20VC Uber CEO, Dara Khosrowshahi on Why Uber Eats is Not Losing the Fight to Doordash Uber's M&A Strategy; A Scorecard Analysis from Careem to Postmates & Skip Why Uber's Investment in Scooters was a Mistake Secret to Marriage, Parenting & High Per

In a candid conversation with Harry Stebbings on the 20vc podcast, Uber CEO Dara Khosrowshahi reflects on his leadership journey, the challenges during his tenure, and the strategic decisions shaping Uber's global presence. Khosrowshahi discusses Uber's competitive stance with DoorDash, emphasizing Uber Eats' global scale and lessons learned in the US market. He credits previous CEO Travis Kalanick for setting a high talent bar but acknowledges the need to rebuild Uber's brand. Khosrowshahi also touches on the impact of the pandemic, which led to tough but transformative decisions for the company. Throughout the discussion, he underscores the importance of resilience, adaptability, and maintaining a balance between embracing risk and learning from failures. Additionally, Khosrowshahi shares personal insights, revealing how his family's history and his wife's perspective influence his approach to business and life.

• Uber operates with a wartime mentality, facing challenges daily.
• Uber Eats is on par with DoorDash globally, indicating a strong market position.
• The company has learned from its experiences in the U.S. and plans to adapt its operations accordingly.

"Uber definitely has been wartime. Like it's wartime every day. I think the first thing we haven't lost a lead Uber eats is actually as big as Doordash on a global basis."

This quote emphasizes the competitive nature of Uber's business and their significant presence in the food delivery sector, matching DoorDash's scale on a global level.

• Dara Khosrowshahi has been the CEO of Uber since 2017, managing the business in over 70 countries.
• Previously, he was the CEO of Expedia and CFO of IAC Travel.
• Dara is on the board of directors for Expedia and Catalyst.org and was on the board of the New York Times.

"Dara was previously CEO of Expedia, which he grew into one of the world's largest online travel companies."

This quote outlines Dara's previous leadership role at Expedia, highlighting his experience in managing and growing a major online company.

• Dara's family lost their business in Iran, which has fueled a collective ambition to rebuild and achieve success.
• The loss strengthened family bonds and instilled a sense of shared success rather than individual triumphs.
• Dara attributes his family's influence on his perspective of success, emphasizing joint achievements.

"You've got a next generation that is incredibly passionate and ambitious... for me, success is joint success. It's shared success."

Dara reflects on how his family's past and the drive to rebuild what was lost have shaped his and his family's approach to ambition and success, valuing collective achievements over individual ones.

• Dara's family values the pursuit of excellence over material worthiness or rebuilding wealth.
• Hard work and diligence on a daily basis are the measures of worthiness for Dara.
• The pursuit of excellence is a continuous process, not focused on an end state.

"But for us, being worthy is not about an end state. It's about going all in, putting in the effort, being diligent, working hard, and that's what drives."

This quote captures Dara's belief that worthiness is derived from the consistent pursuit of excellence and effort, rather than reaching a specific goal or restoring past wealth.

• Dara was initially hesitant to join Uber but was convinced by the potential impact he could have on the company and society.
• He was encouraged to consider the opportunity to lead Uber due to its significance in the tech industry and the real-world implications of its technology.
• Dara advises considering who you work with, the impact you can have, and the company's impact on the world when making career decisions.

"And Uber is a truly important company in our society... I can make a difference, and it's an important company. So I jumped at the opportunity."

Dara explains his thought process behind accepting the role at Uber, where he was motivated by the significant influence he could have on a company that has a considerable impact on society.

• Dara has not had much time for introspection since joining Uber, being focused on the company and its opportunities.
• He believes that learning about oneself comes with time and is not his immediate priority.

"Right now, I'm just learning about the company, about the opportunity, and just going as hard and fast as I can."

This quote emphasizes Dara's commitment to understanding and growing Uber, putting personal reflection on hold while he concentrates on the company's needs.

• High performance for leaders is measured by sustained results over time, not just short-term achievements.
• Dara believes that the true test of a CEO's performance is how the company does after they leave.
• He values building a strong team and maintaining long-term excellence.

"High performance in a particular quarter any year. But to me, high performances sustain excellence over a long period of time."

This quote defines Dara's perspective on leadership performance, focusing on consistency and long-term results rather than immediate success.

