Dara Khosrowshahi with Patrick O'Shaughnessy
Show: Invest Like the Best
Cleaned and reformatted from published transcript or auto-generated captions — punctuation added, filler removed, restructured for readability. Not verbatim. For exact quotes, refer to the original.
Patrick O'Shaughnessy
I have to begin with the story you were just telling me about how you took this job, how you heard about it. I want to know what the company felt like to you when you showed up, how that's evolved, and very importantly what the current moment feels like — which I think is the most interesting question for the business possible. But I love the origins. How did you hear about this job in the first place? What was the backstory?
Dara Khosrowshahi
I'd been at Expedia for 13 years, CEO, working with Barry Diller, and I loved the experience and I loved where I was. At the time Uber was in the news all the time. It seemed pretty chaotic and pretty difficult. Then a headhunter called me out of the blue and said, 'Are you interested in the Uber CEO job?' And at the time I said, no effing way — who would even think about it? I had a considerably lower profile as you can imagine. So I kind of blew it off.
Then I was at the Sun Valley conference, the Allen & Company conference, having a drink with Daniel Ek and my wife, and Daniel said, 'Hey Dara, did a headhunter call you? I recommended you for the job. I thought you'd be great for it.' And I was like, 'Oh, that's why it happened. Are you crazy? I've been at Expedia for 13 years. I'm so happy with what I'm doing.' And I remember Daniel looks at me and he's like, 'Dara, since when is life about happiness? It's about impact. Uber is a company that has impact on the world. It's important. It's in trouble. Why wouldn't you take a shot at this?'
A lot of people come to Uber because of the impact the company has in the world. We're shaping how the world moves. We've got over 10 million couriers and drivers on the platform. I wanted to go to a place where I could make a difference. When I started investment banking at Allen & Company it was amazing, the best company in the world, but I thought — investment banking isn't really changing the world. For me it was about having impact at a company that was having fundamental impact on how people live. We'd had a couple of beers, my wife Sid was there, and the next morning in the parking lot I remember calling the headhunter and saying, 'Tell me more.' That's how it all started.
Patrick O'Shaughnessy
So you show up, there's a process, you take the job. What's the impression on day one through ten? What did it feel like?
Dara Khosrowshahi
Complete chaos. Travis hadn't been the lead of the company for some period of time, and there was a committee of executives who'd been running it for a few months. The company was in the public sphere in many bad ways — lots going on internally and externally — and the business itself was very dynamic and hugely competitive. It would have been difficult enough without any of the external distractions. The business fundamentally was strong, but it was going through a lot of change and chaos, both in terms of the board and the stability of the management team. With time and a lot of work with my team, we were able to bring some order to the chaos, and it's turned out to be a great ride.
Patrick O'Shaughnessy
How did you do that? If you were teaching an HBS seminar on a leader establishing order and structure in a chaotic situation — what's the how?
Dara Khosrowshahi
The most important how is simplifying the situation and breaking down what seems like an unassailable problem into its component parts. It's vector mathematics. If you have a three-dimensional complex interaction, you break it down to each dimension, solve each one, bring it all together, and you can solve pretty complex equations. The same is true in business.
When I got to Uber there were distinct areas I had to take care of. At the board level, the board was fighting for control — focused on who's going to control the future of the company versus what that future was going to be. So we brought in a new chairman, Ron Sugar, who's become my partner through all the years and really brought the board together: this isn't about who controls it, it's about the fate of the company. The company had also lost trust with stakeholders, regulators, the public, so we went on a listening tour, understood the issues, and started acting and communicating — the concerns of stakeholders were just as important as our own.
Then with employees, it's putting together the team. There was a lot of talent inside Uber, but some folks were stuck in the old world and had to get off. Andrew McDonald, our president and COO, predated me and has come through many years. And we brought in new members like Tony West, who's been with me ever since. If you focus on each distinct problem, what seems like chaos becomes small surmountable problems. You can't control what gets solved when, but over a period of time things get better.
Patrick O'Shaughnessy
In situations like that, what have you learned about managing your own stress so you don't get personally overwhelmed by chaos?
Dara Khosrowshahi
I think I'm lucky. Sid, my wife, calls me a robot — I don't get stressed out by situations. We lost everything when we came here from Iran, absolutely lost everything, and I saw it destroy my father.
Patrick O'Shaughnessy
How old were you?
