In 2010, when Uber operated only in San Francisco and only with black cars, the San Francisco Municipal Transportation Agency sent it a cease and desist order alleging that the company was violating existing transportation regulations. CEO Travis Kalanick was firm in his decision about how to respond to the cease and desist order: “We ignore it.”
Source: Mike Isaac’s Super Pumped, p.91-92
Frustrated with unreliable San Francisco taxis, Garrett Camp (later co-founder of Uber) used a “trick” of calling all major taxi services in San Francisco to ask for a pickup. He would use whichever taxi came first, meaning the rest would drive over and find no customer.
Source: Mike Isaac’s Super Pumped, p.69 (calling this “a dick move”)
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)
In the midst of a series of scandals, Uber retained former US Attorney General Eric Holder to review the company’s practices and problems. The report recommended forty-seven changes, including restructuring Uber’s board of directors, restricting alcohol and drug use at company events, and firing then SVP of business Emil Michael .
Reviewing the version of the Holder report available to the public, one compliance consultant described the findings as “one of the most remarkable discussions of a complete workplace culture disaster that has ever been rendered for a multi-billion business.” The consultant continued: “If you changed some of the business and legal language, you might well think you were reading a report on Animal House.” (quote from New Yorker)
The version available to the public (linked above) is just 13 pages long and focused on recommended improvements, but Mike Isaac’s Super Pumped (p. 324) reports that the full report was “hundreds of pages long” and listed numerous specific concerns. Isaac summarized:
It was … a winding, repetitive list of infractions that had occurred across Uber’s hundreds of global offices, including sexual assault and physical violence. The company had numerous outstanding lawsuits against it, and would likely face many more.
No one outside Uber’s Board of Directors would see the full text of the report. (Isaac p. 330)
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.
Business Insider reported that Eric Holder’s report recommended that Uber’s SVP of Business, Emil Michael, leave the company. BI noted that this recommendation was, for whatever reason, not included in the version of the Holder report available to the public. But, consistent with BI’s reporting, Michael left Uber in June 2017.
Uber CEO Travis Kalanick had been especially close to Michael. BI characterized Michael as Kalanick’s “wingman.”
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.