This book was a total page turner. It has everything you’d want from a good story
- famous, familiar characters like Travis Kalanick, Anthony Levandowski, Bill Gurley, Larry Page, Susan Fowler, Masayoshi San
- incredible events - both good and bad
- behind-the-curtains peek into a familar product and a hypergrowth tech company
- diverse, international stage
- high stakes power struggle with compelling characters
- complicated plot - the line between good and evil is not so clear
I looked forward to the next chapter just as much as I’d look forward to the next episode of Game of Thrones.
If any of this sounds like your cup of tea, pick up the book and start reading it!
Otherwise, keep on reading and I’ll share what I enjoyed most about this book.
My reasons for loving this book (spoilers!)
The book made me respect and understand Travis Kalanick
Before I read the book, I knew of Travis Kalanick from Uber’s press stories over the last decade. I thought he was an obnoxious, negligent businessman that got lucky by being in the right place at the right time. I thought that he had no redeeming qualities and that I’d probably do his job better than he could.
As I read the book though, I had to revise my opinion.
A precocious child, he picked up his father’s skills with mathematics, impressing others with his ability to speed through arithmetic in his head where other classmates needed pencil and paper.
Kalanick himself was no slouch on the SAT. He scored a 1580, just twenty points shy of perfect, and whipped through the math portion of the test with plenty of time to spare. Friends remember his savant-like math abilities. “We were driving across town in Los Angeles once, and Kalanick saw a street sign that said we were seventeen miles from where we were going,” recalled Sean Stanton, a friend and former colleague. “He looked down at the speedometer and saw our average speed, and in a few seconds rattled off how long it would take us to get there so we could make it in time for our meeting. I mean, who does that?”
He and his computer science friends took full advantage of their T1 connection. They battled each other in games like Quake, Doom, and StarCraft. File-sharing parties were common; groups spent hours trading and downloading music, movies, and images, swapping files as if they were baseball cards.
Travis was a math whiz with a degree in Computer Science?! He was more similar to me than I thought, and easier to relate to. If I knew him in school, I’d consider him a fellow nerd.
Uber was not Travis’s first company. He founded two peer to peer file sharing companies before he worked for Uber - Scour and Red Swoosh. Let’s look at the quandries that Travis dealt with at these companies:
At one point, when Red Swoosh was running out of money, an employee dipped into the company’s payroll tax withholdings—money a company reserves to pay the IRS the taxes it owes—to fund operations.
He was later informed by an advisor that the company might be committing tax fraud. This would stick with Kalanick for years; he felt betrayed, put in legal jeopardy by a colleague
That cycle repeated for the next few years at Red Swoosh. Kalanick would run out of money, then secure a last-minute deal with a larger tech company and keep his business alive for another few months. He’d then find a way to parlay that deal into yet another venture investment, bailing out the company for a year or so longer.
Red Swoosh ran out of money, and one of its employees was committing tax fraud. Travis kept negotiating deals and investment rounds to keep the company alive. He kept the company alive for six years before he finally negotiated a sale:
Finally, after six years of tireless hustling, Kalanick negotiated his best deal yet: he sold Red Swoosh to Akamai for nearly $20 million. After taxes, Travis personally netted roughly $2 million.
I respect people that have gone through the trenches of building a company. Real experiences like these harden you for your next battle.
After the Red Swoosh sale, Travis didn’t exactly live a life of the rich and famous. He started a blog and advised young startups from his apartment in San Francisco’s Castro District.
For Kalanick, blogging was a way of marketing himself, along with the occasional talk delivered at startup mixers and cocktail parties.
Kalanick wanted to be a fixer like The Wolf. After buying his hilltop house in the Castro, Kalanick started investing small amounts of money in various startups with the understanding that he’d be available as their own personal fixer, willing to swoop in and solve problems whenever a founder needed his help. Got a problem with an agitated investor? The Wolf can handle it. Don’t know the first thing about hiring new engineers? Just call The Wolf. Maybe you have late-night thoughts on your company’s next move and want to talk it out. Never fear, The Wolf is here.
Travis is very relatable here. This is pretty much what I would do if I made it big - write an interesting blog, help young entrepreneurs make it, and earn a nickname like “The Wolf”!
When Travis became Uber CEO, he gave early employees autonomy and responsibility.
Kalanick trusted his employees with significant power. Each city’s general manager became a quasi-chief executive, given the autonomy to make significant financial decisions. Everyone was responsible for “owning” their position. Empowering his workers, Kalanick believed, was better than trying to micromanage every city.
that sense of freewheeling autonomy made employees lionize Kalanick’s leadership. It was as if Kalanick had hired a private army of mini-entrepreneurs and given them one mandate: Conquer.
