Diary of A CEO: with Uber CEO Dara Khosrowshahi (Transcript)

He passed away a couple of years ago, so it’s tough for me to talk about it. Let me try again.

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, so I communicated with him in Iran. But expression of feelings and frustration were not something that my family did. You just dealt with the situation.

So yeah, I think I suffer from over-stoicism and then breaking down every once in a while, as you just saw.

STEVEN BARTLETT: It’s a familiar story of the men that I’ve interviewed who grew up with that kind of emotional composure enforced and modeled to them.

DARA KHOSROWSHAHI: Yeah, I don’t know if it was enforced — it wasn’t implicit. 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 or communicate it to everyone. 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.

On Fatherhood and Breaking the Cycle

STEVEN BARTLETT: How does — because I’m not a father yet —

DARA KHOSROWSHAHI: Yes.

STEVEN BARTLETT: But I’m approaching that. I’ve just proposed to my fiancée, and we’re in the process now of bringing children into the world, hopefully. And it’s one of the things I think a lot about — how do I stop my own stoicism passing on to my children?

DARA KHOSROWSHAHI: First of all, fatherhood, parenthood, is so humbling. You have such a picture in your mind as to how you’re going to raise your family, what your kids are going to be like, and they just become their own people. And it’s such a beautiful process to see.

At first there’s this alarm — “Oh my God, I’m losing control. I’ve done everything, I’ve planned everything. This is how I’m going to raise kids.” But then real life gets in the way. It is absolutely exhausting. So you probably execute on 80% of your plan, and you’re 20% imperfect because you are exhausted and you’re working and you’ve got a career.

And at some point, you see these kids kind of move off into this completely unexpected territory. For me, being a bit of a control freak, I thought, “This is not good. They’re doing their own thing.” But then you step back and you think, “This is absolutely gorgeous what’s happening.”

The advice I would give in terms of being a parent is just spend the time with the kids. That is the magic — not what you do or the particular tactics, but the investment in them and the time spent with them. The rest you can’t control. But what you can control is that connection.

Childhood Photos and a Mother’s Words

STEVEN BARTLETT: I went back and looked through lots of different photos of where you lived and where you grew up to try and get a picture of your world in an early context. And all these photos look incredible. I think that was your fifth birthday.

DARA KHOSROWSHAHI: Oh, wow. I had hair back then. My mom loved to dress us up in little doll outfits.

STEVEN BARTLETT: I can tell. Here’s another one.

DARA KHOSROWSHAHI: Lord, look at that. I’m definitely not going to do that to my kids.

STEVEN BARTLETT: Age 4 in London — a photo of you and your cousins there. And another one.

DARA KHOSROWSHAHI: Family was everywhere for us.

STEVEN BARTLETT: And again, another one with a beautiful haircut there.

DARA KHOSROWSHAHI: It was a great childhood. It was amazing.

STEVEN BARTLETT: I spoke to your mum, Lily. I hope —

DARA KHOSROWSHAHI: Well, how’d it go? We’ll see.

STEVEN BARTLETT: She said — I’ll play the audio file just so people can hear it.

LILY KHOSROWSHAHI (audio clip): “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.”

Building Impact: From Iran’s Factories to Silicon Valley

DARA KHOSROWSHAHI: I can’t say I remember that conversation, but one of my early experiences that really imprinted on me was when we went to visit one of my dad’s family factories. My dad was in charge of designing factories, building them, operating them. And the respect that the factory population had for him — the excitement they had that his family was visiting — was just really cool.

The way that he treated them, he knew everyone’s name. He treated them with such respect. It really imprinted on me. There was this care. It wasn’t, “The boss is coming and there’s fear.” For me, that ability to build a life where you have impact on a lot of people, but it’s positive, building impact — where you have the broad respect of those folks — it really imprinted on me.

So I always wanted that. When we came to the States, making money was important. I don’t want to say, “Oh, I didn’t care about it,” because we lost everything. My first job was investment banking. What’s the goal of investment banking? Have fun but make money. And so that was a priority for me.

But then as I matured in life, as I knew I had safety — okay, yes, I can make money, I can provide for my family, I can support my mom and dad — then building an enterprise, having that feeling that I saw with my father, that connection with his team, became something really important to me.

Arriving in America at Nine Years Old

STEVEN BARTLETT: When you came to New York, you were eight, nine years old?

DARA KHOSROWSHAHI: Nine years old, yes.

STEVEN BARTLETT: If I’d asked you at nine years old, when you arrived in New York, what you wanted to do when you were older, what would you have said?

DARA KHOSROWSHAHI: I have no idea. I wanted to make my dad proud. That was it. I wasn’t motivated by a specific target at all. I just wanted to make my family proud.

STEVEN BARTLETT: Why make your dad proud?

DARA KHOSROWSHAHI: He’s always been an important figure in my life. Part of it is that I never got to know him that well as an individual, because when I was younger, he was working all the time. He would show up once in a while for dinner — we always had family dinners together. And then he went away, and then I went off to work. So I never really got to know the person that he was.

But there’s this sense of duty, this hope that he’s somewhere — or maybe he’s not someplace. Making my father proud has always been a strong undercurrent in my life.

The Road to Brown University

STEVEN BARTLETT: So you’re nine years old, you’ve arrived in New York City. You do end up going off to college sometime later.

DARA KHOSROWSHAHI: Yes, I went to Brown University, studied engineering there.

STEVEN BARTLETT: How do you think about that choice at that time, and how determinant that was of your trajectory in your life — that decision to go to that university and study that subject?

Engineering, Investment Banking, and the Road to CEO

DARA KHOSROWSHAHI: 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, and those equations being able to represent something in real life and then magically that something in real life 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 BARTLETT: Engineers make good CEOs, great CEOs, if you step back.

DARA KHOSROWSHAHI: 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. It’s an organism and it’s a machine at the same time. And to some extent the job of the CEO is engineering. How do I set up the company to achieve the goals that I set for shareholders, set for my board? It’s a giant engineering problem. And to me that’s fascinating — the putting together the pieces to get to what you perceive to be the goal.

And one of the really important things is you’ve got to pick the right goals. That is one giant problem solving engineering challenge, and it’s one of the most fascinating parts of my job.

STEVEN BARTLETT: I want to get into that — the practical company building, how you organize an organization to be a well functioning machine, setting goals and all that stuff. After college you go into investment banking for a period of time?

DARA KHOSROWSHAHI: Yeah, I worked there for eight years in risk arbitrage to begin with, and then mergers and acquisition advisory work as well.

STEVEN BARTLETT: And that experience, I was reading, taught you about betting on people?

DARA KHOSROWSHAHI: Yes.

STEVEN BARTLETT: Versus other things. What do you mean by betting on people, and why is that important?

DARA KHOSROWSHAHI: It was actually a lesson that I learned from Herbert Allen, who was running Allen & Co. at the time. The Allen family started the company, and he always told me — and at the time I didn’t really listen to him — he always said, “Dara, always bet on people. Companies go. There are good companies, bad companies, but great people stay great all the time.”

And one of the things that made Allen & Co. really special — investment banking can be a dog-eat-dog sport, but Allen & Co. really cultivated relationships with people whom they perceived to be great, both in terms of potential and in terms of character. Of all the investment banks, that loyalty, that making a bet on a person and then staying with them through their whole careers, is a pattern of how that place works. And it’s definitely something that I learned there.

STEVEN BARTLETT: What is it about one’s character that makes them qualify as a great person?

DARA KHOSROWSHAHI: You look for success, honor, loyalty — people who will tell you what they’re going to do, whether it’s good or bad, and then follow through on their promises.

STEVEN BARTLETT: Hard work. I’m surprised that wasn’t mentioned.

DARA KHOSROWSHAHI: Well, that comes with success.

STEVEN BARTLETT: Okay, right.

DARA KHOSROWSHAHI: Talent and hard work. You put those two together and —

STEVEN BARTLETT: Why did you leave Allen & Co.?

DARA KHOSROWSHAHI: I left Allen & Co. because I met Barry Diller. He was a client of mine. We got to meet in a big, unfriendly, hostile tender offer for Paramount at the time. There’s another one happening for Paramount now, as we speak. And he was the one person I thought — I was going to be an Allen & Co. lifer. I thought I was going to be there forever. My older brother Kaveh is an Allen & Co. lifer. It’s the only job he’s had in his life. But Barry was the one person who I thought, if I get a chance to work for this person, I’m going to jump at it. And I did.

