I got close to this reporter and met up with her in my office. One day she was running like 20 minutes late, but I wanted to be there at the door when she got there. I looked at my system she's like I'm taking an Uber. I'm really trying to sleep, but I'm in an Uber. I'll be there soon. Okay, I can see where Ubers that are coming to where I am are going to be there and she's in one. When she got there I was like, "Great. It's okay that you were late. I waited upstairs until you got here and I tracked you on the system, came downstairs and met you." That was the comment I made. A couple months later it's like New York general manager stalking a journalist. Now that's some bad faith. And Ben Smith at BuzzFeed is a piece of and he's still a piece of Welcome to the early podcast where we interview the best and the brightest who've built the world's most innovative companies. Hosted by me, Max Crowley. Tune in weekly for new episodes and please, please, please like, subscribe, and share. And now for today's episode, let's go. Well, welcome to the podcast. Hello, Josh. Thanks for joining us. Hello, Max. It's a pleasure to be here. Josh, where did you grow up? Forest Hills, Queens, New York City. Born and raised. And actually I have spent the majority of my life here with it with only a couple of exceptions like summer camp. That's it. Every other time I've been in New York. How did your family end up living in Queens? My mom grew up in New Jersey, my dad in Connecticut and New York was the average. But Forest Hills, Queens was a great place to grow up. It's like a nice mix. It's in the city proper, but it has some suburban attributes. I had a subway stop. But also some people had backyards and it was close enough to Manhattan to really be able to go there a lot, spend a lot of time there. It was great. I really liked it. How'd they end up there? I think they had friends who lived there. I mean, how does anyone end up anywhere? I don't know. I The New York thing's super interesting to me of just the people that live that grow up in such close proximity to Manhattan. I mean, that's got to in a good way got to sort of harden you a bit and Yeah, I mean I went to high school in Manhattan. I've been around New York. I mean I just have a probably speed about me that's kind of New Yorkie. I walk fast. I'm impatient. There's certainly a vibe you get here. I think it's there's a similar thing if you're from LA or you spend a lot of time out there, there's a different way about you. Cuz you went to Stuyvesant, right? I did. And that's like a great school. It was I had some friends who went there. You took a test to get in. It's a SAT style test you take in seventh grade and if you're good enough at math and English and taking that test then you get in and I did go there. I'm actually wearing the sweatshirt from there which is unusual. I kind of am in still in my roll out of bed outfit. I don't take the kids to school outfit where all the other dads are just for work and I guess I am too, but it's more sweatshirt than button-down shirt. And so yeah, I did. I went there. It's a math and science focused high school. There's a few like that here. Bronx Science for context. So will your kids go there? No, my kids are in a school now that goes through high school. I mean I would like them to, but I'm not I'm not really in charge. Yeah, I maybe. I don't know. I have a 10-year-old and a 7-year-old so we're not we're not quite there, but I think it would be unusual for them to leave their school that they're in now which goes into senior year of high school. So probably not. I mean math and science even, you know, 25 years ago or whenever you were in high school, you know, uh that sounds like I'm sorry. I sorry that I came off totally that Yeah, it's true, but that's that's that's pretty crazy. Yeah, I mean I know I went to high school 30 years ago. I started high school I'm trying to be nice. 1996. Uh yeah, I'm old. But but math and science, I mean it's even more clear, I guess, to me how the importance of math and science Like how do you feel about that in retrospect? Um yeah, I mean I've I've certainly always been a math guy. The English side, I guess, I was good enough or I'm good enough at the math side to leverage Shout some of my deficiencies on the English side, but math has always been a good one for me since I was very little. It's sort of a link to my more analytical side, why I'm into computers, and why engineering has come kind of naturally to me, why I probably did well at Uber. I like math. It's probably just some innate feature of me, so I leaned into it. You end up at Columbia, so you continue the New York New York. You're just like not going to leave the island. That's it, forever. Not going to leave. I will go to any college that will accept me that is in this 10-square-mile block. It's a little bigger than that, actually. But, yep. Stayed here. So, I'm in high school in the '90s. Uh I'm in a computer science seminar where I get a desktop of my own in that classroom, and it has high-speed internet, which at that time I didn't have in my in my home. Most people didn't. And so, I got into uh this new website called eBay. I started selling stuff on eBay at like 16 or 17. And I did sort of a form of that through college, started a website, was selling on eBay and on the web. Really selling anything I can get my hands on. Off-season apparel ended up being kind of a thing that I focused on. Old designer jeans, things like this. Worked with another guy, did that through college for a bit. And then, after school, kind of continued on that path, sort of transitioned a bit into helping companies sell online. So, now it's like '04, '05, '06. Businesses that are in the real world that also want to try out this internet thing. And I was always the kid who would help with setting up your computer or your you know, I just kind of had like an intuition about it, I guess. And that led me to IAC, where I started helping them sell funny shirts on their web on one of their websites that they had bought. But, uh uh you know, after IAC bought uh CollegeHumor, they hired some people to help run that. And so, I did the retail side of that for a a years. And then, had another kind of few random startup jobs, typically in marketing and operations, and eventually found my way to Uber. It looked when I joined, I think