Dara Khosrowshahi on Leading Uber, Marketplace Trade-offs and Learning from Mistakes

Uber CEO Dara Khosrowshahi tells Harry Stebbings that his job includes making mistakes and learning from them. In this 2023 interview he discusses the family history that shaped him, joining Uber, marketplace decisions, acquisitions and leadership.

His family lost its business and wealth in Iran, but Khosrowshahi says it did not lose its sense of family. He sees the next generation’s ambition as an effort to rebuild what their parents created. Shared success with family or a team matters more to him than individual celebration.

Harry describes tying self-worth to rebuilding after loss. Khosrowshahi says his family’s focus was less on money or a final state than on the pursuit of excellence. For him, being worthy on a given day means putting in the effort, whether or not the outcome works.

After thirteen years at Expedia, he initially rejected the opportunity to lead Uber. Spotify’s Daniel Ek challenged him to think about impact: Uber was important and Khosrowshahi might make a difference. That helped him reconsider the role.

He describes Uber as a technology company whose products affect the physical world, pointing to more than five million people earning on its platform at the time of the interview. His career test is whether he can learn from the people around him, have an impact at the company and work for an organization that affects the world.

Khosrowshahi says he has had little time for introspection about the transition. The work is difficult rather than always fun, but he loves it and remains focused on learning about the business and moving ahead.

He defines senior leadership performance through sustained output, not a strong quarter or a single year. Building a team and an organization capable of performing over many years, including after the CEO leaves, is part of the test.

A leader must be willing to be misunderstood for a long time, he says. Former boss Barry Diller told him that merely agreeing with the obvious would produce average results. Khosrowshahi tries to notice groupthink, make a considered non-obvious choice and accept responsibility for its consequences.

He describes both Expedia’s technical turnaround and his work at Uber as demanding, wartime-like situations. At Expedia the team had to keep the business running while rebuilding its platform; he says he is comfortable continuing through setbacks.

Uber’s marketplace imposes natural constraints: supply and demand change by location and time. He says the company thinks about being “trip obsessed,” because a successful match must work for riders and drivers, or for diners, restaurants and couriers.

Khosrowshahi says the platform was making roughly two billion such trips in the most recent quarter and had more than five million earners. These are his figures for the interview period. He says the company’s effect on earners and cities creates responsibilities that can slow decisions but should improve long-term choices.

He agrees that long-term capital allocation matters, but says leaders must first earn the ability to invest. Near-term resource choices and the team that executes them are essential to sustaining the business over a longer horizon.

He considers Uber’s marketplace technology a successful investment. Its teams train machine-learning systems to balance supply and demand across time and geography. His claim that the investment produced significant returns is a company leader’s assessment, with no quantified return supplied here.

He sees the company’s autonomous vehicle development business and owned bikes and scooters as examples of going outside its strengths. Uber, he says, is better at connecting supply and demand than building hardware; it still had an investment in Lime, a business focused on that area.

Focusing on the core need not prevent expansion. Khosrowshahi says Uber Eats and Uber Freight began as adjacent projects but used the company’s existing skills in matching supply and demand. In his view, those investments helped redefine what became core.

Harry asks whether Uber Eats lost the lead to DoorDash. Khosrowshahi disputes that characterization globally, asserting that the two were comparable in size worldwide and predicting Uber could be more profitable because rides and delivery share a platform. The interview provides no independent data establishing those claims.

He credits DoorDash for betting early on suburbs and restaurant selection, while Uber Eats initially emphasized urban centers and fast delivery. He says the suburban market proved larger than Uber expected and that its inherited bias toward five-minute arrival times led it to make the wrong early bet.

Uber’s response, he says, was to expand suburban coverage and selection. In his example, many customers would choose 200 restaurants with a predictable 35-minute arrival over 100 restaurants in 25 minutes. This is his description of customer preference, not evidence supplied in the interview.

He calls Australia, France and Taiwan strong markets and singles out Australia for its combination of mobility, delivery and membership. These are his qualitative assessments of Uber’s business at that time.

Khosrowshahi says Uber’s acquisition of Careem was a bet on its founders and their plans for mobility, delivery and payments in the Middle East. He regards the region’s business as successful and Careem as part of that success.

