They got together and they said, "Look, we're all going to pony up $1,000." There were 1,800 taxis, 1,800 medallions, and they said, "Let's offer Eric $1.8 million to sabotage it, to just basically turn Uber off in Philadelphia." The funniest part about this thing is that mere thought that I had the ability to completely sabotage Uber in Philadelphia. Could I have screwed things up for a couple days? 100%. Could I have sent some really messed up text messages out on the driver line? Definitely. But was I going to be able to shut the entire thing down or a company that had tens of millions of dollars in the bank at the time? There's no chance. 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. Eric Wymer, thanks for joining the podcast. You're welcome. Thanks for having me. Good to see you, dude. Yeah, you too. What's uh what's the origin story for you? Been a bit of an evolution, I'd say. The hair was a lot shorter. There was a lot more Ralph Lauren closet than there is now. The the jeans were tighter, too. The jeans were a lot tighter. I've gone tighter jeans. There's this dichotomy, East Coast and West Coast. The West Coast tends to have a lot baggier jeans. All right. So, where are you from? Originally from Reading, Pennsylvania. It's about an hour and a half west of Philadelphia. I grew up there. Spent most of my life in Pennsylvania in the early days. Went to college at Penn State and then after college ended up moving to New York. So, that was first time of feranging outside of Pennsylvania. What do you think was important about your childhood that starts to play into both your career and then you've jived with the California thing? I see it in you. What do you think stands out from your childhood? Pennsylvania was an amazing place to grow up. Having a yard, being able to run around with your friends, coming home in the wee hours of the morning, but your parents knowing that you're safe. I think there were a couple things early on that started to form me into the person that I would be. One was just sports. Sports was a huge part of my life growing up. My entire family was into sports. I played football. I spent a lot of my time on football. back to football as the first startup because it was 14 16 hours a day that you were either thinking about it. It was a lot different though. There was the physical component at times in startups you feel it physically although a lot of it is the mental side but football for me flexed both of those muscles mental and physical. I found myself more addicted to that adrenaline rush through that experience. And then post school how did you end up in New York? So, I ended up getting a job at Goldman Sachs. First job out of school. Penn State was not a target school for Goldman Sachs. Very few Penn State people there, but was able to network my way in. Met a couple really good people in a middle office division there in the finance division and they came to campus. Was able to mix it up with them a bit. Went in for an interview. Ended up getting the role. I think this was in October of 2010. So, I graduated in 2011. I basically had a job the fall before I graduated. The rest of that year was like hands off. I did what I needed to do. I went to college, got a job at a reputable place, and super excited about that. But it's funny looking back given how short the tenure was there. Also, University of Iowa was not like Accentur's breeding ground. Very few other people got hired from there. But it's it's funny how you just end up working your way in and and that's all that matters. Hustle your way in. So you're working for Goldman. Great job. You're already exceeding expectations or whatever you want to call it. But then you're like, I'm doing a hard pivot. I want to do this Uber thing. You cold outreach to Ryan Graves on email. It's also funny how these origin stories have some similarities. It's wild. Also the misfit nature of kind of all of us that totally the land of misfit toys. We all came together. How did that start for you? How did you come across the Uber thing? What were you thinking about that time? Funny enough, a girl that I had a crush on in college knew about Uber. So, she was working at one of the big recruiting firms that would look for executives at tech startups. So, it was very connected in the VC scene. I didn't even know what a VC was at this point. I was working at Goldman. All of my work was going into this line item in a report at the end of the month. So it felt a little bit meaningless even though I know ultimately it wasn't and it was having an impact but the impact was very hard to see. So I ran into this girl in the city and described that I wasn't loving the position at Goldman. She said you should check out a few of these startups Uber, Pinterest, and Square. Looking back today, it's hilarious. All of those companies became unicorns. They obviously had really good information on the founders, on the investors that backed those companies, the traction, and I started digging. And as I was looking at those companies, Uber for me was just the obvious choice at the time, and I'm sure it was similar for the reasons that you joined, but it seemed like a really cool product. I tested it out in New York. I remember hitting a button and a town car showing up and just that initial reaction that you have. The original interaction with the product was something I think really special and that a lot of us related to and you've needed to be obsessed and excited about it in order to do what we ultimately all did there. I connected some dots. I saw that Ryan Graves was the head of operations and I was like he has a non-traditional background. Yes. Right. He wasn't the Ivy League person for me. you give me like a little bit and I'm going to run at it 100%. I remember sending him an email and I said, "Look, I work at Goldman Sachs. I hate my job." I said something, I think, about the Padres's cuz I knew he was a Padres's fan and I was a big Phillies fan at the time and he asked me if I could get on a call with him. I think he was in London at the time. So, I got up at 4:00 a.m. or something, New York time one morning. We had like a 20minute conversation. I think he checked the boxes. This guy works at Goldman Sachs. he sounds really excited about this product. Let's move him on to the next round. So that's how it kicked off, but it was very much a shot in the dark at the time that ended up working out. The same thing with me with Ryan Graves where you see his background and he was randomly doing Peopleoft implementations at GE, which I was doing at Accenture or something like that. It was like the same thing. Yeah. You're like, wait, if this guy can do it, well then I can. So where does it go from there? You do the interview process, analytics test, all that. when does Philadelphia come in the equation? Did you think about doing a New York job? How did that all work out? I think it's interesting. So, at