THE TAKEDOWN OF TRAVIS KALANICK: The untold story of Uber's infighting, backstabbing, and multi-million-dollar exit packages
Twenty-four hours before Travis Kalanick would make a snap decision that would ultimately force him out of his job, the Uber CEO was relaxing at a rented house in Malibu with several friends.
It was a Sunday afternoon and he was ready for a nap. But as his eyes began to close his phone buzzed.
"Have you seen this?" a friend asked, sending a link to a tweet by a former Uber engineer named Susan Fowler. She had written a blog post titled "Reflecting On One Very, Very Strange Year At Uber" recounting appalling allegations of sexual harassment and retaliation at the company Kalanick had cofounded.
Emil Michael, Kalanick's confidant and Uber's senior vice president of business, burst into the room, waving his phone. He had seen the post.
Kalanick didn't know who Susan Fowler was, but he knew this was a problem.
His life at Uber was about to unravel.
This is the story of how one of the most powerful people in Silicon Valley - who had built-in protections and seemed untouchable - made a series of decisions that cost him his job and ravaged his reputation all within six months.
It's also a look inside an epic boardroom battle that broke Silicon Valley's sacred rules, with investors usurping power from the board to overthrow a visionary and revered, if problematic, founder.
And it's a tale of how backstabbing, greed, mistrust, and a crisis of conscience overwhelmed insiders at the world's most valuable tech startup, with friends and colleagues turning into enemies, all using their wits to move and countermove against one another.
"What we went through in 2017 - you probably have friends who have gotten divorced, and it's, like, the relationships are gone," one insider said.
Business Insider spoke with dozens of people in Uber at all levels over the course of six months to chronicle the chaotic period that ended Kalanick's reign. The stories they shared were corroborated by testimony, documents, and text messages.
The people we spoke with credited Kalanick's wits and tenacity for Uber's spectacular rise; but they also agreed that Kalanick's downfall was largely his own doing. His fast-moving, win-at-all-costs mentality created a corporate culture that has been written about ad nauseam.
What has not been written about is Kalanick's mindset and the circumstances that drove his actions during this fateful period. Who was advising him? Who betrayed him? And what was going through his mind?
One part of what drove Kalanick to the brink was simple: He was terrified of a hashtag.
If Donald Trump had never been elected, Kalanick might still be CEO
That hashtag #deleteuber was born after the 2016 US presidential election, a few weeks after Uber's Washington, DC, policy team suggested to the head of policy and communications, Rachel Whetstone, that Kalanick join President-elect Donald Trump's business-advisory board.
Whetstone, along with others at the company, believed it would be good for Uber to have a seat at the table. Kalanick agreed and became one of a dozen CEOs to join the council, alongside JPMorgan's Jamie Dimon and General Motors' Mary Barra.
Whetstone and Kalanick have since said that was a colossal mistake.
At the time Uber was in a good place. It was operating in more than 425 cities in 72 countries, had 30 million monthly users, and was looking at ending the year with $6.6 billion in net revenues - more than double the previous year.
The company had also put some major legal and public-relations disasters behind it.
It had settled several lawsuits, including a case alleging that staffers had used a secret "God View" feature of its software to stalk a reporter and a $100 million lawsuit with drivers over their being classified as independent contractors.
Uber was also past a 2014 rape case in New Delhi, India, which resulted in Uber being banned from that city for a short time. The next year, the woman, who alleged she had been raped by an Uber driver, sued the company for $18 million. Uber hired an Indian law firm to investigate, and the company agreed to settle her case for $3 million.
"If you'd have asked me on December, 31, 2016, I'd have said, 'We're good. We've cleaned up. Everything's going to be fine,'" one former executive said.
The good feeling didn't last long. In January 2017, shortly after Trump had been sworn into office, the new US president signed an executive order barring people from seven predominantly Muslim countries, and Uber got caught in the crossfire.
Protesters stormed Kennedy Airport, and in solidarity the New York taxi union went on strike. With no cabs available, Uber and Lyft - Uber's archrival in the ride-hailing market - were swamped with ride requests. Uber tweeted it was turning off "surge pricing" (the higher fees it charges during high-demand periods) to show that it wasn't profiteering. But the move backfired: The tweet looked to many like a promotional ploy as people remembered the CEO was on Trump's business council. And #deleteuber went viral.