STEVEN BARTLETT: Why? Why Barry?

DARA KHOSROWSHAHI: He’s spectacular. He was spectacular. He is spectacular. A doer. I met him in a circumstance where he lost. It was his giant hostile tender offer, bids going back and forth between the winner, Viacom, and Barry. Ultimately, Barry stepped away, and we were planning an announcement. You can imagine all these fancy PR people sitting around a table — how do we present a loss as a win?

STEVEN BARTLETT: So he bid for a company and he didn’t get it.

DARA KHOSROWSHAHI: He didn’t get it. He walked away. He didn’t get it because he walked away, which in hindsight was a mistake — he could have paid more. And then in the release where he walked away, I think the release was, “They won, we lost. Next.” And he was a constant motion machine. They won, we lost. Next. What’s next? Let’s go. And that’s the kind of person I wanted to work for.

On Losing, Learning, and Moving Forward

STEVEN BARTLETT: In business, losing is part of the game.

DARA KHOSROWSHAHI: Absolutely. But then calling it out — not bullshitting, not like, “Oh, we tried our best in the circumstances.” They won, we lost. Next. It’s okay.

STEVEN BARTLETT: Does it matter how you lose?

DARA KHOSROWSHAHI: Absolutely it does. And I find companies guilty of two things. One is ignoring losses, papering over them. And then sometimes being obsessive about the loss — inspecting it, what happened, let’s do a summary, let’s meet, what went wrong. For me, it’s somewhere in the middle, which is: recognize that you lost, say it — because it’s important to say it — analyze it, but then move on.

The next time, you hope to have learned some kind of judgment to avoid that kind of a loss. But it doesn’t mean you’re going to avoid losing at all. If you’re not taking shots, you’re not missing, you’re not losing. So for me, it’s constantly moving and taking your shots — losing, learning, next. Losing, learning, next. That constant motion is what I want to see. That constant motion and learning is what excites me.

STEVEN BARTLETT: This is business advice, but also life advice generally, because a lot of people who I meet will ask questions that sound a lot like what you just said. It’s dealing with rejection, dealing with taking an L, and how that L then stays with them — sometimes for a decade, sometimes for 15 years — and holds them back, hurts their confidence, means that they don’t take any more shots. And this can cause a sort of downward confidence spiral.

DARA KHOSROWSHAHI: 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 BARTLETT: You have a difficulty dealing with rejection in your personal life?

DARA KHOSROWSHAHI: Very much, yeah.

STEVEN BARTLETT: What kind of rejection?

DARA KHOSROWSHAHI: Any kind of rejection, conflict. It’s something that I’ve fought my whole life. Because I was one of the younger cousins, because I was the youngest brother, I just kind of didn’t have rights. So I went with the flow. And going with the flow means you’re going with a current. I didn’t cause trouble, and that has followed me in my personal life.

In my professional life, I don’t have as much trouble there. I guess my professional life, to some extent, is a mask — because I get to be aggressive, I get to lose. It’s something that Sid, my wife, has really helped me with. But it is something in my personal life where I’m generally conflict avoidant.

STEVEN BARTLETT: You’re conflict avoidant in your personal life. Interesting.

DARA KHOSROWSHAHI: Yeah, definitely.

STEVEN BARTLETT: That’s not good in a relationship.

DARA KHOSROWSHAHI: No, 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. I’m still on a learning journey there, I’ll tell you that.

From Expedia to the CEO Chair

STEVEN BARTLETT: Eventually, you go on to becoming the CEO of Expedia. There were a couple of CEOs that came before you, but you became the third and took that company in a very different direction. Very different job, going from investment banking to being a CEO.

DARA KHOSROWSHAHI: Yeah. There was a journey there, because I went from banking to running deals, and I knew that I liked how companies worked. The thing that I liked about investment banking was that I got to see a lot — really smart people, really cool companies being built. But I couldn’t go along with that journey. I was jealous of the journey that these CEOs were moving on.

So when M&A became a bridge to working at a company and building it, I moved from M&A to CFO — Chief Financial Officer — because that’s, to some extent, finance, but it’s also being the CEO’s partner and helping the CEO build. I always knew the direction I wanted to go in, which was: at some point, I want to actually be an operator.

And then I had the opportunity to take over Expedia. The CEO at the time, Eric Blatchford, said the big company thing wasn’t for him, so he resigned. And honestly, Barry didn’t have an alternative.

STEVEN BARTLETT: Barry was the owner.

DARA KHOSROWSHAHI: Barry was the CEO and chairman of IAC, which was the parent company of what became Expedia. The head of IAC Travel resigned. I raised my hand and said, “Maybe I could do it.” Barry was desperate — he had no one else. So he promoted me to be CEO of IAC Travel. And IAC Travel was going through some difficult times, so we spun it off as Expedia. That’s when I became the CEO of Expedia, the public company, and I moved from the Netherlands to Seattle.

STEVEN BARTLETT: In your job just before you took on that role as CEO, you were buying businesses — mergers and acquisitions. What are some of the companies that you bought?

DARA KHOSROWSHAHI: We bought a lot of companies. We bought Ticketmaster, we bought Match.com, bought Expedia, Hotels.com. And it was all around a theme that Barry and I were fascinated with — the movement of commerce online.

It was during that time, the late 90s, early 2000s, and we saw it happening with our very own eyes, really, with home shopping. It was a flat screen, a television, and you were offering products and people were calling up, buying those products electronically. And just the medium change — from a TV screen to an Internet screen, and instead of calling, you could use HTTP. So while the medium changed, we kind of saw this opportunity to take advantage of the change of platform.

Match.com, essentially, in the olden days — you had online dating, but you would call a number. You’d be like, “My name is Dara and I’m six foot two,” and you’d describe yourself and you’d hear other recordings and you would get matched up based on someone who seemed nice. And all of that just moved online. That was what Match.com was.

Same thing with Ticketmaster. In the olden days, you would go to a Tower Records — have you ever been to a Tower Records? So there were these things called record stores, and they also had a desk where they would sell concert tickets. You would either call for a concert ticket or you would physically go and buy one. And there were lines — Tower Records lines. And all of that moved online.

Same thing with travel, right? You would call a travel agent. So there was this movement of retail and phone commerce to online commerce, and we identified the early players making that shift. Personals, ticketing, and travel were the ones we went for, because at the time, Amazon was doing everything else — physical fulfillment. What we were going for were essentially electronic transactions that did not require physical fulfillment. Travel, because it’s a virtual good. Ticketing. Match.com, which was personals. There was a pattern around the madness, so to speak. But we went out and bought all these companies. It was a really great time.

Spotting Great Companies and Pattern Recognition in Transitions

STEVEN BARTLETT: I’ve got two questions that emerge then. One is, again, I’m really interested to understand how you would look for talent or how you think about what a great company is. Are we looking at the company culture, were you looking at the founders? Was there something else? Was it the profitability?

And the other one is just really intrigued as to what this period of your life and thereafter taught you about how to spot opportunity and transition. Because that is a transitional moment of technology. And I think there is a certain pattern recognition one can develop as to know what to bet on in these moments of transition where there’s huge skepticism — “the Internet’s not going to be anything.”

So two questions there. One is how do you spot great companies? And then the second is patterns in transition.

DARA KHOSROWSHAHI: So I’d say they’re related, which is 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 they’re going, how much should you invest, what’s the return, how large is the market going to be.

But there were companies that were 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.” That was it.

And to some extent it’s a self-reinforcing cycle, which is yes, the great management teams and the great founders were the ones who were able to identify the opportunity and hit that opportunity faster than anyone else — recognize that opportunity and execute on it faster than anyone else. So to some extent, the companies who were in the lead of course had the best management teams and the best founding teams. And when those two things matched, that was when we jumped.

And then the last thing I would tell you in terms of pattern recognition is that 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.

So I do think one of the key pieces of pattern recognition for me is that humans think about success and transitions in a linear way, because time is linear.

STEVEN BARTLETT: What do you mean by that? For someone that doesn’t — they think of it going like this?