Dara Khosrowshahi
I was nine years old. My father, along with his family, built an incredible family business. We came here, we lost everything, but then we rebuilt. For whatever reason, worrying doesn't help. Overthinking things doesn't help — it only makes things worse. I'm able to approach things from an engineering mindset: what are the problems, let me list them, let me have an approach to solving each of them, test and learn. Not everything improved in a linear path, but being stressed out — what's the point? Who cares?
Patrick O'Shaughnessy
Can you say a little more about what that experience was like, watching your dad go through that at that young age?
Dara Khosrowshahi
We came to the States and got to stay with my uncle Nasi. The adjustment for us wasn't very difficult, but as I grew up I observed my father, who when I was a kid was a giant of a man, become less giant. He lost that spark. He wasn't able to begin again here in the US. He did his very best — he was an entrepreneur, he tried his hand at a lot of things. It drove myself and my brothers to rebuild. Many immigrants have a chip on our shoulder and I had a particularly big one. But at the same time, I didn't want work or fortune to break me as a person. So I was able to separate the two: do I want to do well? Absolutely. But in the end I know who I am, and I'm always going to be that same person. I'm not going to let the chaos of the world affect me mentally.
Patrick O'Shaughnessy
This is a selfish question because I have kids growing up fast. My guess is you wouldn't press the red button to undo the experience you had, because it made you who you are. How do you think about your own kids, who maybe won't have an experience that shapes them in a similar way?
Dara Khosrowshahi
God, I'm figuring it out as we go. Being a parent is so humbling, but I think we're doing our kids a disservice by giving them too much and being around too much. On the weekends my mom would be like, 'Get out of here and come back for dinner, figure it out.' The helicopter parenting, being around your kids all the time — you want to love your kids, you want them to be absolutely loved and appreciated, but it's the challenges in life that form you, and it's the overcoming of them that gives humans a profound satisfaction. If you as a parent are overcoming those challenges for your kids, you're actually doing them a disservice long term. A happy life is not necessarily an easy life. So Sid and I co-parent in a way where we're not going to do everything for the kids. They come home, they're responsible for their homework. They've got to learn how to make it in this world themselves, within the scope of family, which will prepare them for the outside world.
Patrick O'Shaughnessy
If we zoom all the way to today, it seems from the outside like the most interesting time to be running this business. The opportunity is so massive, the threats are real, the new entrants are fascinating. What does it feel like to run this today? What feels like the central question to answer as the leader?
Dara Khosrowshahi
Every single year I've been at Uber has been a challenge. The challenge and opportunity now is the rise of AI, both as an internal tool for how we build. What's different about Uber is that we don't just exist in the digital sphere. Our experiences are digital first in terms of your interaction with the platform, but then they're delivered or fulfilled in the real world, where all kinds of things happen. You've got a determinative structure in the app, but then probabilistic outcomes in the real world — traffic, a driver cancelling, your food being late. We've used AI tools to build out our system for much longer than most companies.
Now, with AI in the digital world — the ability to build much larger models that know more about you, anticipate what you want more accurately, and turn an engineer into a super engineer — and then the rise of physical AI, autonomous vehicles, drones, and how they're going to change how we interact with consumers in the real world — I've never seen a pace of change so fast. It's incredibly exciting.
Patrick O'Shaughnessy
What's your mandate to your team, given how fast things are changing and how much more each person can now do?
Dara Khosrowshahi
I'm not a top-down driver. We have a bottoms-up culture — I want people inventing all over the company. I don't want to be that single point of failure, so I hesitate to drive mandates. AI adoption at the company has been occurring in all parts of the business, because we're an ML-native company in terms of where the technology came from: engineers, how they scope and build and debug, on-call, platform migrations, all the way to our legal and marketing teams. Where I come in is pushing the teams to use the power of AI to rebuild systems and processes from the bottoms up. It could be a decent first step to have AI optimise 20 or 30% of a process in speed or cost — but to rebuild it from the ground up, that's much harder, and that's where I'm really pushing the teams to think from first principles.
Patrick O'Shaughnessy
What's the most amazing thing you've seen someone do with the technology at Uber?
Dara Khosrowshahi
The most amazing thing is that the impact is showing up in all kinds of random corners of the company. We've got devs in India who all of a sudden are driving 10x the code commits they used to, using autonomous agents all over the place. The uptake isn't at all predictable in terms of who's racing ahead with this new technology. It's up to us to find those people and promote the rebels inside the company. We want the rebels to win here.
Patrick O'Shaughnessy
One of the interesting questions today is the actual latent demand for intelligence. Have you had an experience like mine, where at first you tell your team to burn tokens, use as much intelligence as possible, and then there's a moment where you realise — wow, this is expensive?
