The Uber CEO’s story is a masterclass in resilience, radical honesty, and relentless motion.
When Dara Khosrowshahi was nine years old, revolutionary guards stormed into his family’s backyard in Iran. A gun went off. Bullets tore through the living room window. His mother looked at the shattered glass and made a decision: they were leaving.
That single moment — the rug pulled out from under an entire family — forged one of the most consequential business leaders of our generation.
Today, Dara runs Uber, a company worth over $160 billion that completes 40 million trips a day across the globe. When he took the job in 2017, Uber was hemorrhaging roughly $3 billion a year. Today it generates nearly $9.8 billion in free cash flow annually. But the numbers only tell half the story.
The real story is about what it takes to build something — and keep building — when you’ve already watched everything be taken away.
Lesson 1: The Floor Can Always Be Pulled Out. Never Forget That.
Most people in positions of power start to feel safe. Dara never has.
“At my core, I never feel safe. That feeling of having the rug pulled out from under you — of building everything and losing it — that’s a feeling that never leaves you.”
His family’s industrial empire in Iran was wiped out overnight by the 1978 Islamic Revolution. His father, a proud and accomplished man, was broken by it. His mother, who had never worked a day in her life, became a salesperson in suburban New York to keep the family afloat. His father was then trapped in Iran for six years, unable to get an exit visa, while Dara grew up without him.
He had a heart attack on the plane home.
This backstory isn’t just a compelling origin tale. It’s the operating system behind every business decision Dara makes. The paranoia is a feature, not a bug. The restlessness is structural. The hunger is not manufactured — it was installed by experience.
The lesson: Comfort is the enemy of greatness. The leaders who sustain long-term success are the ones who can never quite relax into their wins.
Lesson 2: Radical Honesty Is a Competitive Advantage
Three months into his tenure at Expedia, the Head of HR pulled him aside and told him he was “scaring people.” His response? That was probably the point.
Dara believes that the biggest failure mode of CEOs isn’t making wrong decisions — it’s receiving wrong information that leads to wrong decisions.
“Your whole life as a CEO is a version of the world that your team wants you to see.”
His solution is disarmingly simple: if you want people to tell you the truth, you have to go first.
“The way to get transparency from your team is — you’ve got to give it to them.”
At Expedia, he found a broken codebase, coasting technology leadership, and a company quietly heading toward exponential decay. He said so. Loudly. Some people couldn’t handle it and left. He considered that a feature, not a bug.
He also builds what he calls “random direct channels” — impromptu conversations with engineers four levels below him. Why engineers?
“Engineers often don’t give a damn. They’ll tell me anything and everything. There’s a kind of disrespect for authority that I love.”
The lesson: As a leader, the single most valuable thing you can do is make it psychologically safe for your team to surface problems fast. The only way to do that is to model it yourself.
Lesson 3: Work Hard Is a Skill — and Most People Don’t Treat It Like One
In a culture that sometimes romanticizes “work-life balance” to the point of paralysis, Dara is refreshingly direct:
“The most important skill in life is the skill of working hard. And it’s not a skill you can just decide you’re going to do.”
He’s careful to distinguish hard work from mere busyness. It’s grim determination. It’s structured discipline. It’s the thing that separates Ronaldo from every other talented footballer who didn’t make it.
“I’m not going to let anyone out-work me. And that’s a huge advantage that compounds over time.”
At Uber, this isn’t a motivational poster — it’s embedded in the company’s values. One of them is simply: Embrace the Grind.
He also draws a sharp line between flexibility and coasting. You can have dinner with your family every night at 6pm and still check emails at 9:30pm. You can wake up at 5:30am and be present at your kid’s soccer game. The two are not in conflict — unless you’re using “balance” as a polished excuse for lower output.
The lesson: Hard work is a learnable skill, but it must be built over time and modeled from the top. Neither Ronaldo’s talent nor your MBA will substitute for it.
Lesson 4: How to Read a Moment of Transition Before Everyone Else Does
Before Uber, Dara spent years at Barry Diller’s company doing mergers and acquisitions — buying companies like Match.com, Ticketmaster, Hotels.com, and Expedia itself. The pattern behind every deal was the same:
“Humans think about success and transitions in a linear way because time is linear. But companies — especially technology companies — move exponentially.”
