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In 1961, two MIT professors beat roulette in Las Vegas. Not by counting. Not by luck. With a shoebox of transistors taped to their stomachs. Their edge was 44 percent over the house. The casino never figured out how. One of them invented the mathematics behind the internet. The other invented the modern hedge fund. His name was Claude Shannon. Yes, that Claude Shannon. In the summer of 1961 he built the world's first wearable computer in his basement in Cambridge. He wore it into a Nevada casino under his shirt. His partner was a 28-year-old math professor named Ed Thorp. Thorp tapped his toe when the ball passed a mark. Shannon's computer did the physics. It sang the answer into Thorp's ear as one of eight musical tones. Which quarter of the wheel the ball would land in. It worked. They tested it in Reno, then took it into the pit. The edge held. The device is now in a glass case at the MIT Museum. Credited as the first wearable computer in history. They quit after a few trips. The earpiece wire kept breaking. And in 1961 the wrong pit boss noticed and things got physical. Shannon wanted no part of that. He was a professor. Thorp had no such problem. He took the math to blackjack, wrote Beat the Dealer in 1962, and by 1964 every casino in Nevada had rewritten the rules to stop him. In 1969 he opened Princeton Newport Partners. Nineteen years. 20 percent a year. No losing quarter. Shannon went back to Cambridge and ran his own money. His personal portfolio compounded at 28 percent a year for 30 years. Better than any fund manager alive at the time. Nobody knew until his wife opened his books after he died. Two MIT professors. One shoebox. One summer in Nevada. The blueprint for the entire hedge fund industry. Thorp is 93. Shannon died in 2001. The shoebox is behind glass in Cambridge. Vegas learned to change the rules. Wall Street never did.

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Insurance is the oldest of the four ways. It is a nine-trillion-dollar global industry. The equation underneath it was invented in 1560 by a broke Italian gambler. His name was Girolamo Cardano. He wrote a book called Liber de Ludo Aleae. A short manual on how to win at dice. Nobody in finance read it for four hundred years. Then in 1996 a ninety-year-old man in New York wrote a book that traced every modern risk model back to that manual. He called it Against the Gods. One thesis. Every dollar of premium ever collected on Earth is a footnote to a gambler scribbling in Milan. His name was Peter Bernstein. He founded the Journal of Portfolio Management in 1974 and ran money at Bernstein-Macaulay before that. Wall Street called him the historian of risk. In 2008 a small production company filmed him for thirteen minutes. He walked through the entire five-hundred-year arc. Cardano to Pascal to Fermat to Black-Scholes. Then he stopped and said the industry had built glass towers on the back of an idea a broke Italian scribbled to settle a card debt. He died the following summer. Age ninety. Reinsurance premiums crossed six hundred billion dollars last year. Every actuary on Earth prices catastrophe risk with the same expected-value framework Cardano invented to shave the house edge in Milan. The video is thirteen minutes and twenty-two seconds long. Free. Eleven years on YouTube. Twenty-nine thousand people have watched it. Almost none of them work in insurance.

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The man who invented modern fantasy didn't publish his first novel until he was forty-five. By that age, J.R.R. Tolkien had already built a respectable life. He was an Oxford professor, an expert in ancient languages, with a wife and four children and a settled academic career. He was exactly the kind of man who might reasonably have decided that the shape of his life was already fixed. The work he would be remembered for, he had not yet even begun... The story, which Tolkien told himself, is that one summer he was grading examination papers, when he turned a page and found that a student had left it blank. Without quite knowing why, he wrote a single sentence on it: "In a hole in the ground there lived a hobbit." He did not know what a hobbit was. He had spent years inventing languages and mythologies as a private passion, and telling stories to his own children, never imagining any of it would reach the world. But that one line began to grow. It became a story, and then a book, and in 1937, at the age of forty-five, Tolkien published The Hobbit. It was a success, and his publisher asked for a sequel. Tolkien warned them it might take some time. It took 17 years... He wrote it in the margins of a demanding full-time job, revising endlessly, doubting it often. When The Lord of the Rings was finally published, in 1954 and 1955, he was in his early sixties. That book, begun as a middle-aged professor's private side project, went on to sell well over a hundred million copies, to invent modern fantasy as we know it, and to reshape the imagination of the entire world. Tolkien already had a full and respectable life behind him. And still, the thing he is remembered for, the thing that outlived him and reached hundreds of millions of people, was something he began at forty-five, at an age when it would have been the easiest thing in the world to tell himself he had already missed his chance. He didn't. It's never as late as it feels.

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