Dara Khosrowshahi
We're dealing with it now. We blew through our AI budget for the whole year in a quarter, and it's forcing us to adjust. We're going to meter headcount increases, because to the extent my engineers are getting more efficient, their throughput is increasing — they're becoming superhuman in output. My view right now is: drive adoption, encourage usage across the company, but also drive efficiency. We've got over $10 billion in free cash flow, which is great, but it's on well over 10 billion trips a year — we're not a high-margin business. We want efficiency to lower prices for riders and give more earnings to our earners. So we use the more expensive frontier models to explore — a new interaction here, an experiment there — and once we scale some of these experiences we bring in more efficient models, more efficient on a token basis, or open source, at lower cost. Exploration is go, go, go; efficiency and scaling is what we're also talking about.
Patrick O'Shaughnessy
You're one of a small handful of companies in this AI-meets-the-physical-world zone, with a scaled brand and distribution, an aggregator of demand. How do you think about that challenge and opportunity as one of the few companies with the right to win in how this new technology links up to the physical world?
Dara Khosrowshahi
First, there's an enormous opportunity in something that's boring but wonderful boring: just building larger models. Our feed and search models are probably 10,000 times bigger than our older models, able to take much more data about you and predict what you're going to search for. Now we have universal search — if you search for something, it's not just classified as rides or eats or grocery; we show you everything available across our services. Today, when you take an Uber ride, three-quarters of the time we can guess where you're going, and it's a one-tap interaction that can only improve. As it relates to the real world, we can anticipate what's happening much more effectively, and the form factor is going to change — drones getting food to your home, AVs taking you from place to place. Some of it is immediate, but there's a ton of opportunity going forward.
Patrick O'Shaughnessy
What do you think has to be true for Uber to win the demand-aggregator top slot in AV specifically?
Dara Khosrowshahi
Supply. We're a supply company. The more drivers we have in the marketplace, the more restaurants we wire up, the more latent demand we have. It's one of the lessons I learned coming from Expedia to Uber. At Expedia we were a demand-first company — how many consumers can we get to the website — and then we'd build out hotel and flight inventory in response. At Uber everything is upside down. One of our most significant growth opportunities right now is building out our supply not just in the big cities but in sparse markets — the suburbs, the next 50 cities, the next 200 cities in a country. The first thing we do is go out and recruit drivers, merchants, restaurants, groceries, couriers, and then the demand shows up. The biggest opportunity and challenge is securing every single car that's going to take you from A to B, every restaurant, every retailer. If we do that, the demand will take care of itself.
Patrick O'Shaughnessy
In AV specifically, what does that feel like? It feels like we're at the very early part of the S-curve. What is the state of AVs to you?
Dara Khosrowshahi
It's very early, but it's moving very fast. We've got over 30 partnerships now with incredible partners — from Waymo to Nuro and Lucid, to Nvidia, which is building not just compute and sensors but a software driver now, to companies like Waabi and Wayve, WeRide, Pony AI. Just like in foundation models, there isn't going to be a single winner — there'll be many players, open-source and smaller models too — and we're seeing the same acceleration in AV development. We want to be your go-to-market solution for companies building out these digital drivers, and we let them focus on building the driver while we build the services around them. We're securing depots and charging in cities where the regulatory landscape is moving the right way, working with fleet partners, securing financing — we just announced a billion-dollar financing line with Santander for EV and AV fleets — and working on autonomous insurance.
We're building the entire ecosystem so someone who builds a driver can get those cars on the road with all the supporting infrastructure. We're collecting data in the streets as we speak that we can feed to the model, and when they hit market we've got instant demand. What we're seeing is that consumers love the product, and AVs on our network are 30% or more busier than ones that aren't — in trips per vehicle per day and revenue per vehicle per day — which makes a huge difference to the ROI of investing in these expensive cars.
Patrick O'Shaughnessy
What has surprised you most so far about the product of AVs?
Dara Khosrowshahi
How quickly magic turns to normal. When I first experienced Uber, in New York City while I was at Expedia, I thought, oh my god, this is absolutely magical — push a button and a car shows up in five minutes. Next day you're like, where's my damn car? It was six and a half minutes, how dare they. With AVs you get in and it's magical — the cars are nice, there's a sense of privacy and peace, you play your own music. For the first two minutes you're like, oh my god, look at what's happening. Then minute three, you're doing the same thing you always do. What's magical now is going to seem normal to all of us 10 years from now. We want to make sure these AVs aren't just available for rich people in the middle of cities — we want them available everywhere. The speed to market is going to be fast, and the interactions are going to normalise faster than you think.
