The Diary Of A CEO: Dara Khosrowshahi Interview Transcript — Uber CEO
Guest: Dara Khosrowshahi — CEO of Uber Host: Steven Bartlett — The Diary Of A CEO Show: The Diary Of A CEO Duration: 01:43:17 (103 minutes) Source: YouTube Deep Dive: Uber CEO Dara Khosrowshahi: AI Disruption, Autonomous Vehicles & Insecurity-Driven Leadership
Table of Contents
- Opening Highlights (00:00:00)
- Iranian Revolution & Immigration to America (00:02:48)
- Brown University, Investment Banking & Betting on People (00:16:04)
- Building the Expedia Empire (00:24:40)
- The Birth of Uber & Jevons Paradox (00:33:09)
- Leadership & Radical Transparency (00:43:36)
- The Religion of Hard Work (00:51:26)
- Continuous Improvement & Risk-Taking (00:54:13)
- Uber’s Values Reset & Bold Bets (01:02:43)
- AI’s Massive Impact on Jobs (01:13:54)
- Autonomous Vehicles & the Future of 9.4 Million Drivers (01:23:45)
- Daniel Ek’s Advice, Father’s Wisdom & Farewell (01:37:53)
1. Opening Highlights
Dara: You come to Uber, you’re going to work your ass off. And if you’re not performing, we’re going to let you know.
Steven: But do you ever worry that they might not be able to deal with the truth?
Dara: Then they can leave. Because the most important skill in life is the skill of working hard. And when you see the top athletes, Ronaldo, Michael Jordan, of course they’re talented. But the thing that’s different about them is they work their asses off. And that’s a learned skill. That’s not something you’re born with. You may be smarter, more talented, et cetera, but I’m not going to let anyone outwork me.
Steven: And with that mentality, when you joined Uber, Uber was losing 3 billion pounds per year. Now it generates 8.5 billion in free cash flow every year. But it seems that you were forged in such a way that you were gonna be relentless.
Dara: Yeah. And it really started with being born in Iran, with the Islamic Revolution in 1978. We were not safe there. And I remember at one point we had these Revolutionary Guards come into the backyard and bullets went through our living room. So my family came to the US to rebuild their lives.
Steven: You were eight, nine years old.
Dara: Yeah. And it really destroyed my dad. Sorry. It’s tough for me to talk about it. All right, let me try again. Seeing that has put me on a road where I just wanted to make my family proud. So I studied bioelectrical engineering, and then my first job was investment banking. And I got to see the process of big companies being built. And then I had the opportunity to take over Expedia.
Steven: And in your 12 years as CEO, Expedia sales increased from 2.1 billion to 8.8 billion. And you were the highest paid CEO of a US tech company.
Dara: And I left it all behind to get Uber.
2. Iranian Revolution & Immigration to America
Steven: I’ve looked through your story. You were the CEO of Expedia at one point. You’re currently the CEO of Uber and you’ve turned that company from a loss making company to a highly profitable company. Your story starts in a very interesting way. Can you take me to that earliest context so I can understand how and why you are the way that you are?
Dara: I think that for me, the events that shaped my life and maybe a part of who I am really started with my being born in Iran. And Iran at the time was modernizing, becoming a modern society. And my family built a pretty big industrial company that everyone was quite proud of in Iran. We lost all of that with the Revolution in 1978 and my family had to come to the US to rebuild their lives.
Steven: You had to come to the US?
Dara: We were not safe there. One of my uncles actually was a cabinet member of the Shah’s who had just been toppled. And at one point we had these Revolutionary Guards come into the backyard. They were actually going after our neighbor’s house and one of their guns went off and bullets went through our living room, shattered the glass in the living room. And at that point my mom’s like, we’re not safe being here. So we had to come to the US. And I do think that event to some extent, has shaped not just me, but my family, in that the rebuilding of our lives, of our economic lives, to some extent, we’re all trying to rebuild what we lost in Iran.
Steven: Do you look back on that and can you identify any sort of fingerprints that were left on you from that time that have defined you in a business capacity?
Dara: I think at my core, I never feel safe. When the experience of losing everything. And for the kids, it was fine for the kids, but seeing my parents lose everything, and it really destroyed my dad. His losing his value to the world as he saw it, really hurt his inner being. And I do think, to some extent, seeing that has put me on a road where I wanna rebuild, I wanna make my family proud. But at the same time, that feeling of having the rug pulled out of you, of building everything, that’s a feeling that never leaves you. I think Americans underestimate what this place represents in its ideals. Which is, if you build something, it’s yours. There’s a rule of law, can’t be taken away from you. That is not true for the majority of the population of the world. And so I think for me, there’s a drive to build. And it’s at the same time, never, ever, ever taking anything for granted, never being satisfied. Because the minute you take things for granted, then that rug can be pulled out from under you.