He describes Postmates as a different acquisition: it helped Uber expand selection and scale on the US West Coast, particularly Los Angeles. He says the Postmates app retained loyal users while integrating the backend with Uber infrastructure reduced costs.

Asked to grade acquisitions, he names Careem and Uber Freight’s Transplace as successes or potential successes, noting the latter was still early in development. He describes the electric bike company Jump as a failure and says Uber underestimated the difficulty of combining hardware, firmware, manufacturing and shipping.

Mistakes are part of taking risk, he argues, but excuses prevent learning. He wants people to recognize errors early, take responsibility, learn and improve. He says Uber would remain focused on software for the time being while keeping an open mind about future opportunities.

He uses the distinction between one-way and two-way doors: move quickly on decisions that can be reversed, but give consequential, hard-to-reverse decisions more consideration. He also says public companies must maintain a cushion—a “budget” for mistakes—while meeting investors’ expectations for financial results.

Harry asks whether almost every acquisition can be reversed. Khosrowshahi responds that the size of a mistake and its effects on third parties matter. Even when a change can technically be undone, reversal may have substantial costs.

He says Uber moves more carefully when changing features for earners than for riders or diners because people depend on the platform for their income. An error in payment, pricing or routing can have a large effect on someone working 20 or 40 hours a week. This is the CEO’s account of the company’s approach.

For difficult decisions he often turns first to his wife, whom he calls his top adviser. He values her judgment of people and her willingness to challenge him. He also consults chair Ron Sugar, Barry Diller and others.

When assessing technical talent, he looks for people who can explain complex matters simply and share their knowledge. To him, clear explanations signal clarity of thought and generosity rather than an attempt to demonstrate superiority.

Khosrowshahi says he starts by trusting his team and giving autonomy, then expects accountability. Accountability does not mean avoiding all errors: it means taking responsibility, learning and improving. He describes himself as generally calm, though he gets angry occasionally.

Asked about marriage, he cautions that each relationship differs. What works for him and his wife, he says, is that they like spending time together as well as loving each other. He says he wants to be fully present with his children when he is with them.

Harry criticizes what he sees as generational entitlement. Khosrowshahi agrees that adversity and mistakes can help people grow and says he had sometimes been too protective as a parent, while also praising the capability and hard work of people at Uber. These are personal views, not evidence about an entire generation.

When he arrived, Uber’s board had conflicts over control. He says he wanted it focused on the company’s success, and worked with incoming chair Ron Sugar to reshape it. He considers the resulting board effective; the interview gives his perspective on that transition.

The transition also meant combining long-serving employees and newer managers. Khosrowshahi says the pandemic brought them together, but acknowledging a change from “Uber 1.0” to “Uber 2.0” was difficult for some veterans. He says the earlier company also had entrepreneurial energy, innovation and a high talent bar.

He names Isaac Asimov’s Foundation as a book that captured his imagination after arriving from Iran, and mentions The Splendid and the Vile. Asked about predecessor Travis Kalanick, he credits the talent he recruited but says damage to Uber’s corporate reputation took time to repair.

Khosrowshahi says he and Kalanick speak occasionally and that Uber works with Kalanick’s dark-kitchen business. He credits Diller for opportunities over more than twenty years and admires his continuing curiosity.

He calls the pandemic his most painful professional lesson. He says Uber lost 85% of its volume overnight while the business was already losing $2 billion, and responded with business sales and significant layoffs. He believes the period sharpened its focus and helped Uber Eats expand; the precise volume and loss definitions are not specified in the interview.

His advice to himself on the eve of becoming CEO would be to move faster. He needed to meet people and gather input, but in retrospect thinks some early decisions could have been made sooner.

Uber can still improve the clarity of decision ownership, he says. Products that operate in the physical world require input from engineering, product, operations and legal teams, making it harder to know who has the final call.

Asked where Uber and he will be in five years, Khosrowshahi says he does not know and deliberately avoids a fixed picture. He worries that a detailed forecast could make him discount contradictory evidence; he prefers to listen, read and identify unexpected signals early.

Harry thanks Khosrowshahi for the conversation, and the guest thanks him in return.