the time, New York didn't have any openings. But I think what stood out to Graves in the email that I sent was I mentioned something about Philly. Just anything about Philly. Anything? Yeah. Looking back, well, maybe I shouldn't have said anything about Philly. No, I'm a big Knicks fan. Exactly. Just grab a sports team from any city you want to live in and that would have worked. I remember him mentioning something at the end of the call. He said, "What do you think about Philadelphia?" And I said, "I think it's a great city." I didn't really know what to say. I didn't understand where it was going in the conversation. And ultimately, they wanted to bring someone into Philadelphia to be the driver operations manager to launch the market. And so, they veered me down that path in the interview process. So did the analytics test and then spoke to Austin. Had that conversation. I think I was at my parents house in Pennsylvania at the time. I'm almost certain they called me back the same day and then just offered me the job. That was kind of the start of it. Were you nervous about the Philadelphia piece or you were like whatever, I'm going to move. No, I definitely did not want to leave New York. And then it was funny because I think a month or weeks later I see that people are being hired for the New York market. I was gonna say because we're always hiring. Totally. Jeremy got hired a month later. Some of our closest friends. It It's just funny looking back. But very grateful for that path because I think being in that market on a smaller team allowed me to really develop in a way that I may not have if I was on a bigger team and maybe got lost in the shuffle. Being the number two, the number three. Yeah. Versus being at the wheel is is a different scenario. So, what are the early days of of the Philadelphia market like? I mean, you're box of iPhones, start calling drivers, start onboarding. What was all that like? There were a lot of iPhone boxes and not enough cars to put them in in the early days. The early days, we were in a 100 square foot room when we first started. There were three of us. So, I had actually referred a friend from college, Megan Norman, to come in and be the community manager. And so, her, myself, and Adria were basically in this tiny room with three desks, and you couldn't turn your chair all the way around without somehow touching one of the other people in the room. And the iPhone boxes were going up halfway to the ceiling. It was a really challenging market. So, a little bit history on the on the Philadelphia limo market is there were probably only 200 250 cars total that were licensed, which was really challenging for Uber because the whole Uber model was you're creating this demand that wasn't historically there. And so, in order to do that, you had to put a lot of cars on the road so that people knew that you could get low ETAs and that the service was available. It's so important when it's all new. And so we had a really hard time early on just figuring out how are we going to scale this thing. So the demand wasn't really the issue. Once you kind of got things launched and we did our press and people were talking about it, you built relationships with the community, things started to move. But it was really really tough on the supply side. And that ended up being my core focus which was challenging as a 20 3year-old coming out of a very structured environment into one with zero structure. How quickly do you realize that you need to get more cars on the road? Again to set the stage here, this is a fixed number of cars in a city. It's fixed for whatever reason. People don't want there to be more supply. And now you as a child, effectively a 23-year-old have to figure out, hey, we have to get more cars on the road. It took us a little while to figure out what the constraint was. So ultimately the constraint was that it cost about $10,000 to get a license in Philadelphia to be a limousine. I'm not sure what it costs to be a taxi. There was a separate process, but in short, it was cost prohibitive to any bluecollar worker or anyone wanting to start one of those companies to get into business. I mean, it was just astronomical. In other cities, it was $50, $75 for a permit. And then on top of that, you need a car, you need licenses, you need insurance, you need everything else that goes along with just operating the vehicle and the business. So, it was a challenge. I think ultimately once we got through the list of all the limo companies and we were asking for referrals and things like that, what we realized is there were just no independent contractors. I think that was the biggest signal that we got that, hey, look, we're going to have to figure out another way to scale this thing. And as you know, this model worked a lot better with a single person and a car versus a company that had 25 cars and 50 drivers. It just the economics were a lot better for the owner operator and it was hard to have another person in the mix trying to scheme off the top. There's just not enough profit in the whole equation. So then what do you guys do? You guys create a secret limo company. This was the most Uber thing we did in the early days there, which was, okay, there aren't enough cars in circulation, so we're going to create them. And we spun up this company. It was called GageN LLC. So Uber means above or greater than. Gagan in German means against. And the whole concept there was that the Philadelphia Parking Authority, they call it the PPA, was a very, very twisted organization. $10,000 to get a license. There was obviously a reason for that. They were protecting the current owners who were probably fueling their pockets with cash. The entire thing was corrupt. And so, we launched this new business, Gagen LLC. But the interesting thing is you have to go through an approval process with all of the existing companies and they once you're preliminarily approved they put you up to a vote and so everyone has to vote and they have to say sure we're okay with this new company coming in because that's how the world works. Well they didn't know it was Uber who is standing in who is standing in is like the boss or whatever. So we created some type of legal structure where you know Travis was some type of owner in GageN and it was a subsidiary of Uber but Uber never showed up on any of the documentation and I don't think anyone expected us at the time to go and create a limo company and get a license. So they passed. Everybody said sure that's okay. Yeah, gagen sounds great. And we I remember we had a lobbyist or someone on our legal team basically standing in at that meeting. You find quickly that you have to get the right team on board politically to get a lot of this stuff done. So great lobbyist, great communications person, great lawyer, awesome legal team, not just our internal legal team at Uber. You're getting local folks that know the