The Exchanges

Q Speaking of that kind of discomfort with going with the crowd, would you say that you're a wartime CEO? Would you say that's your natural preference?

A I think, you know, Expedia was, it was, I was at Expedia for 13 years, and it did feel like wartime. It was a big turnaround, and turnarounds in business are difficult. Turnarounds in technology are harder, and for example, with Expedia, we had to undergo a giant re-platforming of the whole technical platform, so you had to keep the business going, and then rebuild the technical platform, which was pretty tough. Now, it was wartime, Not in the public eye. Uh, and then Uber definitely has, has been wartime. Like it's, it's, it's a wartime every day. Although, although I think we're, we're really getting a handle on the business and I'd say we're winning, but I do feel comfortable in difficult situations. I don't take setbacks too seriously. I just keep pushing. So am I comfortable in wartime? Reasonably.

AI assessment note: “So am I comfortable in wartime? Reasonably.”

Q from Shopify on the show the other day, and in his brilliantly kind of Germanic and disciplined way, he said to me, Harry, the best businesses, they have constraints. Uh, I'm clearly an impersonator for a second job. Um, uh, when you think about the constraints on Uber, what do you think are the natural constraints? And are there any artificial constraints you place on the business or the team?

A Tons of constraints. And, and I think it's what makes the business Interesting. I think the first constraint that comes up is that we are a marketplace business. So our supply and demand is variable, but it is variable on a real-time basis, spatially, time-based, etc. And that variability and predictability make it very challenging to kind of make the marketplace worse, so to speak. So the natural constraint, we talk, for example, at Uber about being customer-obsessed. But the thing is, you know, we have multiple customers, so actually a value of the company is being trip obsessed. The magic happens when you match supply and demand. You bring that rider and driver together, or you bring that eater together with the restaurant, with the courier, and that magical match happens. And that magical match can happen only when it's on a basis that makes all two or three parties happy. That's a very interesting business challenge. And so for us, for example, our value is being trip obsessed. It's about what do you have to orchestrate to bring together that connection on a real time basis? Now in this last quarter, two billion times a quarter. That to me is a super interesting constraint. And then related to that is what I talked about earlier, which is the impact that Uber has on the real world. You know, we are an incredibly important entity in terms of Transportation and cities in ter…

AI assessment note: “I think the first constraint that comes up is that we are a marketplace business.”

Q I do have to ask you, you mentioned kind of the globalization. You acquired Kareem. Talk to me about the decision-making process there, and another anonymous friend. In hindsight, are you happy you made the acquisition?

A Yeah, very happy. I mean, for, for me, it was a bet on, um, Medasser and Magnus, who were the founders at Kareem, and they're still with the company. They're incredibly talented entrepreneurs. And Kareem, actually, early on, Was looking to build a mobility business, delivery business, and a payments business in the Middle East. Uh, the Middle East, it's the demographics in the Middle East are great demographics. It's a young demo coming online. And the bet that Kareem was making in this platform, uh, building out a mobility delivery and payments business was something that we can learn from. And the Middle Eastern business for us has been enormously successful and Kareem is absolutely a part of that success.

AI assessment note: “Yeah, very happy. I mean, for, for me, it was a bet on”

Q I think when you have such a big transition, you learn about yourself in many ways. What did you learn about yourself as a leader, as a person, when making the transition from Expedia to Uber?

A You know, Harry, honestly, I haven't had time to think about that. I'm not particularly introspective and it may be a strength. It may be a weakness. Um, I'm here to do a job. Uh, I love it. A friend of mine was asking me, are you having fun? I'm like, no, I'm not having fun. It's too hard, but I love what I'm doing, but we're mid path, you know, and, uh, maybe in another five years, I'll have time to think and learn and kind of be introspective about what I learned about myself. Right now, I'm just learning about the company, about the opportunity, and, and just going, just going as hard and fast as I can.

AI assessment note: “honestly, I haven't had time to think about that. I'm not particularly introspective”

Q Final one for you, Dara. Next five years, so it's twenty-twenty-eight. Where will we be then, and where will you be then?

A Oh, I, I have no idea. Um, I'm not a planner, Harry. Like, I just, I, I feel like if I have too clear a sense of what's going to happen in the next five years, I'm going to ignore any input that disagrees with that picture, and I'm going to be like, Getting, holding on to input that agrees with that picture. So, I actually very specifically, like, I'm very open-minded to what's happening in the last, in the next five years. Think about five years ago. Could you have ever predicted where we are now? Right? And so, predictions that are valuable, the obvious stuff you can predict, but the most valuable input is actually quite unobvious and very difficult to predict. And so, as opposed to trying to predict, I want to be open. Like, I, I'm very humble, and I don't know what's going to happen five years from now, but I want to see signal, I want to talk to everyone, I want to read anything and everything I can, so that I can see that signal sooner than anyone else, and I don't want to have a bias, because it's, if you're human, if you see signal that goes against your bias, you're going to tend to ignore it at least the first couple times, unless it, until it becomes unignorable, so to speak.

AI assessment note: “I have no idea. Um, I'm not a planner, Harry.”

Q How did Barry Diller influence you as a leader? What a hero.

A Oh, uh, in every way. In every way. He's, he's been my I, I worked for him for over 20 years. Uh, I think that I'm here because of him, because of the shots that he took, because he, the opportunities that he gave me. Uh, and, and I think what's extraordinary about Barry is, despite all of his accomplishments, he is still unbelievably curious. He, he has a thirst for knowledge that I have not seen, you know, I've never seen, but also, as, as you get older, you kind of think you figure it out. I think if he has Barry, he's like, I haven't figured anything out. I'm still going. Uh, and that curiosity and that drive is, is pretty extraordinary, and it's definitely shaped me.