you're already there, but I was probably employee in the 30s or 40s, and when I got there, it had this a sensibility and it kind of looked like the companies I'd worked for up until then. This is in series A, series B, still getting still getting things going, still at the point where everyone is contributing individually. There are managers, but you need to get your hands dirty. This is still startup mode. I was hired to run New York at a time there's a couple other guys already in the mix. Each city had three guys doing stuff in those first few cities, and so it was really an all hands on deck kind of thing. When I joined Uber New York, we probably had 50 cars on the road doing a few dozen rides a day. It certainly wasn't zero when I got there, but it was pretty close to it relative to where it would end up going. That was kind of my my sweet spot. Not there from zero to one, but as soon as something got going, that's where I would get in the mix. You inherited It wasn't a total disaster, but it wasn't necessarily working, if I remember correctly, because the regulatory scheme in New York is more complicated. The strategies of other cities didn't resonate as easily in New York. So, yes, you inherited something, but it may not have even been the right thing. I mean, you really had to build it from the ground up, from what I remember. a bunch of myth around this, and I don't even necessarily know what really happened, but there was some So, when they were going to launch a city, they'd throw launchers in the mix who would turn up in the city with like machetes through the jungle, you know, how like Trout used to say, and just kind of forge a path that way, and then they would hire a team, and that team would take it from there. And it seemed like New York was the first city outside of San Francisco to get that treatment. So, they'd say, "Okay, we're going to go do that there in this new place." At the same time as a bunch of other cities. I've always explained it as it was like the the first one out and maybe they didn't quite have the rhythm down yet. And if you didn't believe if you didn't look at it and say I see a path clearly from where I'm sitting to this being ubiquitous household name. If you didn't believe then working for Travis probably wouldn't feel like a great thing like wouldn't have been a very good experience. And so what I sort of understood is the the folks who were involved there at the middle to end of 2011 uh were not fully on board. Many of them went on to do awesome other things like it you know probably wasn't them. They just were not quite feeling it. They didn't have that rhythm yet. Many years later in an exit interview or towards the end of my time or maybe the employee I'm thinking of was moving to San Francisco to take a a role there. She said to me when I interviewed with you pretty early on you drew me a picture verbally of a world covered in Ubers not in kind of like a creepy bed way but town cars or oh yeah to carry things as ubiquitous in New York City as the yellow cab. And when he said that I didn't really believe it but now it's true. And you saw that. It certainly seems obvious in retrospect but I just saw when I got there it was happening. There was clearly only a problem on one side of the business which is on the supply side. The demand every day at 4:00 p.m. 5:00 p.m. the service would become unusable because everyone would request. They would all want their ride. There were people who wanted widgets and we couldn't create enough widgets where a widget is a trip somewhere. That's a really good problem to have. You know what I mean? You're selling something and you can't keep up with demand. If you're running a double-sided thing and one side has a ton of volume and the other doesn't. If the side that doesn't have the volume is the supply side that's a very good situation to be in. I just saw that okay. We just need to hire infinity drivers. Just get as many drivers in the mix as we can and this will work out. You mentioned regulatory stuff in New York. I know that myth is a nowhere is the taxi cartel stronger than in New York and the taxi limousine commissioner so bad and De Blasio and the De Blasio piece is true, but in reality actually New York's regulatory situation made it much easier for Uber to scale. I'll explain why. So, is it cool to get into this right now? Like I'm about to go full full kind of Uber school mode. All right, hold on. How did you actually get the job? How did you even get in the mix? I was at a wine direct-to-consumer startup for about a year in 2011. Just the next one of the ones I would do. E-commerce. I was employee seven. There is like $50 million from Excel or some And it was we're going to redo wine. I'm not really a wine guy, but I became one for a year. By the end of that year I knew wasn't meant to be. So, on December 26th, I was in the office. The office was empty. I mean, I'm Jewish, so there was, you know, I don't have any like attachments. It's such a nice I love Christmas so much because everyone else is celebrating with their families and I don't have to. It's like the nicest day of the year for me. I went into the office the next day. I was just looking for new jobs. I was sitting over there. And on Crunchbase, there was a job for New York head of Uber. And I had used it a couple of times. So, this is December. When it came into New York in April of that previous year of the year we're at the end of, I tried it. It was really expensive. I was like, this is cool. It's too expensive. I'm never going to use it. Then I was going to an airport once at like 5:00 in the morning. I was like, well, this would be a good use for it because I'm in Manhattan, but like going to the Avenue block and waiting for a yellow cab to show up. By the hours, I tried Uber and it didn't work. There were no vehicles on the road when I did it, but I got an email later in the day from the community guy at the time saying, "Hey, we saw you tried using Uber. It didn't work. We're really sorry about this. This is what we would later call a zero when you open the app and there are zero cars available. I got a zero and they had a thing where they would email you, "Sorry, you know, there were no vehicles. Here's five bucks off your next ride." That kind of pattern, that interaction is super common now in e-commerce and and in everything. At