Kalanick called Trump's travel ban "unjust," and 48 hours later, on February 2, he quit Trump's business council - the first CEO to do so - but it was too late.
By week's end, more than 200,000 people had deleted their Uber accounts, a loss of 5% of the company's market share. Worse, they were leaping from Uber to Lyft. That week, Lyft passed Uber in the App Store for the first time.
In a snap, Uber lost "millions of dollars - easily millions of dollars," one insider told Business Insider and multiple others confirmed.
Losing business to competitors was what Kalanick feared most, and he grew determined that #deleteuber would never happen again.
"That was the beginning," a former Uber exec said.
The hashtag returns
By mid-February, #deleteuber had slowed to a trickle and Uber's top executives were exhausted. Kalanick and Michael booked their trip to Malibu for what was supposed to be a weekend of rest and recovery.
Instead, Kalanick was reading Fowler's post describing a "Game of Thrones"-style culture within in his company, where managers stabbed one another in the back and sexism and sexual harassment ran rampant - and HR didn't seem to care.
The post had been up for only a few hours by the time Kalanick saw it, but it had already gone viral. People with millions of Twitter followers, including tech-industry bigwigs and mainstream celebrities, were publicly trashing Uber.
To Kalanick's horror the #deleteuber hashtag was trending again.
At the rented house, Kalanick and Michael leaped into crisis mode with Michael calling advisers for ideas on how to tame the situation and Kalanick consulting his executives.
Whetstone helped Kalanick craft a statement, and at 3 p.m. he tweeted a promise to investigate the allegations, vowing that any Uber employee who behaved the way Fowler described would be fired. The two men worked until 3 a.m. and then hopped on a flight back to Uber's headquarters, in San Francisco.
The next day, Monday morning, Kalanick huddled with a small team at the office to plot damage control. The room included board member Arianna Huffington, company president Jeff Jones, PR chief Whetstone, and head of HR Liane Hornsey.
They spitballed ideas about how to respond to the growing PR crisis, including sharing unflattering information about Fowler during her time at the company and commenting on her harasser (who had been fired months before Fowler wrote her post).
But they quickly shelved such tactics and focused on the promised investigation. Do it in-house or hire someone? Whetstone warned against bringing in an outsider as third-party investigations could easily snowball. But Kalanick, with #deleteuber on his mind, thought an internal investigation would make Uber look like it had something to hide. He wanted an outsider.
In that case, Whetstone suggested they hire former US Attorney General Eric Holder. He had already done some work for Uber since leaving the Obama administration. Kalanick liked the idea and asked his team to get Holder on board. He didn't care how much it cost and wouldn't limit Holder's access.
"That decision was made in an instant," one person said. Within hours Holder had signed on.
Kalanick didn't realize it at the time, but he had just hired his executioner. As one former executive put it, "If you put anything under a microscope for long enough, you're going to find it moves."
A Google lawsuit and an Uber executive's $100 million severance demand
Three days later, on February 23, Waymo - the self-driving-car company spun off from Google - slapped Uber with a $2.6 billion lawsuit. The suit alleged that Google's former star engineer, Anthony Levandowski, had stolen self-driving technology from his previous employer and brought it to Uber when Uber bought his autonomous-truck startup, Otto, in a deal worth $680 million. (Google had already sued Levandowski personally.)
Google rarely sues anyone. When asked why Waymo would sue Uber, one former Googler theorized that while Google founders Larry Page and Sergey Brin are generous with their handpicked leaders (they had paid Levandowski $120 million, according to filings from the suit), they may take action if they feel betrayed.
The Waymo lawsuit unnerved Uber's board, especially Bill Gurley, whose firm, Benchmark, was Uber's largest venture-capital investor. Gurley is a Silicon Valley investing legend who has backed successful startups for decades and is known for condemning Silicon Valley's excessive ways. Gurley had bet on Uber in 2011, when the company was two years old and had 25 employees. Benchmark's stake was now worth billions and accounted for most of his firm's returns. This lawsuit threatened those billions.
On top of that, Gurley felt duped by Kalanick, who had vouched for Levandowski. Kalanick had called Levandowski a "visionary" when he argued for the Otto acquisition at an April 2016 board meeting. Not everyone liked the idea. Michael, the company's head dealmaker, hated it. He thought the price was too high.
The concerns didn't make Kalanick change his mind, but he did take some protective steps. The full payout relied on the Otto team hitting a bunch of milestones. (Uber has paid Levandowski only $100,000 to date.)
