Podcast Summary

The Diary Of A CEO with Steven Bartlett

Guest: Dara Khosrowshahi, CEO of Uber
Episode Title: Uber CEO: At Uber, If You Don’t Perform, You’re Out! Uber Was Losing $3b A Year
Release Date: February 23, 2026

Episode Overview

In this insightful and at times deeply personal episode, Steven Bartlett speaks with Dara Khosrowshahi, the CEO of Uber, about the company's dramatic turnaround, the mindset required for high performance—both personally and professionally—and the profound impact of emerging technologies like AI and autonomous vehicles on society and work. Dara shares the story of his early life as a refugee from Iran, the lessons he learned from his father, and how these experiences have shaped his relentless drive as a leader. The conversation delves into leadership philosophy, the specifics of managing and transforming massive organizations, the realities of risk and failure, and how to foster cultures of honesty and continuous improvement. The episode is rich with honest reflections, practical insights, and a direct, no-nonsense examination of the future of work.

Key Discussion Points & Insights

Dara’s Early Life: The Formative Years

• Background and Refugee Experience

  • Born in Iran, Dara’s family lost everything in the Islamic Revolution of 1978 and emigrated to the US for safety ([04:52]).
  • Dara reflects on the impact of “having the rug pulled out from under you” and the driving sense of never feeling truly safe, feeding his work ethic and need to rebuild ([06:30]).
  • His father, once a respected industrialist, was separated from the family for six years, leaving Dara’s mother to raise the children and start working for the first time ([07:50], [08:02]).

• The Lasting Influence of His Father

  • Dara confides that seeing his father's pain in losing everything and his sense of value deeply affected him ([06:30], [10:02]).
  • His aim was always to make his father proud, though their relationship was shaped by cultural stoicism ([16:09], [16:24]).

"I never feel safe... that feeling of having the floor, you know, the rug pulled out of you... never leaves you.”
– Dara ([06:30])

Building High-Performing Organizations

• Betting on People, Not Just Companies

  • Learned from Herbert Allen at Allen & Co: “Always bet on people. Companies go, but great people stay great all the time.” ([19:24])
  • Talent and character trump everything else in sustainable business performance ([20:23]).

• Transition from Finance to Leadership

  • Dara’s path moved from investment banking to CFO and eventually CEO, learning that leadership and operational skill outweigh purely financial wizardry ([26:14], [38:17]).
  • Early failure in hiring at Expedia led him to run the primary business himself, developing his operational “chops” ([38:17]).

• Building a Culture of Hard Work and Relentlessness

  • Hard work is “the most important skill in life”—one he deliberately cultivates in both his teams and his children ([54:02]).
  • At Uber: “You come to Uber, you're going to work your ass off. If you're not performing, we're going to let you know.” ([01:07], [48:58], [54:02])

“You can work hard and at the same time you can have flexibility. But I’m not going to let anyone outwork me.”
– Dara ([54:05])

Practical Company Building and Culture Change

• Turning Around Expedia

  • Found the company “coasting” after years of success—required fast, often painful change, including substantial turnover ([41:06], [48:20]).
  • Emphasizes radical honesty and transparency as a leader to get the same back from the team ([45:09], [47:59]).
  • “If I’m going to err with my company, I’m going to err in telling the truth and potentially scaring someone away. I'll take that.” ([45:09])

• Goal Setting and Continuous Improvement

  • Every Uber team has rigorous, tracked goals, though the art is in setting the right (truly ambitious) targets ([63:05]).
  • Uber organizes around “shots on goal”—taking fast, frequent, iterative risks toward improvement and innovation ([58:43]).

“It's not good enough to get better. We have to get better faster than our competitors, because our competitors are all getting better as well.”
– Dara ([57:59])

• Values and Company DNA

  • Uber's values are unique and operational, e.g. “Go get it” and “Great minds don’t think alike”—not generic statements ([64:03]).
  • The value “Do the right thing, period” is intentionally open-ended, requiring personal judgment ([64:03]).

• On Handling Failure

  • Recognize and analyze losses, but move forward quickly; don’t obsess (“They won, we lost. Next.”) ([22:00]).