people making the decisions at the PPA. We're playing the game essentially. So, we played the game and we came out of it for $10,000. We had a license that we would ultimately then license hundreds and hundreds, who knows, maybe thousands today of new vehicles, four, five, six, 7xing the total supply of cars in a market. Do you remember was the approval process internally difficult at that time to to go do this thing? No. Once we recognized that the supply was so small, I remember Travis was talking to Adria and he said something like, "Oh, Toronto only had 300 cars when we first started." Now, it was a lot easier in Toronto to get a license. It wasn't cost prohibitive like it was in Philadelphia, but the point there is that's all it takes. It just takes a little bit of confidence in that, oh, we've seen something like this before. We can absolutely do this again. And that was the beauty of Uber. We just had free reign to problem solve. And Travis, the executives at the company were trusting in the local teams to come to them with these recommendations. The other thing is Travis would go super deep on these things. He came down and spoke to the PPA at one point. like he was involved in the Philly regulations for a period of time until, you know, the company continued to grow and he needed to take a step back and we had to throw some other people internally on it. It was a wild ride setting that whole thing up. I'm sure there's a bunch of these examples in tech, but it's so crazy that there wasn't enough supply in all these markets for this business. This is just one of the headwinds that would have happened of being like, well, you just can't do this business because there's not enough supply. and instead it was just like well let's just create unlimited amounts of supply and that'll solve the problem in some ways. I don't think that mentality can be underestimated because 99 out of 100 people would give up. 99 out of 100 people would say, "Oh, there's this massive barrier to entry here. We're not going to do this." But it was the opposite at Uber. And I think that's something that we all take away as a gift from this. Whereas now you look at a problem and you're like, "Okay, what's on the other side of it? What's the opportunity that comes with that problem?" Because in most cases when you're creating a new market or creating a marketplace, you're going to run into these massive, massive speed bumps. And just knowing that there's probably something really nice on the other side if you can just get yourself to the other side, I think is probably one of the best things I I took away from that. Yeah, absolutely. and and that that the opportunity is created in that whole mess and that these crazy regulatory environments actually if you can figure out how to get above them and beyond them, it creates the opportunity. So what was the situation where you got offered a bribe to throw the company under the bus or what? $1.8 million or something. Yeah. So that's where Philly gets its rep, you know. So you got you got more than you bargain for with this. Hey, are you do you like Philadelphia? Exactly. one minute conversation around my love for the Phillies and all of a sudden I'm throwing myself into a crazy situation. So we had one driver, he was one of the independent operators. This guy's name was Aziz. Super close with Aziz. He would feed us information because he was seeing how the environment was changing. I'd go to the airport and I'd walk around and talk to all the limo drivers there to try to get them on the platform, hoping that I'd find a driver or a company that I hadn't spoken to yet. the taxi drivers were giving me the death stare every time I went down there. But Aziz would take me. So he would introduce me like a warm intro to a lot of these people. So forever grateful for him just being the man back then and just seeing the opportunity that was at stake. So essentially the group of taxi folks kind of got together and they would meet frequently and let's call it there were four or five people who held the majority of the medallions. So they got together and they said look we're all going to pony up $1,000. There were 1,800 taxis 1,800 medallions. And they said let's offer Eric $1.8 million to sabotage it to just basically turn Uber off in Philadelphia. The funniest part about this thing is the mere thought that I had the ability to completely sabotage Uber in Philadelphia. Could I have screwed things up for a couple days? 100%. Could I have sent some really messed up text messages out on the driver line? Definitely. But was I going to be able to shut the entire thing down or company that had tens of millions of dollars in the bank at the time? There's no chance. But it was funny. So, I declined. Just for the record, to be clear, let's get this on the book. You know, there was a great answer cuz I was literally going to say, "How would you even do it? It's so crazy." Yeah. It's like the OJ thing, right? I write a book about how I would have done it. But to be clear, I never I didn't do it. Yeah. I did not take the money. All my money is hardearned money. Were you ever nervous at that point? because those obviously if people are willing to do that, they see that this is a no joke seismic shift in the market and they're probably willing to do a lot of things to make sure it doesn't happen. I was definitely nervous at points. I was nervous very early on when we realized that the way we were operating was very gray, but that was where Uber played. It wasn't black or white. If it was, it was hard for us to go in there. But if it was gray, then we were able to start operating and then fight our good fight along the way. And so I remember being nervous early on because I was like, are we breaking the law? And that felt weird again as a 23-year-old kid with no work experience. I don't know. I guess I generally followed the rules for most of my life. Like just didn't do anything super far outside of those bounds. And then you started to get comfortable with it where you knew you were fighting for a greater good than what those regulations had been written for. But again, we were in that kind of gray area. We continued down that path. And I think the thing that Travis did really well was just getting everyone to believe. And it's pretty amazing what you can accomplish if you believe or if you have a group of people that believe. I think if Uber in a nutshell is just a bunch of people believing that that needed to exist and then everything needed to change. Totally. I mean, you and I are in Tahoe in September 2012. There's about 100 people at the company. We do like one of the first company events where the whole company meets up. That's one of those seminal moments where you you felt we were all just geared up, ready to go, would have done anything, and you're really believing in Travis and what was ahead of us and you're feeling like this thing's