Uber: Hustle & War

The book Super Pumped: The Battle for Uber is a great breakdown of the violence that outlined Travis Kalanick’s regime and Uber’s corresponding rise.

Every once in a while you read a fun Silicon Valley tip, like how Airbnb found they could increase growth by sending professional photographers to hosts.

Then there’s Uber and how they openly skirted city regulations, shadowbanned transportation authorities and enforcers, attempted to deceive Apple’s App Store team, and possibly had a hand in stealing intellectual property from Google’s autonomous driving division.

It’s metal. More aptly, warlike.

Uber resembled a feudal monarchy, and one that was on a crusade. 

“It was as if Kalanick had hired a private army of mini-entrepreneurs and given them one mandate: Conquer. Everyone was a founder of their own city-level fiefdom.”

Mike Isaac, Super Pumped: The Battle for Uber

The workforce rode out under the blessing and banner of their king, Travis Kalanick. Under his decree, nothing was off limits. Current and ex-Uber employees undoubtedly reminisce about the glory days—if only behind closed doors.

Kalanick spurned, deceived, and overwhelmed anybody between him and his mission. It was his willingness to do so that initially earned respect from his employees and investors. They knew what they were getting: an entrepreneur with an otherworldly drive. His attributes fit Peter Thiel’s “Founder Distribution” well, a theory of how founders oscillate between the most extreme traits of individuals.

Founders: anywhere but average. Diagram from the book “Zero to One” by Peter Thiel & Blake Masters.

He was weak when Michael Ovitz cleverly sued to receive favorable investment terms for Kalanick’s first company, Scour, and later backstabbing them by selling all of his shares.

Strong as he stood up to city authorities, taxi unions, app scammers, and organized crime, responding with an arsenal of clever—and at times unethical—engineering techniques and a willingness to burn capital on tickets and fines. Breaking the law was a cost of business.

He was poor when he dropped out of college and lived at his parent’s apartment, and rich when Uber became one of the fastest growing companies in history.

He was flagrantly disagreeable to CEOs, politicians, and activists, yet a charismatic visionary for his company and backers. 

At one point the hero of the story and another the villain.

In other words, a founder.


In Our Oriental Heritage, Will Durant writes: “A nation is born stoic, and dies epicurean.” 

Similarly, a startup’s flame is brightest at its inception, when founder mimicry is still active. Uber began as a communal identity around Travis Kalanick and his value of ‘hustle’. This created an echo chamber that enabled them to pursue their goals without any of the delay or pesky thoughtfulness that comes with more democratic thinking. Durant is describing the disintegration of the collective into individuals. We have a great sense of what Uber was like under Travis Kalanick, but little of that identity remains today—and nothing has truly replaced it.  

Meanwhile, ‘hustle’ has become brutally out-of-fashion, or cancelled. This is despite the fact that it was the defining characteristic of Uber’s success. There are admirable qualities derived from hustle, but it has unfortunately become associated with vapid technology bro-culture. Most importantly, the dogged spirit it represents is in stark contrast to the startup culture du jour; one that is unremarkably cozy. We’re now ensconced in “The Start-up of You”, a blanket weaved with individualist threads and anti-corporate patches.

Conformity is misunderstood. It’s necessary for a group to achieve great things—to focus on a single goal in spirit—just as diversity and individualism is necessary to determine what is great. Once celebrated (see William Whyte’s The Organization Man), we have come to under-emphasize conformity’s crucial role in the beginning of any institution.

The Fall of a Wartime CEO

These violent delights have violent ends.

Dolores, quoting Shakespeare, in “Westworld”

Kalanick’s fall from leadership is consonant with the Girardian theme of scapegoating. An example of this would be the Biblical story of Jesus Christ dying on the cross, ostensibly so our sins would be forgiven through the crucifixion of an innocent individual. For Uber, at some point the sexism, drug-use, unethical business practices, and overall toxic culture was threatening its very existence. Customers, drivers, and venture capitalists were clamoring for a sacrifice, and they needed a scapegoat.

Children inherit the sins of their father, and startups inherit the sins of their founder.

Let’s stay far away from comparisons of Travis Kalanick to Jesus Christ. But the Girardian similarity stands: for Uber to live, Kalanick had to die.

Metaphorically, of course. 

The degree to which Kalanick was responsible for Uber’s travesties, and thus deserving of disgrace and his ensuring downfall, can’t be traced objectively. Rene Girard posited that the victim of a mob was always innocent. But responsibility is somewhat besides the point, because Travis Kalanick is undoubtedly a Wartime CEO, and with war comes violence.

In order to be ordained, violence cloaks itself under the illusion of control. The guise of a plan allows pockets of Hobbesian acts to occur.

It only takes a trickle to break the dam. There are always crimes of war.

Ben Horowitz describes companies as operating in two phases: Peacetime and Wartime. Peacetime is marked by consistent growth, processes, and planning. Wartime means there’s an existential threat at play; stop f*cking around. CEOs that excel in one mode are often not cut out for the other.

Kalanick fought every battle like it was his last, no matter the enemy. Uber went up against city authorities, Google, Apple, China, and more—and came out alive. 

The backers of Uber’s war chest, the venture capitalists, had to rescind their support of Kalanick when it became clear he would not stop wrestling in the mud. His once-treasured aggressiveness had become a liability, his creative spark threatening to ignite their pile of cash.

They thought they were playing within certain boundaries, with a clear goalpost. Kalanick plays with boundaries, and only knows how to up the ante. 

Peacetime CEO knows that proper protocol leads to winning. Wartime CEO violates protocol in order to win.

Peacetime CEO spends time defining the culture. Wartime CEO lets the war define the culture.

Peacetime CEO strives not to use profanity. Wartime CEO sometimes uses profanity purposefully.

Peacetime CEO does not raise her voice. Wartime CEO rarely speaks in a normal tone.

Peacetime CEO works to minimize conflict. Wartime CEO heightens the contradictions.

Ben Horowitz, Peacetime CEO/Wartime CEO

The dust has settled with Uber, and Kalanick is no longer involved.

So, what do generals do during times of peace? They prepare for war.

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