Steven: Your father, there was a moment where he got trapped in Iran and wasn’t granted an exit visa for about six years.
Dara: Yes. My mother was raising us alone in Tarrytown, New York, 45 minutes north of New York City. She went from a life of never having to work to becoming a salesperson to make some money. She did it all herself, and she really stepped up. I remember when he left, he was like a giant compared to me. And then when he came back, it was my sophomore year at college, and he still saw me as a kid. He wanted to drive me to college. He had a heart attack on the plane coming back. He was a diminished person to some extent. But it was great that I had many, many years with him since then.
Steven: Your mother referenced how you didn’t mention him much, but when he returned, you broke down in tears.
Dara: (Becomes emotional) He passed away a couple years ago, so it’s tough for me to talk about it. He was a very stoic man, so he kept it all inside. And we were taught to do the same thing, but we wrote letters together, and they’re beautiful letters. He wrote poetry. But expression of feelings and frustration were not something that my family did. You just dealt with the situation. So I think I suffer from over stoicism and then breaking down every once in a while, as you just saw.
Steven: It’s a familiar story of the men that I’ve interviewed that grew up with that kind of emotional composure enforced and modeled to them.
Dara: It wasn’t enforced. We were a very loving family, but my father was very humble. He did not believe that just because you’re in a position of power, you should project that power. There was a stoicism inside my family, which is don’t complain. So it was a weird combination of stoicism and love at the same time.
Preparing for Fatherhood
Steven: I’m not a father yet, but I’m approaching that. I’ve just proposed to my fiance. One of the things I think a lot about is how do I stop my own stoicism passing on to my children?
Dara: First of all, fatherhood, parenthood is so humbling. You have such a picture in your mind as to how you’re gonna raise your family, what your kids are gonna be like, and they just become their own people. And it’s such a beautiful process to see. At first there’s this alarm — I’m losing control. But then you step back and you’re like, this is absolutely gorgeous what’s happening. So the advice that I would just give in terms of being a parent is just spend the time with the kids. That is the magic — it’s not what you do or the particular tactics, but it’s the investment in them and the time spent with them.
The Factory Visit That Left a Mark
Steven: I went back and looked through lots of different photos of where you lived and where you grew up.
Dara: Oh, wow. I had hair back then. My mom loved to dress us up in little doll outfits. Family was everywhere for us. It was a great childhood.
Steven: Your mum said: “When he was very little, he told me that he wants to do something important in the world. And he said becoming wealthy is not his priority, but making a change is.”
Dara: I can’t say I remember that conversation. But one of my early experiences that really imprinted on me was we went to visit one of my dad’s factories. And the respect that the workers had for him. He knew everyone’s name, he treated them with such respect. That ability to build a life where you have impact on a lot of people, but it’s positive, building impact — that really imprinted on me. When we came to the States, making money was important. I don’t want to BS and say I didn’t care about it because we lost everything. But then as I matured in life, building an enterprise, having that connection with the team that I saw with my father, became really important to me.
Making Dad Proud
Steven: When you came to New York at nine years old, if I’d asked you what you wanted to do when you were older, what would you have said?
Dara: I have no idea. I want to make my dad proud. That was it. I wasn’t motivated for a specific target at all. I just wanted to make my family proud.
Steven: Why “make my dad proud”?
Dara: He’s always been an important figure in my life. Part of it is that I never really got to know him that well as an individual. When I was younger, he was working all the time, then he went away, then I worked. I never really got to know the person that he was. But there’s this sense of duty. Making my father proud has always been a strong undercurrent in my life.
3. Brown University, Investment Banking & Betting on People
Steven: You’re nine years old, you’ve arrived in New York City. You do end up going off to college.
Dara: Yes, I went to Brown University, studied engineering there.
Steven: How determinant was that choice of your trajectory?
Dara: My father always said you can do anything in your life as long as either you’re a doctor or an engineer. And I picked engineering. I just loved the problem solving aspect of engineering and all the layers of equations being able to represent something in real life and then magically that something following what it should theoretically. The problem solving aspect in engineering fascinated me. I absolutely loved it and I think it serves me to this day.
Steven: Engineers make good CEOs, great CEOs if you step back.
Dara: Companies are just machines, right? They’re machines that are run by people. And over a period of time you actually try to automate some of the stuff that the people do and then you send the people off to do new stuff that can’t be automated. To some extent the job of the CEO is engineering. How do I set up the company to achieve the goals? It’s a giant engineering problem. And one of the really important things is you got to pick the right goals.
Steven: After college you go into investment banking?
Dara: Yeah, I worked there for eight years in risk arbitrage to begin with and then mergers and acquisition advisory work.
Steven: That experience taught you about betting on people?
Dara: It was actually a lesson from Herbert Allen, who was running Allen & Co. He always told me, “Dara, always bet on people. Companies go — there are good companies, bad companies — but great people stay great all the time.” Allen & Co. really cultivated relationships with people whom they perceived to be great. Both in terms of potential and in terms of character. That loyalty, that making a bet on a person and then staying with them through their whole careers, is definitely something that I learned there.