special. Totally. As a founder now, I think about that moment a lot, a lot more than people would probably think I do. And it's because there was an energy in that speech, for lack of better words. It was a speech. It reminded you of, I don't know, if you're going to war or something and they're firing you up, leaders firing you up, but there was just a level of charisma there that I think is so so critical to galvanizing a group of people together to achieve a really tough goal. And the tough goal for us at the time was how do we just get this product to be ubiquitous? How do we get it everywhere and really push this thing forward and goes back to that greater good? I think we all felt like we were fighting for a greater good. I can still feel that energy. We're all in a circle. Travis is speaking to us. I don't know if we had just played dodgeball or if that was the next day. There was a lot of camaraderie and a lot of us knew each other via Skype through these instant messaging channels and that was the first time a lot of us were able to get together in person. And by the way, we're all working so much that you could talk to people on Skype more than you were talking to your friends that you lived with. And so bringing everybody into the same place was really special. I try to take that with me today to get people together in person because there's just nothing like it. You can't emulate that in-person feeling and the way that you build camaraderie that way. No, it was distributed workforce before that was Zoom and everything that the world that we live in today. Yeah. And then we all came together and it was like, whoa, I know you from Skype, which is the messaging app that we use at the time. Then we do workation together a couple months later. So workation is basically New Year's was always the biggest day of the year, night of the year for Uber. Travis's idea was let's get everybody together, meet in one place or then end up being in a few places, work from there on that day, build camaraderie, may maybe also do a hackathon of some kind. Again, another really important moment showing the hustle and the energy and that your life is really handed over to this thing. That was the best, especially at those ages. We loved it. What do you take from those experiences now as you're a founder and you think about building culture and the hustle and the belief? It's so interesting because it's probably one of the smartest things Travis did looking back. You got all of these people in the company together at the most critical time for the company and you got them to only think about the company. It was amazing, but it didn't feel like that because you were having fun. You were spending time with your colleagues. You were doing all these other things. I mean, we went to Miami. We were working a lot, but we were also having a lot of fun. We went to some clubs. We did a lot of interesting things when we were there. It was much more than just the work. But I remember I think it was New Year's Eve night. 90% of the house you guys went on a walk to the beach or something to see fireworks and was going down in Philly and I stayed in. I didn't partake in that because I knew I had to be on the lines and be talking to drivers and things like that. But that was just the culture that was created. The way I would connect those dots today is that culture is very very very difficult to change over time from what I've seen. And so that to me that was early enough where you had 100 people and Travis did those workations before before we were there. There were a couple. There was one in Thailand and maybe one in Mexico or something. I went the year. I went to Costa Rica the year before. Okay. So, you had done it. I think Travis had done that with other companies. So, he saw what type of impact that can have on a group of people when you get people together in person and you're not in your 9 to5 environment in the office and you're living together in a house. He had figured that formula out. But the earlier you do this stuff, the better because as the company gets bigger and bigger, it's just so hard to shift. It's not an accident that these massive companies that you have today have a very distinct culture. It's because changing the culture happens to be really really difficult and sometimes the founders are no longer at the company and the founders are the culture carriers. The culture it can still hang on even when the founder is not there in certain ways. So that's kind of what I've taken away from it is just trying to focus on the culture a lot earlier, just knowing that it's going to be more difficult to change over time. So even if it's two, three things that you just want to make sure you hammer home, get it right in the beginning because it's going to be difficult later. And and I've talked to people that still obviously we've been gone from Uber for a long time now, but I've talked to people that work with Uber and they've still got some of their in. Obviously DAR is very different but there's still some stuff in the ethos about regulatory and dealing with partners and other things that like that just continues to exist there even as people change over it's just part of the system is Uber scales like many of us you go from individual contributor to very quickly manager and now managing teams what was it like dealing with that I'm good at my job I'm very focused on it I know what to do every day now hey manage a bunch of people sort of doing the same thing. By the time I made the transition to be a manager, I was a strong individual contributor. I knew how to manage up. I knew how to ensure I was hitting on things that were important that would move the business forward. I felt like I had a strong intuition for the business. But I was a terrible manager when I started. Managing people is so difficult. Somebody told me and it was someone at Uber. I'm just forgetting who it was, but the way they described management was just you suck less at it over time, which I thought was really interesting. I think it's true. I don't think you can ever be a perfect manager, nor do you really want to be a perfect manager. So, making that transition was the most value I found from it was watching other people who I admired doing it and taking tips from them and pulling bits and pieces along the way. But the biggest transition for me personally was getting out of this mentality that I don't have to do everything. And now understanding that you have to delegate to a team who's going to execute on those things, but you need to be there with them along the way, holding them accountable, checking in, knocking down walls. That was a big big leap for me because I get so much energy off executing. That was a difficult transition, but again, sitting next to other really smart people who were way better managers than I was helped me learn along the way. And then by the end of it, by the time I