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there's a tweet and Uber is totally illegal in DC and that started the Washington Post paying I mean it was just nonstop from that moment this 83-year-old taxi cab commissioner requested an Uber took it to the Mayflower Hotel and had the press and you know the DCTC enforcement agent there impounding the vehicle we were fighting for our jobs and for what we had built for the drivers and it was very clear to everyone this thing was working and we just fought for our lives for the next 5 6 months 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 Rachel Hol thanks for joining the podcast great to see you Max great to see you this is the first inperson podcast so I love it I I'm honored to have you here East Coast represent yes New York City Live From New York so you were born in New York born and raised in New York yep where did you grow up and how did that shape you totally well grew up on the upper west side you know once a New Yorker always a New Yorker and I spent like an abnormal amount of time commuting places right because I'd take the bus to school I'd go to tennis I'd be on the subway I'd be on the bus and um and frankly usually avoiding a taxi um at all costs worst case scenario worst case scenario it was slow it was expensive um and I had kind of like pretty well optimized um you know the subway uh situation at that point but spent a lot of time thinking about how to get around well we'll fast forward a lot I was in San Francisco suddenly I'm in San Francisco there's no way to get around there's no parking there's literally mountains between everything so you can't walk and the public transit is terrible um and the cabs are extremely unreliable and it was like a source of constant frustration um and that was in 2010 and someone was like you know there's a new thing called Uber transportation becomes sort of a fabric of your your life in some ways it's life right I mean if you're debating going to meet friends or go somewhere with friends I tend to be this won't surprise you the friend that wanted to go home early and so you know hanging out I was I was big on 8 hours of sleep like pre Ariana being big on 8 hours maybe like an Irish exit too EXA s away know but then you're like standing on a street corner alone in San Francisco and you're like this is not safe at all yeah um and so it was very much sort of in the conscience in a way it was never in New York yeah it's San Francisco pre Uber was one of those cities where it it just didn't even make sense before Uber to leave your house half the time I mean it was really crazy um and so and and Uber completely transformed that City and even you know when I was started to you know first kind of got um was aware of uber was the very beginning of of 2011 and I remember it was like your get out of jail free card right it was Uber black only it was extremely expensive um but you always knew you could get home and you could get home safely and it really transformed where I would go to dinner and when I'd meet my friends um just knowing that that option existed and when I looked at you know then fast forward to kind of starting to think about um you know where I was going to work and things like that a lot of the things that were sort of big in in 2011 were like the social media monitoring app and it's like the world will be better if we don't know you know who has more social media influence right who un who won exactly but like the world is definitely better because we can all get around more easily and I just found it was like really impacting my daily life in a way that very few things were at the time so cuz you graduate from Stanford NBA 2010 2010 which Uber doesn't even barely exist at that point first ride was what June of 2010 so did you I mean you go into NBA 2008 so first first was that a difficult decision was that a no-brainer to do NBA CU I know you know people that are in their mid-20s think about that and then what was your expectation for what you would do coming out coming out yeah so you know I was at um I I went to college in amer um small Liber arts school by you know happen stance found Bane and and did spent three years doing consulting work um spent sort of 6 months on an externship there so got a little taste of like what um you know what what sort of startup life was I actually worked for um the uh the company that did all the online parts of Major League Baseball which was super fun bam or whatever bam bam yeah there you go but Disney purchased bam I mean it's like one it's an unbelievable asset and Company very cool but this is 20 you know 2007 actually we put all the um the the pitch FX technology in all the ballparks you could actually see the um you know now which of course is everywhere um the kind of Strike Zone technology but um but that was a little bit of a taste of what like a tech startup was like and um you know I looked at a few things um and uh and just decided like I really didn't know what I wanted to do honestly and so you know why not spend a bunch of money at at business Camp um and and uh you know Stanford was a great place to pontificate on on what you want to do with your life but I think what I really learned there was what I was I I wasn't going to be the person who was like the best Finance person or like the amazing marketer like the Ops wizard but I was like pretty good at all of them um and so that's what kind of Drew me more to that like GM skill set because it really is about you know taking a lot of different you know disperate piece of information being able to make a decision and and weigh all those tradeoffs um from one another and so I actually spent I spent a year after after business school at Clorox CU I very quickly realized like the one area I actually didn't have experience in was marketing okay so I had seen almost everything from a uh a bane perspective like a little bit of everything and and marketing was definitely the area that I did not have much experience and so spent a year a year at claro and great training I mean seeing how like a number one brand Works was amazing but I also was like I'm not a patient person by nature and you know spending kind of 10 years to get the corporate two jobs up was not going to be for me um it was it's funny they had a um it was sort of around our first review we had to write like what jobs we might be interested in uh at Clorox and I wrote Like You Know Chief of