Uber’s Icarus

New York Times technology writer Mike Isaac won the Gerald Loeb Award for distinguished business reporting for his coverage of Uber. He details how Uber radically transformed transportation while breaking laws and accumulating multiple scandals. Isaac presents former Uber CEO Travis Kalanick’s leadership journey as hubristic, epitomizing Silicon Valley tech culture at its best and worst. He provides an in-depth, perceptive view of one of Silicon Valley’s most controversial multibillion-dollar companies.

NPR, Fortune, Bloomberg and The Sunday New York Times chose this as one of the Best Books of the Year. The New York Times Book Review named it an Editor’s Choice and said, “Isaac is great at the ticktock of events as they unfold, but his best work comes when he steps back to examine the bigger picture.” John Carreyrou, author of the best-selling Bad Blood, said, “Aside from being a delicious read, Mike Isaac’s account is also teeming with new revelations that will shock and outrage you.”

A Cautionary Tale

After Travis Kalanick founded Uber in 2009, Isaac details how the company expanded in five years from a start-up into operating in hundreds of cities worldwide. The ride-sharing service grew quickly – despite, the author repeatedly points out, laws and regulations prohibiting its services. Isaac depicts Kalanick as believing Uber championed innovation by harnessing technology’s ability to improve people’s lives. Violating local laws didn’t go against the company’s values, because, Isaac writes, Kalanick cited “Principled Confrontation,” as one of Uber’s values. 

The saga of Uber – which is, essentially, the story of Travis Kalanick – is a tale of hubris and excess set against a technological revolution, with billions of dollars and the future of transportation at stake.Mike Isaac

The author reveals that Uber recruited former CIA, FBI and NSA employees to surveil government officials who might impede Uber. Because Kalanick’s lack of legal or ethical oversight resulted in the company’s valuation plummeting tens of billions of dollars and led to six federal investigations, Isaac presents Kalanick’s hubris and aggression as a cautionary tale.

Silicon Valley is teeming with people with big ideas and empty bank accounts. It is a town where being first to an idea doesn’t always mean you’ll end up the winner.Mike Isaac

Garrett Camp and Kalanick launched UberCab which dispatched private black cars. As Isaac explains, venture capitalists and CEOs expensed UberCab rides, and the company grew.

Fines

The San Francisco Municipal Transportation Agency, Isaac discloses, served the company with a cease and desist order. It threatened the company with fines of up to $5,000 per trip and warned Kalanick and other employees that they would spend up to 90 days in jail for each day that UberCab continued operating.

Isaac relates how Kalanick told his team to ignore the order: He renamed the company Uber, and it illegally entered markets in new cities, absorbing fines along the way. Isaac cites the example of Philadelphia’s local Public Utility Commission which fined Uber $12 million for roughly 20,000 violations. Kalanick, Isaac recounts, viewed fines as a business expense.

Investors

Benchmark Capital invested $11 million in Uber, based only, Isaac found, on a handshake deal with Kalanick. Uber attracted investors, the author believes, by creating scarcity. The company made potential investors work to get meetings. Google Ventures invested $250 million, but Kalanick, the author says, treated it as he did all investors, for example, refusing to give Google updates on Uber’s progress.

Isaac finds amusement in Kalanick being regarded as symptomatic of the jerks who created the culture people saw in tech companies. Kalanick, the author notes, made misogynistic remarks in interviews, damaging his credibility.

War

Uber launched UberX in 2014, paying ordinary people to drive its customers. Kalanick, Isaac emphasizes, wanted to bankrupt Lyft and created a secret program, “Hell,” to lure Lyft drivers to Uber.

One Lyft executive grew so paranoid about being followed by Uber that he walked out onto his porch, lifted both middle fingers in the air and waved them around, sending a message to the spies he was absolutely sure were watching.Mike Isaac

Isaac tells how Uber formed a Secret Services Group (SSG) of former Secret Service, FBI and CIA operatives who anonymously gained access to private WhatsApp group chats by impersonating Uber drivers, gathering intelligence about how drivers were organizing and whether they were planning strikes.

Muslim Workers

Isaac recounts that in 2017, President Donald Trump banned people from countries with high Muslim populations from entering the United States. The New York Taxi Workers Alliance – which included many Muslim drivers – went on strike. Isaac relates that Kalanick let Uber complete airport pickups while drivers were striking, and he sought a seat on Trump’s business advisory council. Isaac reports that more than 500,000 people deleted their Uber apps in a week, and Kalanick left Trump’s council.

Ouster

Isaac lists multiple scandals – a federal investigation, lawsuits and reports of sexual assault. Uber commissioned an investigation, the Holder Report, by Covington & Burlington. The author uncovered the report’s suggestion that Kalanick should step down.

I wondered if there would be a new generation of Travis Kalanick protégés soon. What would they think of the founder’s rise and the path he took to get there?Mike Isaac

Kalanick finally resigned in 2017, Isaac notes, after venture capital firms that owned 26% of Uber’s economic stock and roughly 40% of its voting shares pressured him. Isaac offers a coda: In 2019, Uber hit public markets at $42 a share, right after Lyft’s debut at $72 a share – a major defeat and Kalanick’s true legacy.

Hubris

The author savors and abhors Kalanick’s hubris, arrogance and disregard for norms. Happily, though, Isaac does not present a morality tale. He remains a cool observer and acknowledges the dominant fact of Kalanick’s ascent: Most of his tactics worked, and Uber’s success depended on them. Then, suddenly, they worked no more, and Kalanick’s juvenile escapades and attitudes undid him. Isaac provides great fun and deadly serious cautions. He notes the impotence of old norms in the face of determined entrepreneurs and marvels at how long Kalanick managed to endure without, apparently, growing up. In that, Isaac provides a comprehensive overview of a profound cultural and business shift and ponders Kalanick’s likely effect on up-and-coming entrepreneurs.

Other fine works addressing Silicon Valley hubris and its discontents include John Carreyrou’s Bad Blood; Reeves Wiedeman’s Billion Dollar Loser; and Brad Stone’s The Upstarts.