DARA KHOSROWSHAHI: Yeah. Everything kind of moves this way. Your schedule is relatively linear. You sleep seven hours a day — your life is a linear life. But company success and company momentum, especially with new technologies, where if there’s a technology that’s truly better than the other technology, within the virtual world there’s absolutely no friction holding it back.

These companies move in an exponential way in terms of their growth and ultimately in terms of their value. So whereas most people, when they project out to the future, they see a straight line — what actually happens is a hockey stick. And that’s where the opportunity is. It’s the spread between the hockey stick and the straight line. And it’s very difficult for people to process that.

Those were the companies that we identified. Online travel was a hockey stick. Personals was a hockey stick. Ticketing was a hockey stick.

Jevons Paradox and the Birth of Uber

STEVEN BARTLETT: I heard about the — is it Jevons Paradox?

DARA KHOSROWSHAHI: Yes.

STEVEN BARTLETT: Which I think kind of overlaps with what you’re saying there. When things become easier, faster, cheaper, people do them not incrementally more, but exceptionally more often.

DARA KHOSROWSHAHI: I mean, that’s the definition of Uber. And we can get to that at some point. Originally it was built as a black car service, so to speak.

STEVEN BARTLETT: Can you tell me where it came from? Because a lot of history has now moved forward and people have forgotten the story of how it came to be.

DARA KHOSROWSHAHI: To a large extent, the founding was before me, but it was Garrett Camp who was one of the founders. He had this idea, and I think it was born in Paris. It was a snowy day in Paris and they couldn’t find a black car. It was a bunch of young tech guys thinking, “How cool would it be to pick up my phone and call a black car?” And that was the core idea — you can use your phone to call a black car.

He brought on Travis Kalanick. Travis was the operator and the co-founder. And to your point on Jevons Paradox, people thought, “Well, what’s the size of the black car marketplace?” And it was a couple of billion dollars. Or, “What’s the size of the taxi industry?” And it was more than a couple of billion dollars. But what they didn’t see at the time was that if you radically make something either more convenient or cheaper, the market expands beyond how you calculate it.

So the Uber size and scale now is way beyond the original marketplace of black cars or taxis. The company today is a result of Jevons Paradox and timing.

The Role of Timing in Uber’s Success

STEVEN BARTLETT: We often don’t think much about the luck of timing. “Luck” is an interesting word to use, but how important timing is — and other foundational factors — in enabling a company like Uber to exist. When you think about the timing of Uber, what are the foundations that made it possible?

DARA KHOSROWSHAHI: It was the mobile revolution. It was mobile data technology and the iPhone coming together. In the early days, one of the geniuses of Travis was that he would hire these market managers who would be GMs of new cities they would expand into. They would literally go to the city with a bag full of iPhones and give them away to black car drivers to get them to come onto Uber, because at the time 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 to understand that there’s a pattern here — “I’m going to replicate that pattern all around the world and raise as much capital as I have to in order to get there faster than anyone else.” That was the magic.

Yes, there’s luck in there. But if that founding team hadn’t been as aggressive in blitzscaling — which is a term that folks used all around the world — the company wouldn’t be what it is today.

From Investment Banking to Expedia: Learning to Lead

STEVEN BARTLETT: Your transition out of investment banking into Expedia — CFO, then CEO. There’s a stereotype in business that investment bankers and CFOs don’t necessarily make the best CEOs, because they might stereotypically over-financialize, maybe be less risk-tolerant. And when I spoke to Barry, he did say the following. I’ll just play it for you because it’s better coming from him.

VIDEO CLIP BEGINS:

BARRY DILLER: He was not an active leader because his career up until then had been on the financial side of things. So he really had not yet had the experience or opportunity to manage people. That came in a difficult way to him. 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.

VIDEO CLIP ENDS:

DARA KHOSROWSHAHI: Yeah, growing up under Barry was — and by the way, I wouldn’t be where I am today without him. Not him as a mentor, because he’s not really a mentoring kind of guy, but him as my leader, learning from him.

I’d say the experience that really shaped me as it relates to Expedia was that I did come in as more of a financial leader. Our leadership at Expedia.com failed. I hired a person, had to fire them, hired a second person — complete disaster. So I was 0 for 2 in terms of hiring for our largest business. This business was 50% of our profits, and I was 0 for 2 in hiring.

So I went to Barry and the board and said, “If I miss hiring the third person to run the biggest part of our business, then you should fire me.” Barry quickly agreed — “Yes, of course we will.”

So I said, “Obviously, I don’t understand enough about the job to find the right person. I think I’ve got to take the job myself for six months to a year to understand what the job actually entails, so I can then go find the right person.”

And so for what turned out to be five or six years, I ran both the holding company — Expedia Inc., which is a public company — and I ran Expedia.com. I was President of the largest part of the company.

That experience taught me my operating chops. It taught me how to actually operate a company — how to run something. And that’s a very different skill set from capital allocation and financial wizardry. That’s important, but what I discovered was that operating a company, leading it, organizing it, setting up the goals, getting the right team together — that’s the part of the job that I loved.

It took me a while to get there. My whole early career was in the financial sector, which I enjoyed. But I didn’t find my true love — which is operations, running companies, running a technology company — until way, way later in my career.

And I think now I’ve got both. I’ve got that financial foundation because it has to work. But the operations and leadership part of the business is something that I love. And watching Barry take responsibility, take shots, go against the grain as aggressively as he consistently did — I think that has made me a much better operator than I would have been with any other boss.

STEVEN BARTLETT: Three months into that role, the head of HR told you that you were scaring people.

DARA KHOSROWSHAHI: I’d forgotten about that. I think that was my job. Yeah.

STEVEN BARTLETT: What’s the context there?

The Art of Transparency and Hard Work

DARA KHOSROWSHAHI: The context was that, first of all, turnarounds in technology are really hard. We were talking about the momentum thing. When momentum is positive in the technology sector, if momentum turns negative, it is remarkably difficult to turn it around. Yahoo is hanging on, but it was a great company, and you see where it is now. It’s brutal when you get it wrong. And it always takes longer than you think.

It goes to when I was talking about linear versus exponential. 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 f*ing disaster.

So what I saw with Expedia was a technology company whose technology engine was broken. The code base was old, had not been reinvested in, technology leadership was coasting, and that really alarmed me. And one of the things that I learned from Barry in terms of leadership is that when a bell is rung, when you see something, when you see a pattern, you have to act. You can’t wait for a second.

So in my mind, once I figured out, “Oh my God, this really is a turnaround. This isn’t like a company that I’ve got to tune. This company, if I don’t move and move hard and fast, is going to start on that exponential decay curve.” I had to move quickly.

One of the skills that I learned from Barry is transparency. Whenever he wanted to understand an issue, he wanted to go to the source. He didn’t want a summary, and it didn’t matter where that source was — whether it’s a junior analyst or a president. He wanted to hear from the source because what he didn’t want to lose is the fidelity of the issue.

When there’s an issue, it goes through the analyst, the associate, the vice president, the SVP, and whatever. By the time it’s summarized for you as the CEO, it’s lost everything. And usually at each level it’s like, “Hey, do we really want to tell them that? Why don’t we phrase it this way?” So your whole life as a CEO is a version of the world that your team wants you to see. If you’ve got a good team, usually it has more to do with reality than not. But you are subject to your team and the information flow that gets to you.

Barry always wanted to go to the source. He would just cut through levels, get to the core of the idea. And then once he did, he would move fast. For me, I’ve held onto that, but I’ve also turned it the other way — one of the ways in which I can depend on getting the real truth from you is by being honest with you.

Human beings are good bullshit meters, so to speak. When you’re the CEO and you’re talking to your staff and giving all the business talk — “We’re doing this, but last quarter we had some certain challenges” — they see you bullshitting them. So why the hell should they tell you the truth? If their boss isn’t telling them the good stuff, why should they give the good stuff back to the boss?

For me, it was almost like 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. Otherwise you’re going to filter yourself.

STEVEN BARTLETT: But do you ever worry that they might not be able to deal with the truth?

DARA KHOSROWSHAHI: Then they can leave. And I think that’s what my head of HR was saying — I was scaring the hell out of people because I’m like, “We have a real problem here and we’ve got to come together.”