left Uber, my biggest accomplishment, my biggest takeaway, the thing I felt the most joy from was actually seeing the people on my team grow, take on new roles, helping them get new roles when we decided to move the office from Vegas and consolidate into Los Angeles. So, it's interesting how that progresses and develops over time, but it can definitely be a scary experience when you're at that point. And I guess I was 25 managing people who had Ivy League MBAs that were 5 years my senior. Every single person I was managing was a lot smarter than me. Let's put it that way. It's you're thrust into it really quickly in a high growth environment. And it's a and like everything is sink or swim and that one's notoriously difficult for sure. Similar. Yeah. Had to learn, have gotten better at I hope get get less sucky at. The reason that you and I were in those positions, I think it was Steve Jobs that said the best managers are the best individual contributors. There's a reason for that. You know, the entire business from front to back. And so your ability to help someone else with an issue that they're having and to be able to keep the compass in the right direction, you have a much higher likelihood of being successful at that than somebody who comes in externally who doesn't have that context. It takes a while to ramp up. Absolutely. Speaking about scaling, you end up also helping Uber expand very quickly in the United States. You end up doing the Uber everywhere project that we had. We started in a city like Philadelphia or Chicago or New York, but then you have to start to go out to the suburbs and go out to smaller cities and still requires the startup standup activation of a market drivers and getting riders. So what was that experience like? How did Uber scale this so quickly in these markets? Yeah, there was a funny anecdote that Lyft launched this thing called Lyft a Palooa. A lot of these things that we did looking back were driven by what Lyft was doing too, what competitors were doing. And some of that was just staying up to speed on what the newest tech was or what certain angles were with new product lines like Uber X. So Lyft launched I think it was 12 markets on a single day. Now once we actually looked into this they may have had one or two drivers in a market but they didn't have the mentality that we had. The mentality we had was when we go into a market we're doing it right. There's going to be cars available. We're going to invest in it. We're going to ensure everybody in town knows what we're doing. They took a different approach and it it was first shot to the stomach because they had demonstrated this hyper scale in a way that we were wondering why we hadn't done it, why we weren't responsible for something like that. And so we actually met in New York. It was a small group of us and I remember the presentation that the leadership team went through to kind of pitch us on this concept. But they said, "Look, we need to launch all of these secondary and tertiary markets on the east coast and we need to do it quickly." And so it was this really cool challenge moving from single market management in Philly to rewriting the playbook on how we launch markets because at that time there had been this launch playbook that everyone talks about. Just so everyone knows, the launch playbook was a Google doc with links to other documents. It wasn't like a Bible that was found in some temple somewhere. It was just a document. The original name of it was If Austin Dies. I didn't realize that. That's a fun fact. Then that was basically like Austin the original launcher and her just documenting everything that she knew about this. And don't get me wrong, you need to document everything, especially early on at a startup because otherwise, how are you going to train anyone else on how to do their job? But I'm simplifying it. But we created a new version of that playbook based on we were looking at cities based on population density and we were figuring out where we wanted to go next. And at one point we were able to launch I believe it was 10 markets in a single day. We ended up launching about 25 in a year. And then there were two other teams. There was a West Coast Uber everywhere team and a Midwest one. So combined, I think we did probably close to 75 to 100 cities in a very short period of time. But the technology had gotten so much better. We introduced Uber X. If you were doing that just with limos, it would have been very hard to do it remotely. But with Uber X, almost anyone with a personal vehicle was eligible. And then switch it over. You didn't have to give the driver an iPhone. That was probably the biggest thing that ultimately led to us being able to do it 100% remote because we used to go in and rent a conference room at a hotel, bring in a hundred drivers. Remember doing this in Orlando and it was almost like a town hall. You're having this conversation getting them pumped up about earning on Uber and you had to give them an iPhone. So, it took forever. But then we were launching Charleston, South Carolina and BYOD, right? Bring your own device. They could download the app. Why did it take so long? Was there some sort of Dude, I don't know. It's insane. Is it just because a lot of people iPhone penetration wasn't as high as it? That's definitely probably part of it. So, part of it was that not enough drivers had an iPhone. It was an iPhone app. So, then you have to rebuild it for Android. Or was it because you could only use the Uber app when you were on the backgrounding? The backgrounding was probably an issue, too. Anyways, guess we don't need to figure that out right now. But it is strange that it took so long. Then it was uh Blake that ended up doing the whole got all the devices back which is one of the craziest things I've ever watched. Like I was like and he's the man. He's at OpenAI now. He's always been at a bunch of ser. So I was like dude you were one of the most competent individuals ever because that was an impossible mission. It was like go get all of these iPhones back from around the world. I remember he used to send this chart and it was just every single iPhone's coming back and you're like dude one of the best execution jobs of all time. Maybe I'll I'll get him on the pod. You end up how do you end up in Vegas then? So you end up launching a bunch of these markets and then I think it's Rachel Hold comes to you and says hey we need some help in Vegas and and is in addition to that you keep raising your hand and just doing whatever. And I think that's an important anecdote about you generally and also something that that's kind of what you need to do especially in these in these environments where it's it's growing just jump on any opportunity. Yeah, totally. I mean, you did the same thing. It I guess I got a bit of a reputation for just being down for anything and smile on your face. Being single was important at the