Patrick O'Shaughnessy
I'm interested in the build-partner-buy decision you're making in a million ways. You've got capital, free cash, infrastructure, and the demand aggregation you've built. How do you think about partnering with companies like Waymo, which you could certainly see becoming a competitor if they get a big enough network?
Dara Khosrowshahi
It's a coexistence I'm quite used to from the travel business. Think about OTAs, online travel agents — they compete with a Marriott, with a Delta, with an independent hotel for the consumer, all of whom are building their own direct channels and loyalty programs. But at the same time those hotels want incremental consumers from the platforms, because they have a big box to fill and want to drive utilisation. The returns for a hotel that's 70% full versus 90% full are night and day. The same is true in Uber Eats — we work with McDonald's, Starbucks, Chipotle, all of whom also compete with us to some extent. And the same will be true of a subset of AVs like Waymo: of course they want to build their own brand and channel, but we can drive more utilisation for them when their cars are on our network. The same is true of Zoox, of Nuro. Wayve is focused on building one end-to-end model they license to OEMs, and we'll be responsible for the demand. There'll be lots of models — it's not going to be black or white, only compete or only work together. It'll be an amalgamation of business models, as there already is in travel and food.
Patrick O'Shaughnessy
What's your premortem for this going wrong? If it's five years from now and Uber has screwed up this opportunity, what's the most likely reason?
Dara Khosrowshahi
I don't think it's necessarily an Uber thing — it's a big question for the industry. You've seen how powerful AI is, but also how unpopular it is with the general public. In the corporate world we're amazed and driving utilisation, but the way these AI models interact with the average person is: yeah, search got a little better, but if it's going to drive up my electricity cost or cost my cousin's job, that doesn't feel good. The same will be true of AVs. It's terrific technology, it's going to be safer than human beings, but how does it interact with emergency service providers? How do we make sure it's available to everybody, not just the wealthy? We've got to have these dialogues with regulators, with real people living in cities, with our drivers whose earnings may get affected. In Austin and Atlanta, where we have two big partnerships with Waymo, drivers on the Uber platform are making more money, and the number of drivers joining is increasing, because AVs are actually adding incremental demand. So we have good news early, but we've got to communicate and move at the pace society is prepared for, otherwise there'll be a backlash.
Patrick O'Shaughnessy
If I assume the public-perception part is solved, what would the same premortem answer be for something you do control?
Dara Khosrowshahi
Access to supply. That's why we have a partnership with basically every AV provider, whether in mobility, delivery, or freight. We need access to supply, and we're investing time and capital. I think we're in a great position to be the largest amalgamator of AV supply, just like we're the largest amalgamator of transportation services around the world.
Patrick O'Shaughnessy
If we assume the success scenario, where Uber is the clear demand-aggregator winner of AVs, what does that unlock on the other side — consumer experiences or things that aren't currently possible?
Dara Khosrowshahi
We think it's another trillion-dollar marketplace. Over a long period we'll see the cost of AV software come down and the cost of hardware come down — usually 30 to 40% per generation. The Lucid midsize that Lucid and Nuro are building for us together would be a $60,000–$70,000 car. At those prices you can bring the cost of transportation down for the population, and what we see is that as we bring costs down, demand goes up. When Uber launched, people sized the market on the taxi market — we're multiple times bigger than the taxi market. I see the same potential with AV, in cost, reliability, and safety. And then delivery: if it's done with a drone, instead of a 25-to-30-minute delivery you get habituated to a 10-to-15-minute delivery — cheaper, faster, better. It will change how society operates.
Patrick O'Shaughnessy
Do you think there should be a Foxconn-like contract manufacturer for AVs? The stat I heard in San Francisco surprised me — I badly overestimated how many Waymos are driving around. It seems you can be hyper-efficient, but the downside is maybe you can't hit the production to get costs down.
Dara Khosrowshahi
It's happening as we speak. Many of the traditional OEMs we talk to now see that L4 driving is a reality much closer than they thought, and they're investing in L4-ready systems. Over the next two to four years the traditional players will get there. Right now the cars are being manufactured in the hundreds and thousands; it'll get to the tens of thousands, the hundreds of thousands. Each vehicle probably drives three to four times what a human does, so the efficacy of one AV is substantially higher. And we're seeing newer-generation Foxconns — they exist in China, where the players' capabilities and bill of materials are incredibly impressive. We need that kind of low-cost player in the western hemisphere; it's being worked on, but we're not there yet. The Chinese capability in manufacturing, in both quality and cost, is at this point unrivalled.