A good decision-making framework for me is: if I make a mistake, where do I want to make the mistake? 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. Because if that person doesn’t want to face the truth, if he or she’s not up for the fight, then they should go someplace else. They can have a good career elsewhere.

So for me as a leader, I’ve always believed in transparency. Partly because I think you attract the right people, and partly 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.

It’s incredibly important as a leader of any organization to build the channels and build the kind of culture that surfaces problems to you quickly. And you always have to have your random direct channels. If you think about organizations as organisms, they have their own incentives. My staff’s incentive is to control the information that gets to me — not because they’re bad people, it’s just their job, because I can get overwhelmed. Who do I meet with? What’s my schedule? Is this person worthy of meeting the CEO?

My fight is I just set up a bunch of random touchpoints. I’ll meet with engineers four levels down consistently, because usually they’ve got the kind of personality where they don’t give a damn. They’ll tell me anything and everything. And they like putting the CEO down. That’s great.

STEVEN BARTLETT: They like putting the CEO down?

DARA KHOSROWSHAHI: Engineers often don’t like authority. And code is like the biggest authority buster — it’s the truth. So I find a lot of engineers have a personality where they’ll just tell you what it’s like. Their value is in something else, and there’s a kind of disrespect for authority that I love.

STEVEN BARTLETT: I’ve found in my companies that there’s sometimes a 24-year-old young woman who will just tell me the truth.

DARA KHOSROWSHAHI: Yeah. And she’s the one you want to hang out with.

STEVEN BARTLETT: She’s the one I always go and ask for an opinion.

DARA KHOSROWSHAHI: Absolutely. You’ve got to have your own channels, but the way to get transparency from your team is — first, you’ve got to give it to them.

Turning Around a Coasting Culture

STEVEN BARTLETT: Was the culture hard-working when you arrived? Because you used the word “coasting” to describe some of the team when you arrived at Expedia.

DARA KHOSROWSHAHI: Medium. The company had been successful for a long time and had coasted on that success to some extent. So I needed to turn over the team — the entire team — very, very quickly and get some hungry people in there.

STEVEN BARTLETT: The entire team?

DARA KHOSROWSHAHI: Almost the entire team. Yeah. It was rough going for a while, but then you have mission-oriented people who are trying to prove themselves, and it’s part of the renewal that every company has to go through. We turned it around. It was tough going, but we really turned it around. And that was when I learned, “Hey, my love is running things. It’s great. It’s the best part of my job.”

STEVEN BARTLETT: How did you get that company to work hard? Because there are so many people listening right now who are in a company that might have been successful, coasting, maybe two decades in. This is an ultimate question in executive management — how do you turn around the culture of a big company, or even a 200-person company?

DARA KHOSROWSHAHI: It’s very difficult. And sometimes the shortcut is just changing people. It’s finding the people who you believe will line up with your cultural mechanisms — how you work, your values — and then embodying those values and mechanisms as examples, and making sure that your team embodies those values and passes them down through the organization.

Part of working hard is, for example, sending emails to the team on a Saturday, and if I don’t get a response on Saturday, sending them an email on Sunday with a question mark — “What’s going on?”

At Expedia, in hindsight, we worked intensely and went hard, but not as hard as I’d like. Because Expedia was selling vacations — the product we were selling was about turning yourself off. So we did talk about work-life balance.

At Uber, it’s different. 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, and it’s a company that’s making a difference in the world. You’re going to learn so much, and while you will have worked hard, you’re going to have a great time.

But don’t come here if you want to coast. I’m very clear about that. And I should have been more clear at Expedia, but we were selling vacations, so I couldn’t be quite that direct.

The Skill of Working Hard

STEVEN BARTLETT: In your 12 years as CEO, Expedia stock rose 550% and sales increased 400% — from $2.1 billion to $8.8 billion. And you were the highest-paid CEO of a US tech company, with a pay package of $94.1 million.

DARA KHOSROWSHAHI: I left it all behind to go to Uber.

STEVEN BARTLETT: You left it all behind.

DARA KHOSROWSHAHI: It was a big options package that I never vested. But it’s all good. It was a great run.

STEVEN BARTLETT: I’m so intrigued about this point of hard work, because I think ten years ago, saying what you just said was very taboo.

DARA KHOSROWSHAHI: Yes.

STEVEN BARTLETT: It feels to me more in vogue now.

DARA KHOSROWSHAHI: We’re freed now. Yes.

STEVEN BARTLETT: You’re freed now.

DARA KHOSROWSHAHI: Yes, indeed. Sometimes people ask, “What advice would you give to young people?” And to me, 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 have.

Way too many people focus on whether they should be a computer programmer or a doctor, or study the liberal arts. Now that anyone can vibe-code, just learn to work hard.

When you see the top athletes, of course they’re talented — their talent level is world-class. But the thing that’s different about the elite athletes versus the non-elite athletes is they work their asses off. They’re disciplined, they’re structured, they’re relentless. Look at Ronaldo, look at Michael Jordan. The same thing is true in all of life — in business, in personal life.

For me with my kids, I just want to teach them how to work hard. Growing up, as a banker, as an executive, I told myself: I’m not going to let anyone outwork me. And if that’s true, then they may be smarter, more talented, but I’m not going to let anyone outwork me. That’s a huge advantage. And over a period of time, that advantage compounds.

I want that in our company. I want Uber to be an incredibly hard-working company.

STEVEN BARTLETT: Comes at a cost though, no? Working hard.

Work Ethic, Culture, and Continuous Improvement

DARA KHOSROWSHAHI: It comes at a trade off. And we believe in flexibility. So people confuse lack of flexibility with working hard. You can work hard and at the same time you can have flexibility. So if you want to have dinner with your family — and I’m religious about having dinners with my family 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. So of course there are trade offs, and life is about trade offs.

STEVEN BARTLETT: I think one of the most important things I’ve learned from interviewing CEOs — and generally we’ve gone through a transition of COVID and remote work and then come back into everyone being in the office again — is actually the most important thing is what you just said, which is being honest with people so that they can make decisions for themselves in their lives.

DARA KHOSROWSHAHI: Absolutely.

STEVEN BARTLETT: I think the thing that one might describe as toxic is when you say something publicly, but then when they arrive, it’s a completely different deal. But what you’re doing is you’re being honest, and you’re therefore allowing people to make decisions for themselves in their own lives.

DARA KHOSROWSHAHI: And I’m allowing them to be honest back to me.

STEVEN BARTLETT: Yeah. And that’s a company culture that someone like me would be attracted to.

DARA KHOSROWSHAHI: Absolutely.

STEVEN BARTLETT: But there are lots of people listening that couldn’t think of anything worse.

DARA KHOSROWSHAHI: And that’s okay.

STEVEN BARTLETT: Yes. Yeah.

DARA KHOSROWSHAHI: There are plenty of companies that they could find, or plenty of causes that they can find. It’s fine.

Learning to Work Hard

STEVEN BARTLETT: You said “learn to work hard.” Learn?

DARA KHOSROWSHAHI: It’s a skill.

STEVEN BARTLETT: Really?

DARA KHOSROWSHAHI: Yes, of course it is. The idea of just staying focused on something, 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. I see it in people all the time. There’s just this grim determination. At Uber, there’s actually a saying inside one of our values: “Embrace the grind.” Embrace it. That’s a learned skill. That’s not something you’re born with. Maybe there’s an element that you’re born with.

STEVEN BARTLETT: Have you ever seen someone who isn’t a hard worker become a really hard worker? An exceptionally hard worker?

DARA KHOSROWSHAHI: That’s a good question. No. Doesn’t occur to me. Have you?

STEVEN BARTLETT: No. I heard — I think it might have been Brian Chesky at Airbnb or Elon — say that he’s never seen someone who wasn’t a hard worker become a really hard worker.

DARA KHOSROWSHAHI: That’s interesting.

STEVEN BARTLETT: And this is why I’m trying to —

DARA KHOSROWSHAHI: — come up with someone. I’m failing so far.

STEVEN BARTLETT: And maybe I might posit that it’s somewhat to do with your childhood, your early context, which you didn’t choose.

DARA KHOSROWSHAHI: I was also working hard here, but —

STEVEN BARTLETT: — you were forged in such a way that you were going to be relentless.