Steven: What is it about one’s character that makes them a great person?
Dara: You look for success, honor, loyalty, people who will tell you what they’re gonna do, whether it’s good or bad, and then follow through on their promises.
Meeting Barry Diller & Dealing with Rejection
Steven: Why did you leave Allen?
Dara: I left Allen because I met Barry Diller. He was a client of mine. We got to meet in a big deal — an unfriendly hostile tender offer for Paramount. He was the one person I thought, if I get a chance to work for this person, I’m going to jump at it.
Steven: Why Barry?
Dara: He’s spectacular. A doer. I met him in a circumstance where he lost. This giant hostile tender offer — Viacom won, Barry walked away. And all these fancy PR people were sitting around a table figuring out how to present a loss as a win. And the release was basically, “They won, we lost. Next.” He was a constant motion machine. They won, we lost. What’s next? Let’s go. And that’s the kind of person I wanted to work for.
Steven: In business, losing is part of the game.
Dara: Absolutely. But then calling it out — not bullshitting. “They won, we lost. Next.” It’s okay. I find companies guilty of two things. One is ignoring losses, papering over losses. And then sometimes being obsessive about the loss — inspecting it, what happened, let’s do a summary. For me, it’s somewhere in the middle. Recognize why you lost, say it, analyze it, but then move on. And the next time you hope to have learned some kind of judgment to avoid that kind of a loss. But if you’re not taking shots, you’re not missing, you’re not losing. That constant motion and learning is what excites me.
Steven: This is business advice but also life advice. A lot of people deal with rejection and that rejection stays with them for a decade, holds them back.
Dara: And listen, I’m talking a big game. But I will tell you, in my personal life, I can’t deal with rejection. I have a really hard time dealing with rejection. Professional life, no problem whatsoever. So in the end, we’re all humans after all.
Steven: You have a difficulty dealing with rejection in your personal life?
Dara: Very much, yeah. Any kind of rejection, conflict. Because I was the youngest cousin, the youngest brother, I just went with the flow. And that has followed me in my personal life. In my professional life, I don’t have as much trouble — I guess it’s to some extent a mask, because I get to be aggressive, I get to lose. It is something that Sid, my wife, has really helped me with. But in my personal life, generally I’m conflict avoidant.
Steven: That’s not good in a relationship.
Dara: No. That’s why Sid’s helping me out. I’m much better now. But when I take those issues on, I have to fight myself. There’s some core of me saying, just let it go. But that’s how resentment builds, and that’s how relationships over a long period of time start moving the wrong way. So it is something that is at my core, but I actively fight, and I’m getting better at it.
4. Building the Expedia Empire
Steven: Eventually, you go on to becoming the CEO of Expedia.
Dara: Yeah. There was a journey — I went from banking to running deals, and I knew that I liked how companies worked. So I moved from M&A to CFO, because that’s finance but it’s also being the CEO’s partner. I always knew the direction — at some point, I want to actually be an operator. The CEO at the time resigned. Barry didn’t have an alternative. I raised my hand, Barry was desperate, so he promoted me to CEO of IAC Travel, which we spun off as Expedia.
Buying Ticketmaster, Match.com & Expedia
Steven: Before you were CEO, you were buying businesses. What are some of the companies that you bought?
Dara: We bought a lot. We bought Ticketmaster, we bought Match.com, bought Expedia, Hotels.com. It was all about the theme that Barry and I were fascinated with — the movement of commerce online. Late 90s, early 2000. We saw it happening with home shopping — a flat screen television and people calling up, buying products electronically. The medium changed from TV to internet, from calling to HTTP. Match.com — in the old days you’d call a number, describe yourself, hear recordings. Ticketmaster — you’d go to Tower Records or call for concert tickets. Travel — you’d call a travel agent. All of that moved online. What we were going for were essentially electronic transactions that did not require physical fulfillment — travel, ticketing, personals. Because Amazon was doing everything else.
How to Spot Great Companies
Steven: How do you spot great companies? And what patterns did you see in transition?
Dara: They’re related. We would spot great companies just by observing who was taking the lead in these transitions. These transitions are difficult — you can’t predict exactly where things are going, how quickly. But there were companies emerging as the leaders and I would just identify the leaders and cold call these folks up and say, I want to come in and talk to you.
The last thing I would tell you — we never completed a successful deal because we got the company cheap. We actually overpaid for every single great company that we bought. But we overpaid based on what the market thought at the time, not what the reality turned out to be.
Humans think about success and transitions in a linear way because time is linear. Your schedule is relatively linear. But company success and company momentum, especially with new technologies — where there’s a technology that’s truly better and within the virtual world there’s absolutely no friction holding it back — these companies move in an exponential way. Most people project the future as a straight line. What actually happens is a hockey stick. And that’s where the opportunity is — the spread between the hockey stick and the straight line.