After their time at Uber, Kalanick wanted his troops to go off and start their own companies. He saw the very act of founding a company as a virtue unto itself.
I can see how this city based management style helped Uber grow so quickly in so many cities. If all the important decisions for Uber’s growth were being made in San Francisco, there’s no way that Uber would have taken over the world as quickly.
I also think it’s no accident that the early Uber team is described as Travis’s “private army”. Travis would ask his soldiers to break local laws, stand up to its enemies, and play dirty to win. I’m not sure he would have succeeded if his employees thought they were cogs in the machine at a boring office job.
Uber’s stories of dirty tactics and ruthless competition are incredible
Uber started competing head to head with Lyft and Sidecar, and they held nothing back.
Graves, Geidt, and especially Kalanick weren’t above playing dirty. They started booking secret meetings with regulators in San Francisco and encouraging them to go after Lyft and Sidecar.
every race he [Travis] enters, in anything where he’s asked to compete against others, he seeks nothing less than utter domination.
Kalanick enjoyed the fight. At first he began to needle John Zimmer, Lyft’s co-founder, on Twitter. In playful jabs, he would troll Zimmer by asking about Lyft’s insurance policies, business practices, and other seemingly esoteric shoptalk. Then he would start picking Zimmer and Lyft’s business apart.
Kalanick didn’t really want to buy Lyft, anyway. He wasn’t into Zimmer. Something about the Lyft president’s personality irked Kalanick. The Uber CEO didn’t want to work alongside Zimmer. He wanted to professionally humiliate him.
Kalanick took pleasure in hurting Green and Zimmer, and showed them no mercy.
It is surprising for me to learn that Travis treated his competitors like sworn enemies. In my day job, I’ve seen my coworkers disrespect and belittle competitors, but I have never seen company leaders go after a competitor publically and with this level of intensity.
Uber also hired spies to gather intelligence on Lyft executives and on driver initiatives.
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.
Another entity, the Strategic Services Group, the SSG for short, employed the most clandestine tactics of the bunch. It was made up of ex-CIA, Secret Service, and FBI operatives, and hired subcontractors on special anonymous contracts with Uber so that their names couldn’t be traced back to the company. This outfit of black-hat spies engaged in a wide range of activities, some of which eventually spun out of Uber’s control.
Undercover operations could include impersonating Uber drivers to gain access to closed WhatsApp group chats, hoping to gather intelligence on whether drivers were organizing or planning to strike against Uber.
The budgets for these black ops departments were obfuscated; Kalanick had purview over them. Nevertheless, Kalanick okayed budgets that spun into the tens of millions for surveillance activity, global operations, and information collection […] Buying intelligence from third-party firms to gain an edge was normal.
I didn’t think that companies hired professional spies to follow competitors and impersonate drivers. I thought I could come up with creative ideas for a company to beat its competitors. Uber’s tactics make me feel like my “creative ideas” are child’s play.
Real people went through serious and tragic events as Uber grew in cities
Often, as white collar tech employees, we forget that our work affects real people. In Uber’s case, the app sometimes affected drivers, employees and customers in extreme, emotional and hard hitting ways.
As general manager of Uber’s Milan office, she worked overtime to convince Uber drivers to stay on the road, even as taxi operators would hail Ubers to their location, pull drivers out of their cars, and beat them. And one night when Lucini was returning home from work, she found a sign hung from a power line not far from her apartment. On the sign was Lucini’s home address, and a message calling her a prostitute who provided her “services” to Milan’s transportation chief.
Taxi cartels in areas like Las Vegas and elsewhere had deep ties to organized crime, which meant serious and sometimes violent retaliation. Cars were stolen. Sometimes taxi owners would assault drivers and set their cars aflame.
Cabbies were aghast. Doug Schifter, a livery driver from Manhattan, faced financial ruin after the rise of Uber wrecked his income driving for traditional car services. Schifter drove to City Hall in Lower Manhattan on a cold Monday morning in February 2018, put a shotgun to his head, and pulled the trigger. “When the industry started in 1981, I averaged 40–50 hours,” Schifter wrote in a final post to his Facebook page. “I cannot survive any longer with working 120 hours! I am not a Slave and I refuse to be one.”
Wow - employees are being intimidated by tough guys, and drivers are taking their own lives as a result of pricing changes. No company wants its work to lead to events like these.