Additionally, Uber's head lawyer, Salle Yoo, authorized an investigation into Levandowski and other Otto team members, to ensure they didn't bring over any Waymo technology. This was not an unusual preacquisition legal step, one person explained. Engineers sometimes have backup files on their computers or cloud accounts, perhaps unintentionally.
But the method she chose to conduct this investigation wound up burning everyone.
A member of Yoo's team hired an outside law firm that, in turn, hired an investigator, a cybersecurity company called Stroz Friedberg. It completed its inquiry before the Otto deal closed, in August 2016, and issued a report concluding that Levandowski did possess Waymo's files - thousands of them - and that it had tried, somewhat inconclusively, to verify if he deleted them all.
Stroz Friedberg's findings should have been a major red flag, enough to kill the deal, one insider told us. But neither Kalanick nor Yoo ever read the report, nor did the board, before the Otto deal closed, several people told Business Insider.
Why they didn't read it remains a contentious issue among those involved. The ignorance was by design, according to one person close to the situation. Stroz Friedberg's report was handled by an outside lawyer to prevent anyone at Uber from discovering confidential technology from Levandowski and using that information to make business decisions.
But the net result was that Gurley and the board didn't learn about the Stroz Friedberg report until it was unearthed, months later, as part of the Waymo trial. When Gurley finally read it, in May 2017, he was incensed. Kalanick, he thought, had misled him about the entire Otto acquisition. In a deposition, Gurley testified that not disclosing the report to the board "crossed a line of violating fraud and fiduciary duty."
Kalanick was hardly any happier with the situation, and he blamed Yoo.
Salle Yoo had joined Uber as its first in-house lawyer, in 2012, when the company was just a 90-person startup, and for most of their time together they had a good relationship. But as Uber grew bigger and more complex and her team swelled to 290 people, Kalanick felt that too many legal issues were falling through the cracks with serious consequences, including lawsuits.
To Yoo, Kalanick was the problem. She felt that she was kept out of the loop on matters that could affect the company's legal risk. For instance, as part of this lawsuit, she testified that she wanted Uber to fire Levandowski long before it did and that she was excluded from critical discussions about the engineer that took place while she was on away on a trip.
On her way out the door, she asked for a $100 million severance package.
Yoo thought it was only fair; she had seen male executives ask for huge exit packages and get them. She had spent her career at Uber encouraging women to lean in.
Kalanick had no intention of agreeing to that huge sum.
Her final package, worth tens of millions, amounted to less than two-thirds of her initial demand. But it contained a kicker: If Uber gave a better severance deal to another employee, the company had to come back to her and match the difference.
Yoo's departure wouldn't become official for months. It was announced in September, after Uber had hired its new CEO. But Yoo had worked well with Gurley, and with her departure Kalanick lost his long-time head lawyer, who should have been a powerful ally.
Why Uber's head of communications Rachel Whetstone really quit
As Whetstone had warned, within weeks, Holder's investigation had started to sprawl. The board committee that Holder reported to - which included Gurley, Huffington, and David Bonderman, a founding partner of private-equity firm TPG - authorized a second law firm, Perkins Coie, to look into allegations of sexual harassment, bullying, and retaliation. Those were the original charges leveled by Fowler. The committee then tasked Holder with looking into Uber's corporate culture.
As Holder interviewed employees and combed through emails and chat records, morale inside the company went from low to "rock bottom," said one former executive: "People were confused, disappointed, angry."
Unhappy employees gossip - among themselves, with outsiders, and with journalists. Almost every day a new nightmare story about Kalanick and Uber was published.
There was a meltdown between Kalanick and an Uber driver, Fawzi Kamel, wherein the CEO was shown in a video scolding the man.
It leaked that a star Uber hire, Amit Singhal, had been fired from his former employer, Google, for failing to disclose a sexual-harassment allegation.
Vice president Ed Baker suddenly resigned amid allegations of sexual misconduct at an Uber party.
The New York Times reported that the company used a software tool known as "Greyball" to hide Uber cars from not only angry taxi drivers but also, eventually, from regulators in cities around the world.
Jeff Jones, the one-time Target CMO who had joined as president less than a year earlier, resigned soon after the Greyball revelation. On his way out he dissed the company's "beliefs and approach to leadership."
