Shervin Pishevar on Uber, Venture Capital and a Disputed Leadership Crisis

Investor Shervin Pishevar recounts his early investment in Uber and his role as an adviser to Travis Kalanick. In this January 2025 conversation with Harry Stebbings, he also offers a sharply contested account of Uber’s 2017 leadership crisis. Pishevar was an investor, adviser and participant in related litigation; his allegations and interpretations are his own and are not independently established by this interview.

Pishevar begins by remembering his mother, who had recently died. He says she taught in Iran, worked multiple jobs after the family came to the United States, brought him to computer classes and helped buy his first computer. He calls her his first angel investor.

He started his first company while finishing college and working nights as a security guard. He recalls recruiting young developers and later using his sense for talent to identify founders he thought were exceptional.

Pishevar says Sheryl Sandberg mentored him and encouraged him to enter venture capital, introducing him to firms. He joined Menlo Ventures after working as an entrepreneur and angel investor, and recalls early investments including Uber, Warby Parker and Tumblr.

He had pursued a meeting with Kalanick after trying Uber in San Francisco. Pishevar says his father’s experience as a taxi driver helped him understand the market, while introductions from mutual contacts eventually led to a meeting as Uber prepared its Series B.

Pishevar recalls initially losing the deal to another firm. He told Kalanick he remained available if circumstances changed; when Kalanick called from Ireland, he flew to meet him. His lesson is to show up and maintain a relationship even after an initial rejection.

In Dublin, Pishevar says, Kalanick described an ambition to replace car ownership rather than merely compete with taxi and black-car services. That enlarged Pishevar’s view of the potential market and convinced him to offer a term sheet.

He recalls offering a $290 million valuation, briefly raising it to $300 million while awaiting an answer, and Kalanick accepting the earlier figure. He describes a $20 million investment and later secondary exposure. His present-value estimates are his own recollections and depend on holdings, dates and prices.

After about 18 months at Menlo, Pishevar says he negotiated deal-by-deal carry and became an adviser before starting Sherpa Capital. He also says he sold Facebook shares and bought Uber shares personally, leaving himself heavily exposed to that investment.

As a strategic adviser and board observer, he admired Kalanick’s intelligence and drive. He tells a story about a mental mathematics challenge at a party as an example. His praise reflects a close personal and financial relationship, not an independent assessment of leadership.

Asked about criticism of Uber’s hard-driving culture, Pishevar says he thought the culture was excellent and that building quickly required intensity. This is his perspective as an ally; the interview does not independently resolve employees’ differing experiences or the workplace concerns discussed later.

He thinks Uber should have responded more quickly to Lyft’s early service. In his account, Kalanick initially sought action from local authorities instead of immediately launching an equivalent product, giving Lyft time to grow. His attribution of later market share to that delay is a counterfactual judgment.

Pishevar says he helped recruit Emil Michael as Kalanick’s senior business partner. Michael initially chose another role; a later encounter during an Asia trip revived the discussion. Pishevar credits him with a major role in fundraising and expansion.

He recalls introducing Kalanick to TPG’s David Bonderman and Jim Coulter and traveling in Asia with them. Pishevar describes an introduction to Baidu that led toward Uber’s China venture. These are his recollections of a complex set of relationships and transactions.

He says competing in China cost substantial money but thought the size of the market justified the effort. He reports that Sherpa invested in Uber China and later in Didi after the businesses combined; those financial interests are relevant to his evaluation.

Pishevar describes using special-purpose vehicles and co-investment to bring additional capital into Uber. He also recounts a financing structure he calls Waverly loans in connection with secondary shares and TPG. The conversation is his account, not advice on tax or transaction structure.

On later fundraising, he describes Michael creating a competitive process among investors and recalls a valuation increase between rounds. He believes large amounts of capital were necessary to subsidize a global marketplace of drivers and riders.

For city launches, Pishevar says he brought celebrities into the investor base and enlisted well-known people as early riders. He recalls Edward Norton participating in the Los Angeles launch and says the approach was adapted in other markets.

Pishevar says the operating business was still growing when board conflict intensified. He attributes the crisis to investor Bill Gurley and Benchmark, arguing that they wanted an earlier public offering. This is the account of a participant who opposed them; the interview does not present Benchmark’s response or independently establish motives.

He alleges that Gurley hired private investigators and held meetings aimed at removing Kalanick. The interview provides no independent evidence or response from Gurley to assess those allegations. They should not be treated as established fact.

The discussion turns to engineer Susan Fowler’s public account of workplace harassment. Pishevar describes her experience and says Uber then commissioned an independent workplace investigation. His characterization is not a substitute for the underlying allegations, the investigation’s full findings or responses from those involved.

Pishevar says he viewed the proposed investigation as a potential trap and argues that an investigation could be misused. He also claims its report did not find wrongdoing by him or Kalanick. Those are his interpretations and claims; the interview does not supply the complete report or establish that workplace concerns were unfounded.

He recounts Kalanick’s mother’s death in a boating accident and says investors subsequently asked Kalanick to resign as CEO. Pishevar alleges they exploited a vulnerable moment. The interview does not establish their intent or offer the investors’ account.