the time in 2011, and for whatever reason, it struck me as a really good interaction. I was like, "That's interesting." I opened the app, took no action. I just opened the app. Couldn't do the thing I wanted, closed the app. You knew and you reached out and you made this interaction with me. That's really smart. I just remembered that. Then when I saw that ad for the head of New York, the job ad was really funny. It was like, "Get unlimited SUV rides, travel around like a European diplomat." I love that. I thought that was so funny. So, I wrote a cover letter and sent my resume. I've heard that when you put a job up a board, you get a thousand things and they're all and now they're written by AI and they make no sense. But I do the exact opposite. I applied for like one job in a month and I'm like, "I'm just going to nail this thing." And so, and just hoping cover letter. I did the cover letter, I did the resume, sent it to Ryan I like triangulated a bit. I was like, "Who do I want to send this to?" And they're like, "graves.ryan@gmail.com." That is his email address. I hope you publish the famous the famous tweet the famous It was like, "Yeah, it was like, here's a tip, call me." It was I didn't know about that story. I don't know anything. I don't know about Travis. I don't know anything. I was like, "This is cool." That's kind of my thing. Is the product cool? Will I be like, "This is interesting?" And even wine, though not a wine guy, I just thought thought it was interesting. I thought it was interesting. I wanted to do it. So, I send that email and I got a call back within the hour from Ryan Graves. He's like, "You're the Busted Tees guy. You do funny shirts for CollegeHumor." Oh. I love I It's like, "I love Busted, man." And I was like, "That's so funny." And now that was like notable Ryan Graves. It's all right, Graves. But it's funny just to fast forward. We I had an arch rival, Nerdy Shirts, that was right out of LA. And the head of that was William Barnes. And they hired William Barnes to run LA. So, Graves I guess either accidentally or whatever found the two funny t-shirt operator guys. And put them in charge of the two co- largest cities. Yeah. And he's like become one of my best friends from Uber. I don't even think he started Nerdy Shirt. I think he like bought it and then ran it. Way more legit. I just got a job. But I did a good job there. And we grew that a lot. We were selling millions of dollars of these Nerdy Shirts. Very topical. Something would happen in the world and we would make a shirt about it. Did you know Did you know William at the time though? Like were you Nerdy Shirt. I hated them. They were They were the number two and they would do all sorts of nasty like SEO on us. And I was like I like hated them. As I hate any competitor. And then it ends when did you know when it ends and it's all good. But it was so fun when we discovered that it was so funny. But anyway, Ryan calls me. He's like, "Who's Bust-A-Tee's guy? I see their ads everywhere. Love it. Let's talk." I'm like, "Okay." And we shot the And then great. We have a thing. You'll do this analytics test. And then you'll come test us. Know me Travis. And that went down over the next two or three weeks. I was there mid-January. And I was there the week after for GM Summit. And when I was there in mid-January for my Newber thing for the like Uber University is what they would eventually call it. But Were you at my Newber camp? Like they were doing them only every few months. So maybe I know you started in like August or September. August of that year? Yeah. I was so pre pre-camps and all that. Yeah. So maybe Chapin was there with me. He was He started before me. But it was He was sort of zoned for that. For that. I I It might have been too cuz I started Yeah. And instead Yeah, maybe yeah. Those are the guys who were in New York when I got there. It was the three of us for a bit. So I got the job, you know, it felt slow motion cuz I was so excited about it. But it all went down pretty fast. And then they made the offer. Um I've always been a transportation guy in kind of the way I'm a map guy. I like maps. I love the subway. I have a very good subway knowledge better than probably most New Yorkers from spending a lot of time on it and being interested in it. So, it felt like a very, very good fit for me. Um it felt really good. And honestly, there for 5 and 1/2 years and for many, particularly the first three, I'd like wake up in the morning, I can't believe I have this job. This is This is great. This is so fun. I'm having a great time. Part of that's cuz we were doing really well, really from the beginning. It started doing well right away because we fixed the supply problem. That's sort of all it was. I mean, that's a bit of an understatement, but that was a big part of it. I certainly didn't have the understanding or wherewithal that you did at that time. I was just kind of like along for the ride and hey, I think this is awesome. Certainly in retrospect, the fact that there was almost unlimited demand and that you could capture the demand with more supply is just crazy, especially now working in other business or businesses or doing other things. You almost always have a product market fit {slash} demand problem. Uber never still, to this day, never has that problem. Yeah, I mean, I think there are moments in time where technological waves um can really get you there. And so, in Uber's case, it was a new computing thing, mobile device, the like mobile phone with internet everywhere and then the iPhone 3G with GPS everywhere. The original iPhone in '07 did not have any GPS. It had a cell tower like approximation, but you couldn't run it off that. The 3G one had GPS, and so that's 2008. So, really, Uber was invented the year that it became possible. Now we have these computers that know where they are. That's a huge tech shift. The idea for Uber is great, but it's a product a bit of of the moment. And there was a lot of companies who did it, and I think we won because we were the best at it. But that kind of idea like, oh, like transportation can be really quickly solved in a profound way because of these things. I think we're in a similar moment now with AI. When we talk in a bit about the thing that I do now, that's part of the success of that, just how what I just said was the part of the success