5. The Birth of Uber & Jevons Paradox
Steven: Can you tell me where Uber came from?
Dara: The founding was before me. It was Garrett Camp, one of the founders. I think it was born in Paris — a snowy day, they couldn’t find a black car. A bunch of young tech guys thinking, how cool would it be to pick up my phone and call a black car? He brought on Travis Kalanick as the operator and founder.
And to the point on Jevons Paradox — people thought, what’s the size of the black car marketplace? A couple billion dollars. What’s the taxi industry? More than that. But what they didn’t see was that if you radically make something either more convenient or cheaper, the market expands beyond how you calculate it. The Uber size and scale now is way beyond the original marketplace of black cars and taxis. The company today is a result of Jevons Paradox.
The Luck of Timing
Steven: Timing. How important was timing in enabling a company like Uber to exist?
Dara: It was a mobile revolution. Mobile data technology, the iPhone coming together. In the early days, one of the geniuses of Travis was he would hire market managers to expand into new cities and they would literally go with a bag full of iPhones, giving away iPhones to black car drivers to get them on Uber. Because a lot of them didn’t have smartphones. So the onset of the smartphone was that beautiful magic of timing coming together. And then the aggressiveness of that founding team — understanding the pattern and replicating it all around the world, raising as much capital as needed to get there faster than anyone else. Yes, there’s luck in there, but if that founding team hadn’t been as aggressive in blitzscaling, the company wouldn’t be what it is today.
From CFO to Operator
Steven: There’s a stereotype that investment bankers and CFOs don’t necessarily make the best CEOs. What did Barry say about you?
Dara: Barry said: “He was running out to leave because his career until then has been on the financial side of things. He really had not yet had the experience to manage people. And he mastered it. It didn’t take him all that long. He mastered how to become a leader and he mastered how to take ultimate responsibility for a company.”
Growing up under Barry shaped me. But the experience that really shaped me as it relates to Expedia — I came in as more of a financial leader. Our leadership at Expedia.com failed. I had to fire the first person, hired a second person — complete disaster. I was 0 for 2 in hiring for our largest business, 50% of our profits. So I went to Barry and the board and said, if I miss hiring the third person, then you should fire me. Barry quickly agreed.
So I said, I’ve got to take the job myself for six months to a year to understand what the job entails. What turned out to be five or six years, I ran both the holding company and the largest part of the company. That experience taught me my operating chops. How do you operate a company? How do you run something? That’s a very different skill set from capital allocation. What I discovered was operating a company, leading a company, organizing it, setting up the goals, getting the right team together — that’s the part of the job that I loved.
Three Months In: Scaring People
Dara: Three months into that role, my head of HR told me I was scaring people. Turnarounds in technology are really hard. Just like the curves up are exponential, curves down are exponential as well. The first couple of years look bad, but they’re not that bad. But you know in your mind that ten years from now, it’s going to be a disaster.
What I saw with Expedia was a technology company whose technology engine was broken. Code base was old, had not been reinvested in, technology leadership was coasting. One of the things I learned from Barry is that when you see something, when you see a pattern, you have to act. You can’t wait.
Barry always wanted to go to the source. He didn’t want a summary. It didn’t matter where that source was — a junior analyst or a president — he wanted to hear from the source. Because when there’s an issue and it goes through the analyst and the associate and the VP and SVP, by the time it’s summarized for you as CEO, it’s lost everything. Every level is like, do we really want to tell them that?
So your whole life as a CEO is a version of the world that your team wants you to see. Barry always wanted to go to the source, cut through levels, get to the core, and then move fast. For me, one of the ways I can depend on getting the real stuff from people is by being honest with them first. When you’re the CEO giving all the business talk and bullshitting, they see it. So why should they tell you the truth? For me, it was almost a self-defense mechanism — 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.
6. Leadership & Radical Transparency
Steven: Do you ever worry that they might not be able to deal with the truth?
Dara: Then they can leave. I think my head of HR was saying I was scaring the shit out of people because I’m like, we have a real problem here and we’ve gotta come together. If I’m gonna err with my company, I’m gonna err in telling the truth and potentially scaring someone away. I’ll take that. Because if that person doesn’t wanna face the truth, if he or she’s not up for the fight, then they should go someplace else.
As a leader, I’ve always, always believed in transparency. Partially because you attract the right people and partially because then I’m going to get the good information to act on. Usually the failures I see with CEOs aren’t because they made the wrong decisions — it’s because they were getting the wrong data that led to the wrong decisions. So it’s incredibly important as a leader to build the culture that surfaces problems to you quickly.
