Leaders Playbook: Inside Uber 1/21/26

0:00Trading at Schwab is powered by Ameritrade, giving you even more specialized support than ever before, like access to the Trade Desk, our team of passionate traders ready to tackle anything from the most complex trading questions to a simple strategy gut check. Need assistance? No problem. Get 24-7 professional answers and live help and access support by phone, email, and in-platform chat. That's how Schwab is here for you, to help you trade brilliantly. Learn more at schwab.com slash trading. Men are struggling with their mental health at some of the highest rates we've ever seen, but most aren't getting the support they need, and that needs to change.

0:36I'm Dr. Guy Winch, your host for Season 3 of The Visibility Gap, presented by Cigna Healthcare. This season, we're focusing on men's mental health, bringing together real stories and expert insight to explore the pressures men face every day and why opening up can feel so difficult. Join us for the new season wherever you stream your podcasts. On this episode of Leaders Playbook. We're doing 36 million rides a day. Inside Uber, the global tech giant that's transforming transportation and food delivery. I started driving people around myself. Meet the CEO who jumped in the driver's seat to turn around a toxic culture and a business weighed down by billions in losses.

1:19Running Uber has been an incredible challenge. His strategy to drive change. We had to reinvent our culture to be able to grow in the right way. Regain customers' trust. Leadership sometimes is swimming against the current. And find opportunities when 85 % of revenue evaporated overnight. You have to go into wartime mode. Plus, how he's positioning his team to future-proof the business. I think long-term it's going to be a massive societal shift. Leaders Playbook Uber starts now. I'm meeting Uber CEO Dara Khosrowshahi at the company's office in Lower Manhattan. He joined Uber in 2017 after spending more than a decade growing Expedia into one of the world's largest online travel companies.

2:02There he worked alongside billionaire tech titan Barry Diller, who promoted him to CEO when he was just 36 years old. When Khosrowshahi left Expedia to run Uber, the ride-sharing platform was in crisis. I'm here to discover the leadership skills that enabled him to turn a troubled tech company into a profitable, publicly traded global powerhouse. When you took over Uber back in 2017, you took on the role of CEO. It was struggling with so many issues. What made you decide to take on that challenge? For me, it was about the impact that Uber has on everyday life. It was a tough decision because I had been running Expedia for 13 years.

2:44I'd been working with Barry. It was an incredible partnership. But I remember talking to my dad and he said that when a company that's a verb asks you to run it, just say yes. Running Uber has been an incredible challenge and it was a challenge that I was up for. To understand what Khazrashoggi was taking on, let's go back to the beginning. Uber was founded in 2009 by Travis Kalanick and Garrett Camp. It disrupted the taxi industry with a user-friendly app that made it easy for passengers to connect with drivers. Uber's president, Andrew McDonald, joined the company in its early days. Uber in 2012 was a luxury product.

3:22It was mostly black cars at that time. And so it was a premium service. And it was just a really fun place to start out and build. And we were going global. We were raising money. We were growing the team. In 2016, despite reporting$18.8 billion in gross bookings, the company reported a net loss of more than$3 billion. In 2017, it got worse. Uber's co-founder and CEO Travis Kalanick was investigated following a series of scandals and allegations of a toxic work culture. Uber's top investors ultimately forced him out. Just before Dara stepped in, we literally had no CEO. We were just trying to keep the trains on the tracks.

4:02We had tons of executives and leadership departures. Internal morale was really challenged. Travis was an incredibly talented leader, and I would tell you that I could not have accomplished what he accomplished in the founding of the company. He had to be aggressive in order to build the company into what it was. So in some ways, I think he was the right leader at founding, and I was the right leader to take the company and scale going forward. So you saw the opportunity to have this huge impact, but at the time there were so many mission-critical issues. How did you decide what to tackle first?

4:39Well, I think any CEO has to deal with a multiplicity of problems. And for me, it's about, it's part of my engineering training to some extent. It's taking complex problems that have multiple dimensions and splitting them up into kind of individual pieces. And for Uber, we had to reinvent our culture to be able to grow in the right way. we really had to rebuild our relationship with regulators and our driver base or courier base and build the trust that's necessary in building a business the right way. And then, of course, we were losing billions of dollars in terms of profitability, and we had to turn that around.

5:17For me, it was about separating each of those issues, creating a plan, and then executing against each of them. And while the job is not done, we have been able to move forward in all of those areas pretty significantly over the past couple years. McDonald recalls the challenges facing Khazr Shahi as a new CEO. We had daily press stories hitting the news about things that were happening at Uber. You know, usually those were bad headlines. We had tons of sort of internal leaks. I think, interestingly, Dara just took that right head on. He spoke from the heart. He was clear about what he didn't know.