of Uber. The right time, the right thing is invented, you can kind of ride that very, very legitimately. So, everyone getting an iPhone is the big thing and then making Uber is like the next dimension down, I think. And then having the App Store and a few other pieces of that that just didn't, you know, end up being Totally. Right, App Store wasn't a thing right away, so you needed that, too. That must have been like '09 or something. All right, so then going back to like the first 12 months of Uber, let's say, to wild time, maybe you can get into the sort of regulatory scheme there and the different things that you guys had to do. And then, you know, just what was the best decision you made during that time and what was something you would have done differently? At this point in Uber for my first year, year and a half, Uber was explicitly Uber Black, what it's called right now, us partnering with licensed operators in each city. Every major city has a concept of renting a limousine or a black car for the executive-level guy who's being picked up at the law firm or she's getting picked up at the bank, fancy transportation. Those tend to be regulated at the at the state level or within a city. We would partner with those people who already had an analog version of that business with a dial-a-car. You would call someone, they would send that car, the car was nice, it opened the door, the guy's in a suit. That whole construct kind of existed. We layered onto that in the early years. When we exhausted those systems and the demand exceeded what we could do with those systems and Lyft came in and Sidecar were like, "Forget those systems, anyone can do it." And they did that and cities were all The way Uber does it, which is totally legal and within the system. That's bad, but Sidecar and Lyft, like, that's good. Way to go. confused regulators and thought, "That's okay, we'll just do it that way, too." And we did it and did it much bigger and better. That That moment that I just described didn't ever come in New York City. So, in New York, for a couple of reasons, we never really exhausted that original style of Uber. The regulators there, unlike those in other cities, never did and never will come around to, "Yeah, anyone could just drive the car." That's never going to happen in New York. Part of that is just because the system is so vast. There was already just tens of thousands of vehicles were in that system already, and we've expanded it a lot, but sort of within the confines of the laws that were written in the 1980s. Because of that, because we sort of stuck with the traditional style, we never run background checks on drivers because they do that with their city, because they're already professional drivers sort of operating in the government-defined system that New York City has. Because of that, the profile of the driver is very different than in rideshare cities. It is in essence a full-time job. It is not something you can viably do for 10 hours a week. It is not a gig. It has to be a profession because there are structural things in New York like drivers owning their own insurance, congestion laws, and things like this that it it only is sensible to do it as your full-time occupation. So, it's just a very different pitch. That in some ways makes it harder, and in some ways makes it easier. I found net-net admitted a little bit easier, because once you got the driver, because the commitment is so large, we were sort of eating all that up front. Once I find that guy who's willing to really go all in and do this, then he's going to be with you for a few years, versus a guy who's just like, "I have a car. I want to try this. You paid to acquire me. I do the background check. I go out for 1 week. It's not for me. I give up." In some ways, that version is like fairer and and and better, and we would like to have that in New York, or we would have liked to have that in New York. But, with the reg- you get the regulatory regime you get, not always the one you want. And Uber New York does it the way that I just said, and in some ways it's a little bit easier to scale that way. What's the best decision you made in the first 18 months? We did a very large driver incentive for like new new drivers got $1,000 cash. We could do that because of the dynamic I just outlined. Like once we get a driver, their you know, so-called lifetime value could be measured in the thousands or tens of thousands. The $1,000 fee was pretty good and it got people's attention. It also got me into rooms where all drivers that were working in like bases, there are 60 drivers that form a franchise and they operate out of a building somewhere and they and they have an operator and the operator takes the phone calls and dispatches. We can convert that whole system over to Uber. There were so many fundamental ways that we were better like tolls. Tolls were a huge pain for drivers at the time because they would take their fancy rider home to Connecticut over a bridge, easy pass the bridge, then have to write up a separate receipt for the toll. We're like, "Geo fence. When you drive through, it will automatically add it." And drivers were so skeptical that that would work. That's not I so how are you even It's magic. Yeah, there's a lot of things where I was showing magic to people that never seen it before. So, going deep in the community, the $1,000 referral bonus was a good one. Letting my guys on the Uber team kind of run their own thing. I was pretty hands-off. I managed the way I like to be managed, I guess. So, I mean hopefully they felt like they had ownership over what they were doing. Um, you know, all all good stuff. Um, the next question is more interesting. You know, um, there's nothing like reading an article in the news about a thing you know super well because you learn that there's a pretty wide delta a lot of times between the way something is written about in the press and the reality. Most things you read about and you don't know about them, so you take, you know, like, "Okay, that I guess that's right." It was pretty amazing reading the way Uber was covered in the press, particularly locally, versus the realities that I knew. This is a little more than the first year. This is probably for me year year three when we were getting big enough to hate. I was there for 5 and 1/2 years. Act one, first couple