Uber faced unfathomable challenges in the international market
In China, Uber wanted to win in the market at all costs. Chinese customers responded to Uber’s incentives in a way that was hard to predict:
he [Travis] noted that in just nine months, the number of trips taken in Chengdu and Hangzhou were more than four hundred times the number of trips taken in New York, one of Uber’s largest cities, when those markets were the same age. What Kalanick left out was the fact that in many cities, more than half of those trips were fake, a complete waste of money brought in by investors.
But in China, drivers and riders colluded to scam Uber out of billions in incentives, divvying the rewards … drivers seeking a fake ride would ask for “an injection,” a reference to the small, red digital pin that signaled a user’s location inside the Uber app. A “nurse,” or scammer, could respond in kind to give a “shot” to the original poster by creating a new fake account and going on a fake ride with the driver. The two parties would then split the bonus incentive payment from Uber. Repeated over and over across dozens of cities, small driver bonuses mushroomed into millions in squandered cash … scammer would request rides from his “passenger” phones, and use his “driver” phones to accept those rides. He would then drive around the streets of Chengdu with dozens of phones spread across the front and back seats of his car, racking up fares for each of the “trips” he was completing for his fake customers.
Some scammers created giant makeshift circuit boards filled with hundreds of slots to insert SIM cards, the small microchips that allow mobile phones to communicate with a cellular network. Each SIM card in the circuit board acted as a new number that could automatically respond to a verification text for a newly created account, which the scammers then used to rack up more fake rides and bonuses.”
The ingenuity of these scammers is very surprising to me. They built custom circuit boards with hundreds of SIM card slots so that they could take fake rides on Uber and earn incentive bonsues.
Their Chinese competitor, DiDi, went even further - they planted engineers inside Uber as corporate spies.
One of DiDi’s preferred tactics was to send new recruits over to Uber to join as engineers. As soon as they were hired they acted as moles, feeding proprietary Uber information back to DiDi and carrying out corporate sabotage on some of Uber’s internal systems.
When I heard that corporate espionage was involved, it became clear to me that the conflict between Uber and DiDi was less like competition and more like war.
In India, Local taxi companies hated Uber and initimidated employees with violence.
In Mumbai, local taxi operators muscled up at Uber’s offices and tried to intimidate employees. Violence was not uncommon; in Bangalore, whenever BD took a ride home from work, he refused to let Uber drivers take him directly to his house; he knew competitors might follow him.
An angry mob of drivers—some who drove for Uber, others employed by taxi organizations all too happy to stoke anger—showed up outside of Uber’s offices in early 2017 with the dead body of the thirty-four-year-old driver, M Kondaiah, dumping the corpse on the company’s front doorstep.
Drivers and passengers in India and Brazil experienced horrifying, violent crime.
The man took out a canister, doused his body in gasoline and then brandished a lighter, threatening to set himself ablaze unless Uber raised its rates again.
Yadav switched off his cell phone, making the two untraceable to police or Uber headquarters. He found a secluded area, parked the car, climbed in the back seat and raped the young woman.
For six weeks, Uber employees in India even brought their parents and families into hotels with them; taxi officials were beating up Uber employees in the street.
[In Brazil,] Osvaldo Luis Modolo Filho, a fifty-two-year-old driver, was murdered by a teenage couple who hailed a ride using a fake name and chose to pay in cash. After stabbing Modolo repeatedly with a pair of blue-handled kitchen knives, the couple took off in Modolo’s black SUV, leaving him in the middle of the street.
At least sixteen drivers were murdered in Brazil before Kalanick’s product team improved identity verification and security in the app.
Nobody expects their white-collar office job to lead to violent crime like suicide, rape and murder. Despite knowing that such events happen every day in cities around the world, my heart becomes heavy upon learning of such human suffering.
The power struggle between the Uber CEO and the board gives a glimpse into high stakes corporate politicking
As Uber started to get bad press, Bill Gurley thought that Uber needed to make major changes, and replace Travis with another CEO.
It [the Eric Holder report] was hundreds of pages long, a winding, repetitive list of infractions that had occurred across Uber’s hundreds of global offices, including sexual assault and physical violence. After Ryan Graves read the report, he felt he needed to vomit.
Gurley and Bonderman worried Holder’s recommendations might not have gone far enough, since they stopped short of pushing Kalanick out for good. Some members of the executive leadership team were convinced Huffington had leaned on Holder and Tammy Albarrán, Holder’s partner, to convince them not to recommend Kalanick’s termination in the final report.
Travis Kalanick didn’t trust VCs and gave himself supervoting shares to keep his power.
Whenever Camp, Graves, or anyone else in Kalanick’s orbit began to chafe at his actions, he usually responded with some version of the same placative sentiment: “Do you know how much money I’m going to make you?”