Whatever Uber's other issues, it now had a serious PR problem, and its communications leaders couldn't - or didn't want to - get the situation under control, depending on who you ask.
But it was one story in particular that caused Kalanick's inner circle to turn on one another.
In late March, tech-industry news site The Information published a story about a group of Uber executives - including Kalanick, his then girlfriend, Gabi Holzwarth, and Emil Michael - visiting a South Korean karaoke bar in 2014. That bar turned out to be more like an escort service, featuring women with numbers taped on them.
When the story came out, it included a reference to that phone call and portrayed Whetstone as being sympathetic to Holzwarth and asking her if anyone from Uber had expensed the night in the karaoke bar. The story also said that Whetstone had reported the call to the legal team, which turned the information over to Holder's investigators, citing someone "with direct knowledge of the matter."
Kalanick was not pleased. As his head of PR, he felt Whetstone was supposed to be defending the company from stories like these, not be part of them.
Whetstone had already had a reputation inside the company as being difficult to work with, becoming easily upset, or even irrational. She routinely threatened to quit, but would then cool down and change her mind. Or Kalanick talked her down and encouraged her to stay.
Kalanick indulged her at first, feeling she was a good resource for the company. But over time, he felt, she had become too much drama to deal with.
Other people at Uber saw Whetstone differently. One employee described her as "intellectually honest." Whetstone was already rich from her years at Google and wasn't under the spell of potential wealth, which drove other top players at Uber. "That made her feel like she could speak truth to power with Travis," a former executive said. "She wasn't part of the group of yes-men who would never disagree with him."
For her part, Whetstone had become disillusioned with Uber. In her role as a powerful woman in the company, she was someone who many troubled employees and other insiders felt comfortable venting to. As these people shared stories with her, Whetstone began to see Uber differently. She became angry.
She saw a company that needed to grow up, but that under Kalanick wouldn't.
Uber's defiance was baked in. It was Kalanick's greatest strength when Uber was small, but as Uber grew it became the company's greatest weakness, aided by a leadership posse who viewed new governance and controls as annoying, big-company bureaucracy.
After Whetstone's name appeared in The Information story, the increasingly smaller circle close to Kalanick saw it as evidence that Uber's real problem was its PR team.
The company's culture wasn't toxic, they reasoned, but it was perceived that way because of an endless stream of negative stories leaked to the press, while those who wrote about their positive experiences didn't get their due.
Not only was Whetstone doing a poor job of defending the company, they believed, she was riling other employees and stirring up gossip. Kalanick talked to her about these concerns. The subtext was alarming: the implication that she was somehow the source of the leaks.
Such intimations were both insulting and potentially career-ruining. A PR person found to be leaking would almost definitely never work again - even if leaking about a toxic culture would spark necessary changes and be considered the ethical thing to do.
Once again, in early April, Whetstone quit. The next day, as she had before, she changed her mind.
This time, however, Kalanick accepted her resignation. Over dinner, they amicably negotiated an exit package involving millions of dollars' worth of stock that vested over time and agreed on a face-saving explanation that kept Whetstone on as a consultant.
On April 11, her resignation was announced and Kalanick publicly praised her as she left, calling her "a force of nature, an extraordinary talent and an amazing player-coach who has built a first-class organization."
Tensions grow between Kalanick and Gurley
In the early days, when the company was tiny, Bill Gurley and Travis Kalanick worked closely together. Gurley particularly admired Kalanick's recruiting talents, like the way he could charm big names into joining the company, including President Obama's campaign manager, David Plouffe; VMware star engineer Thuan Pham; and Target CMO Jeff Jones.
Gurley pushed Kalanick to find a mentor. In 2015 he and Michael arranged for Kalanick to meet legendary CEO coach Bill Campbell, who had advised Steve Jobs and Google's Larry Page, among others. Kalanick was all in, but shortly after their first meeting, Campbell was diagnosed with cancer and stopped taking on new clients.
As the company had been without a CFO since 2015, Gurley pressed Kalanick to hire a new one, someone qualified to run a multibillion-dollar company, arguing this person could be like a mentor. A strong CFO creates internal controls that would detect "the red flags that allow the company to understand when there are problems," as one person described. Other execs - among them Salle Yoo - echoed Gurley's urging for a CFO, "year after year, month after month," one person described. The suggestion fell on deaf ears.
As Uber grew, Gurley and Kalanick began to disagree on a number of issues. Gurley was cautious. He wanted Kalanick to stop burning so much money, taper off the growth plans, and increase the bottom line.