years is like oh my god, these Uber guys are geniuses. They are just they're so smart. Their neon tank tops and their ice cream trucks and all that stuff. They are so clever. Uh fighting in a battle. Yeah, these guys are amazing. That was act one. And then in my like 2 and 1/2 years in, mid 2014, I you just sort of felt it begin to change a bit. We did some rate cuts, piss off some drivers, piss off some government, you know, start to be hated. And then so act two is like these guys are the worst ever, right? And so neither of those things are true. We were neither the best ever nor the worst ever. There in some ways we were the best and maybe even some ways we were the worst. But it was just so crazy. And so I'd read articles in like BuzzFeed that this New York driver makes $1.27 per hour. And it's on their website, on their homepage, on Twitter, people talking about it. The thing is everyone's pay is individual to them. Everyone Everyone Every Uber driver is is a snowflake. That's a joke, but doing a truly random thing. They are driving around, getting jobs, getting a percentage of that fee each time, having a certain amount of downtime. I mean, there's truly randomness. So you could have a thousand drivers on the road. Each driver is going to have a truly random experience. That randomness is going to impact how much they make. If you quantify that per hour, do you is that per hour from when the moment they left their home until the moment they get home? Is it while they're on duty with the app? Is it while there's a someone in their car? There's a lot of ways to cut that. So since it's random, surely there is a driver who goes out and he sits in his car. For whatever reason, he gets no jobs and his hourly rate is quite bad. And then there's the other guy who on the other end of the thing who is so good at Uber and knows exactly where to be. He works exactly the right hours and he makes a lot of money. Then there's everyone in the middle, but that's a true distribution, right? Um it's there's a lot of randomness there. You might not like it and you might think it's not fair, but it's fundamentally how taxis work also. In a situation where a person is sort of on their own, they get the equipment, they go, they make money as they work. There's variables in there that impact how much they make. And I really had a hard time since I've been saying driver hiring was the biggest part of the whole thing. Having big articles in the media that sort of socialize this idea that Uber pays, you know, slave wages. That Uber is just a Uber is just a hollow app. You know, the drivers are working for peanuts, for $1.47 an hour. Now, I'm not saying drivers are are getting rich, nor am I saying it's the job I want my kids to have. It is a job that my father had briefly, but it is what it is. We offered a version of it that was better than the existing version. If you were driving a taxi, driving for Uber was better in a lot of ways. If you were driving for a for-hire franchise thing that gets radio dispatch outside of a building in Queens, this was better than that. And I would I was comfortable with that. And so it was very hard to read things in the news that sort of implied otherwise with very selective drivers on Uber make a dollar 47 an hour. It's like, well, perhaps that one did one time, but it's certainly not regular. Would Would we be onboarding hundreds of new drivers a week who come in through the main channel of referrals from other drivers? Would that be happening? The proof is in the pudding a little bit. Can't you see that? You come to meet me and the driver support center is filled to the brim of people who want to get in on this. Can't you kind of see that maybe you don't have that right? I just was not very successful with those arguments. So, Travis was like, "Why are people Why is the media in your city writing this horse that you and I know is not true? Get in their face." And that was a mistake. And so, I very much He let me What I loved about Travis What I love about Travis is he was always comfortable with me being me. And everyone being themselves. I mean, be yourself was one of our values. It was mocked, but I think it was it was real. And I I did appreciate that he I felt like I could be the unedited version of myself with him, and that he enjoyed those instincts and made me feel good about them. For that And that's why I That's why I was there for as as long as I was. I've never been able to survive another place for more than a year or two because it just People just certain people just drive me crazy, and he was just like, "You be you, and it's fine." And he's like, "Hey, you're going to let a reporter like that basically spread like libel, you know, like slander us, say we pay people a dollar 47 an hour? Like, we shouldn't let that stand." I'm like, "You You're goddamn right we shouldn't." That's some intense stuff. I mean, it's our This is In that moment, our life's work. We're working very hard. We are giving legitimate opportunities to people. There are people for whom it doesn't work out, but the but the vast majority, particularly in New York, was that it was working out. There were things about the driver relationship that I would do differently if I could do it again. I think rate cuts at times were highly justified, and at other times were not. I think we did them in both situations in New York. I think the the last one we did in the 2016-17 range was probably a price cut that shouldn't have happened. We might have gone too deep. And that's evidenced by the fact that they charge more now. Uh but, the system gets more efficient, and yield per hour, how much a driver can do per hour, goes up over time as Uber grows generally. More drivers on the road, more riders increases the liquidity of the system. It brings wait times down. It keeps drivers busier. It's this beautiful thing that happens. But, that's like a hard thing to explain to a reporter who like majored in English. There was a couple of dominoes that fell that I was sort of near and it blew up in my face a little bit in 2014 when I was really trying to engage with a reporter who I feel wrote things like drivers make a dollar 50 an hour in bad faith. I wanted to prove to her that she had it wrong. I got close to this reporter and met up with her in my office. One day she was running like 20 minutes late, but I