time because any other responsibilities, you know, you better not have any family or whatever else to deal with. Totally. Totally. You better not have any other responsibility. You have a pet, you're fired. So, I got a call. I was living in DC at the time. I was working at the regional office down there. I got a call from Rachel and she said, "Hey, we're going to make a leadership change in Vegas. Do you think you could help us out?" And I think a few seconds later, I was like, "Sure." I had a girlfriend at the time. Go break up with her. I No. The the the terrible thing is like I fully committed to that without even talking to my girlfriend at the time. Look, it's not as if she wouldn't have been supportive at the time. It was the obvious move. It was a great opportunity, but I think what I didn't understand at the time was how long I would end up being there. So, she asked me when I could go and I think it was a Tuesday night and I said, "I don't know, Thursday." So, they fly me to LA. This is a piece of the story that I didn't tell you before. I'm in the office in the LA office. They thought, "Hey, come get them integrated." The LA office was the regional office. So, a lot of the leadership was there. So, I come in, I'm, you know, high-fiving people, seeing people that I knew already. I sit down at a desk and Barnes is in his office letting go of the current Vegas GM. And so, I am sitting in the office while this guy is getting let go, about to replace this guy. Unbeknownst, yeah, he has no idea why I'm there. And then the next day we're all flying as a troop into Vegas to rewrite the narrative. The whole thing was crazy. Was not prepared for that at all. And I guess he just showed up in the LA office to to just meet with people. It wasn't planned. No. But then they were like, "Well, we've got to let this guy go like now. His replacement just arrived. His replacement's eating lunch right behind you. He's smiling." And this was a very Uber thing, but every conference room was a was a fishbowl. So you're just firsthand view of everything going on in every single one of these. There were no closed offices. So when you take over Vegas, what was wrong at the time? What had not gone correctly? And what did you do to rectify the situation? It was so interesting. There was a guy named David Pickerell there. He's got his own company now. Super successful guy. But I walk into the office and I'm doing the initial conversations just with the team to figure out what the hell is going on in this place. Basically, David is running the entire market. There's three or four people on the team and mind you, Vegas is growing exponentially. It also happens to be one of the most profitable businesses from a margin standpoint just given how small the team is, how centralized a lot of other functions are. It was a different time at the company. So, it launched so much later than a lot of these markets. So was able to take advantage of all this new tech that we had, these new teams, these resources. But David's running this market, 100,000 trips a week or something like that. It's no small operation. And what I recognized very early on was they were just focused on the wrong things. Running Uber Chopper multiple times a week. There's this interesting parallel between what they were doing and how it would be if you just tried partying in Vegas for a month straight. Everything is at your disposal. You're a an arms length away from the best party you've ever been to. Alcohol, anything you can get your hands on. And it it felt similar. Uber Chopper was one of those things. It should have been used very very infrequently. It was to create buzz. It was to just show people what else we can do, how else we can leverage the application, not for daily trips, you know, to take a spin around the strip. it was just a little bit wacky. So, there was a prioritization exercise. I remember sitting there at a whiteboard and we just put a a list down of all the things that they were working on and it became very easy to just strip back the ones that we didn't think were making a big impact. Look, I'm not going to say I came in there and, you know, miraculously just fixed the market. It was a team effort and we just dumbed it down to what are the most important things we need to work on right now based on higher level goals and we just pushed forward but we grew that thing into a very very large market hundreds of thousands of trips on a weekly basis and it was a very small team. When did the deals with hotels come into place and how important is that? cuz that was one of the gating factors was that they were like screw this, we're not going to let Ubers drop off or pick up in on the strip. And obviously without that, it's hard to do Vegas without having that. Totally. So 40 million people visit Vegas on a yearly basis. Now that number is outdated, so maybe it's 45 by now. But we were winning with Tourist, which made sense, right? Uber had operations globally. We had more operations in the US than Lyft, but Lyft was winning on the local side. So in local zip codes, their market share was actually bigger than ours. And so we were trying to figure that whole puzzle out. But we had a very strong belief that in order to win Vegas, you have to win the tourists. And it was almost just this indication of how the company was doing overall at a national scale. So we focused on the hotels. We set up deals with MGM, with Caesars. That was really cool. Getting to work with Marshall and Emil. Just a different part of the business that I hadn't been able to experience before. And also us walking into these casino exacts conference rooms with jeans and a t-shirt on and they're in full suit. It was hilarious. There'd be 20 of them and there were three of us, but we had something that they cared about. That was the interesting leverage point. But the other really, really critical, a quarter of trips in Vegas were to and from the airport. Think about that for a second. That's huge, right? I think in most markets it was probably 10%. 