AI assessment note: “that curiosity and that drive is, is pretty extraordinary, and it's definitely shaped me.”

Q by that is like, you know, in business or in investing, you make mistakes, and it's very easy to let that plague your future decision-making process. Ah, we'll never do anything in hardware again. Well, that might be wrong, and it might be a good thing for Uber to do something in five years, 10 years, who knows? Um, how do you keep a plastic mind with each new decision?

A Well, I think that if you're not making mistakes, Then you're not doing your job. You're not taking risks. You know, like if I didn't want to make mistakes, I'd, I'd be a treasury bond manager, right? Like my job is to make mistakes and learn from them. So like, I, I don't mind when people make mistakes. What I, what I mind is if they're not self-reflective, first of all, they don't recognize it and they don't make excuses, right? That the problem with excuses suck anyway, but the problem with excuses is you're not learning, right? So Face up to the mistake. Identify early. Take responsibility. Learn from it. And then help that shape who you are going forward. And that, who you are, hopefully, is a little bit better. And the same applies to companies. Like, we absolutely should be making mistakes. If we're not making mistakes, we're playing it too safe. We're not, you know, we're not growing. Like, that's, that is part of being an organism. So I'd say for me, I don't mind making mistakes. I just, I just want to, it's the old fail fast. Um, there are some decisions where you really have to take your time, right? So decisions that it's the old one way door, two way doors. The key is, uh, identifying two way doors, moving fast through them, and then taking your time on the one way door to make that considered decision. And maybe it comes back to something that we started with, whi…

AI assessment note: “I always want to keep my mind open, eyes open, see what's going on”

Q by that is like, you know, in business or in investing, you make mistakes, and it's very easy to let that plague your future decision-making process. Ah, we'll never do anything in hardware again. Well, that might be wrong, and it might be a good thing for Uber to do something in five years, 10 years, who knows? Um, how do you keep a plastic mind with each new decision?

A Well, I think that if you're not making mistakes, Then you're not doing your job. You're not taking risks. You know, like if I didn't want to make mistakes, I'd, I'd be a treasury bond manager, right? Like my job is to make mistakes and learn from them. So like, I, I don't mind when people make mistakes. What I, what I mind is if they're not self-reflective, first of all, they don't recognize it and they don't make excuses, right? That the problem with excuses suck anyway, but the problem with excuses is you're not learning, right? So Face up to the mistake. Identify early. Take responsibility. Learn from it. And then help that shape who you are going forward. And that, who you are, hopefully, is a little bit better. And the same applies to companies. Like, we absolutely should be making mistakes. If we're not making mistakes, we're playing it too safe. We're not, you know, we're not growing. Like, that's, that is part of being an organism. So I'd say for me, I don't mind making mistakes. I just, I just want to, it's the old fail fast. Um, there are some decisions where you really have to take your time, right? So decisions that it's the old one way door, two way doors. The key is, uh, identifying two way doors, moving fast through them, and then taking your time on the one way door to make that considered decision. And maybe it comes back to something that we started with, whi…

AI assessment note: “I always want to keep my mind open, eyes open, see what's going on, be curious”

Q What do you think, what do you, what do you think makes her an incredible judge of people as something where I suck?

A I love people in general, and I'm always going to look at your best side. She takes a much more judgmental view of people, and she's got a very high bar for her, you know, people that she engages with. She just, like, is able to call bullshit in .one seconds, and so I think that, actually, I like people, like, I want to like you. I want to believe in you. I want us to do something really cool together. That's my natural bent. And so she really helps me and she's, she can be critical. She's sometimes critical of me and herself as well, but we're, we're great partners and, and even on business stuff, like I talked through business issues with her and listen, if you can't explain simply deep business issues or even deep technical issues, like one of the things that I, that I always look for in terms of engineering and technical talent is I'll ask them questions. And if there, there are some of them that try to use their technical talent, like to Lord over you as power over you, they, they, they demonstrate to you how much smarter they are than you. And then there's a different kind of person who explains things simply. They want you to understand. They want to share their knowledge. That latter kind of technical talent is a kind of technical talent that I'm looking for, which is like, tell me why, tell me how this works. If they are able to simply explain a deep technical problem,…

AI assessment note: “She takes a much more judgmental view of people... able to call bullshit”

Q What do you think, what do you, what do you think makes her an incredible judge of people as something where I suck?

A I love people in general, and I'm always going to look at your best side. She takes a much more judgmental view of people, and she's got a very high bar for her, you know, people that she engages with. She just, like, is able to call bullshit in .one seconds, and so I think that, actually, I like people, like, I want to like you. I want to believe in you. I want us to do something really cool together. That's my natural bent. And so she really helps me and she's, she can be critical. She's sometimes critical of me and herself as well, but we're, we're great partners and, and even on business stuff, like I talked through business issues with her and listen, if you can't explain simply deep business issues or even deep technical issues, like one of the things that I, that I always look for in terms of engineering and technical talent is I'll ask them questions. And if there, there are some of them that try to use their technical talent, like to Lord over you as power over you, they, they, they demonstrate to you how much smarter they are than you. And then there's a different kind of person who explains things simply. They want you to understand. They want to share their knowledge. That latter kind of technical talent is a kind of technical talent that I'm looking for, which is like, tell me why, tell me how this works. If they are able to simply explain a deep technical problem,…

AI assessment note: “She takes a much more judgmental view of people, and she's got a very high bar”