• Leaders must be willing to endure being misunderstood and maintain their course despite criticism.
• Dara values unique, non-obvious decisions and is comfortable going against the grain if it means doing his job effectively.

"As a leader, you have to be willing to bust out of the obvious, do something nonobvious, different, surprising, and then stick to that decision."

Dara discusses the importance of making bold decisions and standing by them, even when they are not immediately understood or accepted by others.## Groupthink and Discomfort with Consensus

• Dara Khosrowshahi expresses discomfort when his opinions align with the majority, as it suggests potential groupthink.
• He prefers to seek opportunities in disagreement or contrarian views.

So, actually, if I agree with everyone, it makes me distinctly uncomfortable.

Dara suggests that agreeing with everyone makes him uneasy, which implies he values independent thinking and the avoidance of groupthink.

• Dara Khosrowshahi describes his experiences at Expedia and Uber as 'wartime', indicating periods of significant challenges and turnarounds.
• He feels comfortable in difficult situations and doesn't take setbacks too seriously, which is indicative of his resilience.

Now, it was wartime, not in the public eye. And then Uber definitely has been wartime, like it's wartime every day.

Dara refers to his leadership experiences, particularly at Uber, as being akin to 'wartime', emphasizing the constant challenges and high-pressure environment.

• Khosrowshahi acknowledges the presence of numerous constraints in business, which he believes makes the business interesting.
• He discusses the unique challenges of operating a marketplace business, such as the real-time variability of supply and demand.
• The focus at Uber is on being 'trip obsessed', which is about matching supply and demand to satisfy all parties involved.
• He also highlights the responsibility Uber has due to its significant impact on transportation and earning power for millions.

Tons of constraints. And I think it's what makes the business interesting.

Dara acknowledges that constraints are inherent in business and contribute to making it interesting, particularly in the context of Uber's marketplace dynamics.

• Khosrowshahi agrees that CEOs need to be good at capital allocation for long-term success.
• He emphasizes the importance of earning the right to invest capital by managing resources effectively in the short term.
• Tactical resource allocation and having the right team to execute plans are crucial in the short term.

From a long term basis, yes. From a short term basis, you've got to earn the right to invest your capital.

Dara agrees that capital allocation is vital for CEOs, but stresses the importance of proving one's ability to manage resources effectively in the short term before making long-term investments.

• Khosrowshahi believes Uber has excelled in marketplace technology, where significant resources have been effectively used.
• He acknowledges mistakes in allocating capital to ventures outside of Uber's core competencies, such as the self-driving and hardware businesses.
• Learning from these experiences, Uber has refocused on its strengths in connecting supply and demand.

Where we got it wrong was when we went outside of our core.

Dara reflects on past capital allocation decisions, admitting that investing in areas outside of Uber's core expertise was a mistake.

• Khosrowshahi discusses the balance between focusing on core business and exploring adjacent products and markets.
• Investments in future innovations should utilize the company's core skill set and have a clear advantage or 'right to win'.
• Uber Eats and Uber Freight are examples of successful expansions that leveraged Uber's expertise in real-time supply and demand matching.

I think that, and by the way, you always want to be expanding the core, so to speak.

Dara explains the importance of expanding the core business while ensuring that new ventures align with the company's existing strengths.

• Khosrowshahi clarifies that Uber Eats is as large as Doordash on a global scale and discusses the strategic bets that influenced their market positions.
• Uber Eats initially focused on speed and urban centers, while Doordash targeted the suburbs and restaurant selection.
• Uber Eats has since adapted by improving selection and managing customer expectations regarding delivery times.

I think the first thing that I would tell my anonymous friend is that we haven't lost the lead.

Dara addresses the perception of competition in the food delivery market, emphasizing Uber Eats' global presence and ongoing strategy adjustments.

• Khosrowshahi expresses satisfaction with the acquisition of Careem, citing the talent of its founders and the strategic fit with Uber's vision for the Middle East.
• The acquisition of Postmates was driven by the goal of consolidation in the US delivery market and has led to cost savings through backend integration.
• He views the Careem acquisition as particularly successful due to its alignment with Uber's broader business objectives.

Yeah, very happy. For me, it was a bet on Madassa and Magnus, who were the founders at Kareem.

