TThe Diary of a CEO
← All episodes
23 February 2026

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

8Frameworks
12Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take47:00

Uber's Offer Is Demanding Work, Agency, Learning—and No Coasting

Khosrowshahi describes Uber's culture in unusually explicit terms: demanding work, direct performance feedback, and exit when performance does not improve. In exchange, he says employees can have meaningful agency, learn quickly, and contribute to an important company. He also distinguishes flexibility from low intensity, noting that he protects family dinner and returns to email later; this is his stated operating philosophy, not evidence that the model suits every worker.

  • Khosrowshahi says candidates should know the intensity before joining
  • He presents agency, learning, and impact as part of the employment exchange
  • Poor performance is addressed directly and can lead to removal
  • He argues that schedule flexibility and demanding output can coexist
  • He accepts that many people should choose a different culture

don't come here if you want to coast

Dara Khosrowshahi · 49:30

You can work hard and at the same time you can have flexibility

Dara Khosrowshahi · 53:00
#work culture#performance#flexibility#uber
Hot Take51:30

Khosrowshahi Calls Hard Work Life's Most Important Skill

Khosrowshahi argues that disciplined, structured, relentless effort compounds into an advantage and should be taught as a skill. He compares the pattern with elite athletes and says his own rule is not to let others outwork him. However, when asked for an example of a non-hard-working person becoming exceptional at it, he cannot recall one, leaving his claim that the skill is learned unresolved within the episode.

  • He prioritises capacity for hard work over choosing a fashionable profession
  • He associates elite performance with discipline, structure, and relentlessness
  • He believes sustained effort compounds over time
  • The conversation does not establish how reliably the skill can be acquired
  • His view is a personal leadership belief rather than a demonstrated universal fact

the most important skill in life is the skill of working hard

Dara Khosrowshahi · 51:30

That's a learned skill

Dara Khosrowshahi · 54:30
#hard work#discipline#performance#learning

Explainer· 3

Explainer1:14:30

Uber Runs on Many Local AI Models, Not One General Intelligence

Khosrowshahi says Uber's pricing, routing, matching, and order batching depend on smaller AI models trained on local problems and stitched into a wider operating system. He argues that this history makes the company comfortable with probabilistic systems that work most of the time but can produce unexpected failures. His description concerns Uber's own architecture and experience rather than a general safety endorsement of AI.

  • AI contributes to pricing, routing, matching, and courier batching
  • The system must operate across very different cities
  • Khosrowshahi describes local models being combined into a larger service
  • He says probabilistic failures create an uncertainty layer the company must handle
  • Uber positions itself as an applied-AI company rather than a foundation-model research lab

we have built the entire company on small AI models

Dara Khosrowshahi · 1:15:00

we're comfortable with the uncertainty layer of AI

Dara Khosrowshahi · 1:15:30
#ai#uber#machine learning#operations
Explainer1:19:00

Uber Sees Coding Shift From Manual Writing to Agent Orchestration

Khosrowshahi says about 90% of Uber engineers use some form of AI tool and roughly 30% are power users showing a clear difference in code-output measures such as diffs. He expects coding work to move increasingly toward orchestrating agents and designing systems. He says near-term efficiency gains would make him hire more engineers to move faster, while acknowledging that later gains might shift investment from headcount toward agents and computing capacity.

  • The usage and power-user percentages are Khosrowshahi's estimates for Uber
  • He cites code diffs as one productivity indicator rather than a complete quality measure
  • He expects the engineer's role to contain more orchestration
  • Near-term productivity gains could increase Uber's engineering ambition
  • He treats future headcount substitution as possible rather than certain

about 90% of our coders are using AI

Dara Khosrowshahi · 1:19:00

It becomes more of an orchestration job versus a manual writing job

Dara Khosrowshahi · 1:20:00
#ai coding#engineers#agents#productivity
Explainer1:22:00

Khosrowshahi Sees Real-Time Learning as AI's Missing Capability

Khosrowshahi argues that people can update during a conversation, while deployed foundation models generally depend on large pre-training and post-training cycles rather than continuously changing in the moment. He distinguishes applications that bring fresh real-world signals around a model from the model itself learning. He presents real-time learning as the capability that would make him more seriously consider universal replaceability, while saying he has not yet seen it.

  • Humans can alter behaviour from immediate interaction
  • Khosrowshahi describes model releases as fixed until engineers produce a later version
  • Applications can supply current signals without the base model itself learning
  • His distinction is a high-level explanation, not a comprehensive technical taxonomy
  • He identifies real-time learning as an important threshold in his own judgement

the AI agents aren't learning

Dara Khosrowshahi · 1:23:00

I haven't seen a model that can learn real time

Dara Khosrowshahi · 1:23:30
#ai#learning#foundation models#agents

Story· 3

Story04:00

Losing Everything in Iran Shaped Khosrowshahi's Drive to Rebuild

Khosrowshahi says his family lost its industrial business during the 1978 Iranian Revolution and left after armed guards pursuing a neighbour fired bullets through the family's living room. He connects watching his parents rebuild—and seeing the loss damage his father—with a lasting sense that security can disappear and a drive to make his family proud.