DARA KHOSROWSHAHI: Yeah. Relentless is right. I think at one point, Jeff Bezos was going to call Amazon “Relentless.” That was the name he was thinking about for the company.

And that is what I see in successful technology companies — there is this relentlessness. At Uber, we have lots of different groups that are trying to do different things, but 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 and improve it.

So as an organism, every part of the company — whether it’s a payments team in terms of new payment types or payment success, or the fraud team, or the mobile app team in terms of conversions — every team is set up, organized, and goal-driven around improving everything that they do. The whole company, in small ways, is constantly improving, never ever stopping.

And it is not good enough to get better. We have to get better faster than our competitors, because our competitors are all getting better as well. So it’s basically who can adapt faster — either to the reality of the market as it is today, or the prediction of the market as you see it tomorrow. The speed of change and the identification of the opportunity — those are the two factors I think are most important.

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. And then, of course, there’s identifying the opportunity and going after it. Those are the two things you really have to get right.

STEVEN BARTLETT: If you’re taking two shots, not only are you going to get two data points of information, but you’re also increasing your probability of having a successful shot by like 100%.

DARA KHOSROWSHAHI: Shots on goal. Just shots on goal.

Building a Culture of Continuous Improvement

STEVEN BARTLETT: How do you create a culture of continuous improvement? Because successful companies, as you highlighted earlier, become complacent with their victories. They like to take some time off and celebrate — high five, and then chill. And the studies show, in this big meta-analysis where they looked at successful companies, that they become risk averse because of loss aversion. They have something to lose now, so they just protect it.

DARA KHOSROWSHAHI: I think the good news, to some extent with Uber, is that we’ve always been a company that has had a chip on its shoulder. The company had a chip on its shoulder when it was founded and had to fight taxi unions for its very existence. Then the disaster happened with Travis leaving and a new CEO coming in — that was a really, really difficult time. Then we went through COVID, which was again a disaster for the company, but ultimately prepared us to do better. Then people saying it was a tough IPO, that Uber was never going to get profitable. And today we’re incredibly successful.

But we’ve got the challenge and the opportunity of AI and autonomous vehicles. So we’ve always been a company that has been, I would say, underestimated. And that feeds into our culture — we are a hungry company.

I do think we’re sometimes guilty of getting complacent in little ways. But I have a leadership team that, when they see complacency, more often than not, they identify it and they get it the hell out. It’s a team that is not satisfied, that’s always driving. And I love that about us.

Balancing Success and Ambition

STEVEN BARTLETT: How does one balance enjoying the success and the accomplishments? I mean, you’ve turned this company around into a highly profitable business. Everyone I’ve spoken to — many of our mutual friends — have talked lovingly about the impact you’ve had on the business. The numbers speak for themselves. When you joined Uber, Uber was losing $2.5 to $3 billion per year. Now it generates $8.5 billion in free cash flow every year.

DARA KHOSROWSHAHI: $9.8 billion in the last year. But they’re counting.

STEVEN BARTLETT: You’re counting — $9.8 billion. Incredible. Celebrate. Chill.

DARA KHOSROWSHAHI: Well, you can celebrate and not chill. We take those moments. It’s cool to run a company that’s so important. It’s cool to run a company that’s hitting record after record after record. And we do celebrate those records and those milestones — maybe not enough. And again, it goes to: what mistake would you rather make? I’d rather make the mistake of celebrating a little too little and being a little driven and pushing forward.

But the success itself — succeeding is almost a celebration in and of itself. And when you’re succeeding in such a competitive field, I just find a deep sense of satisfaction there. And I think my team does too.

Taking Smart Risks

STEVEN BARTLETT: How do you get the team to take the risks that they need to take? Is there something you do? Do you incentivize them on the amount of shots they take? How do you do that?

DARA KHOSROWSHAHI: One is they’re always moving fast. That’s what we do — we push. We’re constantly pushing the pace of the company in terms of execution. So I think that helps.

But I do think there’s a mechanism I’ve talked to the team about, which is taking smart risks. I think you’re absolutely right — as companies get bigger and more successful, they tend to become more risk averse. And it should be the exact opposite, because you can take more risks and make more mistakes when you’ve got $9.8 billion in cash flow to protect yourself against some of those mistakes.

So I have, in the past two years, pushed the team actively to push the envelope in terms of risk. Don’t be defensive, be offensive. And it comes from my challenging the teams, talking about it, setting examples of sometimes failing and then saying it’s okay and moving on — and sometimes making decisions that are seen as more risky than not. That setting of example then allows the company to follow.

Goal Setting and Company Values

STEVEN BARTLETT: So if I was in one of your teams, how do you think about goal setting?

DARA KHOSROWSHAHI: All the teams have different business goals. The ads team has to drive technology-driven incremental ad dollars per year, or customer satisfaction, customer NPS, and so on. Every team has its own goals, and they organize against those goals, execute on those goals, and 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 becomes the issue — are you setting the right goals? Are they too ambitious? Are they not ambitious enough? And sometimes people can game the system. So we use it, but I can’t tell you that it’s perfect.

STEVEN BARTLETT: What about values? You talked earlier about values. A lot of companies go and do an offsite, write some words on a wall — ambition, enthusiasm, courage, whatever. What do you think of that sort of corporate habit of defining values?

DARA KHOSROWSHAHI: 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 of the company. And so it was very important for me to go and inspect the culture of the company and change it. It was a statement.

The culture had, I think, some cool stuff in there, some cool ideas. Like, for example, there was one value that was “toe stepping.” And the idea of toe stepping is what you and I talked about earlier, which is we want to challenge each other within the organization. And so if I have to step on your toes and tell you something that you don’t want to hear, I’m allowed to, even though it hurts you, because the truth is more important. So sometimes the truth hurts, and that’s okay. That was the idea of toe stepping.

And what happened was sometimes those values became weaponized, where toe stepping, whose spirit came from a place of “we want to speak the truth,” became an excuse to be a jerk. So the values in and of themselves can be great or terrible based on how you execute on them.

Rebuilding Uber’s Values

When I first came in, we had to redo the values. There’s a saying by Jeff Bezos that I love, which is that the value system of the company appears to some extent — if you say “thou shalt,” you’re going to fail, because the company shall. And the approach that we first took was that we would actually crowdsource the value system. We had a vote for all the employees in the company — “What values do you think should be part of the new Uber?” We took all the signal, edited it, and came up with a new list of values.

And there was one value that I wrote myself. It was mine, and it was “Do the right thing, period.” It wasn’t crowdsourced. It was just that. And usually with these values, there’s a whole explanation. But people are like, “Well, what does ‘do the right thing, period’ mean?” You have to figure it out. And for me, it was a message to the whole company: if you work at Uber, you have a responsibility, and I’m not going to tell you exactly what to do. Use your judgment. It’s our expectation that you use your judgment to do the right thing.

And sometimes doing the right thing isn’t clear — should I go after my business goals? Should I compromise on a business goal because safety is in question? Of course you should. Safety comes first before business. But we were putting that weight and that responsibility within the employees.

But the rest of the value system that was crowdsourced? It was forgettable. It was the kind of stuff like passion, ambition, teamwork. What company doesn’t believe in teamwork? Give me a break.

So Nikki Krishnamurthy, who runs People, she pushed me to reset the values four or five years in. By then, I felt like I did have a right to have a point of view. I’d been there. We weren’t quite done with the turnaround, but I was a part of the company. And then we came up with a value set which is different.

“Do the right thing” was the only one that survived from the original set. But for example, “Go get it” is one of our top values now. And the idea of “Go get it” is literally what we do — we help people go or get it, right? Rides and Eats. So it’s kind of fun in terms of what we do. But it’s an attitude: we as a company are go-getters. We’re going to be aggressive, we’re going to push, we’re going to move fast, we play to win.

And then there’s one that I really like: “Great minds don’t think alike.” We came up with a set of values which I think is unusual and describes how we are different as a company, and it’s really true to who we are.

STEVEN BARTLETT: How important is this attitude of failure and experimentation, especially in a world that’s transitioning as fast as the one we’re in? When you listen to people like Ray Kurzweil and his predictions of the future, he says that if you’re 10 now, by the age of 60, you’ll experience a year’s change in, I think, 11 days. Just this sort of exponential acceleration.