I set up a bunch of random direct channels. I’ll meet with engineers 4 levels down consistently because usually they’ve got the kind of personality where they don’t give a shit. They’ll tell me anything. And they like putting the CEO down. Engineers often don’t like authority, and code is the biggest authority buster. It’s the truth. So I find a lot of engineers have a personality which is — yeah, I’m gonna tell you what it’s like. There’s a kind of disrespect for authority that I love.
Turning Around Culture: Sometimes the Shortcut is Changing People
Steven: Was the culture hard working when you arrived at Expedia?
Dara: I think the company had been successful for a long time and had coasted on that success. So I needed to turn over the team. Almost the entire team, very quickly. It was rough going, but we really turned around.
Steven: How do you turn around the culture of a big company?
Dara: It’s very difficult. And sometimes the shortcut is just change of people. Finding the people who line up with your cultural mechanisms, embodying those values as examples, and then making sure your team imbues them down the organization.
At Uber — you come to Uber, you’re going to work your ass off. We’re going to be really demanding. If you’re not performing, we’re going to let you know. And if you don’t fix it, we’re going to push you out. But while it will be incredibly hard, you will have real agency at the company. We’re a big company, but individuals can make a big difference. Don’t come here if you want to coast. And I’m very clear about that.
7. The Religion of Hard Work
Steven: In your 12 years as CEO, Expedia stock rose 550%, sales increased 400% from 2.1 billion to 8.8 billion. You were the highest paid CEO of a US tech company at 94.1 million. And you left it all behind.
Dara: It was a big options package that I never vested. But it’s all good. It was a great run.
Steven: This point about hard work — 10 years ago saying this was very taboo.
Dara: We’re freed now. Sometimes people ask what advice I’d give to young people. The most important skill in life is the skill of working hard. Too many people focus on should you be a computer programmer or a doctor or study liberal arts. Just learn to work hard.
When you see the top athletes — their talent level is world class. But the thing that’s different about the elite athletes is they work their asses off. They’re disciplined, structured, relentless. Ronaldo, Michael Jordan. The same thing is true in all of life. With my kids, I just want to teach them how to work hard. As a banker, as an executive, I’m not gonna let anyone outwork me. And I think that’s a huge advantage. Over a period of time, that advantage compounds. And I want that in our company. I want Uber to be an incredibly hard working company.
Steven: Comes at a cost though?
Dara: Yes. It comes at a trade off. And we believe in flexibility. People confuse lack of flexibility with working hard. You can work hard and have flexibility. If you want to have dinner with your family — I’m religious about that. When I’m in town, 6 to 8, absolutely, spend that time with my family. But at 9:30pm, I’m checking emails. When I wake up at 5:30am, I’m checking emails. Life is about trade offs.
Steven: I think the most important thing is what you just said — being honest with people so that they can make decisions for themselves.
Dara: And I’m allowing them to be honest back to me.
Steven: That’s a company culture that someone like me would be attracted to. But there’s lots of people listening that couldn’t think of anything worse.
Dara: And that’s okay. There are plenty of companies that they could find. It’s fine.
8. Continuous Improvement & Risk-Taking
Steven: You said learn to work hard. Really, it’s a skill?
Dara: Yes, of course. The idea of staying focused, not being discouraged by failing, trying over and over again and just working harder than others — it’s not something you can turn on and off. At Uber there’s a saying inside one of our values: “Embrace the grind.” That’s a learned skill. That’s not something you’re born with.
Steven: Have you ever seen someone who isn’t a hard worker become a really hard worker?
Dara: That’s a good question. No. Have you?
Steven: No. I think Brian Chesky or Elon said the same thing.
Dara: I’m trying to come up with someone. I’m failing.
Every Team, Every Day, Improving
Dara: At Uber, each and every team is built and targeted on optimizing and improving their own particular function. There isn’t a piece of the company that is not improving every single day. And if they’re not improving fast enough, someone else is going to take their place. Whether it’s the payments team, the fraud team, the mobile app team — every team is organized for and goal-set on improving everything that they do.
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. Who can adapt faster to the reality of the market today or the prediction of the market tomorrow? That’s the two factors — speed of change and identification of opportunity. If you can work fast, you’re accelerating time. Every one shot that you take, I can take two shots. I’ve got more time than you do.
Steven: If you’re taking two shots, you’re also increasing your probability of success by 100%.
Dara: Shot on goal. Just shot on goal.
Creating a Culture of Continuous Improvement
Steven: Successful companies become complacent, risk averse. How do you create a culture of continuous improvement?
Dara: The good news with Uber is that we’ve always been a company that has had a chip on its shoulder. The company had to fight taxi unions for its very existence. Then the disaster with Travis leaving. Then COVID. Then “Uber’s never going to get profitable.” We’ve always been underestimated. And that feeds into our culture — this is a hungry company. When my leadership team sees complacency, they identify it and get it the hell out.
Steven: Under your leadership, Uber went from losing 2.5 to 3 billion per year to 9.8 billion in free cash flow. How do you balance enjoying the success?