10 to 15%. But 25% of the trips go to and from the airport. Well, for anybody who's taken an Uber from the Las Vegas airport, I am sorry. I'm so sorry because it is still a miserable experience. Yes. You're going to the parking garage. You have to walk to parking garage. the second floor. You used to have to go to the mezzanine level. So, you'd go to the second floor and you'd be like, "Where the hell is this Uber lot?" You have to walk up the stairs. The reason that still happens the way it does is because when a taxi goes and picks up at the airport, they pay a fee to the airport. And so, we came in with this whole pitch. Hey, we'll give you x amount of dollars on the ingress and egress to give us the front of the house, but the taxis have been supporting the airport for so long. It was just a a hill we we weren't able to climb fast enough. So maybe one day. Sounds like Uber's trying to put taxis on their platform now anyway. Yeah. Yeah. What ends up being your couple of really core learnings from the Uber experience? I think one of the biggest ones is just to not operate under a sense of fear. I think we all took that away where a problem comes up, it's an opportunity. And that mentality, like I said before, cannot be underestimated when you're building a business because the reality is things are going to go wrong all the time, multiple times a day. So that was a big takeaway for me. I think the other thing is just the importance of hiring really talented people around you. Uber would not have succeeded the way it did without the caliber of team that it had. And so ultimately the people you surround yourself with at the table are going to be the ones that get the business to this desirable place in the future. And so you got to spend time thinking about that and and putting a lot of energy and effort into it. And part of that is the culture too because you have to do a little bit of sales on how you get people into the organization and then what makes them stay. So there's a lot to unpack there, but those would be the two core takeaways. Something that I think is great about you and and even if grown admiring you is your ability to change and pivot very quickly. If you're in a situation that you think no longer feels good for you, you can pull out quickly. You've had jobs that were relatively quick. you've been in potential co-founder situations that you've decided to reverse out of. You've been engaged before, you no longer are engaged. And you know, I even a time I would make fun of you that you were changing cars all the time, which was like I did change cars a lot at least a couple times. Where do you think that comes from? And you know, again, one of the reasons I think it's a great quality about you is that it's allowed you to then put yourself in positions that end up being great, but you've had to go to through some pain to get there. There's a bit to unpack here. So, in business, I think we reverse decisions all the time. You have to think about it. When you fire someone, you reverse a decision. You hired them. That was your decision. But now, you have to go back on it and you have to let that person go. But you have reasons for that. I think ultimately with me and and look I have spent a lot of time on some inner work to ensure that I'm able to handle these situations hopefully prevent a lot of these situations from happening like doing the work up front but in a lot of these scenarios the thing that's constant is just being true to myself and so I would say one of my superpowers is I know how my gut feels and that ends up being really important especially early on with a business You don't know. You don't have data to tell you exactly what to do or to make some of these decisions. And you have to relentlessly make decisions and trust your gut and trust your instinct. You have to look at the anecdotes, look at all these signs that the world universe is giving you and you have to go. And so there have been numerous situations in my life where I've probably not spent enough time upfront thinking about what it was I wanted or what it was that was important to me. And so I would make a decision and then I would sit with it and my gut would just be wrenching. My stomach would be flipped upside down and my body was just trying to tell me this is not right for you. And so then what would I do? then I would have to have a really hard conversation with someone about that. So whether it's deciding that joining a company as a co-founder wasn't the right thing for me. Well, that was a really tough conversation. So the way I look at it is those tough conversations just set me up to have more tough conversations in the future. But I've done a lot of work. I have a life coach and one of the things she always says to me is thinking creates reality. Well, so if we all take a second to think about that, if we can create our reality by thinking, we'd probably spend a lot more time thinking and thinking positive and thinking positive 100%. So that's what I've learned and taken away from it. Now, does that mean I'll never have to reverse a decision again? No. But I am a lot more clear about what it is I want in a lot of these core areas of my life. Whereas when I was going through the elementary phases of being a professional, I think it was a lot harder. And the same goes for personal relationships. The same goes for friendships and anything else we want to end up spending our time on. So I appreciate that. It's been a really cool learning experience for me and I I really take that to heart to just spend more time thinking. I know the life coach for you has been really transformative. What else from that experience has helped sort of shape who you are today? So I think before the life coaching, so 2019 was when I started it and I did a couple very intensive 2 years. Then I took a little break for a while and then I picked it up again this past August. It sounds like a drug. When I'm not with my life coach, I feel a lot less accountable. I feel a little bit like life is happening to me versus I'm driving the life that I want to live. And so a lot of the work was spent upfront in designing what I want my life to be like across every area, relationships, friendships, community, career, love, all these different areas. And once you're very clear on just where you want to be in those areas and where you are today, you see the gap and then it's just like business. You say, "Okay, what do you have to do to close that gap? How do you get yourself there?" And I think that's enabled me to just be number one just a lot happier as a human, which I think is the most important thing. I would hope that the people around me say I treat them better and right there's that whole aspect of it but I also think I've just accelerated my ability to be an effective entrepreneur to start companies to bring people around me to solve really tough things. So it's the best me money I've ever spent hands down. So you leave Uber it's obviously a crazy experience and super intense and you do just a bunch of awesome things. Obviously the company is super successful. You then leave you're trying to figure out what to do next. You've now really morphed into this entrepreneur, you know, and again I know there was this this path for you getting there and again trying things and restarting things and whatever else. What has been that journey overall as you found professional success or a professional path and maybe you know talk more about what you're working on now? Yeah, so I tested a lot of things. Did some angel investing. I think that was my test to see if I could be an investor. I'm a terrible angel investor. Do not follow any of my investments. Not not as bad as me, but I'm the worst. Turns out it's really hard, right? It's really hard to know if something's