wanted to be there at the door when she got there. So, I looked at my She's like, "I'm taking an Uber. I'm really trying to sleep, but I'm in an Uber. I'll be there soon." Okay. I can see where Ubers that are coming to where I am are going to be there and she's in one. When she got there, I was like, "Great. It's okay that you were late. I waited upstairs until you got here and I tracked you on the system, came downstairs and met you." That was a comment I made. A couple months later, it's like New York general manager stalking a journalist. Now, that's some bad faith And Ben Smith at BuzzFeed is a piece of and he still is a piece of And I told him that on Twitter the other like a month ago. I was like, "You're a piece of shit." Like that's bad faith. And then he tricked a meal into saying he knew it was off the record and he took sort of like a bad a joke in bad faith. A lot of bad faith reporting. And I'm not here to defend anyone, even really me, but I just told you a story about that he was tracking me thing and it was like I was in You were coming to meet me. I told you it was not nefarious. She got a ton of attention and got a job at the LA Times and all this stuff and it's like Okay, that's fine. But, it really Oh, it kind of up my my life for a bit. I mean, when I went later, I was part of a VC fund that raised 60 million bucks and I'm diligence for that. What was this thing with you tracking journalist? Am I talking about this 10 years later? Like that's unbelievable. Um I mean, dude, it and it resonates. I mean, I had that uh New Yorker article. I don't know if you How many of you remember that? I never went on those trips. I was like, nothing good will come of these trips. Not going to Austin, and not going to anywhere or Vegas, you know, I mean, I did go to some of them. But, what happened? You You were just a little casual. You're casual. Cash and cocky. Casual and cocky. I just But, like, look, I mean, it everything resonates, as you said, because it was we believed so much in what we were doing. I mean, to have that belief in what you're doing every day is so great. And then it ended up being a you know, a short time. It We didn't stop believing what we were doing. It's just the world celebrated it for a bit, and then the world wanted it to to kill us for a bit about it. And so, it was this wild dichotomy where you still believe so much in what you're doing. Um and I look, I just got sucked up in a moment, and I got taken advantage of by some people. Like, look, I I I bear the responsibility of that, and I'm in some ways glad it happened cuz I learned a lot. But, it is wild how you're never as good as you are when you're on top, and you're never as bad as you are when you're when you're on the bottom. Yeah. Yeah, 100%. I think people don't realize the thing grew really fast. In a normal situation, when you have enough success to be written about in a New Yorker article, there's other infrastructure in place to make sure you don't do what you did. You know what I mean? But, like, things happened fast, and it's like, we'll hire a comms person or two, and that'll be fine. You can't be everywhere. We're highly distributed. Highly suc- you know, the distribution angle, like, we're in all these different cities, each sort of operating in some some ways independently. And it's a it is what it is. It's a problem. happens. Yeah. But, I like, we were like, grown-up business size, but still startup mentality. That was the problem. So, kind of maybe your defining moment, if I'm correct or not, is de Blasio, the regulatory sort of scheme there that pops up and tries to fix supply and really mess with the core of how we did business and you ran an unbelievable campaign to really push that back. I mean, what what are you most proud of from from that campaign looking back on it? Anyone who's listening and not familiar with it, you know, the there was definitely a vibe among the country that Uber goes into their into their city and they break all the rules and then they get the rules changed and then they live happily ever after. This was mid-that strategy. If you look back now to 10 years ago or even more like 12 years ago, 13 years ago when they changed the first laws in Colorado, I think. There is a degree to which that's true. We invented a new kind of transportation or lifted or side car did or whatever and we made it popular. The culture became comfortable with getting into a car with another human without them having a taxi license which ultimately is kind of a meaningless thing. As long as the person is a fundamentally safe in whatever agreeable way, it's fine. You get where you're going. We really changed changed the country in that way. That was not a thing, now that is a thing. It's not still not a thing in New York, but the vibe at the time was these guys, Silicon Valley bros come in and do this thing. What must have been frustrating for the New York industry taxi and limo is that that wasn't what was happening in New York. In New York, a bunch of guys came in and also girls of course. My team was basically always half and half just by accident and played by the rules here and just crushed everybody. Like just totally destroyed everybody. Just by you know, people always say like the worst of all must have been that taxi and limousine commission, right? The truth is they were all actually very fair to us. They were true believer regulators appointed by Bloomberg, not as partisan, didn't probably didn't always like us personally, but they knew that we actually just filled out paperwork better than anyone else. We wrote some software to fill out paperwork. We always had our paperwork in order. We submitted records better than anyone else. We replied to any any requests better than anyone else. We were a little bad kid who was trying to be good and was super good and just and and that resonated with them. And when I think back at the time, the commission was never a problem. Ever. It was City Hall. So, Bill de Blasio in 2015, you know, this is probably like July. There were some there were some footprints up until this in like May or April. There is a US There is an article in some paper where taxi commissions had gotten a whiff of this like, you know, the way to get Uber is talk about traffic and congestion. They're making too much traffic. It's bad for the environment. You can't