Patrick O'Shaughnessy
Can you teach me about drones? I'll never forget that Amazon video from 10 years ago — it felt like the future was coming, my sandwich in five minutes. And no drone has yet shown up at my house. What's the story with the technology?
Dara Khosrowshahi
The biggest issue is battery density — the ability of a battery to lift itself and then lift the payload, and the requisite range and recharging needs. Joby is building drones for people, that's happening, and drones for food and grocery are going to start hitting real scale over the next two to five years. It's going to cost more than a human delivery to start with, but the ramp of the technology — larger payloads, operating in whatever weather, accurately getting a payload right in front of your house — is all moving in the right direction. Is it going to be a big part of our lives two years from now? No. But five to 10 years from now it's going to become more and more normal.
Patrick O'Shaughnessy
I'm interested in the regional differences. What have you learned watching AVs start to happen in the US versus Europe versus the Middle East?
Dara Khosrowshahi
The Middle East is going fast. Abu Dhabi, Dubai, Saudi Arabia — they're on it. The regulators are very entrepreneurial; they want to lean into new technology. Those services are happening today, with no vehicle operators in Abu Dhabi and Dubai. The US is certainly happening — the Californias and Texases of the world — but we want the right discussions at a regulatory level. It's going to take longer in a New York, in a Boston. And Europe is starting to happen — we're starting commercial robotaxi in Europe, and I think we'll have pilots in London before the end of the year. Europe is recognising it can't be left behind, and the European OEMs are a huge player in manufacturing and employment there.
Patrick O'Shaughnessy
Another US-versus-international story is that as you've gone international with Uber Eats, you've won the number-one position more often. What has the US experience in that category taught you that's impacted how you approach an international market?
Dara Khosrowshahi
The basics are the same. You've got to get selection right, sign up your merchants. When I look at the serviceable addressable market in the cities we operate in, we've probably signed up 40 to 50% of the restaurants and merchants that could be on our platform. Then it's about reliability — every time you order something, we get it right, we don't make mistakes, we deliver within 30 minutes. Our magic sauce is cross-platform. We started with mobility and can increasingly upsell the mobility customer the delivery product — when you open your mobility app on Uber, you see Eats right there, and about 13% of Eats bookings come from the mobility business. We get a bunch of free customers from mobility, and then we have Uber One, our membership program — 50 million members, growing 50% year on year. The way I look at it, we're kind of like Netflix: for the same price you get more content than anyone else. Discounts on mobility, surge protection, free delivery, no fees on groceries $60 or more, now 10% back on hotels. If we build a loyalty program bigger than anyone else's, plus the cross-platform magic, we can get to number one and have higher margins than our competitors — and we're proving it out market after market.
Patrick O'Shaughnessy
So much of the story is being good at getting supply. What does excellence look like there? What's the key to being great at aggregating supply?
Dara Khosrowshahi
Honestly, we're okay at it — I think we can get a lot better. I want more of our team members to put themselves in the shoes of our suppliers: to drive more, to stand behind the counter of a restaurant. All our employees are crazy users of Uber Eats and Uber rides, but we don't put ourselves in the shoes of our merchants. Partly because I was going crazy at home, but partly because I wanted to understand what a driver and courier experience feels like, I bought an ebike and started delivering food in San Francisco. Our drivers, couriers and merchants are on our platform much longer than the typical consumer. A consumer is in and out — maybe a 30-second interaction, once or twice a day. A driver has her app open six, eight, ten hours a day. So the premium on quality is higher. A P95 bug happens to a consumer maybe once a month; for a driver on the app six hours a day it's happening every week. We have a value at our company — building with heart. I'm an engineer at heart, very numerical, but there's a craft to building, a humanity in our service. Driving people in my Tesla and delivering food in San Francisco for a couple of years — that's what it takes to be a better builder and to be better at amalgamating supply.
Patrick O'Shaughnessy
What surprised you most when you were doing the deliveries?
Dara Khosrowshahi
How hard it was. Going into the restaurant, figuring out where to pick up, making sure you got the order right. About 50% of orders are batched, so you pick up two deliveries sometimes at the same restaurant or another one, and you've got to get everything right. There's a reason things go wrong in the real world — there's a lot to process for couriers and drivers, and then you have to deal with real-world traffic. For a consumer you push a button and your food shows up, it's all easy. For that driver and courier, there's a lot more going on, and processing everything can be a challenge.