Staff to the CEO um you know a Corp Dev job and they're like I don't think you like understood what you were to do I was like no I did um but kind of doing the next marketing rotation was just not going to be for me and so um you know and I also was looking at at getting back to the east coast um at the time my uh now husband was in DC um and so was like looking very casually at at was in DC and was like totally unexcited about everything it was when living social was really big yes and I just like hate breakage business models well in Chicago we had the grou you had group exactly so you know you know the exact thing so that's all the jobs were like all the startup kind of cool fun job was B jobs were basically Living Social people ex living social and I was just like I'm not I don't believe that business I it's it's crazy because people ask me about what tech companies I was interested in in 2010 and it's like Groupon was the only one that I like really knew well totally and I don't want to do that that's it was exact same thing and it was to the point where I was like I couldn't even like get myself to finish my resume I was so unexcited about the stuff and then I'm like oh my God is this like a relationship problem or is it a job problem and then a business school classmate of mine was like oh you know uh Uber is is looking at at at the East Coast in some cities um I think DC is one of them and like in 24hour I like read the job description I was like someone wrote a job description for me and it was just that moment of like this is exactly what I want to do and like I'm going to make this happen so then what did how did you get in touch with them well you know so first of all I should say it was it was patney okay um who shout out patney shout out to patney who said to um you know a a friend of hers um from tpg who was one of my friends um admins was like that was the original lock in and so Susie was like you gota uh you got to reach out so I you know first submitted everything through you know the the regular channels I'm God knows if anyone from Uber ever was going to check that but then Ryan Graves exactly he was sitting on the job he was sitting ready on the job portal exactly there was no recruiter I mean there was no one to pay um but then you know quickly found like everyone I knew that had any um connections to Ryan and it was actually it was my boss from mlbam it was um Haley barno who's now at at first round and you know she was the Birch boo CEO and first round head back Uber obviously and and Birchbox who I was like okay those are my you know I don't want to go more than three I don't want to be the crazy person but kind of pinged in to Travis and Ryan every um every possible way and you know I actually preparation for this read through some of those old emails so it's like a fun walk down memory lane wow I need some some of those screenshots if you're to share exactly it was like Ryan you know Ryan being like let's chat you know and so all lowercase exactly and then and then also love Ryan typical Ryan fashion though it was like Rachel Rachel Rachel Ryan response Rachel you know which so I I I quickly realized I had to uh had to be assistant yes well worth it yes and patchy referred Sam Gman too so I it I hope she got all those referal ref shares she deserves every one of them those very important shares the early ones the pre the pre many split referal shares yes the uh yeah I mean Ryan my first Skype with him he was three hours late and I would remember being so frustrated but at the same time I I the same thing for me I wanted the job and so and I was like why is he doing this but it doesn't matter and and then when I got the job did the same thing to so many people because we were running doing a 100 things at the same time for sure exactly exactly and then when you get it it's like salvation and you're like oh my God thank God I didn't turn out or or whatever it's a good it's a good um you know reminder for life like yes all right so I know that when you were doing the interview process Travis calls out the MBA as maybe a negative not a positive I had gotten through the Athena's you know exam statistics Exam I had gotten through multiple Ryan interviews I had my blog post I had my 100 day plan and I'll also add cuz I think it's a good it's just like good reminder for life on Tuesday it was a Tuesday afternoon when Ryan pinged me and was like okay let's do the 100 day plan and you know they said You Know Travis has got some time on 9:00 a.m. on Friday morning or in two weeks and I was like I will take 9:00 a.m. on Friday morning hell yeah let's go and it didn't you know I was working at the time I to put together this 100 day plan but it's a good you know it's a good reminder and again in in looking at these emails I had friends who were like do they know you work you know but it's just that's the that's got to be the mentality if you you know go to a school like Stanford you know as they're pitching you on kind of why your life will change post post MBA they're basically like you know every job you'll ever get is because there's some Stanford connection that opens some door which largely actually is quite accurate um but here I am sitting talking to Travis who's like it's bad enough you finish college but like why on Earth did you spend two years getting an MBA um 00,000 exactly time money like what were you thinking start a company um and you know it's it was I was the first Michael pow started before me but I was the first MBA hire that they had made and then of course subsequently like so many of the GMS had had a very similar background um and I think part of that is just because like there was no prep for Uber right um being there you know there was no Playbook there was no oh what's the distributed GM model Uber invented all that and so you know really the best preparation in some ways was like being able to be dropped in situations and just figure it out um and actually there's a lot of parallels to to some of the some consulting stuff too where you know you're dropped in a new client you're dropped in a new case I did a lot of private Equity work there they'd be like these two week projects where you'd have like a day to get totally up to speed on everything and you were you had this mentality of like EV you can solve any problem we can get any information um I mean in the case of b sometimes you're willing to pay a lot more than we were at Uber