5:56And I think this was really important for our employees to hear why he was joining the company, which for him was the chance to change the world. One of my challenges coming in was to come in and really help the company understand just how important we are to the world. And that sometimes in order to speed up, you have to slow down. You have to have a dialogue with your constituencies. You've got to talk to regulators. You've got to allow your drivers to have a voice. And that was all part of the transition of culture. Before Khazr Shahi joined Uber, one of its published core values was always be hustling.

6:31He had to make a change. Our most important, I say, cultural value at Uber is pretty simple. It's do the right thing, period. No exceptions. And I remember when I introduced that cultural value to our employees, many of them asked, well, what does that mean? You know, give me a handbook for doing the right thing. But the fact is that doing the right thing in one circumstance may be different from another circumstance. What I wanted to message your team is, each one of you has a responsibility when you come into work. You represent Uber. And that means you have to be thoughtful about your decisions, because with the scope that we have, we have a lot of power, and you really have to think about your constituencies before you exercise that power.

7:12How did you tackle this balance between maintaining the spark and also telling your employees here, we have to change the way we're doing things? I think I was lucky in some ways. The company was in crisis. If I'd taken over and everything was going great, the question would be, why are you trying to change something that is perfect? So I had the right to come in as the new leader and change where we wanted to change, but also keep consistent that entrepreneurial spirit, the great talent that we had at the company, really combining the two. And I did the same thing with the management team. STEPHANIE SY One of your big challenges, in addition to managing these relationships and these various constituencies, was winning back trust.

7:54And there were trust and safety concerns. There was a whole campaign to get riders to drop Uber in favor of Lyft. How did you deal with that? DAVID BUCKLEY, CEO, Gaining back trust is really difficult. The fact is that it doesn't happen overnight. One of the most important moments when I came to Uber was actually we have these all-hands meetings where our employees ask any and all questions. And one of the employees asked me about our PR problem, the trust problem that you talked about. Well, it's a PR problem. And I say, you know what? If we treat it as a PR problem, we're never going to solve it.

8:30The problem is us. The way to win trust back is act differently. And just as Uber started gaining trust, a global pandemic knocked out 85 % of its business overnight. Coming up. You have to go into wartime mode. And later, I bought a Tesla and I started driving people around myself. What he discovered in the driver's seat.

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10:11Get 24-7 professional answers and live help and access support by phone, email, and in-platform chat. That's how Schwab is here for you, to help you trade brilliantly. Learn more at schwab.com slash trading. Men are struggling with their mental health at some of the highest rates we've ever seen, but most aren't getting the support they need, and that needs to change. I'm Dr. Guy Winch, your host for Season 3 of The Visibility Gap, presented by Cigna Healthcare. This season, we're focusing on men's mental health, bringing together real stories and expert insight to explore the pressures men face every day and why opening up can feel so difficult.

10:49Join us for the new season wherever you stream your podcasts. In 2017, Uber CEO Dara Khazrashahi took over a company in turmoil. He focused on transforming its culture and rebuilding customers' trust. Nearly two years in, in May of 2019, he took the ride-sharing platform public. Less than a year after Uber's IPO, COVID-19 brought ride-sharing demand to a screeching halt. The pandemic was an unimaginable emergency situation. 85 % of our mobility volume disappeared overnight. In those situations, you have to go into wartime mode. and as a leader in wartime mode, you have to be decisive, you have to move quickly, and you have to inspire the team to hopefully understand that you know what you're doing.

11:44And as part of that, I'd say there are two really important things that we did. One is we cut costs, and we had to cut costs because the revenue had disappeared. I think, unfortunately, we laid off close to 25 % of the company. I never imagined I'd come to Uber to do a layoff that big. it was really, really hard, but it was necessary for us to reset. And then the second for us was leading into Uber Eats. People weren't going out anymore, but our Uber Eats business all of a sudden overnight doubled, and it was a lifeline for restaurants. And our drivers who were driving people around all of a sudden could turn around and deliver food.

12:22Fast forward to today, our Uber Eats business, which was less than 10 % of our business, today is just as big as our mobility business. And ultimately, I think five to 10 years from now, our delivery business, which is moving from like food to now grocery and pharmacy and everything you can imagine, ultimately I think is gonna be bigger than our mobility business. We were having a really hard time getting drivers back on the platform because they didn't wanna get sick. We have these driver forms all the time. So I talked to drivers to understand what they think, et cetera. And there was one woman who I was talking to who had been driving for Uber, and she switched over to delivery.