DARA KHOSROWSHAHI: The law of accelerating returns.

STEVEN BARTLETT: Yeah. How do you create a culture or build a team in a world where the correct answer is changing this quickly?

Building a Culture That Embraces Change

DARA KHOSROWSHAHI: I think it is about setting a culture that does embrace change and is constantly challenging itself. And I will give Travis and the founding team credit — there’s this idea that everything they did was terrible, and that’s just not true. We have a very high talent bar at the company. We have always kept a high talent bar and we haven’t compromised.

And what I found is that talented people who are also driven are on a constant hunt for the truth. So culture isn’t enough — you actually need the right people at the company. And I think we’ve got a company that does have a chip on its shoulder, born out of the creation of a new industry. So we’ve experienced it, and we have a group of people who are driven and hungry and are constantly looking for change. And you’ve got a leader and a leadership team that’s pushing the company to do so and doesn’t penalize folks for challenging them. I think it’s the stew that you have to put together — a combination of culture and people.

STEVEN BARTLETT: Do you have any mental case studies of great bets the company has taken that most people wouldn’t have taken, or thought was wrong, or wouldn’t have taken the risk on — that transpired to be critical to your success?

The Taxi Bet: Going Against the Founding of Uber

DARA KHOSROWSHAHI: Well, I think this one will be critical to our success. And there’s a funny one — taxis are one of the fastest growing parts of Uber’s business.

You remember, Uber started as the enemy of taxis and built out this peer-to-peer ride sharing. It was probably five or six years ago that our head of product now, Sachin, worked on building a technology that would allow taxi companies to have their own little Uber. And eventually he came to Uber — thank God — and said, “Well, why don’t we build that into Uber? Why don’t we actually put taxis on Uber?”

Originally, within the company, and I kept in touch with some of the founders just because I want their advice — they built a great company, I’m standing on the shoulders of giants — they said it was the most idiotic thing on earth. “You can’t wire up taxis. They hate us. Acceptance rates will be terrible.” There were lots of technical reasons. They had tried it earlier and it was a total failure.

But I think Sachin, having worked in the industry, combined with my being somewhat ignorant and saying, “Why the hell not try it?” — that combination allowed us to build out a taxi product. And taxis are now the fastest growing segment of the company. It went completely against the founding of the company. But now I hope to have every single taxi in the world wired up to Uber. Why not?

STEVEN BARTLETT: And there’s another alien that’s arrived amongst us, which is AI. Uber has always been somewhat powered, from what I understand, by —

DARA KHOSROWSHAHI: Very much so, to a certain degree.

STEVEN BARTLETT: But the world has changed in the last couple of years as it relates to AI. There’s been a huge acceleration in investment and improvement of the technology. Aside from Uber — you talked earlier about your early childhood and how you grew up with a bit of a paranoia about losing everything, because that’s what you experienced as a young man. You see this technology arrive, which is fundamentally disruptive to all of us, including me as a podcaster. I’ve done the tests and the retention isn’t far off whether it’s me or AI, so it’s slightly concerning. But how do you approach such a disruptive technology? How do you think of it broadly and the impact it’s going to have on society? And are you paranoid?

AI, Autonomous Vehicles, and the Future of Work

DARA KHOSROWSHAHI: I’m not paranoid. I’m not. I guess I was going to say I’m not built that way, but maybe I am. I think my instinct is always just to move forward.

Uber has been built out of an AI core. All of our pricing, all of our routing, who you’re matched with, whether or not a courier batches a trip — which is, do they take two orders or one order — 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. And we’ve got to work on the streets of New York and the streets of Lagos as well.

So we have built the entire company on small AI models that have been trained on local problems and then get stitched together. That’s literally what the company is. So for us, AI is a core skill set. And AI can mess things up, right? Because it’s not heuristics-based. There are emergent issues that come out of an AI that works 96% of the time, and 4% of the time it screws up. So we’re comfortable with the uncertainty layer of AI as a company. I would say we are moving headlong into AI. We’re not one of the research shops, but in terms of applied AI, the team is driving to build newer AI experiences across the company.

But stepping back as a person, the impact on society is going to be enormous. Going back to Kurzweil’s law of accelerating returns — whereas previously society has always been able to adjust to these kinds of shifts because it had time to adjust — AI, quite literally, thinks. And AI will be able to replace the work that 70 to 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 impact.

Now, are they going to be more expensive than humans, cheaper than humans? Who knows? But the capability will be there probably in the next 10 years for intellectual jobs, and probably around 15 to 20 years for physical jobs, because physical AI is harder. Robots, cars — more capital-heavy, takes longer, have to deal with the physical world. So the changes in society are going to be giant.

But my view is you can’t slow down the rate of change. And if you’re a part of that change, at least you can have some say as to how that change imprints on society and on the real world. So for me, I’m leaning in. It’s a very, very exciting time.

STEVEN BARTLETT: 70 to 80% of jobs will be disrupted by AI — that’s broadly what you said there. And the pace of change is going to mean that a lot of people don’t have new jobs to go to. I think that’s the question — the retraining challenge. And people say, “Well, there’s going to be jobs in AI.” But listen, I’ve got some friends that can’t just…

DARA KHOSROWSHAHI: Society’s always adjusted, right? Farming was a huge percentage of our labor force. Now it’s less than 1%.

STEVEN BARTLETT: But the speed at which—

DARA KHOSROWSHAHI: Yeah, I think that’s a real question. And you could argue that AIs will be able to retrain you. The job retraining process is going to change. So of course society is going to adjust. But I do think it raises real questions.

STEVEN BARTLETT: I’ve not been able to get an answer on that, really, from the experts in AI that I’ve interviewed — which is, what do those 70 or 80% of people do? Because we’re seeing in our own business that there are many jobs which we would have hired for previously, across the board, that AI is now doing exceptionally well. And every single day — literally daily — we try to see if the new model, Gemini Pro 3 or whatever, can do things that we’re currently doing manually. And every day we’re getting those little breakthroughs and going, “Oh, okay, now we no longer need to.” And coding is one of those big areas that you talk about a lot, where there’s already been significant disruption at Uber. A lot of your coders are now using AI to—

AI and the Future of Coding at Uber

DARA KHOSROWSHAHI: Yeah, about 90% of our coders are using AI. Now, that’s easy to say, but there are probably 30% of them that are power users. They are showing a clear differentiation in the number of diffs — a diff being a code release that’s different from the last code release. So one of the measurements of productivity is just how many diffs are you putting to the code base?

Uber is just a giant code base. That’s what we are. Our engineers are literally the builders of the company. They are manufacturing the bricks that go into the system, and they are the architects who are thinking about what the system should look like. So while 90% of our engineers are using AI tools of some sort, there’s about 30% of them that are using them at a completely accelerated pace. And it really is changing their productivity in a way that I’ve never seen before.

Ultimately, I do think that 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 or building systems for you. It becomes more of an orchestration job versus a manual writing job. But the job will still be there.

And my attitude is, if my average engineer became 25% more efficient — which we haven’t gotten there yet, but we will — I’m going to hire more engineers because I want to go faster. There are still lots of unsolved problems. But I can imagine, maybe five years from now, as engineers get more and more productive, I may not decide to add engineering headcount. Because at that point, instead of adding an engineer, I should add agents and buy some more GPUs from Nvidia. That may be the investment of the future. We’ll see.

STEVEN BARTLETT: Because thinking about linear versus exponential as well — if we imagine a rate of improvement — in my head I go, won’t there come a time where you as the CEO, or you and an executive team, can tell an agent what you want to build? You can show it the strategy, and theoretically — I can’t figure out how this isn’t going to be possible — the agents will then build. Actually, maybe they don’t even need you to set the strategy. Maybe. But theoretically, if you imagine any rate of improvement in intelligence, maybe at some point they’re going to say, “Well, listen, there’s a better strategy here, Dara.”

DARA KHOSROWSHAHI: One of my team members told me that some teams have built a “Dara AI,” so that they basically make the presentation to the Dara AI as a prep for making a presentation to me. Because by the time something comes to me, there’s been a prep meeting and the slide deck has been beautifully honed. So they use Dara AI to tune their prep.

STEVEN BARTLETT: Are you concerned they might show Dara AI to the board?

