Today's Wisdom - Frederick, Underdogs and Uber

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As a child, Frederick II of Prussia played the flute, wrote poetry in French, corresponded with Voltaire, and dreamed of a life of philosophical reflection. His father, who built one of the most disciplined armies in Europe and once beat his son in public with a cane, viewed Frederick's artistic temperament as a threat to the dynasty. The relationship between them collapsed entirely when at 18 Frederick attempted to flee Prussia with a close friend. The prince was caught, imprisoned, and forced to watch his companion executed in front of him as punishment. It was one of the most formative acts of cruelty in the biography of any major historical figure. The man who emerged from that cell was recognizably different from the boy who had entered it.

When Frederick came to the throne in 1740 at the age of twenty-eight, Europe's major powers had already written Prussia off as a second-tier kingdom with an oversized army and no particular destiny. Within months he had invaded Silesia, a wealthy Austrian province, in a calculated act of aggression that shocked the continent. Frederick fought what became known as the Seven Years War against a coalition that included Austria, France, Russia, and Sweden simultaneously. He was outnumbered in almost every engagement but survived largely through a combination of military genius, strategic flexibility, and an almost inhuman personal stubbornness. He rode at the front of his armies, had multiple horses shot from under him, and kept fighting through winters and defeats that destroyed lesser commanders. By the time peace came in 1763, Prussia had held Silesia and established itself as one of the five great powers of Europe.

What made Frederick genuinely unusual among the monarchs of his era was the contradiction at the center of his character. He was an absolute ruler who described himself as the first servant of the state rather than its master. He abolished torture in Prussia and invited persecuted groups including the French Huguenots and Silesian Protestants to settle and build within his borders. Frederick corresponded with the greatest Enlightenment thinkers of his age and wrote extensively on philosophy, history, and the obligations of kingship. He also ran a surveillance state, maintained a brutal serfdom in the Prussian countryside, and waged wars that killed hundreds of thousands of people in pursuit of territorial ambition. Prussia under Frederick became the template for the modern disciplined state, and the military culture he institutionalised eventually fed directly into the Germany that emerged a century after his death.

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Statisticians, historians, and fans have never fully agreed on a single answer to this question, which is itself part of what makes it worth asking seriously. The candidates span continents and centuries: Greece’s national football team winning the UEFA Euro championship in 2004 against odds of roughly 150 to 1; Robin Söderling defeating Rafael Nadal at the 2009 French Open, ending a 31-match winning streak at Roland Garros; the New York Jets, 18-point underdogs, defeating the Baltimore Colts in Super Bowl III. Each of these sits in a different category of improbability, and measuring them against each other requires thinking carefully about what an upset actually means. Raw odds tell one part of the story. Historical context tells another. The sheer weight of what was supposed to be inevitable tells a third.

On pure statistical improbability, Leicester City's Premier League title has a credible claim to being the most unlikely result in the history of team sports. To understand the scale of it, some context helps. The Premier League is England's top football division, and for the two decades before Leicester won it, the title had been shared almost exclusively between four clubs, all of them backed by hundreds of millions in investment and global commercial empires. Leicester were a provincial club from a city of 350,000 people whose entire squad had cost less than the annual wage bill of several of their rivals. The 5000 to 1 odds assigned to them before the 2015-16 season reflected genuine mathematical reasoning about a club that had finished fourteenth the previous season. The achievement was so statistically aberrant that academics published papers attempting to calculate whether anything comparable had ever happened across any major professional league in any sport.

The case for Buster Douglas defeating Mike Tyson in February 1990 carries a different kind of weight. Tyson had been utterly dominant, stopping twenty-four of his first twenty-eight opponents while projecting an aura of overwhelming physical menace. Douglas was a journeyman who had lost to fighters nobody remembered. What changed in Tokyo was that his mother had died three weeks before the fight, and something in Douglas hardened into a focus that nobody in the sport had seen from him before. He knocked Tyson down in the eighth round, something only one fighter had ever done before him, and finished the fight in the tenth. Yet even Douglas at 42 to 1 looks almost reasonable when placed beside the 1980 US Olympic ice hockey team's victory over the Soviet Union. The Soviet team had won every Olympic gold medal since 1964 and four days before the Olympic semifinal had defeated the same American team 10 to 3 at Madison Square Garden. The Americans were amateur college players with an average age of twenty-two. When the US won 4 to 3, the result was a sporting shock and a cultural detonation in the middle of the Cold War. Between Leicester, Douglas, and Lake Placid, sport has produced three genuinely separate categories of the impossible, and people have been arguing about which one was the most impossible ever since.

Travis Kalanick grew up in Los Angeles, launched two companies before Uber that left him broke and buried in legal battles, and arrived at his third attempt with the disposition of someone who had decided that asking for permission was a form of weakness. When Uber launched in San Francisco in 2010, it was immediately and unambiguously illegal under existing taxi regulations. Kalanick's response to cease-and-desist letters from city authorities was essentially to keep going and grow fast enough that shutting him down would become politically untenable. The strategy worked. By the time regulators in any given city had assembled the legal machinery to act against Uber, the company had hundreds of thousands of users. Kalanick had understood that if you grow fast enough, the public becomes your lobbying army.

The company Kalanick built in Uber's first seven years was one of the most audacious expansions of a private business in modern history. At its peak he was operating in over seventy countries with millions of drivers and had pioneered the gig economy model that restructured how a significant portion of the global workforce thought about employment. He also built an internal culture that reflected his own personality almost perfectly, which turned out to be a serious problem. Uber under Kalanick was defined by a set of company values that included phrases like "always be hustlin'" and "toe-stepping," a corporate philosophy that tacitly encouraged employees to win by any means necessary. A program called Greyball used software to detect and deceive regulators who were attempting to test the Uber app in cities where it was operating illegally, feeding them ghost cars while real drivers served real customers. The company ran a covert intelligence operation called Hell that tracked the movements of Uber drivers who were also working for Lyft, allowing Uber to undercut and poach them. These were products of a culture that had been told, from the very top, that the rules were something that only applied to other people.

The unraveling came in 2017 with a speed that surprised almost everyone who had watched Kalanick operate with apparent impunity for years. A former engineer named Susan Fowler published a blog post describing systemic sexual harassment at the company and a human resources department that had been institutionally incapable of addressing it. The post went viral within hours and became the opening chapter of a broader reckoning. An internal investigation led by former US Attorney General Eric Holder produced a report with 215 recommendations. Kalanick was forced to resign as CEO in June 2017, pressured out by a group of major investors who had concluded that the company could not go public with him in charge. He walked away with billions of dollars in Uber stock. Uber survived, cleaned itself up under new leadership, and eventually went public in 2019. Kalanick went on to launch a ghost kitchen company called CloudKitchens with the same relentless energy he had brought to Uber, apparently having concluded that the lesson of his career was to move faster, not differently.

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