12:59And she was making good money on delivery, but she was making more money in terms of driving people around. And I asked her, well, why don't you shift over to mobility again? Why don't you start using Uber again? And she said, because, Dara, a Big Mac can't give me COVID. That was, I was like, oh, wow, there's fear here. To understand that fear, Kazarshahi put himself in their shoes. I got an e-bike in San Francisco. I started delivering food at first. And I started understanding that our driver-facing product wasn't as good as a rider-facing product or eater-facing product. Just because most of our engineers, you know, they use Uber all the time.

13:35They use Uber Eats all the time. But they weren't using the driver-facing product. I bought a Tesla and I started driving people around myself. And that led to us becoming much more driver-focused. It led us to building a better product and ultimately led to drivers coming back to the platform. Khaasr Shahi shared what he learned with Uber's leadership team, and his action inspired them. The first thing I thought to myself is, I got to get out on the road again. And our other leaders said the same thing. And it sort of had this cascading effect of people not just using the platform as an earner, but documenting their experiences, and then really speeding up the cycle time at which we improved those experiences.

14:14Super important cultural moment. Leadership starts from the top, and it comes from the heart, and it's really genuine, and people follow. As the pandemic waned, demand for rides returned. But there still weren't enough drivers to meet demand, and growth stalled. Khazrashoggi had a decision to make, improve earnings by cutting costs, or double down and lose more money in the near term. The first couple of quarters, I will tell you, were pretty difficult because we were very open to our investors that we were investing hundreds of millions of dollars to getting driver supply back versus Lyft, who was kind of letting the marketplace do its thing.

14:54I was pretty unpopular for a couple of quarters, but you know what? As a CEO, that's a definition of leadership. Leadership isn't going where the current takes you. Leadership sometimes is swimming against the current. It was clear to me, and maybe it wouldn't have been clear if I hadn't driven myself, but because I understood the product, because I put myself in the drivers and courier's shoes, I knew what had to be done. The investment paid off. The pandemic was finally in the rearview mirror. But Kazurashahi faced a massive problem threatening riders, the company and his leadership. You're still facing negative headlines around safety issues.

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16:07This episode is brought to you by Schwab Market Update, an original podcast from Charles Schwab. Join host Keith Lansford for this information-packed daily market preview delivered in 10 minutes or less, including projected stock updates, monetary policy decisions, and key results and statistics that may impact your trading. Download the latest episode and subscribe at schwab.com slash market update podcast or find Schwab Market Update wherever you get your podcasts. Men are struggling with their mental health at some of the highest rates we've ever seen, but most aren't getting the support they need, and that needs to change.

16:44I'm Dr. Guy Winch, your host for Season 3 of The Visibility Gap, presented by Cigna Healthcare. This season, we're focusing on men's mental health, bringing together real stories and expert insight to explore the pressures men face every day and why opening up can feel so difficult. Join us for the new season wherever you stream your podcasts.

17:09By 2025, Uber reported more than a billion trips a month on the platform. So many strangers connecting for rides all around the world has created a safety challenge for over a decade, one that continues to test Khazr-Shahi's leadership. But you're still facing negative headlines around safety issues. Sure. And it's such a complicated situation because you're not just dealing with employees, you're dealing with independent contractors. How do you stay on top of such serious concerns when the people who might be causing the safety issues aren't people who directly work for you? They're contractors.

17:45I think safety, and especially women's safety, is a huge societal problem. And when you have over 8 million drivers on the platform and 180 million consumers on the platform, and they're connecting every single day, we're going to reflect the realities of society. The fact is that violence continues and it's an enormous problem. Our approach there is just using technology to get better every single day. So if you look at the features that we have introduced in terms of, you know, 911 button in the app, the ability for you to track the ride of a loved one, you know, all of my kids, I'm tracking their rides, the ability to have audio recording, the ability to have video recording, All of these safety features are numerically improving the safety of our platform.

18:35Since our first safety report to the last one that we published, the platform is 44 % safer. Now, that's not enough. As long as some of these safety issues happen on our platform, we're not going to be satisfied. But what I can tell you is we're going to be safer tomorrow than we were yesterday. And that's my job to make sure that happens. And so as a leader, your message is just keep driving progress. As you manage all these issues, it's important to know that your expansion has really been global. And as you've expanded around the world, you've had to deal with so many different local issues, local municipalities, taxi companies.