DARA KHOSROWSHAHI: I was like, “Can I see the code for Dara AI?” And Kira said, “No, we’re not showing it to you.”

STEVEN BARTLETT: But is there anything falsifiable in what I just said — about there coming a time in the not-so-distant future, if we imagine exponential—

Real-Time Learning: The Missing Piece

DARA KHOSROWSHAHI: I think where AI is still missing a beat that humans and other creatures have is the ability to learn in real time. So if you think about it, you and I are learning from this conversation, and maybe your behavior is going to change by 0.1% because of what you learn here.

The construct of most large AI models is: capture enormous amounts of data based on the skill set you’re trying to drive, pre-train that model, put it into the real world, and then there’s some post-training of the model based on feedback from the world. And when the model’s released, it’s kind of released. The way the model learns is that 3.5 becomes 3.8 — but 3.5 didn’t learn. The engineers went out and built a new model, 3.8, that might have elements of 3.5. So the AI agents aren’t learning in real time.

Now, a lot of what we’re doing is building around the foundation models, bringing signals from the real world and using the skills that the foundation models have to do good work. So you can—

STEVEN BARTLETT: Yeah, post-training. I’m post-training.

DARA KHOSROWSHAHI: Exactly. So we are post-training, but we’re learning in real time as human beings. And when the models can learn in real time — that, I think, is the point at which I’m going to say, “Yeah, we are all replaceable.” But at this point, I haven’t seen a model that can learn in real time.

Autonomous Vehicles and the 9 Million Drivers

STEVEN BARTLETT: One of the real areas of disruption in AI has been autonomous vehicles. Just before we started recording, I was saying that I have a Tesla in LA, where I live, and it’s staggering that I can get in the car, press a button, and drive two and a half hours to Joshua Tree without having to touch the wheel or the pedals. Now, driving, I think, is one of the biggest professions in the world.

DARA KHOSROWSHAHI: We’ve got 9.5 million drivers and couriers on our platform. We are the largest organizer of flexible work around the world. I think the second largest workforce is the Chinese army. It’s a big group of folks that we’ve organized.

STEVEN BARTLETT: And statistically, there are fewer accidents in an autonomous Tesla than if a human drives it. So it’s safer for my car to drive itself than for me to drive it. That’s true, right? That autonomous driving is currently safer?

DARA KHOSROWSHAHI: That’s true. Waymos are safer. And now you are a backup to the Tesla as a human being. I’ve got a Tesla as well, and once in a while it disengages and I’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 BARTLETT: And we can’t be far away from it just being—

DARA KHOSROWSHAHI: Waymo’s there already, right? You live in LA, they’ve got the Waymos. We work with them in Austin and Atlanta. And by all accounts, Waymo drivers are safer than human beings. That’s going to be true of autonomous vehicles all over the world.

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. So to the extent that these autonomous agents and drivers can be better than humans — and they will be, over a period of time — there’s a real return on human life as a result of this.

STEVEN BARTLETT: Those 9 million drivers’ careers that you have will be out of work. Conceivably. Talking about being honest about the situation.

DARA KHOSROWSHAHI: Yeah, I think again, it goes to physical AI as well. So I think 20 years from now you can imagine that those 9 million will be 20 million AVs. Maybe. But we have time between now and then, partially because we don’t operate in the virtual world — we operate in the physical world. You have to get the regulations up, you have to build the cars, you have to build the sensor stacks, the models have to get there. So there is time between now and then. But you can imagine the majority of our trips being fulfilled by robots of some kind. Probably not 10 years from now, but 15 to 20 years from now, you’re going to start getting there.

STEVEN BARTLETT: What do the 9 million people do?

DARA KHOSROWSHAHI: I don’t know. We are expanding the kind of work that’s available on the platform, partially as a result of it. We used to have only driving as work — now there’s delivering, there are shoppers as well. I think it’ll be a little while before you get AI shoppers.

And now we actually have a team called Uber AI Solutions that allows people to train AI agents and AI models and do all kinds of knowledge-based work on their phone, to extend the kind of work we offer humans on our platform and give them different opportunities to make money. So we are extending the platform. And then the question is, how much of the platform gets automated, and what’s the velocity at which we can extend our platform into other kinds of work versus the velocity of automation? I can’t tell you which is going to go faster.

STEVEN BARTLETT: Hand on heart though, it does appear that unemployment is going to be significantly increased in a world of AI — especially if we imagine this continual rate of improvement. I just can’t—

DARA KHOSROWSHAHI: You would have to think so. Unless, again, historically in societies, new kinds of jobs have come up.

STEVEN BARTLETT: Knowledge jobs, physical jobs.

DARA KHOSROWSHAHI: Yeah.

STEVEN BARTLETT: I mean, now we’ve disrupted both.

The Human Cost of AI Disruption

DARA KHOSROWSHAHI: That’s why there’s a question here, and I do think there’s a real question as to the ability of societies to retrain, the abilities of human beings to retrain themselves. AI is going to be a part of that. But the timing — how fast is it going to go? It’s a real question mark. I think you’re absolutely right. I don’t think it’s going to be a big issue in the next five years, but when you go five plus years, it’s going to become more of an issue for society at large.

STEVEN BARTLETT: It’s interesting because I was thinking, putting two and two together about your father’s journey of coming to the US, losing what he had, losing his job, and the loss of meaning and purpose being really central to him. And I can see that from your face — I think what I interpreted was that he struggled with, as any provider would, the loss of meaning that comes with it. Because jobs aren’t just about money. They give you a sense of worth.

It’s funny, I read a study many years ago that said when they looked at suicide letters, specifically from men — I think it was an Australian study — the sentiment was about not feeling worth—

DARA KHOSROWSHAHI: Yes. For—

STEVEN BARTLETT: —to your family.

DARA KHOSROWSHAHI: Yeah.

STEVEN BARTLETT: And the extreme of that was, “I think my family would actually now be better off without me.” And this kind of, I think, is probably adjacent to this conversation around job displacement — which is, where are we going to find our meaning in a world where the machines have now disrupted our intelligence and our muscles?

DARA KHOSROWSHAHI: Every universal basic income test has failed. The answer you hear from folks is, “Well, the robots are going to do all the work. They’re going to create utility, and so our work won’t have to create utility. People will just have money.” But it goes to exactly what you’re saying — every single test they’ve done, not 20, but they’ve done a couple of tests where a certain section of the population gets income and a similar section doesn’t. And every time, the ones who are getting income do worse in terms of outcomes.

We don’t know the exact reason, but I think it’s related to what you’re saying — market forces that compel someone to work create a perception of self-value. Most people, if they’re driven to succeed, will succeed. And as they succeed, it comes with a very deep and important feeling of, “I am creating value. I’m supporting my family. I’m building this incredible piece of art.” Whatever that value is to you, wherever that meaning comes from — “I’m an incredible parent” — that value is what keeps people going. And I don’t think the government raining money down on society is going to help.

STEVEN BARTLETT: But it’s refreshing to hear your perspective on this, because a lot of the time you’ll hear CEOs in the media just saying, “It’ll be fine. Everyone’s got to figure it out.” And I think that’s such a—

DARA KHOSROWSHAHI: Historically, we have figured it out, so maybe they’re right. But you have to ask whether they’re giving you the real stuff or not.

STEVEN BARTLETT: Yeah. And that’s kind of what I think — I sometimes hear about private conversations, and the private conversations I hear about involve the sheer amount of disruption that they anticipate. And then when I see them on CNBC or at Davos, it’s, “We’ll be fine, we’ll figure it out.” And I understand the incentive, because if they were to start ringing the bell, it might hurt their own chances of innovating and fundraising and all those things. But I think you sit at this sort of happy medium — as the CEO of Uber, you’ve got to pursue the opportunity and the technology. But on the other end, to be honest and say, “Listen, there’s going to be big disruption, and I don’t know the answers.”

DARA KHOSROWSHAHI: I remember a CNBC anchor once — we had an interview, and afterwards she said, “I really like you. You actually answer my questions.” And I’m thinking to myself, what am I not supposed to? The PR training is always — if you get a bad question, don’t answer the question, just pivot to something else. And for me, I’ve sworn to myself — and Noah, who’s up there, is probably going to kill me afterwards — I’m going to answer the question. I’m not going to do the bt. The anchor knows what’s happening, the audience knows what’s happening. So I’ll answer the question. If it’s a bad question, I’ll deal with it.