Patrick O'Shaughnessy
The membership concept — 50 million people — feels like a feature every big business with lots of people on it would want, and some have been great stories: Costco, Amazon. What does each side get out of a great membership program, and how much do you have to tweak and design it versus it being straightforward?
Dara Khosrowshahi
The ideal membership program is one where you have a fixed cost base. A Netflix is investing a certain amount in programming; the cost of selling a membership is customer acquisition, and there's no variable cost for the services you render. Travel membership benefits are often upgrades to rooms or seats that were empty anyway — that's why membership started in the travel business and in entertainment. It becomes much more challenging if your cost to serve is variable. Amazon was the first to take that on: the cost of a Prime membership is higher the more you use it. Amazon walked through that valley of despair — the public markets didn't understand what it was doing and losses kept increasing — but they understood the unit economics, stuck with it, and braved through the early days. I took a lot of inspiration from that.
In the early days of Uber One, when we acquire a member you're less profitable. We're making a prediction that you'll spend more on our platform, even though your first few transactions are less profitable because we're giving you money back — and over your lifetime you'll be more profitable. It took some time to get up to speed. It's solidly profitable now, but the first year of membership is a year we lose money on you, then make money on you two, three, four years out.
Patrick O'Shaughnessy
The next leg of hooking this platform up to the entire world is hotels — full circle to your Expedia days. Walk us through the decision logic. The question behind the question is how you decide to do these big things in the first place. Why do hotels at all?
Dara Khosrowshahi
We tend to be pretty data-oriented, and it's relatively obvious that people who travel a lot tend to use Uber a lot. We're available in over 70 countries. What's the first thing you do when you land at an airport? You open your Uber app. Last year we completed one and a half billion trips for people outside their home city, and about 15% of our trips are to and from airports. So we could identify travelers — a headline use case — and we started thinking, what more could we do for them? What differentiates Uber isn't just the booking experience, but delivering it reliably in the real world; we go much deeper into the fulfilment stack than a typical online travel agent.
We started with trains, launched in the UK and Spain, and saw the same thing over and over: the more you interact with the platform, the more services you use, the more you come back. More content meant more retention. So it was natural to go into hotels — it's a high-value decision. We talked to the various travel companies to make sure we had the best supply, and we made a deal with Expedia, my old company, and we give the vast majority of the economics back to Uber One members. The design spec of hotels is again: how do I make sure your life is more deeply integrated with our services? 10% off hotels, 20% off 10,000 hotels — a great deal you're not going to find elsewhere, and another reason to join Uber One.
Patrick O'Shaughnessy
What's the idealised end state of that part of your business, five or ten years hence?
Dara Khosrowshahi
We want to bring value in the booking experience, but I want the value to carry into the market. You book a hotel in San Francisco; if you open up your email to us, we already have your flight information, so we pre-book an Uber to the airport and from the airport to your hotel, because we know where you're staying. Ideally, as you approach the hotel, we give the front desk a heads-up — or we let you completely bypass the front desk, go straight to your room, maybe use your Uber app as a key. I want to bring some in-market magic to your travel experience. We're already part of your experience in the city; the richer we can make it, the better. We're starting with a booking — we've got to start someplace.
Patrick O'Shaughnessy
Same premortem question — if this doesn't work, why would that be the case?
Dara Khosrowshahi
We've debated whether people's interaction model with our service can change from on-demand to planned. Our brand has always been known as on-demand — push a button, get a car. So there was a question mark: could we go from on-demand to planned? We started with Uber Reserve. In the old days, Uber Reserve let you reserve a car, but it was really an on-demand dispatch trying to get you the car when you expected it. We changed the back end to drive 99%-plus reliability — we pre-book with the driver, the driver accepts, the driver is there before the reserve — and Reserve is now over a $5 billion run rate. It didn't exist five or six years ago. If we give a tangible benefit — higher reliability for a higher price — we can move both demand and supply. That gave us the opening: is reserving your ride fundamentally different from thinking about your vacation two or three months out? Can we stretch that pre-commit, stretch the brand in that temporal direction? I think we can. It's not a slam dunk, but we're giving you great deals to make that plan on Uber.
Patrick O'Shaughnessy
What have you learned about marketing excellence? Both marketing Uber in general, and — as you do more and more — making sure even your own customers know these things exist. Before preparing for this, I didn't know hotels was a thing.