Dara: 9.8 billion last year. We take moments to celebrate. It’s cool to run a company that’s hitting record after record. But if I’m going to make a mistake, I’d rather celebrate a little too little and keep pushing. Success itself is almost a celebration in and of itself.
Encouraging Risk
Steven: How do you get the team to take risks?
Dara: One is they’re always moving fast. That’s what we do. But as companies get bigger and more successful, they tend to become more risk averse. And it should be the exact opposite — you can take more risks, you can make more mistakes because you’ve got 9.8 billion in cash flow to protect yourself. So in the past two years, I’ve pushed the team actively to push the envelope. Don’t be defensive, be offensive. Setting examples — sometimes failing and then saying it’s okay, moving on. That setting the example allows a company to follow.
Goal Setting
Steven: How do you think about goal setting?
Dara: All the teams have different goals — business goals, customer satisfaction, NPS. The ads team has to drive technology driven incremental ad dollars per year. Every team has its own goals and they organize against those goals and execute them. They’re religiously tracked. It’s the best mechanism that we have. I just wish there was a better one, because the art of goal setting itself is the issue — are you setting the right goals? Too ambitious? Not ambitious enough? Sometimes people can game the system.
9. Uber’s Values Reset & Bold Bets
Steven: A lot of companies do an offsite and write some words on a wall. What do you think of that?
Dara: We went through the exercise, failed the first time, succeeded the second time. When I first came to Uber, obviously there was a view that we needed a cultural reset. The culture had some cool stuff — like “Toe Stepping,” the idea that we want to challenge each other within the organization. But sometimes those values became weaponized. Toe Stepping, whose spirit came from speaking the truth, became an excuse to be a jerk. The values in and of themselves can be great or terrible based on how you execute on those values.
When I first came in, we crowdsourced the values — the whole company voted. Most of it was forgettable. Passion, ambition, teamwork. What company doesn’t believe in teamwork? But there was one value that I wrote myself: “Do the Right Thing, Period.” It wasn’t crowdsourced. And people asked, what does that mean? You have to figure it out. It was a message to the whole company — if you work at Uber, you have a responsibility. Use your judgment.
Four or five years in, Nikki Krishnamurthy who runs people pushed me to reset the values. By then I felt I had a right to have a point of view. We came up with a different value set. “Go Get It” — literally what we do, we help people go or get it. But it’s an attitude: we’re go-getters, aggressive, fast-moving, we play to win. “Great Minds Don’t Think Alike.” We came up with values which are unusual and describe how we are different.
The Taxi Bet: Biggest Counter-Intuitive Win
Steven: Any mental case studies of great bets that most people wouldn’t have taken?
Dara: Taxis are one of the fastest growing parts of Uber’s business. Uber started as the enemy of taxis. About five or six years ago, our head of product, Sachin, said, “Why don’t we build taxis on Uber?” Within the company and from some of the founders — they said it’s the most idiotic thing on earth. They hate us. Acceptance rates will be terrible. They had tried it earlier, total failure.
But Sachin’s industry experience and my being ignorant saying “Why the hell not try it?” — that combination allowed us to build a taxi product. Taxi is the fastest growing segment of the company. It went completely against the founding of the company. Now I hope to have every single taxi in the world wired up to Uber. Why not?
10. AI’s Massive Impact on Jobs
Steven: The world has changed in the last couple of years with AI. How do you approach such a disruptive technology? How do you think about its impact on society?
Dara: I think my instinct is always just to go, to move forward. Uber has been built out of an AI core. All of our pricing, routing, matching, whether a courier batches a trip — all of our underlying systems are driven by AI. We do 40 million trips a day. That kind of orchestration can’t be done by heuristic rules. We’ve got to work on the streets of New York and Lagos. So we have built the entire company on small AI models trained on local problems and then stitched together. That’s literally what the company is.
But stepping back as a person — the impact on society is going to be enormous. Going back to Kurzweil’s law of accelerating returns — previously, society has always been able to adjust because it had time to adjust. 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. Intellectual jobs probably 10 years, physical jobs probably 15-20 years. Because physical AI is harder — robots, cars, more capital-heavy, have to deal with the physical world.
The changes are going to be giant. But you can’t slow down the rate of change. And if you are a part of that change, at least you can have some say as to how that change imprints on society. So I’m leaning in. It’s a very exciting time.
Steven: 70 to 80% of jobs will be disrupted. The pace of change means a lot of people don’t have new jobs to go to. The retraining challenge.
Dara: Society’s always adjusted, right? Farming was a huge percentage of our labor force. Now it’s less than 1%.
Steven: But the speed of change…
Dara: That’s a question. And you could argue that AIs will be able to retrain you. Society is going to adjust. But it raises real questions.