STEVEN BARTLETT: I actually don’t like interviewing CEOs, which is funny because of the name of the podcast. Because actors—

DARA KHOSROWSHAHI: CEO. Yeah. I looked before I came on — I’m like, I’m going to look up the CEOs, and there aren’t that many CEOs.

STEVEN BARTLETT: Well, if I looked at your diary, what would I find inside? I would probably find you contending with being a father. Your psychologist might find some things in there about your health. I can see you’re a guy that goes to the gym, and I think it’s all interlinked. I think for you to be an exceptional CEO, you probably think a lot about your past, your childhood, your health, how to optimize. And honestly, you can’t do a podcast like this for 20 years and just hit the same thing every day. You need to be intellectually stimulated. And you and I are both multifaceted creatures, I guess. So that’s why it’s evolved.

DARA KHOSROWSHAHI: Until we become AIs.

STEVEN BARTLETT: Until we become AIs. Yeah. Just closing off on that — what can we do about this from an AI and AV perspective? Is it the government’s responsibility? Is it collective action?

The Road Ahead: Autonomous Vehicles and Society

DARA KHOSROWSHAHI: One thing I do think we don’t talk about enough is that AI can be a force for good. With autonomous vehicles, for example — these drivers are going to be safer than human beings. We can take 35,000 fatalities down to 3,000 fatalities. I also think AV is going to bring down the price of transportation. A big part of our goal is to make on-demand transportation available for everybody. One of the people I was talking to mentioned how Uber has changed her mother’s life — her mom can get around now and just wouldn’t have been able to without it. We want more people to have that experience.

So I do think it’s important to recognize that if fundamental transportation becomes safer and cheaper — going back to Jevons paradox — that’s a good thing for society. I don’t think the answer is to try to slow down the pace of change, because China won’t, for example, if we’re talking about the West. So I think you just have to lean into it.

I think discussions like this are important. I think you look for technology leaders who are talking about it. Dario, for example, at Anthropic, is talking about it — pissing some people off — but I think he’s having good discussions. And I do think that society arming itself to retrain large groups of people at scale is not a skill I see people investing in. I don’t see that as a core capability of any of our countries. If there’s one thing I can point to, it would be that — the retraining machine.

STEVEN BARTLETT: You’ve got four kids.

DARA KHOSROWSHAHI: Yes.

STEVEN BARTLETT: They come to you and say, “Dad, listen — AI, robotics — give me some advice for my future. What should I be doing?”

DARA KHOSROWSHAHI: Work hard, you’re going to be fine. Work hard. Now, the AIs can theoretically work harder than you, but one of the pieces of advice I give to young people is: don’t plan.

I wound up where I am today having not planned a thing. When I was an investment banker, I wasn’t dreaming of becoming a CEO. And what I find is that people who have too much of a career plan, who have too much clarity about what they’re doing, lose their curiosity. Human beings look for positive signal — whether you like it or not, anytime someone agrees with you, it makes you feel a little bit better. Anytime you get a signal that goes against your preconceived notions, either you ignore it or you think, “All right, I’m going to take this on,” but it’s unpleasant.

With career planning, people who have too clear a plan are looking for signals that feed into it — “I’m going to be a vice president by this date, I’m going to make X amount of money by this date.” They’re not looking around, they’re not being curious, they’re not looking for signals that can change their life.

So what I tell some people is: before you go out and try to change the world, let the world change you first. Take input. If you’ve got blinders on because you’re going in one direction, you’re not going to take in all the stimulus coming in from the world.

The one constant I see is that good people are good. I’ve never seen a successful person in a job or a career get there without working hard. And my guess is — I don’t know about you — you kind of wound up where you are kind of by accident. People say, “Well, you got lucky.” I got very lucky to be here. I had so many moments. Some would say I took advantage of that luck. But to some extent, I was able to take advantage of that luck because—

STEVEN BARTLETT: —you were open. Being open.

Daniel Ek’s Advice and the Decision to Join Uber

You jumped from Expedia to Uber, in part helped by some advice that our mutual friend Daniel Ek, the founder of Spotify, gave you. He’s actually just texted me — I texted him saying, “Hey, can you send me a question to ask Dara?” But he said he’s in the middle of a—

DARA KHOSROWSHAHI: He’s texting while we’re talking?

STEVEN BARTLETT: No, just before I walked in. I’ve just looked. He texted me back saying he’s on an earnings call. Never mind. But he said, “Good luck with the interview.” What did Daniel Ek say to you that helped form the decision to go to Uber?

DARA KHOSROWSHAHI: He’s the one who recommended me. I think I was contacted by a headhunter, and he recommended me to that headhunter. I was actually at The Allen & Company Conference — going back in a circle — and we were having a drink one night, and he asked me, “Did the headhunter call you about this Uber role?”

At the time, Uber was a disaster. An absolute disaster. Everyone was reading about it. I was at Expedia, I had just gotten this wonderful contract — as you mentioned at the beginning — so I was going to stay. I love working for Barry. It’s been the best professional partnership of my life. And I said, “Of course I’m not going to go. I’m so happy with what I’m doing at Expedia.”

And Daniel just looks at me — he’s got these cold, Scandinavian eyes — and he says, “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.”

So the next day, I called the headhunter — I had previously said no, I’m not interested — and I said, “Let’s talk.” Daniel was the one who opened me up.

STEVEN BARTLETT: And your dad — he gave you advice?

DARA KHOSROWSHAHI: I talked to my dad, and my dad keeps things simple. He said, “Dada, when a company that’s a verb tells you to run it, you just say yes.” I thought that was good advice.

And ultimately, I think people who come to Uber stay at Uber. They come because of the challenge, but they stay because of the impact. We are building a company that is important to the world. And for me, I could come and have impact on an impactful company — so why the hell not?

STEVEN BARTLETT: And when he says “a company that’s a verb,” he’s referring to the fact that everybody in the taxi or transportation category uses Uber as a verb, even if they’re talking about a competitor.

DARA KHOSROWSHAHI: Exactly right.

Closing Question

STEVEN BARTLETT: And there’s always one company in every sort of industry. We have a closing tradition here where the last guest leaves a question for the next guest, not knowing who they’re leaving it for. And 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?

A Conversation Never Had

DARA KHOSROWSHAHI: It was a conversation with my dad. I told you I came to New York from San Francisco, and it was because my dad was getting very old and he was losing his mental faculties. And 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.

And I wish I could talk to him about his experiences, his younger life, the excitement of building something, and then the losses and regrets he had in life as well. My relationship with him — there was love, no question about love. But we didn’t have the deep kind of conversations that I’m hoping I get to have with my kids. So that’s a conversation I’d love to have. And 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, which is there are some mistakes that you make that are permanent and you can’t get that back. But having genuine conversations and connections with my friends, having a real relationship — not just with my wife and my kids, but actually with my workmates — having those genuine conversations and connections is my way of correcting for the conversation I never had with my dad.

STEVEN BARTLETT: Dara, thank you.

DARA KHOSROWSHAHI: Thank you very much. I appreciate it.

STEVEN BARTLETT: You’re a huge inspiration for me in so many ways, and even more so now, having done so much research on you in preparation for this conversation. Because it is rare to find a leader who has been consistently successful across different domains — who has built this really quite rare skill stack, from investing to CFO, to then being able to transition to CEO — and who has repeatedly contended with moments of transition and given us all frameworks as founders and entrepreneurs for how to deal with that transition. And one of the great ones I take away from you is honesty.

DARA KHOSROWSHAHI: Yeah. Honesty is so powerful. And I’ll tell you, I learned that skill from my wife. She always says people are people, it doesn’t matter — they eat, they sleep. And she treats everybody in her life the same way, regardless of their position.

STEVEN BARTLETT: Like your dad did.

DARA KHOSROWSHAHI: Yeah, yeah. And she’s — honesty, it’s just so powerful.

STEVEN BARTLETT: Thank you so much.

DARA KHOSROWSHAHI: You’re very welcome.

STEVEN BARTLETT: An unbelievable inspiration.

DARA KHOSROWSHAHI: Thank you. I appreciate it.

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