The Diary Of A CEO with Steven Bartlett

Uber CEO: At Uber, If You Don’t Perform, You’re Out! Uber Was Losing $3b A Year

February 23, 2026

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  • The CEO's relentless drive and appetite for risk were fundamentally shaped by his family's experience escaping the Iranian Revolution, instilling a core need to rebuild and never feel safe. 
  • Effective leadership, particularly during turnarounds, requires radical transparency to ensure leaders receive unfiltered, high-fidelity information from the source, even if it initially scares employees. 
  • The ability to work hard is considered the most important learned skill in life, compounding over time to create a significant advantage over talent alone, a principle the CEO actively seeks to embed in Uber's culture. 
  • Successful companies become risk-averse as they grow, but Dara Khosrowshahi actively pushes Uber to be offensive and take smart risks, leveraging their strong cash flow to absorb potential mistakes. 
  • Uber's initial attempt at defining corporate values failed when 'toe-stepping' was weaponized, leading to a successful reset where the value 'do the right thing, period' was introduced to empower employee judgment over rigid rules. 
  • The rapid acceleration of AI, potentially disrupting 70-80% of intellectual jobs within a decade, poses a significant societal challenge regarding the speed of human retraining and finding meaning outside of traditional work. 

Segments

Early Life and Risk Appetite
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(00:00:30)
  • Key Takeaway: Escaping Iran as a child instilled a core feeling of never being safe, driving a need to rebuild and make family proud.
  • Summary: The CEO’s family lost their industrial company during the 1978 Iranian Revolution, forcing them to rebuild their lives in the U.S. Witnessing his parents lose everything, especially his father’s sense of value, created a deep-seated drive to build and never take success for granted. This foundational experience shaped his relentless approach to business.
Career Path and Engineering Mindset
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(00:01:47)
  • Key Takeaway: Engineering provided a fascination with problem-solving that translates directly to CEO work, viewing companies as machines to be optimized.
  • Summary: After studying bioelectrical engineering, the CEO moved into investment banking before taking over Expedia. He views companies as complex machines requiring engineering principles to set up systems that achieve defined goals. Setting the right goals is considered a giant engineering challenge, which he finds fascinating.
Betting on People and Character
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(00:01:43)
  • Key Takeaway: Great people remain great regardless of company performance, making character traits like honor, loyalty, and follow-through crucial for investment.
  • Summary: A key lesson learned in investment banking was to always bet on people, as great individuals maintain their quality even if the company falters. Greatness in character is defined by success, honor, loyalty, and the commitment to follow through on promises. This philosophy led him to leave a stable role to work for Barry Diller.
Handling Losses and Moving Forward
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(00:02:17)
  • Key Takeaway: Losing is an inevitable part of taking shots, requiring recognition of the loss, quick analysis, and immediate forward momentum.
  • Summary: The CEO advocates for a balanced approach to failure: acknowledge the loss, analyze the cause, but avoid obsessive inspection, then immediately move on. If a company is not taking shots, it is not missing, implying a lack of necessary risk-taking. Constant motion and learning from losses are essential for growth, especially in technology.
Personal Conflict Avoidance
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(00:02:33)
  • Key Takeaway: Despite professional aggression, the CEO struggles with personal conflict avoidance, a trait he actively fights against in his relationship.
  • Summary: The CEO admits to being conflict-avoidant in his personal life, contrasting with his aggressive professional persona, which he attributes to being the youngest cousin and brother who learned to ‘go with the flow.’ He recognizes that avoiding conflict builds resentment, making active engagement and honesty crucial for relationship health.
Transitioning from Finance to Operations
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(00:02:53)
  • Key Takeaway: True passion for the CEO role was discovered through operating the business, not just capital allocation, which required taking the largest part of Expedia himself.
  • Summary: After acquiring companies like Ticketmaster and Hotels.com, the CEO realized his true love was operations, not just financial wizardry. He took on the role of running Expedia.com for several years after failing to hire the right leader, learning the operational skills necessary to lead a technology company effectively.
Transparency as a Leadership Tool
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(00:04:17)
  • Key Takeaway: Radical transparency from the CEO is a self-defense mechanism necessary to break through organizational filtering and extract the unvarnished truth from employees.