Dara Khosrowshahi
The surface we have on the phone is very limited, and I've changed my mind on this. Originally my hypothesis was that the marketing team's job is to get as many people onto the apps as possible, and then it's the product team's job to surface the right product at the right time. A small example: with Reserve, we offer the ability to order hot coffee — the driver picks it up on the way, and you have a coffee on the way to the airport. The goal isn't to get you coffee on that ride; it's to make you understand you can get coffee, or other stuff, on Uber. It's about the lifetime value, introducing a new service in a way that feels delightful rather than like an upsell: this is cool, Uber knows me, why not do more with them?
I'd always been much more product — build this from a product standpoint, and marketing just gets people to the app. But my marketing team told me I was an idiot, and I loved it. They're building storylines: Uber Teens getting your kid home from their game, the human interaction when your kid comes home whether they did well or not. There are very human stories in Uber, and those stories help people realise Uber isn't just about getting a ride — it's about giving you your time back across a broad array of services locally.
Patrick O'Shaughnessy
What do you think is more likely in seven years — that I do whatever the next great version of that coffee thing is, or that I just type into my Uber, 'I want a car at this time and I want a coffee'?
Dara Khosrowshahi
I think you'll be talking to your apps in seven years. And I think you'll still have apps, because there are many circumstances where the communication back to you is more efficient in the written word or in pictures — it's not compelling to say your Uber is six minutes away; seeing the picture and tracking the car is. So the inbound interaction is going to move more and more away from apps toward something much more unstructured, and AI makes that possible. Historically you built UIs for a specific interaction optimised for the overall average — our booking experience may not be optimised to you exactly, but it's optimised to overall averages through lots of testing, and there's only one way in. Now we're going to personalise it: when you land in a city, Uber will be different for you than when you're going to work.
Patrick O'Shaughnessy
Think about the people who've influenced you most. What did you learn from Barry Diller?
Dara Khosrowshahi
He's been my business mentor, and in many ways a personal mentor too. The thing I learned from Barry is the value of getting the truth from the source material. The way I first met Barry — I was an analyst at Allen & Company working on the LBO model for Paramount, during the hostile tender offer between Viacom and Paramount. Barry didn't want to talk to the MD or the VP or the associate; he said, 'Who built the model? I'm going to talk to that guy, because if I'm going to raise billions of dollars in debt, I want to know I'm good for it.' I was so nervous, sweating, trying to print out the model, and I took him through it. He wanted to hear straight from the source.
Every time — and I worked for him 20-plus years — it's the filtering that takes the edge out of a story. And it's often the edge that gives you an edge. Everyone has the same reaction to the average; it's that 20%, that P95 situation, that matters. Barry always insisted on going to the source, getting unfiltered data. It was sometimes unpleasant and took more time, but getting to ground truth helped his decisions and gave him the edge to go against the grain. In larger companies, the higher up the organisation you are, the thinner the layer of what's really going on — everything's been processed for you. My schedule today is determined by well-meaning people who want me to use my time in the best way, but it's processed. So it's important to cut through that and get to ground truth, to create some randomness in your information flow. The best way to get to the truth is, first, as a leader, to tell the truth. I'm brutally frank with my team — what's good, what's bad, where I don't know the answers — and that helps me get the truth back from them.
Patrick O'Shaughnessy
What did you learn from the Allens, both the second and the third?
Dara Khosrowshahi
So many things. Herbert Allen very early on told me that he makes bets on people, not companies. You see that with the Allens — they're so loyal, they build friendships and stay with them. Herbert told me companies can do well or poorly during periods, but great people always stay great, so I'm going to bet on people. I was twenty-something, like, 'Yes sir, Mr. Allen,' and that's soaked into me — regardless of circumstance. I made a bet on Barry: I was going to stay at a company all my life, but he was the one person I told myself I'd work with if I had the chance. It was nuts — my salary was gone, it went through a completely entrepreneurial new entity he was building. But I bet on a person, and in my life those personal bets are probably the best ones I've made.
Patrick O'Shaughnessy
Daniel Ek is famous for shadowing CEOs for long periods to watch how they operate. If I shadowed you for a couple of weeks, what do you think I'd take away about how you prosecute your life?
Dara Khosrowshahi
Number one is the transparency I talked about — I want the truth from everybody, I tell the truth, I'm very open with the company at whatever level. I have a lot of fun working with our product leads and engineers; that's the best part of my job. And the last thing is that you'd see a lot of random interactions. I don't want too structured a day, I don't want to meet with just my direct reports. I build out random interactions across the company to get that information. I look for the troublemakers.