get around. The speed of the city from 2008 till present has slowed down 2 mph. It's like, well, you started measuring during a recession. And that could be like, traffic is bad, but it's also an indicator of economic activity and growth. And it's a long story, but basically they lined up a whole set of rules and announced them with the the intention of just jamming us. You know, they announced them like June 27th or something. We were fighting some other issue in Long Island and there had been an issue earlier in the year with the administration in New York wanting to approve app updates. Every time you update your app, they had to approve like UI changes. Just gnarly you do not want. We just come off that. A lobbyist called me or someone I was sitting with and was like, "Hey, this new thing has just rolled out. They did a presser on it. Like, it's baked. This is happening." And what it was was a one-year moratorium, like a break for one year, on Uber's ability or anyone's ability to add new driver registrants. New vehicles will not be welcomed onto the system for a year while we, you know, figure out what's up do a study. We just do an environmental impact study on what's happening here with all these new cars coming on the road. What people didn't get is so you're already so big, you'll pause for a year, it'll be fine. It's like the other thing with rates and and how much people earn. It's like it's not that simple. The reality is that if if we don't keep adding drivers, the system will become unusable because the riders are coming in 25,000 new riders a week or try Uber in New York for like a year. Like it just went on and on and on and on and on. No end in sight. It's more and more and more and more. And that is not going to work. We really went turns it up to 11, met with every newspaper. I was on CNBC like every day on other news stations. We had a rally at City Hall. We went in there with City Council. Just really, you know, the sort of the opposite of like if you can make it here, you can make it anywhere. It's like if you get by the regulators here, you're going to get everywhere. And so we somehow beat it back. They'd come back 3 years later and do it after my time in 2018, but in 2015 we got it So it was like a 3-week marathon fight and we got Eric Adams, then borough president of Brooklyn, now the mayor, we got him to stand with us. He was a big chip to fall. The governor got a question in an interview. He's like, I think that's crazy. I think Uber's great. That was very helpful. He really hates de Blasio. And then we got a couple other people. We got editorial board of New York Times, Daily News, New York Post, all three to weigh in and all say like this is some Just like you never get that. Like you just never get a city all three of the especially the post agreeing with the other two. Like it's just very unusual. And we went we went spoke to all of them and we did some we spent like 5 million in TV ads. Just like political air campaign hammered political and it was other I was like the principal but there was like alone it would have been a total loss. He was like Brad Tusk, Matt Wing, Alex Anthany, Rachel Holt, Justin Kidd, David Plouffe, like all these people really did. And there are other people that I didn't even say. Someone on the team uh none of the people I just said thought of this idea of the like De Blasio view where you would scroll to the option of De Blasio and it would say like 25 minute ETA. Like that cut through. It's so hard to cut through the sort of mathematical scientific bit. How do you cut through to lay people? Like that's the art and what she was able and what that feature did, you know. Genius. Yeah, pretty good. The De Blasio car type cuz you you would click on it and it would say De Blasio and it's like no cars available or 25 minute ETA or whatever. Genius. Yeah, really really good. All right, so looking back what are a couple of the best learnings from being early at Uber working with Travis? But what what stands out the most? Um well, I think an appreciation for this always sounds stupid but this is what I always answer when I get asked this. Like an an appreciation for the scale of the world. So, something that really at first I had a hard time understanding was how are 25,000 people taking their first Uber ride each week in New York City where we've been live for years. What were those people doing? Now they want to Uber like 4 years in and there's 25,000 of them every single week? And that certain things happen with it's hard for the human mind to to fathom 8 million people in a city. That's just not a natural idea. Of course, you know the number, you know what 8 million is. It fills giant stadium 100 times, whatever. You can like say it and you could sort of visualize it. But to experience it and again, I know this sounds so dumb, but there is something there that's not obvious. Like the world is really, really, really big. And since I only have about 10 minutes left, I will use that segue to talk about what I'm doing now. If that's okay. Do it. Hit me. Uh so, I a few years ago decided I really didn't like the business side anymore. I wanted to become an engineer and built an app called Wave. And Wave is an AI note-taking app. Cuz there's an expression, we need one more note-taking app. And so, actually often it's it's the opposite. That was the joke there. People think that they don't need it. But it was really just a learn-to-code exercise for me. Both using AI to help me make it and AI being what the app does. And basically, it's an audio recorder that summarizes what it hears. So, you go to a doctor's visit or a meeting that's in person, like not on a Zoom, brain dump, church service, whatever. You record it, you get a summary of it. And very simple, it's a utility app. About 20,000 paid subscribers now who record about 5,000 hours a day of audio. And that is always very surprising to me because I truly don't know what I'm doing. And it surprised me that someone would want to use that app. But you have to remember the world is really, really big. And I think there's when you spend too much time in circles like this, you start to think that the only way to do something is like have an idea, do a pitch deck, raise a seed, go do it, hire 10 people, try to make a billion dollars. And that's legitimate and it's great if you can pull it