90% of Uber Coders Using AI
Dara: About 90% of our coders are using AI. But there’s probably 30% that are power users. They are showing a clear differentiation in the number of diffs — a diff is a code release that’s different from the last release. So one measurement of productivity is how many diffs are you putting to the code base. Uber’s just a giant code base. Our engineers are the builders of the company — they are manufacturing the bricks that go into the system and they’re architects thinking about what the system should look like.
While 90% are using AI tools, about 30% are using them at a completely accelerated pace. It really is changing their productivity in a way I’ve never ever seen before. Ultimately, the job of a coder is going to change more and more — from actually writing the code to orchestrating agents who are writing the code, from manual writing to orchestration. But the job will still be there. My attitude is, if my average engineer became 25% more efficient, I’m going to hire more engineers because I want to go faster. But maybe five years from now, instead of adding an engineer, I should add agents and buy more GPUs from Nvidia.
When Can AI Replace Us?
Steven: Won’t there come a time where you as the CEO can tell an agent what you want to build?
Dara: One of my team members told me that some teams have built a Dara AI — they basically make the presentation to the Dara AI as a prep for making a presentation to me.
Steven: Are you concerned they might show Dara AI to the board?
Dara: I was like, can I see the code for Dara AI? She’s like, no, we’re not showing it to you.
Steven: But is there anything falsifiable in what I said about exponential improvement?
Dara: Where AI still is missing a beat that humans have is the ability to learn real time. You and I are learning from this conversation. But most large AI models — you capture enormous amounts of data, train the model, put it into the real world, some post-training based on feedback, and when it’s released, it’s kind of released. 3.5 didn’t learn — the engineers built 3.8. So the AI agents aren’t learning.
When the models can learn real time, that, I think, is the point at which I’m going to think, yeah, we are all replaceable. But at this point, I haven’t seen a model that can learn real time.
11. Autonomous Vehicles & the Future of 9.4 Million Drivers
Steven: I have a Tesla in LA. It’s staggering that I can get in the car, press a button and drive two and a half hours to Joshua Tree without touching the wheel or the pedals. Driving is one of the biggest professions in the world.
Dara: We’ve got nine and a half million drivers and couriers on our platform. We are the largest organizer of flexible work around the world. And I think the second largest workforce is the Chinese army.
Steven: And statistically, there’s less accidents in an autonomous Tesla than if a human drives it.
Dara: Waymos are safer. And you are a backup to the Tesla as a human being. Once in a while it disengages and you’ve got to take over. So it’s not necessarily the pure autonomous agent that’s better than humans, but definitely the autonomous agent with a human backup — no question, that’s better than the pure human.
Steven: We can’t be far away from it just being…
Dara: Waymo’s there already. They’ve got them in LA, Austin, Atlanta. By all accounts, Waymo Drivers are safer than human beings. There are a million deaths from driving every year in the world. In the US it’s between 35,000 and 40,000 auto fatalities. To the extent that these autonomous agents can be better than humans — and they will be — there’s a real return on human life.
What Do the 9 Million People Do?
Steven: Those 9 million drivers’ careers will conceivably be out of work. Talking about being honest.
Dara: I think 20 years from now you can imagine those 9 million will be 20 million AVs. But we have time. Because we don’t operate in the virtual world — we operate in the physical world. You have to get the regulations up, build the cars, build the sensor stacks. Probably not 10 years from now. But 15, 20 years from now, you’re gonna start getting there.
Steven: What do the 9 million people do?
Dara: I don’t know. We are expanding the kind of work available on the platform. It used to be only driving, now there’s delivering, shopping. We have a team called Uber AI Solutions that allows people to train AI agents and do knowledge-based work on their phone. So we are extending the platform. The question is how much of the platform gets automated and what’s the velocity at which we can extend versus the velocity of automation. I can’t tell you which is going to go faster.
Steven: Hand on heart, it does appear that unemployment is going to be significantly increased.
Dara: You would have to — unless new kinds of jobs come up. That’s why there’s a question. Five years, not a big issue. Five plus years, it’s gonna become more of an issue for society at large.
Jobs, Meaning & the Failure of Universal Basic Income
Steven: I was thinking about your father’s journey — losing what he had, the loss of meaning. Jobs aren’t just about money. I read a study that in suicide letters from men, the sentiment was about not feeling worth to your family. And the extreme was “my family would be better off without me.” This is adjacent to job displacement — where are we going to find meaning when machines disrupt our intelligence and our muscles?
Dara: Every universal basic income test has failed. The answer people hear is the robots will do all the work, create utility, so people will just have money. But every single test — the ones getting income do worse in outcomes. I think the reason is related to what you’re saying — market forces that drive someone to work create a perception of self-value. Succeeding comes with a very deep feeling of “I am creating value, I’m supporting my family, I’m building this incredible piece of art.” That value is what keeps people going. I don’t think the government raining money down on society is going to help.
CEOs: The Public vs Private Conversation
Steven: It’s refreshing to hear your perspective. A lot of CEOs just say, “It’ll be fine.”
