Super Pumped

Mike Isaac is a technology reporter for the New York Times who wrote extensively about Uber, including in 2017 when Susan Fowler's bombshell Medium essay dropped and Travis Kalanick's reign at Uber started to unravel. This is the extended story of the company in book form, from Kalanick's pre-Uber startup experiences until the end of the postscript in May of 2019 following Uber's IPO.

To non-fiction book publishers of the world: Please make the exposé of dysfunctional, exploitative capitalism and its abusive leaders a major genre. I will be there for each book launch with my wallet in hand. Timely essay journalism is probably more effective from a public interest perspective, but there is nothing like a book-length treatment to dig into the power structures that enable companies like Uber to exist and the critical tipping points that may allow them to be dismantled.

Super Pumped opens with Uber's "X to the x" company-wide party in Las Vegas in October of 2015, which included the announcement of Uber's 14 company values. Value number 12, "Super Pumped," provides the title of this book. (The precise meaning of this value isn't clear, although cult-like devotion to the company is part of it.) But the book as a whole is also a biography of Travis Kalanick, Uber's now-ousted CEO and driving force through most of its existence.

Uber was not Kalanick's first startup. That was Scour, a search engine for file-sharing sites somewhat similar to Napster. Kalanick took venture capital for Scour under threat of a lawsuit from the VC and then lost control of the company, which was sold for parts in bankruptcy court after a lawsuit from the RIAA and MPAA. Kalanick then spent six years barely keeping his second startup, Red Swoosh, alive until it could be sold to Akami for $20 million and a personal profit of $2 million. Both of those experiences left him with a deep distrust of venture capitalists and a determination to keep control of any future company out of the hands of the money people. That sets up one of the themes of Uber's history: a governance structure that gave Kalanick near-total control with very few sanity checks.

If you're not familiar with the Bay Area tech culture or with startup finance, you may not know about the huge fight over control of startups. Historically, it was common for startup founders to give up majority control of their companies to early venture capital funders, and for those funders to then replace the management (and, some would argue, meddle with the company mission) once the company became more mature and was heading for an "exit" (a stock market IPO or acquisition, so-called because those events let early investors sell off their stake and "exit" the company with a profit). Google and Facebook are among the wildly successful companies that broke this mold and retained founder control. Those examples, plus the flood of additional money into tech startups, let more founders or early owners like Kalanick follow suit and refuse to give up a majority stake in the company.

This is an interesting debate because there are good arguments to be made for both models. On one hand, no one likes bankers, who are widely (and not entirely inaccurately) viewed as reluctantly necessary parasites. The process of bringing in professional management at the behest of the VC owners was often very disruptive, came with aggressive layoffs and reorganizations, and in some cases involved dismantling the business for parts or selling it to a competitor rather than continuing to develop a product. The founders usually had a vision for how the company could change the world, or at least its market, and while those visions were often dubious, that sort of mission and focus was often more appealing to the general employees of the company than the VC focus on a lucrative exit.

On the other hand... there's Travis Kalanick.

As Isaac explains, and which I didn't know before reading this book, Kalanick was not the founder of Uber. That's Garrett Camp, who had the initial idea and brought Kalanick on as an advisor. He was happy to mostly step aside early on, however, leaving Kalanick with uncontested control of the company. It's Kalanick who decided on the strategy of aggressive expansion, openly illegal flouting of taxi laws, political hardball, and massive runaway spending to try to break into Asian transportation markets. It's under Kalanick's watch that Uber built systems to hide their activity from police and government regulators. And Kalanick oversaw the culture of pervasive sexual harassment that led to a massive internal investigation and his eventual ouster.

One interesting thread of this book is an argument in favor of banker control, at least as the least-bad option if the alternative is someone like Kalanick. Investors may not be interested in making the world a better place, but they are interested in preserving their investment and not making negative front-page headlines, which means they're less likely to openly break laws, more likely to hire adult supervision, and more likely to make boring and conventional business decisions. It's quite the unappealing choice, though. One comes away from Super Pumped dubious that either Kalanick or his investors have any business being in charge of anything that affects other people's lives.

I obviously came to this book with my own biases and prejudices, and was not expecting to like Kalanick, but it's even worse than I expected. The moment that put my shoulders up around my ears came after Kalanick was recorded screaming at an Uber driver about company policies. When Kalanick was shown that video, Isaac describes him (via, to be clear, second-hand accounts; Isaac was not there) spending the rest of the night literally writhing on the floor, repeating how terrible of a person he is and asking what was wrong with him.

This is, to be explicit, not typically the behavior of someone who is genuinely apologetic about something they've done. This sort of over-the-top, theatrical apology and elaborate groveling is more typical of abusive people after they've been caught. It re-centers the moment away from the person who was abused and back on the abuser, making everything about their pain and their anguish. There are a lot of places in this book where Isaac is willing to ascribe Kalanick's actions to a deep-seated belief in the corruption of the taxi industry, determination to retain control of his company, or aspirations to transform transportation. This moment was when I decided that Isaac, despite his skeptical treatment, was being far too kind, and Kalanick is scary and dangerous. There's further reinforcement of this pattern later in the book when Kalanick attempts to write a message to the company after the Holder report on Uber's culture of sexual harassment was complete, and some very troubling glimmers of it in the small amount that Isaac reports about Kalanick's relationship with his former girlfriend.

Super Pumped is a detailed, mostly-chronological story of the rise of Uber under Kalanick, its growing financial struggles in Asia, its arrogance and political aggressiveness, and then the revelation and aftermath of multiple classes of illegal behavior. It closes with the last fight over control of Uber, one that Kalanick finally lost, and the naming of Khosrowshahi as the new CEO. The detail and clarity are the strengths of this book; the weakness is that Isaac is much more interested in pure reportage than analysis. Super Pumped is a chronological account of events and not much more; Isaac is focused on the process of reporting and the way stories broke rather than on broader implications for society as a whole.

That's forgivable, of course. Not every long-form journalist is (or should be) Michael Lewis. But for me that made Super Pumped good, not great, and not rising to the level of the best books of this type (The Smartest Guys in the Room and Bad Blood). Admittedly, as much of a disaster as Uber was (and arguably is), it's rather hard to compete with the sheer madness of Theranos.

The lack of more contextualization and broader analysis was one disappointment in this book. Another was Isaac's unwillingness to talk more directly about the red flags around Kalanick's behavior, instead deciding to report the facts as he knows them and let the reader draw their own conclusions. (I realize that my desire for the author to engage more directly in the topic is a personal preference that won't be shared by all readers.) A third isn't Isaac's fault: Neither Uber's story nor Kalanick's are over, so while Super Pumped reaches an adequate conclusion after Uber's IPO, I would have liked to read analysis of Kalanick's subsequent sale of all of his Uber stock and his new startup venture. We'll have to wait for that. (I would also love someone to ask him why, after walking away with several billion dollars, he's choosing to found another company, but I doubt I'd get a satisfactory answer.)

But, those disappointments aside, Super Pumped was compulsively readable and filled in numerous details that I'd not previously known. If you like this style of long-form journalism on disasters of capitalism, this is worth your attention.

Someday there is going to be a book like this about WeWork, and I'm going to read the hell out of that.

Rating: 8 out of 10

Reviewed: 2019-12-28