He built Uber to $15B (Uber CEO Travis Kalanick’s right-hand man)

All right, Emil, take me back to Uber trying to enter Italy. I've heard it was a very difficult time and I'm very interested. What was that like?

Why Italy? Why? You're fascinated by the Italian part of Uber, huh?

I am. I'm fascinated by that. I heard you talking on Joe Lonsdale's podcast and saying that the mafia was involved, right?

I used the word taxi mafia a little bit loosely. I'm not saying like the Corleones were involved or anything, uh, but I guess what happened is, uh, it was the most resistant, uh, place to Uber in the world in terms of like what they're willing to do to stop Uber from operating. And by they, I mean the people who had an interest in the taxi system at all. So we had a female manager of the country who was Italian. We tried to hire local people, right, who knew the politics, the culture of the place, and so on. And she was from a prominent family, well-known, all this. And they put posters around the city suggesting that people kill her. And she lived in an apartment. They went up to her apartment and pulled a sign from her apartment across the road to the next apartment. So it was like in the street, like a banner saying that, you know, this person had an affair with the taxi commissioner or something like that, who was permitting Uber to exist. So imagine the fear that would cause in anybody if people were willing to go to that length in your own city to put posters on the wall. So that was some tough stuff.

Yeah.

Wow.

That is, that's crazy. So definitely fascinated the intersection of crime and, you know, stuff like that.

Maybe not per se crime, but, you know, well, breaking and entering into someone's house is not great. Certainly putting posters around saying someone should be killed is probably not consistent with the rules. Yeah.

Yeah, definitely against the rules. Definitely crime. Yeah. The crime in business. And I'm curious, how did you deal with that? Um, how do you help somebody get through that? I'm curious about that. How did Uber help people get through that?

So it's the right question to ask because we felt we were fighting a righteous battle, right? It was righteous that people should be able to plan their lives, you know, going to get to the airport or getting around town at an affordable price, and people should be able to earn money With this asset they have, a lot of people have a car and it's just sitting there. So if they want to turn some extra bucks, everyone wins, right? So we had missionaries at the company. So while they were scared, they still wanted to push forward. So as a leader, you kind of have to balance the actual safety risk for them. So even though they're passionate, you can't make a mistake that puts someone in jeopardy. But at the same time, you're like, is there a way around this? And they were the ones who were like, no, We're going to win, we're going to win. So, I spent way more time on Italy almost than any other country besides China because of this. Like, every week you got to get updates. What's happening? How do we make sure the team's all right? Should we pull out? What should we do? Right? Wow.

I can't even imagine that's how high stress that was. So, you're probably consulting with what, police, consulting with security and consulting with your team, right?

Yeah. Yeah, we have a, we were consulting with the prime, like trying to get our, someone to talk to the prime minister of the whole country to sort of maybe pass a law that overrides, or at least to make sure that they're protecting our people and they're not in jeopardy. Like all, all, all of our resources came to bear to make sure that, uh, you know, people were protected, but we were doing the best we can to win. Wow.

So I'm curious, how did you go about finding people on the ground in different countries? For context, I'm head of growth at Product Hunt. We're doing these global meetups, right? And they're hosted by people on the ground in different countries. And, you know, finding people in places where you're not is a challenge. And it's, uh, you know, the internet makes it easier, obviously. But how did you find the right people?

We had, um, a pretty sophisticated way of doing this, right? And it was invented for our business model, so it's not necessarily applicable to everyone. But what we did is we had something called the launch team, and that launch team was kind of a roving team. It was a bunch of young people, probably single, so they could go live in different countries, and they would go, quote unquote, launch Italy. And they didn't necessarily have to be Italian, but they had to go a plant and office. They had to get the first riders and drivers. They had to get to the country to a certain point, but they couldn't leave until they hired a local general manager. And it was a little bit competitive. How fast could you build a country and then move on to the next one? And the requirements were they had to speak English because we wanted to communicate globally. So obviously they were local, but they had to have a second language. And we had like a profile that we interviewed for relentlessly, you know, passion, analytics. Um, and you ended up with these like, wow, we got a lot of former Bain consultants here. So like they're Italian, but they, they went to a great college, maybe in Europe or in America. And they went to work for a consulting, um, company that taught them analytics and, uh, was a hardworking place. So I'm just giving you some examples of what the formula spit out. Um, and we did that all over the world. Wow. Wow.

That's amazing. So these people who were young kind of launch teams, they'd get hyped up, get a, get a country stoked and go around just meeting people. And did they have like a strategy when like you choose the biggest city, right? That, I mean, or the capital or what?