Dara: Historically, we have figured it out, so maybe they’re right. But you have to ask whether they’re giving you the real stuff.
Steven: I hear about private conversations where the disruption they anticipate is enormous. Then I see them on CNBC or Davos saying everyone will be fine. I understand the incentive. But you sit at this happy medium of pursuing the opportunity while being honest about the disruption.
Dara: I remember a CNBC anchor said after our interview, “I really like you. You actually answer my questions.” I’m thinking, what — am I not supposed to? The PR training is always, if you get a bad question, pivot to something else. But I’ve sworn to myself — I’m gonna answer the question. The anchor knows what’s happening, the audience knows. So I’ll deal with it.
The Retraining Gap
Steven: What can we do about this? Is it the government’s responsibility? Collective action?
Dara: One — I do think autonomous AI can be a force for good. Safer drivers. Taking 35,000 fatalities to 3,000. AV will bring down the price of transportation. Going back to Jevons Paradox, that’s a good thing. I don’t think the answer is to slow down the pace of change — because China won’t. You have to lean into it.
But society arming up to be able to retrain large groups of people at scale — that is not a capability I see anyone investing in. That is not a core capability of any of our countries. If there’s one thing I can come up with, it’s the retraining machine.
Advice to His Kids
Steven: You’ve got four kids. They come to you — “Dad, AI, robotics, give me some advice.”
Dara: Work hard. You’re gonna be fine. The other piece of advice I give to young people is: don’t plan. I wound up where I am today having not planned a thing. I wasn’t dreaming of becoming a CEO when I was a banker.
People who have too much of a career plan lose their curiosity. Human beings look for positive signal. Anytime someone agrees with you, it makes you feel better. Anytime you get signal that goes against your preconceived notions, you either ignore it or reluctantly take it on. With career planning, people who have too clear a plan are looking for signals that feed their plan. They’ve got blinders — not looking around, not being curious, not looking for signal that can change their life.
So what I tell folks is: before you go out and try to change the world, let the world change you first. Take input. Be open. I wound up where I am kind of by accident. People say, well, you got lucky. I got very lucky. But I was able to take advantage of that luck because I was open.
12. Daniel Ek’s Advice, Father’s Wisdom & Farewell
Steven: You jumped from Expedia to Uber, in part helped by Daniel Ek, founder of Spotify?
Dara: He’s the one who recommended me to the headhunter. I was at the Allen & Co. Conference having a drink with him one night. He asked if the headhunter called me about the Uber role. At the time Uber was a disaster. I had just gotten this wonderful contract. I loved working for Barry. I said, of course I’m not gonna go.
Daniel looks at me with his cold, Scandinavian eyes: “Dara, since when is life about being happy? It’s about making impact. Uber is a great company, and you can have an impact on that company. You’ve got to do this.”
The next day, I called the headhunter. Previously I’d said no. The next day I said, let’s talk. So Daniel was the one who opened me up.
Steven: And your dad gave you advice?
Dara: I talked to my dad, and he keeps things simple. He said in Farsi: “Dara, when a company who’s a verb tells you to run it, you just say yes.” I thought that was good advice. Ultimately, people who come to Uber stay at Uber. They come because of the challenge, but they stay because of the impact.
The One Conversation He Wishes He Could Have
Steven: We have a closing tradition. The question left for you is: What is one conversation that if you could rewind time and have, you would have today, but can no longer have?
Dara: It was a conversation with my dad. I told you I came to New York from San Francisco because my dad was getting very old and losing his mental faculties. I’m glad I came back and got to spend time with him. But those last times, when I spent time with him — it wasn’t really him.
I wish I could talk to him about his experiences, his younger life, the excitement of building something, and the loss and regrets he had in life. I never had those deep conversations. My relationship with him had love, no question. But we didn’t have the deep kind of conversations that I’m hoping I get to have with my kids.
You can’t get time back, and that’s one of the tragedies of life. But it’s also one of the beauties of life — some mistakes are permanent. But my having genuine conversations with you, and connections with my friends, and a real relationship not just with my wife and kids but with my workmates — having those genuine conversations and connections is my way of correcting for the conversation I never had with my dad.
Steven: Dara, thank you. You’re a huge inspiration for me in so many ways. It is rare to find a leader who has been consistently successful across different domains — from investing to CFO to CEO — who’s repeatedly contended with moments of transition and given us frameworks for how to deal with that. One of the great ones I take away from you is honesty.
Dara: Honesty is so powerful. And I’ll tell you, I learned that skill from my wife. She’s always like, people are people. Doesn’t matter — they eat, they crap, they have to go to sleep. And she treats everybody in her life the same way, regardless of their position.
Steven: Like your dad did.
Dara: Yeah. And she’s — honesty, it’s just so powerful.
Steven: Thank you so much.
Dara: You’re very welcome. An unbelievable inspiration.
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