Kalanick, meanwhile, began to see Gurley as a drama-filled drag, perpetually appearing on CNBC to whine about a possible tech bubble. He pushed communications with Gurley off to his wingman, Michael; it was a cold-shoulder strategy Kalanick had used with others, including Whetstone, when he felt he didn't need them anymore.
As the troubles of 2017 piled up - the Fowler uproar, Waymo, Uber's leasing business racking up $1 billion in losses (something a CFO might have prevented) - Gurley went from worried to frightened.
"Travis was a wild card," one person close to the situation said. "Something in him needs to break the rules, be a contrarian, even when it's against his own interest. The board felt they couldn't trust him."
Gurley feared Uber was the next Zenefits or, worse, another Theranos, and if he didn't fix it immediately, Uber's value could plummet to zero.
One woman's email pushed Gurley over the edge
In late April, Gurley, who had been texting with Michael nearly every day to stay in the loop, abruptly stopped. His brief explanation was that their relationship had changed.
Gurley was by that time under siege himself, spending 80 hours a week on Uber, daily from 5 a.m. to midnight - board meetings, special sessions, paperwork, powwows with investors. The press was hounding him, too, so much so that in April he changed his phone number.
Gurley began telling his poker buddies that he was a wreck over Uber's culture and the growing number of lawsuits and government investigations that came as a result of issues like Greyball being revealed in the press. He had trouble sleeping. He gained weight. He took up yoga.
It wasn't just Gurley's own money that was on the line. His Benchmark partners, who all hold equal stakes in the firm's investments, were also concerned, as were Benchmark's limited liability partners - the groups who bankroll a venture-capital fund so that it can invest in startups like Uber. They were reading the negative news reports and freaking out about their money too.
And then there were other investment firms that had followed Gurley's lead and poured billions into Uber. The company had raised an unprecedented $15 billion by mid-2016.
Gurley, as a Valley investment legend, knew all of them, and they were calling him demanding he get Uber's culture under control and protect their hides.
That was easier said than done. Kalanick, like many tech founders, had ensured that as his company grew he maintained control. He didn't have absolute power, but it was close. "It didn't start that way and it never fully got there, but, almost in a Frankenstein way, there were these things levered on along the way," one person described.
For instance, Uber's early employees and early-stage investors had shares with super voting rights (that is, 10 votes for every share), but all later-stage investors and employees had no votes at all per share. Kalanick was one of the largest holders of super voting shares. Between a combination of bylaws and loyalties, Kalanick also controlled enough board seats to make it extremely hard for the board to fire him as CEO.
It was from Katrina Lake, CEO of the apparel-shopping service Stitch Fix, one of Benchmark's other highly successful portfolio companies.
Lake lambasted Gurley for not doing enough to fix Uber. She accused him of shirking his responsibility to make Silicon Valley a better place.
Gurley realized that Benchmark was in a lose-lose situation. The firm's reputation with other tech entrepreneurs would be hurt if he orchestrated a revolt against Kalanick. But it would also suffer if Benchmark appeared to do nothing.
He made a choice: Kalanick had to go, and if the board wouldn't - or couldn't - do it, he'd find another way.
The full Holder report: loaded with allegations
The spring of 2017 dealt Kalanick another painful blow. On May 27, his mother was killed in a boating accident and his father was badly injured.
Despite the infighting, all of Uber's board members and investors reached out to offer condolences.
Except one.
Kalanick heard nothing from Gurley, not even when he saw him for an in-person meeting. It was a bad sign.
A couple of days later, Levandowski pleaded the Fifth Amendment in the Waymo trial and refused to defend Uber. Visionary or not, Kalanick bowed to pressure and fired him.
The press was now publicly speculating about whether Kalanick would be fired, too.
Days after that, on June 6, the results of the Perkins Coie sexual-harassment investigation were revealed. The firm had looked into 215 claims of harassment and other bad behaviors.
Following the report, 20 people were fired, five of them over sexual-harassment allegations. The others were terminated for things like bullying coworkers and retaliating against those who had made complaints to HR.
Kalanick saw the results as a net win for Uber and told his employees so. Out of 15,000 people in the company, only a handful were bad apples and all of them were now gone. That, he pointed out, was a very low percentage, which showed that Uber was largely not a terrible place to work. And no sexual-harassment allegations were ever leveled at Kalanick himself.