Dara speaks positively about the Careem acquisition, attributing the decision to the founders' capabilities and the strategic opportunity in the Middle East.## Acquisition of Jump and Challenges with Hardware

• Uber's acquisition of Jump, an electric bike company, did not meet expectations.
• Dara Khosrowshahi acknowledges that Uber struggled with hardware, contrasting with their software expertise.
• Hardware development involves complexities such as firmware issues, shipping, and manufacturing, which software companies may underestimate.

"There was a company called Jump that we bought, which was electric bikes, and it just didn't work out. We just sucked at hardware."

This quote illustrates Uber's unsuccessful attempt to expand into the hardware sector with the acquisition of Jump, highlighting the challenges they faced due to their inexperience in hardware.

• Dara Khosrowshahi expresses admiration for companies like Apple and Tesla that have successfully built software-hardware businesses from scratch.
• Building a successful hardware business is recognized as an extraordinary accomplishment.

"I have developed a healthy respect for companies like Apple or even the Tesla. It's actually amazing. Building a scale software hardware business from the ground up."

The quote conveys Dara's recognition of the difficulty in creating a successful hardware business and his respect for those who have achieved it.

• Dara Khosrowshahi believes making mistakes is essential for growth and risk-taking in business.
• He emphasizes the importance of learning from mistakes rather than making excuses.
• Being self-reflective, taking responsibility, and being willing to make mistakes are seen as crucial for both personal and company growth.

"My job is to make mistakes and learn from that. So I don't mind when people make mistakes. What I mind is if they're not self reflective."

This quote underlines the significance of self-reflection and learning from mistakes as part of Dara's business philosophy.

• Wall Street demands predictability and is less forgiving of volatility, even if it could lead to greater growth.
• Companies are expected to meet and slightly exceed their financial projections.
• Dara Khosrowshahi mentions a "mistake budget" that allows for some errors without exceeding Wall Street's tolerance.

"The translation layer to that decision-making by Wall Street is the financials that you report on a quarterly basis."

The quote reflects the challenge of balancing innovation and risk-taking with the need to meet Wall Street's expectations for financial stability and predictability.

• Dara Khosrowshahi differentiates between reversible "two-way door" decisions and irreversible "one-way door" decisions.
• One-way door decisions are characterized by their size, potential impact, and the effect on third parties.
• Uber approaches features for earners with caution due to the potential impact on their livelihood.

"So size matters. In this case, I think a second one is, what's the blast radius of the mistake?"

This quote highlights the criteria that Dara uses to assess the magnitude and potential consequences of business decisions.

• Dara Khosrowshahi relies on his wife as a trusted advisor for business and personal decisions.
• He values her judgment of character and her ability to provide critical insights.
• Dara also seeks clarity and generosity of knowledge in his technical team, preferring those who can explain complex issues simply.

"I'm lucky enough actually to have someone that I don't have to call, which is my wife."

The quote reveals the personal support system that Dara has, with his wife playing a significant role in his decision-making process.

• Dara Khosrowshahi starts with full trust in his team, giving them autonomy and holding them accountable for their actions.
• He believes in allowing his team to make mistakes as long as they take responsibility and learn from them.

"I start with full trust, and hopefully you can deserve that trust."

This quote outlines Dara's management style of empowering his team with trust and accountability from the outset.

• Dara Khosrowshahi describes himself as calm and level-headed, which he sees as an asset in both his personal life and professional career.
• He rarely gets angry, preferring to maintain composure in challenging situations.

"I don't lose my shit. I'm pretty calmed. My wife calls me a robot."

The quote illustrates Dara's self-described emotional stability, which he views as beneficial to his leadership role.

• Dara Khosrowshahi attributes the success of his marriage to not only being in love but also genuinely enjoying each other's company.
• He prioritizes spending quality time with his family and believes that liking one's partner is key to a great marriage.

"But what really works for Sid and me is that we're in love, but we're in like, we like each other a lot."

The quote emphasizes the importance of mutual enjoyment and companionship in Dara's view of a successful marriage.

• Dara Khosrowshahi admits to still learning about being a great father.
• He believes in being fully engaged and present with his children, whether at work or with family.
• Dara encourages pushing his children to achieve but ensures he is completely attentive when with them.

"So when I'm with my kids, I'm with them, and we have a great time, and I think that shows that engagement with them."