But when Sacca began attempting to buy up shares of Uber from other early investors—a practice known as “secondary share purchasing”—Kalanick turned on him. The CEO stopped allowing Sacca to attend board meetings as an observer; the two rarely spoke afterwards.
Travis could be so confrontational with other executives and board members at Uber. I haven’t seen conflicts with this kind of intensity in people’s workplace relationships.
To oust Travis, Bill Gurley hatched a secret, elaborate plan with a syndicate of Uber’s VCs.
And he [Bill Gurley] proposed a plan that would rely on all of them [Uber’s VCs] to work together. Gurley knew Kalanick would never step down of his own volition. They had to force his hand. Gurley knew Kalanick, like a rock climber looking for a toehold, would search for any weakness in the syndicate’s attack. With enough time and effort, Kalanick would find one, exploit it, and sink them all. He was a survivor; they needed to box him in. The minute Gurley walked into the hotel room to negotiate a surrender, Travis would tell the six-foot-nine Texan to go fuck himself. They needed a neutral emissary.
They worked through every possible permutation of what could happen when Cohler and Fenton approached Kalanick. (Would Travis throw a fit? Would he accede immediately? Would he lunge over the table and murder them?) They typed up a dozen different versions of the letter they would deliver to Kalanick, one for each possible scenario of the coming showdown. Lawyers at Paul, Weiss—the venerable white-shoe law firm—vetted each draft.
An Uber executive recalled that Kalanick said he was “ready to take Uber’s valuation to zero” before he would ever leave the helm.
Now, as Cohler and Fenton slid his death letter across the table, Kalanick wondered how long they had been plotting his demise. It was the ultimate betrayal. Kalanick was lashing out like a cornered animal. He wouldn’t take it lying down. He wouldn’t accede to their demands. He was going to fight.
Bill planned for every possible response from Travis and forced his hand. It was crazy for me to learn that a company’s investors were bitterly fighting its CEO.
Travis agreed to resign but he probably didn’t see what was coming next.
The story hit the web at just after 1:30 a.m. Eastern Time, as a push notification from the New York Times smartphone app was sent out to the home screens of hundreds of thousands of subscribers simultaneously. “Travis Kalanick resigned as chief executive of Uber after investors began revolting over legal and workplace scandals at the company,” it said. […] Back in Woodside, the members of the syndicate were all in shock. Someone had leaked the entire story to the Times. In the end, all they wanted was Kalanick’s resignation, not his embarrassment. Somehow, in the scrum of the past forty-eight hours, things had gone sideways.
Seeing the tick-tock of events on page A1, followed by an enormous graphic of Kalanick’s face shattered—like pieces of glass—across the front of the business section, was too much for him to bear. He was livid; the venture capitalists screwed him, like he always suspected they would. They made a fool out of him in front of the entire world.
Someone leaked the story to the press, and Travis’s reputation was destroyed in the press. I thought this was a real stab in the back for Travis.
And when Uber began searching for a replacement CEO, both Travis and the VC firm Benchmark pulled out all the stops to influence the decision.
She [Meg Whitman] said that an Uber under Meg Whitman meant the end of Travis Kalanick—music to Benchmark’s ears. One of Kalanick’s allies, who knew of Whitman’s hard-line stance against him, planted the leak with the press to smoke Whitman out.
the firm [Benchmark] filed a lawsuit against Travis Kalanick accusing him of defrauding Uber’s shareholders and breaching his fiduciary duty, a stunning act of open warfare between board members at a high-profile company.
Gurley’s idea in suing the former CEO was to invalidate Kalanick’s rights to those board seats entirely.
The votes [for the new CEO] kept coming in deadlocked; neither side would budge. Then, some believe, Cohler made a miscalculation. The Benchmark partner gave the table an ultimatum: If the board voted for Whitman, Benchmark would drop its lawsuit against Kalanick. It read to the room as an ultimatum. This was the price of peace. Instead of following a fair process to determine the best candidate, Benchmark was effectively holding the board hostage to approve the [replacement CEO] candidate of their choice.
Again, I couldn’t imagine that an investor would file a lawsuit against the CEO that brought them all its returns. And I didn’t think that an investor would pressure the board to vote for a specific replacement CEO, and have it backfire on them.
The book ends with Travis’s departure from Uber, and the entire story arc is gripping, especially if you’re a frequent Uber customer like I am.
Pick up the book and tell me what you thought of it, and of this book review.
Showtime made a TV series out of this book. I haven’t seen it yet. I’ll update this post when I do. If it’s anything like the book, it will be a treat.
Thanks to Kike Ibe for helping me write this post.