Dara Khosrowshahi
As companies get larger, there's always an incentive for people to get along — a single culture, everyone true to it, processes get built, and the troublemakers often get chased away. I want to find those troublemakers and bring them in, because every company is like an organism, and organisms evolve by mutating. Companies that don't mutate, that just sit with a single process and a single information flow — those are the companies that die. So I'm looking for those mutations, those troublemakers, constantly. It requires random interactions, which are less efficient than the structured processes put in front of me, but they often give me the best signal. Sometimes I won't act on it, but if the signal becomes strong enough, I'll move. With AI now, the rate of change inside companies — how information flows, how we work every day — has accelerated by 5x. The companies comfortable with that change will adapt; the ones that say 'we do things a certain way' will have a hard time.
Patrick O'Shaughnessy
One of my favorite charts from this era is the time series of capex of the big technology companies — they all shoot up, except Apple, which is basically flat; they've decided not to play this game. Early on the debate around Uber was whether you'd ever make money. Now you've got $10 billion-plus of free cash flow. How do you prosecute the capital-allocation decision — old-school buybacks versus spending to expand demand, get supply, use these new technologies? Are you Amazon or are you Apple?
Dara Khosrowshahi
Somewhere in between. Capital allocation is more of an art than a science — you can read papers on it, but you have to use judgment in real life. My priority is first organic investment and growth. When I joined, Uber Eats was doing under a billion dollars in gross bookings; it's over 100 billion now, and that took an enormous amount of organic investment. The math is simple: you want your costs to grow slower than your revenue, and good things happen over a long period. Because I came from banking, I'm very comfortable with the power of compounding. So get your core metrics right — user metrics, then financial metrics, expenses growing slower than revenue unless there's a long-term benefit.
When it comes to excess capital, our priorities are to keep building the services we have, invest in algorithms and more engineers, and invest in the new realities of AV — investments in our partners, commits to tens of thousands of AV vehicles, which we'll financialise, like the Santander deal. We've got to be the ones developing the market, so we'll make those capital commitments. The fortunate thing is we've got plenty of cash left over for buybacks — but I prioritise growth and innovation over buybacks. If you're building the company right, you'll do both.
Patrick O'Shaughnessy
You strike me as a confident but not cocky leader. What, if anything, are you insecure about in the business or as a leader right now?
Dara Khosrowshahi
I'm not insecure — again, what good does it do? I'll go back to Barry. I've found that the more successful you are, the more you tend to talk and the less you tend to listen. I see executives who don't want to be talked back to — 'don't you know who I am, I've got authority' — but authority doesn't mean you're right. Barry's the opposite. If you get into an argument with him, oh my god, it's unpleasant, but you bang it out, and the majority of the time, when he realises he's wrong, he's delighted — he lights up, because he just learned. What kind of world is interesting if you're right all the time? The magic happens when you learn. I'm confident, comfortable in my own skin, but I'm a learning creature, and the delight comes from learning — and often that learning comes with pain: the pain of being wrong, of hearing something you don't want to hear, of something unexpected happening. That's what gets me going. If I'm not making mistakes, it's just not very interesting.
Patrick O'Shaughnessy
Is there anyone else who's heavily influenced your way of thinking or behaving?
Dara Khosrowshahi
I'm a bit of a student of business — it came from my investment-banking background; I love how companies shape themselves. One CEO I really admire is Reed Hastings, who built Netflix into the company it is. He's so logical and structured in his thinking, an engineer, but once in a while he's a gambler — and some of those gambles don't work. There's a superpower in being structured in your thinking but not so structured that you can't listen to the troublemakers and have those wild ideas outside conventional wisdom. Those two often go together. Reed innovated in a very structured, deliberate way, and I love what he did with his company and how he thinks.
Patrick O'Shaughnessy
Uber is one of the most interesting business stories — the way Travis willed this thing into existence as a break-down-walls entrepreneur, and the way you've matured it into this behemoth. When I have these conversations, I ask everyone the same closing question: what is the kindest thing that someone's done for you?
Dara Khosrowshahi
I guess it's Sid, my wife, taking me in. We talked about my origin, where I came from, having a chip on the shoulder. Until I met her, I was always living the life I thought I was supposed to, always the person I thought you wanted me to be. When I met her and observed her, she was always the same person — with me, with the kids, with her friends, or at the Sun Valley conference surrounded by unbelievably accomplished billionaires. She was always the same core person; she never changed who she was. Meeting her and seeing her operate finally allowed me to be the person I want to be, versus the person I thought I was supposed to be. That was a gift and a kindness I could never replace.
Patrick O'Shaughnessy
I have a shockingly similar experience with my wife. It's a beautiful place to end. Thanks so much for your time.
Dara Khosrowshahi
Thanks.