Pishevar says the investors presented a letter and threatened to release it if Kalanick did not step down. He regrets the outcome and contrasts it with employees rallying around Sam Altman during a later OpenAI leadership dispute. The situations are not equivalent merely because he draws the comparison.

He says Benchmark later brought a Delaware lawsuit concerning Kalanick’s board seats and describes his own legal response. He claims a judge rejected an effort to remove the seats. The interview does not provide the court documents or full procedural history, so this is his account of the litigation.

Pishevar alleges that a public-relations firm and others circulated a fabricated London police report about him after the Uber dispute. He denies the accusations he says followed and describes pursuing discovery in US courts. The interview does not independently establish who commissioned any activity, the truth of all allegations, or the outcome of each legal proceeding.

He says he obtained communications and a police response that supported his position, and says later anonymous accusations also appeared. Those are his claims. The interview does not present the complainants’ accounts or establish that the separate accusations were false.

Pishevar describes organizing shareholders to challenge Benchmark and exploring a purchase of its stake. He says conversations with SoftBank had already begun before the leadership change and describes the later investment as part of the broader struggle.

He believes Uber would have been worth $1 trillion by the interview date had Kalanick and Michael stayed. He credits subsequent CEO Dara Khosrowshahi with stabilizing and growing the company, but favors the earlier leaders’ potential. The trillion-dollar valuation is an unverifiable counterfactual, not a financial result.

Stebbings asks whether a desire to return capital to investors could justify the board’s actions. Pishevar says no and argues that investors could have waited longer. His estimate of the value of waiting relies on the same hypothetical valuation, not an observed return.

He suggests Google’s own strategic interests and a dispute involving autonomous-driving technology affected its posture toward Uber. These are his interpretations of other parties’ motivations; the interview does not establish that account.

Asked whether the timing of the leadership change was deliberate, Pishevar says the accident was not planned but alleges that investors took advantage of it as part of a broader strategy. That allegation is disputed and unverified in the interview.

Pishevar says he spent millions on investigators and legal proceedings concerning the allegations against him. He describes a pending appeal over discovery from a firm and says he could not publicly identify who he believed hired it. The interview establishes neither a final outcome nor the identity or conduct of any alleged client.

He alleges similar conduct occurred in other venture disputes and argues that investors should be more transparent with founders. The specific accusations about other people and firms are his claims, not findings independently established here.

Looking at venture capital more broadly, he remembers an earlier period of close founder relationships and argues that later capital inflows encouraged excessive valuations. He cites WeWork as a business model he personally declined to fund.

He predicts that self-funded companies, alternative financing and tokenization could change venture capital and broaden access to early-stage investing. Those are views about possible future structures; the interview does not establish regulatory changes or investment outcomes.

Pishevar says liquidity has been difficult for fund investors and links the period to policy and limited exits. He publicly supported Donald Trump and describes his optimism about the incoming administration’s technology and economic policies. These are partisan views and predictions from the time of recording.

He favors privatizing parts of government and says he has invested for years in quantum computing. He expects quantum and AI to advance together. His technology thesis is also relevant to his investment interests.

On Chinese electric vehicles, he discusses subsidies, tariffs and domestic manufacturing, while Stebbings questions how to weigh competition against state support. Their statements are opinions and examples, not a complete assessment of the industry or policy.

Pishevar endorses an estimate of very large AI investment and annual value creation. The numbers are speculative projections presented in conversation, not established returns. He advises smaller funds to cultivate genuine founder relationships rather than compete only on check size.

He predicts quantum computing and AI could eventually help solve hard scientific problems, and speculates about cures for all diseases and dramatically longer lives. These are extraordinary, unverified predictions, not medical evidence or a basis for treatment decisions.

In quick-fire questions, he says he made a few hundred million dollars from Uber and criticizes Steve Ballmer’s tenure at Microsoft while praising Satya Nadella. The financial figure is self-reported and the leadership comparison is his opinion.

He describes becoming a grandfather as a profound change in his life. He also says a small investment in Chris Sacca’s Lowercase fund produced a large return; the amounts are his recollection, not an independently verified fund statement.

Pishevar recounts investing in SpaceX through secondary shares and predicts it could become a trillion-dollar company. He discloses a personal investment and friendship with Elon Musk; the valuation is a forecast made in the interview.

He discusses network states and new cities, a movement in which he says he is involved, and predicts that new jurisdictions will emerge. His involvement is relevant to the enthusiasm of the prediction, which remains speculative.

He regrets missing Pinterest and says Menlo passed on Snapchat after he brought it to the firm. In his view, meeting Pinterest’s founder in person might have changed his judgment. That is a retrospective counterfactual, not a claim about what an investment would have earned.

Asked about funds, he praises 1789, where he says a friend is involved, and criticizes Benchmark. He says the Uber conflict ended friendships. His assessments reflect personal relationships and a long-running dispute.

Looking back, Pishevar says he might have sought more visible employee support for Kalanick. He alleges that other individuals were persuaded to oppose the former CEO, and describes the resulting broken friendships. The interview does not independently establish their motives.

He describes loyalty as both a source of professional success and personal pain. Pishevar closes by saying founders know he will support them in difficult situations, an expression of the value he believes he brings as an investor.