 1905, surface manager Frederick Wells pried a 3,106 carat crystal out of a mine wall in South Africa with his pocket knife, just 18 feet below the surface. The Cullinan was three times the size of the previous record holder, the Excelsior, and it had formed hundreds of kilometers down in the mantle before a kimberlite eruption carried it up intact. This episode traces how a stone of...

Al Capone ended his criminal career plucking a banjo in an Alcatraz prison band. This episode strips away the Scarface myth to follow the real chronology: a barber's son born in Brooklyn in 1899, expelled at 14 for striking a teacher, schooled in extortion as a bouncer at Frankie Yale's Harvard Inn, and slashed three times across the face by Frank Galluccio. He hated the nickname that followed, hi...

The word stockholder once meant something literal: the person who held the longer half of a split wooden stick. This episode follows the tally stick from prehistoric notched bones to the medieval English Exchequer, where a length of squared hazelwood became an unforgeable receipt. Notches were cut across the stick to record a debt, then the wood was split lengthwise through the marks. The lender k...

The infomercial is easy to dismiss as late night filler, but it began as a discovery about dead airtime. In 1949, a 30-minute pitch for the Vitamix blender aired after midnight on WOR-TV in New York and drew more than 130 telephone orders within an hour. The FCC soon capped commercial minutes per hour, and marketers spent the 1970s hunting for loopholes, from album ads padded with long song clips...

In April 1994, James Jebbia opened Supreme on Lafayette Street in Lower Manhattan with the clothing racks pushed to the walls so local kids could skate straight in off the street. The staff were downtown skaters such as Justin Pierce and Harold Hunter, the atmosphere was deliberately intimidating to outsiders, and the red box logo borrowed the look of artist Barbara Kruger's anti-capitalist work....

The 2008 financial crisis erased $11 trillion in household wealth, yet half of the poorest American families saw no decline, because they had no investments to lose. This episode starts decades before the crash, with the 1999 repeal of key parts of the Glass-Steagall Act, a political push for affordable housing, and cheap money from the Federal Reserve. Lenders sold adjustable rate subprime mortga...

In the late 1800s, a Beaumont brick maker and Sunday school teacher named Pattillo Higgins led his class up a small hill called Sour Spring Mound, dropped a lit match, and watched the ground catch fire. He was convinced a salt dome beneath the hill had trapped oil and gas, though geologists insisted the Gulf Coast held none. In 1892 he formed the Gladys City Oil, Gas, and Manufacturing Company, on...