19:12How do you decide when it's worth staying and investing in a city or in a country and when it's not worth it and you should pull out? We want to be everywhere. We're in over 70 countries. We continue to actually expand into new countries now. And ultimately, if we are in a market, we either want to be the number one or two player. And if we're the number two player, we want to have a road to number one. We want to be the top brand. So there are certain markets and certain businesses where we didn't see a road to getting to number one. So, for example, Brazil food delivery. We decided to pull out of Brazil food delivery.

19:46That allowed us to invest in, for example, food delivery in Germany, where we do think we can get to number one. It will take years to get there, but the decision is about ultimately, can we get to number one or not? I'm not going to be satisfied with number two. I never want to be. And I think that creates the opportunity for us to drive to one. With Uber expanding into new markets, Khosrowshahi is leaning into unexpected partnerships for growth. You've been able to turn rivals or frenemies into partners, whether it's taxi companies or you've worked with local municipalities that maybe didn't want you there originally.

20:21How do you approach those relationships? I think you approach those relationships, first of all, by listening. I think that listening is a really underrated executive skill. And the fact is that when you see yourself at odds with someone else, there's a reason there and there may be ways of getting around that. For years and years at our company, taxis were seeing it as a competitor. But then we decided, you know, listen, taxis want business. And we have a huge amount of demand in terms of the audience. 180 million people come to Uber every single day looking for transportation of some kind. Why can't we connect them with taxis?

21:01And as we started having discussions with some of the taxi partners, at first, I'll tell you, they didn't trust us for a minute. But we convinced a couple of them. Come and do business with Uber. And slowly but surely, the results poke for themselves. Like in San Francisco, the average taxi driver who's using Uber is making 20, 25 percent more. That is the perfect solution, which is that's a definition of a win-win. Khazr-Shahi had success turning rivals into partners, creating a growth strategy that didn't rely on acquisitions. I always say that the way to do the best deals is not to have to do any deals at all.

21:36I think that companies that need to do deals to grow then start slipping into doing less high-quality deals. So you've got to put yourself in a position where your organic growth is really, really strong. And organic growth is 18%, 19%. And if you come from that position of strength, then deals become optional. The danger happens when management teams feel like they have to do a deal in order to grow, or they have to do a deal in order to kind of cover for some fault that they have here. It's fun when you make the deal. The integration is like hell. It's terrible. We've got lots of cash flow, but organic growth is always the top priority for me.

22:17As Uber's network expands around the world and technology advances at a record pace, CEO Dara Khazrashoggi is leading the platform so it can compete in the future. If you think about AI, one of the biggest technologies that are coming that's driven by AI is autonomous vehicles in the streets. We elected not to actually build that technology ourselves. That was one part of our business that we divested during COVID, and we are now looking to partner with all of the autonomous partners out in the ecosystem. How do you approach as a leader planning five years into the future when we have no idea what autonomous will look like in five years?

22:56The fact is, if you think you're planning five years into the future, you're kidding yourself. What I'm certain about is that autonomous technology is going to be safer than humans. These digital drivers, they don't get distracted, they don't get tired. We want it to be affordable and available to more people and we're going to invest behind it through these partnerships that we're building. I think long term it's going to be a massive societal shift. We think Uber is really well positioned for that shift. Autonomous vehicles are expensive today. They're going to be, you know, somewhat expensive in the future.

23:30They need to be highly utilized to make a return on that asset. And our platform is the best place for them to be utilized. So I think we've got a significant role to play. But it's a really exciting moment. While positioning Uber to take advantage of advances in technology and coming shifts in consumer behavior, Khazrashahi spends most of his time focused on what's most pressing right now. I'd say general rule of thumb that I've got is you have to spend probably 60 to 70 percent of your time on the near term. And then, you know, I get to have fun with the other 30 percent of my time thinking about the long term.

24:07What's your strategy for developing talent? I have to say I'm not great at hiring people because I like people. So if I'm, you know, if I meet a stranger, I instantly kind of connect with them. but I am good at developing people. And part of that development is getting to know them, listening, and then throwing challenges in front of them and seeing how they do. You want to save them if they're struggling, but unless you're challenging your executives, they're never going to develop. You have access to so much data at Uber, both about what's happening now and what could happen, but you also have a reputation of being a little bit of an instinctive leader.

24:45How do you balance that instinct in the data? So I found that in life, the biggest mistakes that I've made is if my head and heart don't agree. My head is the part of me that's always looking at the data, and I'm a complete data nerd. But I found that with my logical brain, if I truly feel strongly about something and my heart isn't there, I'm missing something. My big rule is when I'm making big decisions in life, the head's got to agree, but the heart's got to be there. When those two come together, I'm ready to move. For Khazr-Shahi's team, his ability to strike that balance is his leadership superpower.