Travis Kalanick, Uber’s co-founder and CEO (until 2017)
After the collapse and bankruptcy of his Scour business, Travis Kalanick envisioned what he called his “revenue business,” designed to get back at the audio and video trade associations that sued his investors and destroyed Scour.
Source: Mike Isaac’s Super Pumped pp.52
After dropping out of college, Travis Kalanick started a company called Scour, which helped users find online files to download. Scour was primarily used to help download illegal files. Mike Isaac’s Super Pumped reports: “Soon, Scour was competing head-to-head with Napster for file-sharing dominance.” Later, Scour’s investors announced being “uncomfortable” with “the copyright implications” of Scour’s business, leading the company to be sold for parts in bankruptcy court. (pp.45-49)
Mike Isaac’s Super Pumped describes a large party Uber hosted for employees — where company leaders anticipated such problematic behavior that they had sharp guidance for employees:
[Kalanick] went on to advise his staff not to throw large kegs off of tall buildings, and mandate no interoffice sex unless coworkers explicitly stated “YES! I will have sex with you” to one another. He also noted that ny puking on hotel grounds would result in a $200 fine. The email set the tone for the rest of the retreat.
(p.23)
Then-CEO Travis Kalanick was indicted in South Korea in December 2014 for violating that country’s transportation law. South Korea’s Ministry of Land, Infrastructure and Transport said that Uber’s provision of paid transportation using unregistered vehicles was “clearly illegal activity,” and that this was the basis of the indictment.
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.
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.
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.
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.
Loooking back at an outside investigator’s report that Uber managers did not receive, Kalanick blamed then-General Counsel Salle Yoo, suggesting that too many legal issues were falling through the cracks of her team.
Planning a response to reports of sexual harassment by employee Susan Fowler, Travis Kalanick and colleagues considered releasing unflattering information about Fowler during her time at Uber. They ultimately did not do so.