The AI Revolution, Autonomous Vehicles & The Future of Work

• Uber’s AI Core

  • Uber has always run on applied AI—pricing, matching riders, routing, batching deliveries ([75:49]).
  • AI now powers nearly every aspect of operations, and 90% of Uber’s engineers use AI tools, with 30% being “power users” ([80:06]).
  • Future engineering may shift from writing code to orchestrating agents and systems ([81:12]).
  • You can't slow down progress; you can only shape its impact ([78:53], [94:28]).

• Anticipating Displacement and Societal Change

  • AI is set to disrupt 70-80% of jobs in the next decade ([78:53]).
  • Dara is honest about the uncertainty this creates: “What do the 9 million people do?” when AVs replace drivers on Uber’s platform? ([87:37])
  • Uber is expanding the variety of work on its platform, but societal retraining is not keeping pace ([88:37], [94:28]).
  • Universal basic income (UBI), so far, doesn’t address the loss of meaning or self-worth from work ([90:32]).

“Every universal income test has failed... People need a sense of value. I don't think raining money down will help.”
– Dara ([90:32])

Leadership Lessons, Advice & Personal Philosophy

• On Hard Work and Parenting Advice

  • “Work hard, you’ll be fine. Don’t over-plan – stay open and let the world change you first.” ([96:19])
  • The skill to relentlessly work hard is learned, often formed in childhood; rarely do non-hard workers become exceptional ([55:59]).

• Taking Risks and "Shots on Goal"

  • The best performers and teams are those constantly moving forward—“next shot on goal”—and learning from failure ([58:51], [59:59]).
  • Uber’s success includes counterintuitive bets, e.g., bringing taxis onto the Uber platform ([70:12]).

• Emphasizing Honesty in Leadership

  • Radical honesty both attracts the right people and builds the foundation for organizational learning ([45:09], [103:33]).
  • “As a boss, I'm going to tell you what's going on because that's the only way I can drag the hard truths back from you.” ([45:09])

"The way to get transparency from your team is first you've got to give it to them." – Dara ([47:59])

Personal Reflections

• Relationship with His Father
  • Most regret is not having a final, deep conversation with his father before his decline ([101:29]).

Notable Quotes & Memorable Moments

On Relentless Work Ethic

"I'm not going to let anyone outwork me... And if that's true, they may be smarter, more talented, etc. But I'm not going to let anyone outwork me. That’s a huge advantage."
– Dara ([54:02])

On Radical Honesty

"If I’m going to err with my company, I’m going to err in telling the truth... I’ll take that. If that person isn’t up for the fight, then they should go someplace else.”
– Dara ([45:09])

On the AI Disruption & Jobs

“AI will be able to replace the work that 70-80% of humans can do over the next 10 years. 10 years is not a lot of time for society to adjust to that kind of an impact.”
– Dara ([75:49])

On Cultural Transformation

"The value system of the company almost...appears. If you say 'thou shalt,' you’re going to fail.”
– Dara referencing Jeff Bezos ([64:03])

On Regret

"If I could have one conversation, it would be with my dad... I wish I could talk to him about his experiences, his younger life, the excitement of building something, and then the loss and regrets he had in life."
– Dara ([101:29])

Timestamps for Major Segments

• Early Life and Refugee Experience: [04:52]–[11:22], [16:03]–[18:03]
• Investment Banking to Expedia to Uber: [19:08]–[29:00]
• Leadership at Expedia: [38:17]–[50:00]
• Hard Work and Company Culture: [54:02]–[57:59]
• Continuous Improvement and Risk: [58:43]–[63:49]
• Values & Culture at Uber: [64:03]–[68:19]
• AI & Automation at Uber, Societal Disruption: [75:49]–[94:28]
• Personal Advice and Reflections: [96:19], [101:29]

Conclusion

This episode offers an unvarnished window into the realities of modern leadership at scale. Dara Khosrowshahi’s journey from refugee child to one of the most recognized CEOs in the world is both inspiring and instructive. He combines candor about the messy, relentless, and sometimes painful process of company transformation with clear-eyed realism about the threats and opportunities of the AI-driven future. The recurring themes are honesty, the value of relentless hard work, openness to change—and the importance of staying human in times of tumultuous technological progress.

Highly recommended for anyone interested in leadership, tech disruption, and personal growth.