going to be successful because it's not just the people. There is timing. There's a market you're going after, right? There's all these other variables, but and you have to spend a lot of time. It makes you appreciate what an investor actually does. You need to spend a lot of time to get really good at that. Tested that out. I tested joining a company. I was uh an executive at a cannabis delivery company for six months. I was doing some really cool marketing and branding type activations. Money got tight. My whole team was the first one to get let off. We required money. We weren't generating revenue. We were requiring it. And then I I did some consulting. I tested a lot of different things. Where I found myself being true to myself was when I kicked a business off the ground with my closest friend out in LA. And that feeling was so pure that I immediately understood that that was the path that I should be on. And I've been on that path ever since. The original business was called Return Mates. Started it after a bad trip to the post office. I was in there for 30 minutes and I came out and my now co-founder was like, "What were you doing for so long?" And told him I was sending back a return. He just said, "That's why I don't shop online." And so it kicked off this whole thing. And then we were like, "Well, we can make the Uber for return pickups." Called it return mates. We'd come to your door, no box, no label. Well, that business has evolved multiple times. Now it's called Sway. But we are the Uber for package delivery and return pickups. And it's been a blast taking a lot of these learnings from the past, even things we probably had PTSD on, and being able to see the forest through the trees a little bit, but getting to work with your best friend on a daily basis, pretty amazing thing. Getting to tackle really hard problems of things that are moving in the physical world, and that's been, I think, a blessing for me is just to to find that path. But again, I think if I would have spent an extra, I don't know, four to six hours in some deep work thinking more about what it was that I really wanted, I probably would have got to that path even a little bit earlier. How do you think you've evolved now as an entrepreneur? Because you have first the path to get to this point where you decide, okay, I'm going to start something. This feels right. Now, I've seen it in you, you know, a swagger or whatever you want to call it over time as you've gotten more comfortable with yourself. Yeah. Being the boss and being entrepreneur, how has that evolved for you? And what do you take from the Uber experience that informs yourself as a day-to-day founder leader of a company? I like that question. There's a belief in yourself, which I think is probably the most critical thing at Uber. I think what they taught us to believe was that you can do it. I remember we were supposed to launch Uber Philly I think in 24 hours. We had zero cars that could be on the road and Austin looked at me and she goes, "How many cars do we have?" It said zero. She's like, "All right, well, we're still launching tomorrow." That at the time was so foreign to me. What do you mean? Logical. Eric was like, "How are we going to launch? We don't have any cars." Well, we put a Craigslist ad up. We got that guy. We asked him to refer a couple other drivers. We had the cars we needed within 24 hours. And so the belief in yourself that you can do something really hard, I think, is probably the most critical thing that I took away. But thinking about my evolution, look, you do something for the first time at least once. So fundraising for me, I'd never fundraised before. Well, I fundraised seven times now. You get repetition. You understand the game. You start to figure out how to play it. You stay in the game. You stay in the game and you polish it. If there's one thing that I would take away from this current experience that wouldn't have been relevant at Uber is that you have to stay in the game as long as you can. Uber never had a cash problem. I'm sure there's a story out there like the Andre where oh we were fighting over a 100 million valuation and 150 million valuation. How about having no cash left as to where I'm putting money in to make payroll? That's a different experience and you only get that when you're sitting in the founder seat and when things aren't up and to the right the entire time. So, I think there were amazing lessons that I learned at Uber that I took away and have helped me evolve as an entrepreneur, but nothing can really compare to those lessons that you face as a founder when you're sitting in that seat. And it's all riding on you, you and your business partner, you and your co-founder, you and your leadership team. It's just different. I rode the wave at Uber. I was carving around. People were putting me in a different break every once in a while, but I was still riding it. With this, I'm like Kelly Slater's wave pull. I want the wave to be like this and then I'm going to go up and come back down. You're orchestrating the whole thing. It's just different. But I wouldn't trade that experience for anything. You need both. You need to know how to be a really good employee so that you know how to treat your employees and you know it from that vantage point. So yeah, I wouldn't I wouldn't trade it. Any advice you would give to someone on the come up trying to figure out their career, trying to figure out how to make it happen, trying to look for something that, you know, brings as much out of them as Uber brought out of us? It's going to sound corny because I think people say it a lot, but it's just start. Do one thing, make an inch of progress because that inch turns into a few inches and then turns into miles and you look back 2 3 4 weeks later and you'll be amazed at what you actually accomplish. I I see that even just with hobbies that I do. I spend a little bit of time on it. You make some progress and then that motivation that you feel from seeing that impact and that progress that you made is just addicting. So you have an idea, you want to start something, just do something. Do a little research, put a deck together, talk to a few investors, talk to your family, talk to your friends, get feedback on it. But do something. And if you do that, I guarantee you will want to come back the next day and do a little bit more and a little bit more and eventually there's going to be something there that you created for yourself. One of the taglines that I have for the show is big things start small. Just do it. Just move forward. That's exactly right. It's also the origin of a lot of us getting the Uber job, which is just send a cold email to somebody cuz you heard Uber is legit, which is a version of of what I did. Many of these stories started that way. That's a great way of putting it, dude. You're the man. Thank you so much for doing this. I appreciate Thanks for having me.