The quote reflects Dara's commitment to being an engaged and attentive parent, fully present in the moments he shares with his children.## Adversity and Generation Softness

• Dara Khosrowshahi discusses the importance of facing adversity and discomfort.
• He acknowledges the criticism of younger generations being too soft but believes they will be fine.
• Dara appreciates the work ethic and capability of the people at Uber.

"It's about adversity. It's about discomfort, making mistakes. All of these things are going to shape you going forward."

This quote emphasizes the belief that challenges and difficulties are crucial for personal growth and development.

• Dara and Harry Stebbings joke about feeling old compared to the younger generation of entrepreneurs.
• Harry, at 26, feels surpassed by even younger founders, while Dara humorously reflects on his own age.

"So I remember, if you think you're old, then I'm dead."

Dara uses humor to address the relative perception of age, especially in the fast-paced tech industry.

• Dara inherited a conflicted board at Uber and prioritized aligning the board with the company's success.
• Significant changes were made, including reshaping the board and bringing in a new chairman.
• The reformed board is now fully committed to Uber's success.

"I need the board to be about the success of Uber versus control of Uber."

Dara underscores his approach to resolving board conflict by focusing on the company's success rather than power struggles.

• The transition from the old guard to a new team at Uber was challenging but ultimately successful.
• Dara had to clearly communicate and act on the changes, especially regarding the company's culture.
• The pandemic served as a unifying crisis that helped the team come together.

"It's about doing the right thing. And I do think that was difficult for some of the old guard, because not everything about old Uber was bad."

This quote highlights the delicate balance of acknowledging the strengths of the past while pushing for necessary cultural changes.

• Dara shares his favorite books, which include Isaac Asimov's "Foundation" series and "The Splendid and the Vile" about Churchill.
• These books have shaped his passion for science and engineering and provided inspiration through historical leadership.

"One extraordinary person, and he really lifted that nation up on his back."

The quote reflects Dara's admiration for Churchill's leadership during a critical time in history.

• Dara values the high bar for talent set by former CEO Travis Kalanick.
• The most significant challenge inherited was the brand damage to Uber, which required rebuilding public sentiment.

"I'll take the talent, because the talent has helped us rebuild."

Dara expresses his belief that the talented individuals at Uber are key to overcoming the company's past challenges.

• Dara does not hang out with Travis but maintains a professional relationship.
• Travis's new venture in dark kitchens collaborates with Uber, showing mutual business interests.

"He's built a dark kitchen company that we do work with, and I think it's the biggest dark kitchen company out there."

The quote highlights the ongoing business connection between Dara and Travis despite the change in leadership.

• Barry Diller has been a significant mentor to Dara, influencing his leadership style and career trajectory.
• Dara admires Barry's unending curiosity and drive for knowledge.

"I work for him for over 20 years. I think that I'm here because of him."

Dara attributes his success and position at Uber to the opportunities and mentorship provided by Barry Diller.

• The pandemic posed a massive challenge to Uber, leading to tough decisions and layoffs.
• These actions allowed Uber to emerge leaner, more focused, and stronger post-pandemic.

"It was an ugly, tough lesson, but it was one that I think we've learned from."

Dara reflects on the hardships faced during the pandemic and the valuable lessons learned that have positioned Uber for future success.

• Dara would advise his past self to make decisions faster upon becoming CEO.
• He acknowledges the need for input but sees value in quicker decision-making.

"Go faster. Go faster. In hindsight, I didn't know what I was getting into."

This advice to his past self emphasizes the importance of agility and decisiveness in leadership roles.

• Dara does not focus on a personal legacy or detailed long-term planning.
• He prefers to remain open-minded and receptive to new information and opportunities.

"I'm very humble and I don't know what's going to happen five years from now."

Dara expresses his humility and preference for adaptability over rigid long-term forecasting.

• Dara identifies decision-making as an area where Uber can improve efficiency.
• The complexity of Uber's business requires input from various departments, which can slow down decisions.

"I think it's actually on the decision making side."

The quote pinpoints decision-making as a critical aspect for Uber to enhance its operational efficiency.

• Both Dara and Harry express their enjoyment of the conversation and gratitude for the opportunity to engage in the podcast.

"Thank you. It was really fun. Appreciate it."

Dara thanks Harry for the interview, indicating a positive interaction and mutual respect between them.