Well, so let me give you a visual. Uh, next to Travis in my desk, we had a globe, like, you know, one of those globes and there were pins in it. Red, yellow, green. Green means we can go, we should go, the rules are friendly or they're neutral. And, uh, you know, it's a big economy or big cities. And then yellow was like, well, the rules are shaky or the economics are weird. And then red was like, they're like, you come here and, uh, it's going to be a felony kind of thing. So obviously you do the greens first, then the yellows, and then you do what you can on the reds. And yes, generally speaking, you go to the biggest city in the country if you can, because that's where transportation is sort of most needed. That's where the people want alternatives and likely can afford alternatives to the current system. But then you branch out into, into every city you can, right? The wait times just get longer as you get to more rural areas, but it works everywhere, right?

Yeah. Yeah. Start with the low hanging fruit, start with the easiest cities, uh, and then move out from there. I assume you had, um, what's the word, lobbying team as well that was, was trying to change laws in countries all over, right? Not just the US. They were, they were trying to change all over, all over.

So back to you, I didn't answer the first part of your question, was like, did this go without a plan? No, we had something called the playbook, and it was literally a written documentation of best practices on how to launch a city. And the launcher and the new general manager responsible for updating that playbook for new information. So every city that was launched after had more nuance, had more data, had more collection of experience so that it became easier and easier.

How much did it take money-wise? Like, how much budget would you allocate for a new city?

I mean, in the beginning, not a lot. In the end, a lot, because we were able to raise a lot of money. And when competitors and copycats started popping up in all these countries, it costs more money to kind of get in there and be competitive and be the market leader.

Yeah, I can't even imagine, like, if I was sending a team to, you know, wherever we're having meetups in Prague and India, like, my strategy would just be like, all right, throw parties, get as many people going and like, like, I don't even know. It's, it's so much operational. Have you always been a very operational person? And do you have any strategies to improve on that?

There was some elements of literally launchers or general managers knocking on the door of black cars that they see in the street saying, hey, here's, you want to earn more money, download this app and, and so on. And it was an element of parties so that people start getting familiar with brand, the who's who of a city. And then you got them free Ubers. And they're like, holy cow, I push a button on my thing, I get this free ride, it's great, some buzz in the city. That was early on. Those kinds of like guerrilla marketing tactics were important. I mean, I actually technically am not an operations guy. I was the business person and I'd never been in a company that was this gritty though, where, you know, you're talking about one by one acquisition of drivers. Riders was a little bit easier. Because you give someone a free ride, you know, they tell a friend, you can market them on the internet, getting a driver set up and getting their payments and getting them to be online and all that stuff. That was harder.

Interesting. And curious, um, dealing with the press, I feel like it's, the press has gotten more and more against tech every year. It feels like, um, for the last 10 to 15 years. Just any advice for tech companies. A lot of founders listen to my podcast, read my newsletter, and are dealing with journalists that hate them. So curious if you have any advice for them.

You know, there's some good news in that 10 years ago there was much fewer outlets. And so when one of the few outlets, TechCrunch, wrote something bad about your company or critical, it caused a lot of ripple effects because there was just such few things, authoritative sources about what was happening in tech. Now there's a lot more. Now they almost like, there's still a lot of negativity, but at least people are listening to other stories and they're not spending as much time on any one. And there's a general skepticism on media generally that Frankly, the media is at fault. That's like not just with tech, with everything. People are like, I don't know, I don't know, I don't know anymore what to believe. So, you know, that's good news in a way. I think the thing that I would advise founders to do now is be— don't be naive in who you engage with, right? The journalists, like bankers, like whoever, they're professionals at making you feel comfortable to talk and to disclose and to whatever. And then all of a sudden you're like, holy cow, I thought this person liked me. It's not— So don't take it personally. It's not about you, right? It's like, not that this reporter betrayed you. It's their job to write something that gets interest, which clicks. And that has a, that has a certain, has to have a certain edge to it. That's not their fault. That's their business model. Right. Um, so don't be naive. Cultivate relationships with the, the reporters who actually do write stuff that's fair, balanced, optimistic. So that when you have a balance, something negative comes out. And I know what Balaji and all these guys are saying is true. It's like, develop your own channels like you do. You have a newsletter, you have a podcast, you talk directly to people on X. And that's another weapon that founders didn't have as much 10 years ago that they have today. And it's hard to balance because that's an extra workload, but As your company gets bigger, that becomes more important.

Yeah, that's right. I've been ghostwriting for founders for the last 3 years and, you know, every startup founder, not every, but a lot of them have ghostwriters because they don't have time to do it. They have time. They send me an idea, you know, and I turn it into something pretty, right? Or they send me a voice note while they're on a walk, right? And every founder like needs to be building their own direct channel, personal brand, uh, as well. So yeah, it, it, it brings the power back to the founders, which I think is so important. And, um, yeah, all about biology. Lulu Miserbi talks about it a lot, going direct. She's, she's absolutely incredible. Amazing. Um, so talking post-Uber, I mean, you've been doing a lot, all sorts of initiatives, investing. Um, curious, what does average day look like and what, what exciting projects are you working on now?