off. But the world is actually so big that you only have to find something you can you can build something that 20,000 people think is interesting, which is really a drop in the bucket of the, you know, United States. It doesn't have to be for everybody. It could be for a tiny percentage of people who are like work in a place where they're not on Zooms all day, which is most people, I think. And they want to and they use iOS and they want to like get in on that AI thing, but they don't know it and they're not on Twitter all day reading about the newest models. They're just like normal people. Understanding that the world is really big from the first thing can make it a little easier to understand that you don't have to make like a business that can be like exceed your wildest expectations can be very small. Uh just cuz the world is so big. Just just find those thousand fans, as they say, like who like the thing that you're doing and that can be enough. That's why the internet is so great. So, the rubric here is like must be gigantic or not useful, but the truth is what it taught me is that actually it's in some ways the opposite. It's like the world is so big that you can just appeal to a very very tiny sliver of it from the back office of your apartment and like do super well. Um and you've done this all yourself. I mean, like with limited assistance. I mean, you you are really a one-man band. Yeah, so 2 days ago the first version of the app released that had someone else's code in it. So, the first 16 months or so was just me. I am starting to expand. You know, there are some there were some issues with the app for a percentage of users that I just couldn't really fix on my own and wanted sort of a gut renovation of the house that the app sits in, I guess would be a way to think about it. So, I am starting to get some help. I have always had some help on the design like look and feel stuff. But the the app itself, certainly the version that people bought in the beginning and really the version until like last week, was all me. Um a lot of AI aid there um because you can really now learn anything with AI. Like that actually is the killer feature. That's like, I want to learn about birds, you know, or making apps or whatever. ChatGPT like it is not a joke, can really teach you anything and it's amazing. Anyone who's willing to put in the time and effort. And so like AI wrote the app, so to say, but I learned an an insane amount along the way. Such that I'll probably doing something like this forever. Um but I am now in a certain mode with Wave that I am starting to try to make it work without me um because it's started to kill me a little bit. To the point where I'm like still in the sweatshirt I put on when I rolled out of bed at noon. So it's it's it's like demanding at this point. Yeah, I mean I do all this I do all the um customer service sort of like Uber style. That for many people would be the first thing that they they outsource. It'll probably be the last thing that I outsource cuz it's such a valuable channel. I mean if like when it's not too crazy, it's direct connection. Yeah, like this weird thing happened in the app. Are you aware of it? Like no, I wasn't, but I can replicate it, so thank you. You know, um and so yeah, I mean I would really like to uh be able to be not involved for a week and not have it break. We're almost there. Only a couple minutes left. So so maybe two meaty questions or ish, but I want to hit both of them. On the AI front, Yeah. what's the next 5 years look like or what's your piece of advice or like, you know, do is how real is this? I mean I'm certainly in ChatGPT every day. What's what does this look like from your perspective over the next 5 years? Yeah, I think it gets it gets better and better, but it will never be as dramatic as like ChatGPT didn't exist to it did exist. Everyone who had that first experience, that's up there with tap a button and a vehicle shows up to drive you somewhere. These sort of very memorable aha moments. There'll be more it'll keep getting better and better, but I think it's primary function is as a human aid. Not different than a word processor, a web browser, a computer in general. It's going to just make life easier. I don't always agree with the kind of way that, you know, sci-fi side kind of does like AI will do all the work for you and you will just draw pictures. I don't know about that. We'll see. I think it's more like it's just sort of going to be in everything. Like I don't know how AI will help you edit this podcast or write the summary or do the show notes. They're just all these little moments in your day-to-day work that I think AI will start to infuse. Um I want to go on vacation. I asked ChatGPT about like you know, I have two kids. One of them is celiac, doesn't eat bread. Like I need to go to a place that will be like flexible with eating and it's like it's got answers. So there's all some of these knowledge positions where the knowledge can be kind of infused in a model. I think they're maybe at risk, but like really they should just use those tools to do their job better and differently, I guess if that makes sense. Yeah. Like if you're like a radiologist, I don't think you're I don't think you're replaced by the model that can read the images, but hopefully you become an operator of one. And you're a lot better at your job. Totally. All right. And then last one, a fun one. What is an interesting piece of content that you've consumed? Article, podcast, you You even You even told me about this before and I was like, oh I got to think of something and not come out and be like, "Duh, I don't know." There's a new All In podcast competitor called This Won't Last. And it's for analogue types, VC operators that are not the besties. I love All-In. I listen every week. Uh and this reminds me of that. It's called This Won't Last. Uh you can Google There've been a couple of episodes of it. So like I got it. It's Zach Weinberg, Roboeis or Roboy, however you say it. Roboy, yeah. Uh a couple other dudes and it's uh the tick Kevin Ryan, yeah. He's the like Kevin Ryan, yeah. godfather of like New York startup web 1.0 like Yeah, incubator. Yeah, everything. Awesome. Josh, you're the best. Thank you so much for doing that. I really appreciate it. You have a good podcast like I like the background. It's good. Good.