  • Summary: The CEO learned from Barry Diller to go directly to the source to maintain fidelity of information, bypassing layers of summary and potential filtering. If a leader is not honest about challenges, employees will filter information back, leading to poor decision-making based on incorrect data. Erring on the side of telling the truth, even if it scares people, ensures the right talent stays and the necessary hard truths surface.
Culture of Hard Work and Relentlessness
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(00:04:51)
  • Key Takeaway: The most important skill is the learned ability to work hard and be relentless, which compounds over time to create a competitive advantage.
  • Summary: The CEO believes that elite performance, seen in top athletes like Jordan and Ronaldo, stems from working relentlessly, a skill that can be learned. He actively fosters this ‘Embrace the Grind’ mentality at Uber, demanding high performance and making it clear that coasting is unacceptable. This relentless pace must be faster than competitors because everyone is improving simultaneously.
Incentivizing Smart Risk Taking
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(01:01:17)
  • Key Takeaway: CEOs must actively set examples by taking and normalizing calculated risks to prevent successful companies from becoming overly risk-averse.
  • Summary: Companies naturally become more risk-averse as they succeed, which is counterproductive given their increased capacity to absorb mistakes. Dara Khosrowshahi actively pushes his team to be offensive, not defensive, by setting examples of sometimes failing and moving on. This leadership approach allows the entire company culture to follow suit in pushing the envelope.
Goal Setting and Culture Values
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(01:02:24)
  • Key Takeaway: Corporate values must be executed correctly, as even positive concepts like ’toe-stepping’ can become excuses for poor behavior if not managed.
  • Summary: Goal setting relies on religiously tracked business objectives, though the art of setting the right ambition level remains imperfect. Uber’s initial values failed when ’toe-stepping’ (speaking uncomfortable truths) was weaponized to excuse being a jerk. The revised value, ‘do the right thing, period,’ was intentionally not crowdsourced to place responsibility and judgment directly on employees.
Navigating Exponential Technological Change
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(01:07:42)
  • Key Takeaway: The exponential acceleration of technology demands a culture constantly challenging itself, as the correct answers are changing too quickly for static planning.
  • Summary: Talented, driven people constantly hunt for the truth, making the right people as crucial as the right culture for adapting to rapid change. Uber’s success stems from a culture born out of creating a new industry, driven by hungry people looking for change. The company’s core is built on small, stitched-together AI models handling complex orchestration like pricing and routing.
Counter-Intuitive Business Bets
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(01:09:34)
  • Key Takeaway: Ignoring industry consensus and embracing ignorance can lead to critical business growth, as demonstrated by Uber integrating taxis.
  • Summary: Despite being founded as the enemy of taxis, Uber successfully integrated taxis into its platform, which is now its fastest-growing segment. Industry founders advised against wiring up taxis, citing past failures and technical issues. The combination of Sachin’s industry knowledge and Dara’s ‘why the hell not try it’ ignorance allowed for this counter-founding success.
AI’s Societal Disruption and Pace
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(01:15:06)
  • Key Takeaway: AI will likely replace 70-80% of human work within 10-20 years, creating a societal adjustment challenge that historical technological shifts did not face due to their slower pace.
  • Summary: Uber’s entire operation, including pricing and routing for 40 million daily trips, is driven by applied AI models. The primary difference between current AI and human learning is the inability of current models to learn in real-time post-release. While physical AI (robotics) will take longer to mature than intellectual AI, societies lack the established capability to retrain large populations at the anticipated speed of disruption.
Advice for Future Careers
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(01:35:37)
  • Key Takeaway: Young people should prioritize curiosity and openness over rigid career planning to capitalize on unexpected opportunities that arise from change.
  • Summary: Dara Khosrowshahi advises his children to simply ‘work hard’ but emphasizes not having too clear a career plan, as this limits curiosity and signal reception. People who plan too rigidly look only for signals that confirm their existing path, missing life-changing opportunities. Success often comes from being open and taking advantage of luck when it appears.
The Value of Honesty and Impact
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(01:38:21)
  • Key Takeaway: The decision to join Uber was driven by the desire to make a significant impact, as advised by Daniel Ek, rather than prioritizing personal happiness.
  • Summary: Daniel Ek convinced Dara Khosrowshahi to leave a happy role at Expedia for the disastrous Uber by stating, ‘Since when is life about being happy? It’s about making impact.’ Dara’s father reinforced this by advising that when a company that is a ‘verb’ asks you to run it, you say yes. The ability to have deep, genuine conversations is a way to correct for past relational regrets.