Um, I, you know, um, it's been a change not being totally devoted to one mission, right? Which I was at 4 different companies, Uber being the most important. Um, but I was, you know, you heard this on the other podcast, I was like 46, single, like I, you know, my parents were living in New York, so I, I was like, okay, let me take some time where I could do several things but balance them out. So they're not one mission that gave me more time control. I could do the family thing for a bit. And so I started working with a few companies. I invested some capital and I worked alongside them as like their chief outside advisor. GoPuff. I was an advisor to Revolut, Brex. I made some just straight investments that were good back in 2018, '19. And I spent a lot of time with founders on the harder problems and interesting opportunities. Raising money, where I'm on the phone at midnight with them, you know, through the good times, M&A, hiring execs, building a team, leadership, these things. So 5 to 10 hours a week working with 4 or 5 companies. That's what my week looks like. Phone calls and Zooms where I have to context switch. But the good news is like I love founders. I love the energy. And then if I could give a little bit of advice at the right time to like change their trajectory, it's super valuable to them and satisfying for me. So right now I'm spending way more time in AI than delivery logistics and, and fintech. And, um, Perplexity AI, that which has an app, a Google search competitor, I like a lot. I'm spending time with some of the legal AI companies. I'm really at this point trying to understand who's going to win besides the hyperscalers for building these foundation models and how. Um, and along the way, I'm meeting as many founders as I can and, and, and and hopefully it will lead to another, the next set of 3 to 5 companies that spend 10 hours, you know, 5, 10 hours a week on, uh, in that way.

Perplexity just became a unicorn yesterday, right? Or announced their unicorn status.

Wow. Yeah.

That's incredible. Do you think they will disrupt Google or is that the plan? I guess.

I mean, I like the search market is enormous, right? It's enormous. And the experience in some ways has not gotten as better, better with at the same trajectory as the rest of tech we use as your iPhone as like anything else. Right. So if anything, it's gotten slightly worse with more blue links and more garbage. So, so is there opportunity for Perplexity to innovate on quality and build a network and get 10% of the market share of Google, which would be like tens of billions of dollars in market cap? Yeah. I think so. And then, you know, that's obviously step one. There's lots of other things you can do with that once you have consumers relying on you, right?

Yeah, that's really interesting. The rest of tech, everything, social media has been exponentially getting better. And here is search, like, linearly improving? Maybe. Like, probably just like parabolically going down, like, for the most part. So that's strange, right? That's really interesting.

Very strange. Like, how many times you search for something some someone off, you're like 7 clicks in, you know, you, it really has not improved in the way some of these other technology things have improved at that rate in the last 10 years.

Yeah. And I feel like, is it because of SEO hackers, like beefing up their websites or is it because Google is getting lazy? I don't know, but some combination. I don't know. It's weird. It's definitely strange. I felt that. Yeah.

Yeah. I mean, there's partially some gaming going on, but it's the greatest money machine ever built. It's like literally, like you could probably take 90% of the Google search team out, a few engineers, and you don't even add an in-ad sales team. It's all online auction and all this stuff. And it prints cash.

It is funny how, you know, uneven it is, how responsible like the search business is for all of Google. Like I have a friend at Google Translate. He's an engineer there, probably gets paid, you know, $200,000, $300,000, right? They don't make any money. The search business just runs the thing. Yeah, it's wild. Yeah.

Yeah. I think the other pillar that's becoming a true pillar there is YouTube. It's becoming sort of a material business unto its own. You would think Google Maps would've had some way of doing that, but it's a great service to humanity, Google Maps, but it hasn't become a pillar of the business. YouTube and search, with search still 10 times bigger, but yeah.

YouTube just released courses too. I saw like paid courses. I think that could be really exciting if they're taking just a small percentage. I mean, everybody's just learning on YouTube now, so why not just, you know, take a small percentage of that? Yeah. Perplexity. Have you used it? Do you find that it's like better than Google a lot of time or?

Yeah. I mean, so number one, it feels like I don't have to hack my brain to figure out what search terms I want to put in. I could just like, it's a little easier to just like block Ah, right. Like you kind of like you would on ChatGPT, you could have much more of a stream of consciousness, which reduces your sort of mental load on starting. And then underneath it, it has like the 10 next questions people ask after the first one, which I think is really, really interesting. And I end up clicking on that and it's much more precise than going to the next link. You're going to the next question and answer. I find it really compelling on that. And I think The stats are showing that like people are finding value every step of the way through their search. And they need to anyway.