Holder's report was presented to the board a few days later. It included a long list of complaints employees had lodged during the investigation into Uber's culture, many of them uncorroborated. The board agreed the full report would remain under lock and key, no copies made, to keep it from leaking to the press. The only way to read it was in law firm's office, under supervision.
Holder's report also contained a list of recommendations for changing the company's culture. First on the list was to reduce Kalanick's responsibilities by hiring a COO, something Kalanick had been trying to do for months anyway.
Samantha Lee/Business InsiderKalanick and Michael.The second recommendation, however, was never publicly revealed.
"It was that Michael should leave the company," a person with knowledge of the matter told Business Insider.
On June 12, Uber announced Michael's departure. His name had been mentioned in some of Uber's scandals over the years and in some of the bad press in 2017, like one involving a second lawsuit over that India rape case. That proved to be unfair, and Michael's name was dropped from the suit accordingly.
Still, according to one person, forcing him to resign was symbolic, a sign that Kalanick did not have an iron grip on the company anymore and couldn't protect his closest allies. The most trusted confidant in Kalanick's ever-smaller circle was now gone. There were very few executives left at Uber who still had Kalanick's back.
On June 13, Uber told its employees and the public about Holder's recommendations for changing its culture. And, with the investigation completed, Kalanick announced he was taking a leave of absence to grieve.
And Gurley was ready to make his move.
Cornered in a Chicago hotel room
Despite going on leave, Kalanick didn't completely stop working. He was still trying to hire a COO.
On June 21, Kalanick held a meeting with a COO candidate and the conversation ran long. The candidate had to fly to Chicago, so Kalanick booked a ticket and flew with him, finishing the interview on the way.
While Kalanick was in his Chicago hotel room, Gurley's partners at Benchmark, Matt Cohler and Peter Fenton, contacted Kalanick, wanting an immediate meeting. Kalanick told them he was in Chicago. They flew there, went to his hotel room, and handed him a letter.
It said that a group of investors were demanding Kalanick's resignation.
The letter gave Kalanick three hours to decide. If he refused to resign, the group would launch a PR campaign against him: more negative press, more #deleteuber.
Kalanick felt like he had no choice.
He negotiated for more time and talked to several people about his options. But he was also physically tired and, having just buried his mother, emotionally exhausted from grief. The famously combative CEO had finally run out of fight.
That evening Kalanick signed the letter. He was no longer the CEO of Uber, the company he loved, that had been his life for the better part of a decade.
Gurley also resigned from the board. He, too, was exhausted.
Gurley also knew that being involved in an investor revolt had burned some bridges with the rest of the board members. Kalanick, who was still a major shareholder, was still on the board, too.
Benchmark's Matt Cohler, who had been friends with Kalanick for years before the Chicago meeting, took Gurley's seat.
But the fight wasn't over.
Benchmark files an unprecedented lawsuit
The board now had the major task of hiring a new CEO.
Stories that Kalanick was hampering the search with the hope of getting himself reinstated began to appear in the press.
These reports angered and hurt Kalanick, who had not only been forced out of his job but felt he was doing everything he could as a board member to find a great replacement.
"Name one thing I did to block the CEO search?" he was heard saying to people.
A revolt was also brewing among the cabal of executives who were running the company now that there was no CEO and no COO.
On July 22, this 16-person management team sent a letter to Uber's board. In it they complained that Kalanick was interfering with their work and demanded relief. Not all of them agreed with the letter, one person said. Some even thought that Kalanick was just trying to be helpful in his own way. But it was signed by "the executive leadership team" representing all of them. This was the second letter the board received from complaining executives. The first one was signed by six of them just before Kalanick had taken his leave.
Benchmark was now convinced that Kalanick was plotting his return and had to be stopped.
On August 10, while Kalanick was on a flight to Seattle to interview Expedia CEO Dara Khosrowshahi for Uber's CEO job, Benchmark filed a suit against him. It accused him of committing fraud over two board seats he controlled and argued that he should be kicked off Uber's board.
The suit shocked the Valley: A VC suing a founder after forcing him to resign was unheard of.
The press was once again feasting, and Kalanick felt duped. He thought by resigning as Benchmark had demanded, he would be avoiding more bad PR for himself and Uber.