  • Khosrowshahi was born into a family that had built an industrial company in Iran
  • The revolution forced the family to leave and rebuild in the United States
  • He says the loss deeply affected his father's sense of value
  • He links the experience with not taking stability for granted

We lost all of that with the revolution in 1978

Dara Khosrowshahi · 04:00

I never feel safe

Dara Khosrowshahi · 05:00
#iran#family#immigration#motivation
Story23:00

Khosrowshahi Says Conflict Avoidance Followed Him Home

Although comfortable with professional conflict and rejection, Khosrowshahi says he has long been conflict-avoidant in personal relationships. He attributes part of the pattern to being the youngest brother and cousin and learning to go with the flow. He says his instinct to let issues go can allow resentment to build, and credits his wife with helping him practise confronting problems more directly.

  • He distinguishes his professional persona from his personal response to conflict
  • His internal impulse is often to let a difficult issue go
  • He believes avoiding the issue can build resentment over time
  • He describes improvement as an active and continuing effort

in my personal life, I can't deal with the rejection

Dara Khosrowshahi · 23:00

that's how resentment builds

Dara Khosrowshahi · 24:30
#conflict#relationships#self-awareness#resentment
Story1:40:00

The Conversation Khosrowshahi Wishes He Had With His Father

Khosrowshahi says he returned to New York as his father aged but could no longer have the deep conversation he wanted because his father's mental faculties had declined. He wishes he had asked about his father's younger life, building a business, loss, and regret. He now tries to correct for that absence by creating genuine conversations and relationships with his children, wife, friends, and colleagues.

  • Love was present, but deep personal conversations were not
  • He wanted to understand both his father's building years and later losses
  • He sees some missed opportunities as permanent
  • He responds by investing in genuine connection with people still in his life

I wish I could talk to him about his experiences

Dara Khosrowshahi · 1:40:30

you can't get time back

Dara Khosrowshahi · 1:41:00
#father#regret#conversation#connection

Q&A· 1

Q&A1:23:30

Autonomous Vehicles Create a Safety Gain and a Work-Displacement Problem

Khosrowshahi says Waymo vehicles are safer than human drivers and argues autonomous transport should eventually reduce fatalities and prices, but the episode provides no cited study with which to verify the comparison. He expects physical deployment to take longer than virtual AI because vehicles, sensors, regulation, and capital must enter the real world. Asked what Uber's millions of drivers and couriers will do if automation dominates, he says he does not know and describes Uber's efforts to add shopping and AI-training work to its platform.

  • The safety comparison is Khosrowshahi's claim in the interview
  • He expects physical AI adoption to lag intellectual automation
  • He imagines a 15-to-20-year horizon before robots fulfil a majority of Uber trips
  • Uber is broadening platform work beyond driving and delivery
  • Khosrowshahi cannot say whether new work will expand faster than automation

What do the 9 million people do? I don't know

Dara Khosrowshahi · 1:26:30

I can't tell you which is going to go faster

Dara Khosrowshahi · 1:27:00
#autonomous vehicles#safety#jobs#uber

Takeaway· 3

Takeaway10:30

Parenthood Taught Khosrowshahi to Trade Control for Time

Khosrowshahi describes parenthood as humbling because children become people their parents cannot fully plan or control. His practical advice is to invest time and preserve connection rather than obsess over tactics or a perfect parenting plan. He presents this as personal experience, not expert guidance.

  • He says exhaustion makes perfect execution of a parenting plan unrealistic
  • Children develop in unexpected directions
  • Stepping back can turn alarm about lost control into appreciation
  • He prioritises time and connection over precise tactics

parenthood is so humbling

Dara Khosrowshahi · 10:30

just spend the time with the kids

Dara Khosrowshahi · 11:30
#parenthood#control#family#connection
Takeaway18:00

Why Allen & Company Bet on People, Not Just Companies

Khosrowshahi recalls Herbert Allen teaching him that companies can rise and fall while great people can remain worth backing across a career. He says Allen & Company cultivated long-term relationships with people it judged strong in both potential and character, looking for honour, loyalty, success, and follow-through.

  • The approach treated a person's whole career as the relationship horizon
  • Potential and character both mattered
  • Khosrowshahi names honour, loyalty, and keeping promises as signals
  • Talent and hard work were connected with demonstrated success

always bet on people

Dara Khosrowshahi, quoting Herbert Allen · 18:30

great people stay great all the time

Dara Khosrowshahi, quoting Herbert Allen · 18:30
#people#character#relationships#talent
Takeaway1:16:00

Khosrowshahi Says Society Lacks a Machine for Mass Retraining

Khosrowshahi predicts that AI capability could replace much of today's intellectual work within ten years and physical work later, while repeatedly acknowledging uncertainty about cost, adoption, and new jobs. He argues that societies historically adjusted because they had more time and says large-scale retraining is not currently a core capability he sees governments building. These are forecasts and judgements from the guest, not established outcomes.

  • His 70-to-80% capability estimate is a prediction, not a measured employment result
  • He separates technical capability from whether AI will be cheaper or adopted
  • He expects disruption to become a larger social issue beyond the next five years
  • He argues that slowing Western technology development would not stop global change
  • His proposed priority is infrastructure capable of retraining large populations

the changes in society are going to be giant

Dara Khosrowshahi · 1:17:00

If there's one thing I can come up with, it would be that is the retraining machine

Dara Khosrowshahi · 1:35:00
#ai#jobs#retraining#society