And when you're evaluating startups to either invest in or spend your time, I'm starting to like get to the point where getting equity in a couple and then like getting offered, you know, do you want to angel invest and stuff? And I haven't, you know, pulled the trigger yet. Scares me, honestly. It's like, you know, I'm, uh, scares me. How do you run through that? How do you make those decisions?

You know, I think it's a lot, it's highly dependent on kind of your financial position. I think people who losing, for losing the money would be an impact to their life. Like it would change the way they operated. That's a dangerous game to play. Even if the company you invest in is a winner, because it'll take 7 to 10 years to get that money out, right? It's on paper. Very few startups are sort of like, okay, they're doing this and then 10x return in 3 years, here's your cash. So you have to be willing to part with that money for a long time, which means you kind of can assume it's gone. And you should only do that up to your means at the time. Now, let's say you do have means. It is, you still have to be thoughtful about what you do because you want to pick the winners if you can. So you have to have an internal philosophy and your philosophy sophistication will grow over time as you do it more, but you have to have a theory. Am I betting on the founder? Am I betting on the market? Am I in order? What are my order of things that I use to evaluate something? And you don't have to be a sophisticated VC. You just have to have your own principles. Like you meet a lot of people, like you have a judgment on, on who's going to be a winner and who's not and what's interesting. And you have to be okay saying no sometimes. And that's hard because sometimes they're often your buddies, right?

Yeah. Yeah, it definitely is. Can you think of any times that you've had to say no on investments that were difficult?

Yeah. I mean, I think that I stopped investing probably like almost 90% in 2021 when things got crazy. I stopped understanding the world. I didn't understand. I was like, I just don't, I like either they're wrong or I'm just an old dude who's, I'm not seeing the future. And it was a lot of Bitcoin and, and, uh, you know, blockchain and, uh, just everything was to the moon. And I was like, I just don't get it anymore. So I'm just going to stop and chill for a while. And that actually was effective because I could tell everyone I'm just not investing. And that's, uh, that's actually easier. But when you're like, when it's hard is when there's someone close to you, you are investing. You know, I think the answer, the polite answer is to give, which, which are true for me. It's like, you know, I'm not interested in this sector. It's just this, this particular thing is, is, I just, I don't, it's, it's not, I, I'm, I, I ration my time. I'm spending time on others, but I really appreciate it. And, um, I hope, I hope I hope it works and I hope I'm like kicking myself for not doing it. Yeah. Yeah.

Long-term games. You've built very solid relationships in Silicon Valley. Is there been any advice to like a young, you know, a lot of my listeners, you know, are college kids who are trying to break in and do that. Do you have any advice to them?

Yeah, I do. And I think there's a reason Silicon Valley is a special place. And just if you think about how special between Apple, Google, Facebook, Uber, Twitter, Airbnb, Dropbox, OpenAI, all are in the 30-mile radius. Like what's the, what magic happens that made that place there? Well, yes. Okay. There was great computer science sort of talent there for a long time when this, when people were making chips and that was like the first technology that the Silicon Valley produced. But the other thing is that there is a culture there of paying it forward without being transactional, just doing favors for people, giving insights, making intros that are valuable without asking for anything in return immediately, playing the long game, sharing knowledge. And that builds a trust circle and a framework of really learning. And if you, that's the long game and it's not, it's not human nature. You're like, well, if I'm doing this, what do I get? And it's hard to do because you're a college kid, you're breaking in, but you want to build solid relationships with people who matter, who could help bring you opportunities that other people aren't seeing. You got to play long game.

Yeah. I was on the phone with the founder earlier. I was like, you know, your Twitter. Like these are people you're going to see in like 40 years on Twitter. Like once you're in Silicon Valley or in startups, you see like we're just going to be here. Like it's the same crew. Like some of my Twitter friends, you know, startup friends, they're coming to my wedding. They're like, you know, close friends. Right. And so that's definitely the way that I've, I've thought about it. I found that so much more than academia, honestly, it was like, people are just so helpful, like just so giving of their time and helpful, playing the long-term game and very, very appreciative of it.

It's a special, that co— I have, I mean, it is, well, I didn't love living in San Francisco. That part of it, that like free learning circle was, was, is just a special thing that I've, I've rarely seen anywhere else in the world.

Yeah. Yeah. Um, cool. These are all, all the main questions. Um, that I wanted to cover. Kind of want to like, I really wanted to talk Uber and operations and everything like that. I don't want to take up too much of your time.

So, well, this is fun. I think congrats for— sounds like you're getting married soon and congrats on really getting out there and making a push on your newsletter and getting in the brains of founders and being curious.

Yeah.

And I think that's a, that's a good posture to be in a very opinionated world. Yeah, so, uh, good luck with that, and I'm psyched for you.

All right, thank you so much.

All right, take care.