Kalanick spent the day at his hotel talking to lawyers. He eventually called Khosrowshahi at 10:30 p.m. and Khosrowshahi agreed to a late-night meeting. It went well and Khosrowshahi decided to pursue the job.
But Kalanick was backing another candidate, former GE CEO Jeff Immelt. And Benchmark had its own candidate, Meg Whitman.
That meant things would get ugly, again.
Strong words in the boardroom
When the board met later, in August, to make its final CEO choice, Immelt quickly learned that he didn't have the votes to be appointed and bowed out.
The board was evenly split between Whitman and Khosrowshahi. They spent two grueling days locked in a room debating the two choices and taking anonymous straw votes.
That idea didn't go over well. Some board members pointed out that if such a damaging suit wasn't absolutely necessary, it should be dropped, and it definitely shouldn't be used as leverage for the CEO vote. Kalanick argued to the board that this was proof that Benchmark's tactics were nothing more than trying to bully people - not just him but the board as well.
Whether that clinched it for Khosrowshahi is a source of controversy among those with knowledge of the situation. But he soon picked up enough straw votes to win.
When the board cast an official on-the-record vote, everyone, even Benchmark, unanimously voted Khosrowshahi in. No one wanted to go on the record as opposing the new CEO from the get-go.
Still, hiring a new CEO wasn't enough for Benchmark and the Uber executives and investors supporting it. Benchmark wanted changes to the stock structure and bylaws to ensure Kalanick could not undermine Khosrowshahi and orchestrate a comeback. As VCs, they had seen such shenanigans before.
"Ninety percent of ousted founders detest the new CEO and try to run them out," one person with knowledge of Benchmark's thinking told Business Insider.
The deal that ended the feud
As he took over the reins of Uber, Khosrowshahi needed to put an end to the drama and dysfunction that had torn the company apart, and he quickly saw his chance.
Kalanick had been angling for months to take on new investment from Japanese tech giant Softbank, which, through its $100 billion Vision Fund, was pumping billions of dollars into hot startups and putting its enormous global power behind those companies.
Softbank had been investing in ride hailing all over the globe and wanted a piece of Uber. But it threatened to throw its weight behind Lyft if an Uber deal didn't materialize - something Kalanick dreaded.
So Khosrowshahi brokered a compromise: As part of the Softbank investment Kalanick wanted, Benchmark would get the governance changes it sought.
In January, when Softbank closed on a 15% stake in Uber, the super voting shares were eliminated (every share now gets one vote) and four new seats were added to the board to dilute Kalanick's control.
A happyish ending for all
When you ask insiders what led to Travis Kalanick's downfall, there are a few things everyone agrees on.
Uber grew too quickly, from 6,700 employees in December 2016 to 15,000 by June 2017, and devolved into chaos before proper HR procedures and seasoned executives could be put in place.
Most blame Kalanick for this, saying he was more focused on world domination than seemingly mundane, operational details.
And the long-term fallout from the feud remains to be seen. Tensions are still high between many former Uber execs.
And it's unclear how the reputational consequences for Benchmark will shake out. By leading a coup against a founder, Benchmark broke a sacred Silicon Valley rule about how it treats the founders it backs, and set a dangerous precedent for other investors and boards.
Although Uber is rehabilitating its public image, it still needs to win in the cutthroat ride-hailing business and do it without a visionary, if problematic, founder at the helm.
Still, for now the storm has passed.
It's been a year since Susan Fowler's blog post and nine months since Kalanick resigned as CEO. Fowler has sold her story for a forthcoming book and movie.
Benchmark sold $900 million in shares to Softbank and got a commitment that Uber would go public by 2019, giving it a path to collect on its billions.
After Kalanick's power was reduced, Benchmark agreed to drop its lawsuit against him.
Whetstone is a vice president of communications at Facebook, and as influential as ever.
Gurley is talking to the press again, sleeping well, and happy.
Kalanick went from a jobless paper billionaire to an actual cash billionaire after he sold $1.4 billion worth of his shares to Softbank. He just announced he is setting up a charitable foundation and investment fund. He remains on Uber's board and still has a huge stake in the company.
And he's now focused on life after Uber.
While he feels that 2017's unrelenting bad PR unfairly villainized Uber, and that the company remains misunderstood, the gut-wrenching ride forced Kalanick to do a lot of reflecting.
"In 2013 Travis was hotheaded," one person described. "By 2017 he was a gentle, diplomatic giant compared to what he was. He's a growing, learning human being."