When most analysts looked at online travel, they saw a modest market. Dara and Diller saw a hockey stick. And they consistently overpaid for every great company they bought — not because they were reckless, but because they understood that the market was radically underestimating where things were going.
This is essentially the Jevons Paradox in action: when you make something dramatically easier, faster, or cheaper, people don’t just do it a little more — they do it exponentially more. The original Uber was conceived as a black car service. No one imagined it would become the world’s largest organizer of flexible work — bigger than the Chinese military by headcount.
The lesson: When evaluating a transition, ask not “how big is the current market?” but “how big does this become if adoption goes exponential?” The spread between those two numbers is where fortunes are made — and lost.
Lesson 5: Losing Is Part of the Game. Obsessing Over It Isn’t.
When Barry Diller lost a hostile takeover bid for Paramount, his official press release was essentially: They won. We lost. Next.
Dara was watching. He never forgot it.
“In business, losing is part of the game. Recognize that you lost, say it — because it’s important to say it — analyze it, but then move on. Constantly moving and learning is what excites me.”
This isn’t indifference. It’s precision. Papering over a loss is dishonest and prevents learning. Obsessing over it is equally useless. The goal is clean accounting: what happened, why, what changes, and then — forward motion.
He admits, though, that in his personal life, he’s conflict-avoidant and struggles deeply with rejection. The professional swagger is partly a constructed environment where he’s given himself permission to lose. The rest of life? Still a work in progress.
The lesson: Build a structure that makes it safe to fail and acknowledge it. The worst outcome isn’t losing — it’s the culture of denial that grows around a loss that is never spoken.
Lesson 6: Great Companies Have a Chip on Their Shoulder
Uber survived taxi union battles. A CEO scandal. A brutal IPO. COVID nearly wiped out its core business. It was told repeatedly it would never be profitable.
Every one of those near-death experiences became fuel.
“We are a hungry company. We’ve always been a company that has been underestimated — and that feeds into our culture.”
Dara is aware that success is the enemy of hunger. As companies grow, they accumulate something to protect — and that protection instinct is the beginning of the end for most. His job, as he sees it, is to keep the chip on the shoulder alive even when the numbers are record-breaking.
One concrete mechanism: he actively pushes teams to take more risks as the company gets bigger, not fewer — because with $9.8 billion in annual cash flow, you can actually afford mistakes that would have killed you at $0.
The lesson: Don’t let success become a defensive posture. The bigger you get, the more shots you can take. Act accordingly.
Lesson 7: Don’t Plan Too Hard
Given his extraordinary trajectory — Iranian refugee, investment banker, CFO, CEO of Expedia, CEO of Uber — you might expect his advice to young people to be: set a 5-year plan, execute relentlessly.
It’s the opposite.
“Before you go out and try to change the world, let the world change you first. People who have too clear a career plan are looking for signals that feed into their plan — and they miss everything else.”
His own journey was a series of accidents. He never planned to be a CEO. He became one because he raised his hand when the Expedia.com division was failing and said he’d run it himself. He never planned to go to Uber. He almost said no — until a friend told him: “Since when is life about being happy? It’s about making impact.”
The next day, he called the headhunter back.
The lesson: Curiosity and openness to signal will take you further than any career map. Plans create blinders. Stay in motion, stay hungry, and let the good opportunities find you when you’re paying attention.
The Question He Wishes He Could Answer
At the end of the interview, Dara was asked: What is one conversation you would have today if you could go back in time?
He didn’t hesitate.
It would be with his father — the man who built an industrial empire, lost it all, spent six years trapped in a country that had turned on him, came home diminished, and died a few years ago without Dara ever really getting to know him as a person.
“I wish I could talk to him about his experiences, his younger life, the excitement of building something — and the losses and regrets he had. We never had those deep conversations. And you can’t get time back.”
He paused.
“My way of correcting for the conversation I never had with my dad is to have genuine connections now — with my wife, my kids, my workmates.”
That’s the part of the story the spreadsheets don’t capture. The part that built the man who built the company. The part that made the relentlessness mean something.
Source: Interview with Dara Khosrowshahi, CEO of Uber, on The Diary of a CEO with Steven Bartlett.
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