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Tensions between Kalanick and mega-investor Bill Gurley

Benchmark Capital general partner Bill Gurley and Travis Kalanick started off thinking highly of each other and working closely, but their relationship deteriorated. Business Insider offers details:

Initially, Gurley saw Kalanick as young and inexperienced, needing guidance and not always listening to advice. Gurley pressed Kalanick to find a mentor and hire an experienced CFO. Later, Gurley wanted Kalanick to stop losing so much money, reduce growth plans, and increase profits.

BI describes Kalanick’s response:

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.

Eventually, Gurley worried that his investment in Uber could be worthless. Worried about Uber’s culture and the many lawsuits and government investigations, he said he had trouble sleeping; he gained weight and took up yoga. His concerns reflected worries about both his own investment and funds from Benchmark’s other partners and investors.

See also Mike Isaac’s Super Pumped (p. 160-161), reporting Kalanick calling Gurley “chicken little” for his supposedly-unfounded concerns.

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Kalanick criticized SVP Whetstone for reporting escort bar visit to investigators

After Uber then-CEO Travis Kalanick and colleagues visited an escort bar and tried to cover it up when asked, one person who had been there contacted Rachel Whetstone, then Uber’s senior vice-president of communications and public policy, seeking guidance. Whetstone in turn reported the matter to Uber’s attorneys, who turned it over to Eric Holder, who was at the time investigating possible improprieties at Uber.

Business Insider described Kalanick’s response:

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.

BI continued, explaining how some at Uber saw Whetstone as “difficult to work with … or even irrational,” but others saw her “speaking truth to power”:

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.

Ultimately Whetstone resigned and Kalanick accepted her resignation. BI reports that Whetstone’s exit package included millions of dollars worth of stock as well as keeping Whetstone on as a consultant to save face.

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Jeff Jones quit, citing differences over “beliefs and approach to leadership”

Jeff Jones quit Uber in March 2017 after less than a year as President of the company. He explained his departure in a statement:

It is now clear, however, that the beliefs and approach to leadership that have guided my career are inconsistent with what I saw and experienced at Uber, and I can no longer continue as president.

Jones had previously served as the Chief Marketing Officer at Target.

Commenting on Jones’ departure, then-CEO Travis Kalanick remarked that “It is unfortunate that [Jones’ departure] was announced through the press.”

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VP of Product and Growth Ed Baker resigned

Ed Baker, who served as Uber’s VP of Product and Growth, resigned after more than three years at Uber. Others at Uber had complained about his behavior. Recode explained:

For example, one person anonymously tipped off board member Arianna Huffington — who is one of the people conducting a wider-ranging investigation into sexism and sexual harassment at the company — via an email that Baker had engaged in a sexual encounter with another employee.

Specifically, said sources, Baker was seen “making out” at an internal Uber event held in Miami three years ago, which was seen by some employees. There was no suggestion of any sexual harassment on his part and the encounter was apparently consensual.

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Fired SVP of Engineering Amit Sighal over allegations of sexual harassment

Amit Sighal joined Uber in January 2017 as SVP of Engineering. The next month, Uber asked him to leave. The stated reason was that he reportedly failed to disclose to Uber a “credible” sexual harassment allegation made against him while at Google.

Sighal had previously worked at Google where he was a “Google Fellow” (a prestigious and limited position) and served as the head of Google’s core search ranking team. Some speculated that he left Google due to the same sexual harassment allegation that caused concern at Uber.

Details from Quartz

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Morale dropped during Holder investigation

Business Insider reports that as Eric Holder investigated activities at Uber, employee morale dropped. His investigation included interviewing employees and reading through emails and chat records. BI says morale was “went from low to ‘rock bottom'” quoting one former executive, who added that “People were confused, disappointed, angry.”

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Salle Yoo demanded $100 million when leaving Uber, got most of it

Business Insider reports that when then-General Counsel Salle Yoo prepared to leave Uber, she sought a $100 million severance package, entailing the repurchase of her Uber shares. Travis Kalanick thought that amount was excessive, but BI says the final amount was “tens of millions” although less than 2/3 of her requested amount.

BI reported Yoo grounding her demand in thoughts about gender:

Yoo thought it was only fair because 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. So she took her own advice, opened her negotiations with Kalanick by shooting high and held her breath.

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Salle Yoo questioned Kalanick’s handling of Levandowski

In addition to insisting that Uber hire outside investigators to check what improper information Otto held, then-General Counsel Salle Yoo questioned other aspects of Kalanick’s handling of that acquisition. Business Insider explains that she said she wanted Uber to fire Levandowski long before the company did so, and also that she was excluded from critical discussions about Levandowski. Business Insider reports that these disagreements led to Yoo’s departure from Uber.

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Company leaders did not read report about confidential material held by Otto

Uber then-General Counsel Salle Yoo had insisted that Uber hire outside investigators to check for confidential information improperly held by Otto, before Uber acquired Otto. The resulting report revealed that Otto CEO Anthony Levandowski had copied Google information. But Uber leaders never saw the report because it was sent to outside counsel. Instead, they learned about the report only incidental to Google’s litigation against Uber alleging theft of Google secrets.

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