to to try to procure that information uh it was a little scrappier either but um you know that mentality ended up being very much the Playbook of like the early Uber moments yeah just figure it out exact I mean there weren't a lot of jobs that were non-technical at technology companies and so that's where I mean Uber really invented the playbook for how someone could be a business leader in marketing and bizdev and supply and all these things that now it's what so many of these companies sort of build you know the infastructure around it it's such a good point because you know this concept of sort of doing what the company does to make money was one of the things that I think was like an important thing I learned from whether it was claro kind of Stanford and then at Clorox where like marketing was the central function um in in a place like Clorox and it's it's not where you would want to be a finance person right like if you want to be a finance person you know go be a Goldman right right if um and if you know if you're an engineer you should be a Google right and I think Uber hit this really unique point between actually the Ops and the tech coming together in a way that I think particularly in the early days as I think as the company scales you should scale through Tech right that's the right way functions get centralized and they get automated and whatever else ex but but that concept of just the operational nature of a company was super unique um and made it you know way more fun for people who aren't Engineers by background to actually have a real impact yeah and we it was scale with humans to start and kind of just do all these things that didn't scale we gave every driver an iPhone we the free Apple Store just the Myriad of things that were just just go go go it doesn't matter that's exactly and I mean customer support being local is like wild in retrospect but it was the fastest way way to scale and to do it correctly yeah and and and it created this sense of ownership this feedback loop um that is really unique and hard to replicate in in most startups and you know now I'm working with on the Venture side working with tons of startups and and Uber is very very special in regard to kind of how it uh how we scaled so when you get going when does DC actually launch so DC launches November of 11 and DC just rips out the gate like it's it's I think at the time so it was basically the fifth City sixth City fifth City and we just launched Boston Chicago was September Seattle was August yeah so sixth yes Sixth and that it was right at that period where actually the night of the Chicago launch was when I got my Uber offer yeah which was like September 20th exactly Boston was my third day okay how Nick Matthews met met Mara the brag tag crew exactly and Mara hadn't started yet Mara started I think a week maybe Nick and Mar I'm not sure if they were may have been a week later but it was it was all right uh right around that time and were you the was Billy and Alex did you hire them or they I did yeah so I hired them um pretty quickly um Billy was um I think it had one conversation or two conversations before I hired him actually funny story there I was like I'm going to be on time to this this is before I actually had started I had I had a call with him because I knew yeah you're like I don't want to experience had been and I and I had an hour before the call I updated my iPhone and it didn't go through and so I'm like running to the Apple Store being like I am going to call this guy I need make this phone call on time and I was late and he didn't let me and then you and then you were never on time to another he never let me live it down exactly so I mean what's the beginning of that experience like for you because if you're you're alone now y I mean people don't quite understand so now it's you Stanford NBA you were working at Clorox before yeah and they're like box of iPhones you're in DC and actually it was because it was one of the only cities where the GM had been hired I think I was the first city GM first first yes cuz we were just doops and Community managers in Chicago no and so they were basically like oh we'll hire the launcher after you so you can like both it's like the blind leading the blind um so it was you know it started as the two of us then Billy joined um and you know we were doing everything from the first thing we did was find a you know a list of the registered drivers from DC DTC which was the at the time the Taxi commission in DC we just started calling um we were working out of husband had a in his office they had like a little conference room that we were working out of and quickly like the line of drivers that were just coming in and out was um was crazy and I remember you know pinging him one night being like what like do you know that the Heat and lights go off in your office at 900 p.m. and he's like no like I've never been there ever been there at 9:00 p.m. and it took us like 2 days to be like you have this problem with your heat like there's like 10 drivers standing like I am yeah exactly it's dark and I'm freezing we need to fix this so DC you launch yes takes off I think I think it was probably the biggest Market out the gate it was very very fast and I think that was a combination of a couple things one um it was priced a little bit lower than some of the other markets and um interesting Supply Dynamics in DC where you've got the Virginia Maryland DC um you know was sort of an unlock because you had you had additional uh Supply and particularly Virginia had like a little bit more lenient um registration uh rules uh than some of the other places and then you know November December and DC is like Peak social season and DC it's very interesting like DC and Boston are like two totally different cities DC is like if you find something cool you tell everyone about it Boston's like I found something cool like I'm going to keep it to myself tell any and um so it it was like a very VI it's a very viral city um and it's a lot of young people and so and the the taxi situation was horrible um and because of the three state rules you couldn't get from DC to you know the from DC to Virginia and you were constantly being turned away and um there's a lot of like history of sort of the where why the DC taxi rules are what they are and they had switch from a zone system which really frustrated people they didn't have dome lights like you could never tell at the time when a taxi even was available or not so it it really had a lot of really really positive characteristics and so and it was of course it's cold at that time so um we really just like could not get drivers on the road fast enough to to satisfy demand particularly on the weekends and so it was off to a great start I actually Travis had me go go out to uh to San Francisco in early January and it was like a little bit of a Victory lap like we had had it was a really good beginning um so everyone's like all excited freaking jealous at that time yeah I was like feeling really good crushing exactly exactly uh feeling really good I literally get back to our office we got kicked out of a couple offices that happened I can imagine imagine constantly um and that's because just for because there's always drivers there D always looking for support and wherever you are you basically ruin the office forever forever they probably today are still drivers AC 1720 exactly End Street and I remember like getting on with Travis and being like the rent is going to be $3500 a month but it's the only way we can stay in this building but we have a private entrance and that was like you know yeah and he was like okay we'll do it you know as long as you on board let me do the math quickly on keep just keep going um so I get we get back I get back to the office Billy Alex and I walk to Starbucks we were I I was Kings of the world debriefing this trip to San Francisco and and we literally walk back in and there's a tweet from the DC the the 83-year-old DC taxi cab commission or being like well the Tweet to be clear the Tweet was not from him the Tweet was somebody commenting on him saying and Uber is totally illegal in DC and we're like oh my God and that started the Washington Post paying I mean it was just it was nonstop from that moment this this 83-year-old taxi cab commissioner then took a requested an Uber took it to the Mayflower hotel which you may remember from Elliot Spitzer Fame and had the press and the you know the DCTC enforcement agent there impounding the vehicle in front of the press um and it really became a just um like we were fighting for our jobs um and for what we had built and and what was clearly going well um and for the drivers and for everyone who was like suddenly in a really good situation who hadn't been just a couple months before and it was very clear to everyone like this thing was working um and it was working in this city it was working really well and we just you know fought for our lives for the next five six months well and and Travis had a keen understanding that every everything was precedent so if you lose in a market it's going to set the stage for every other Market to do the same thing and so DC just became this bellweather of both impact and crazy growth it was clearly taking over more than maybe you know maybe SF but it was clearly winning there and then you had this crazy regulatory front so it became the stage for what's going to happen with this thing is this going to work or not that's exactly right and and in a city where everyone is trained on dealing with regulatory yes everyone's kind of obsessed with the government everyone so it it also was like this is what everyone did does for a living right so it was it wasn't just top of mind for us I mean it was a you know daily weekly Washington Post level story and you know we I remember the first thing Travis said is like okay go hire a lawy laer and I was like I've never hired a lawyer like how do I hire a lawyer he's like go ask you know go find the best lawyer ask a bunch of questions and go figure it out and so that was obviously I had never done that before and that's one of many things like that and then fast forward to the middle of February so we finally get the the meeting with the DC C taxi cab commissioner and um Travis is on the phone um they didn't have actually a speaker phone in the office so I'm like my my iPhone is playing the role of speaker phone uh in in early 2012 the tech is not where it needs to be the tech is not where it needs to be but like speaker phones were pretty common place with the exception of the DC TC um and uh and so I point out the rule that says you know a sedan is a six sad I can probably still recite it six Fenger fewer um vehicle that's um you know that's dispatched um and on the basis of time and distance and so uh I was like but what about this rule uh they were like it's not allowed you can't charge on the base of time distance and um and the other thing just to point out is like all the complaints that cities had were like these silly things like why why can you not charge on time and distance why could you only charge on like of course you could charge on time limousines said this is an hour right or in Miami it would be like you need to request the car more than 45 minutes before it shows up even if it's around the corner and a meter in a meter is a time and distance yeah of course and these they're just all purely protectionist rules and um and so they were like consider that a typo I was like I'm not going to consider a typo we're going to keep going the law Is AO you're going to keep going exactly um and uh yeah and like that's what you know it was that that's what we were dealing with so I mean obviously you know for someone who doesn't have a ton of contact so I mean Uber X becomes an even more aggressive sort of is This legal what is great I mean how this was all Uber black this is all Uber black so this is regulated cars that they were all licensed they were all insured they were all licensed by the state right not individuals um I mean we're effectively a reservation system at that point exactly and a reservation and a A system that said you know it's based on how long the ride is and how far it goes and uh and you know then really over the course of that year it was a long negotiation to get that codified um into law but but to to your point about you know Travis's preci honestly on on the fact that this is all precedence um one point you know they wanted to put a a rule in place that said that Uber's minimum at the time was the minimum and that we couldn't drop below that and of course you know that would have totally changed the trajectory of ubx and um and even though it wasn't it didn't to me honestly didn't feel like okay that's a Gib we could make in theory um you know he was right because it would have totally changed the course of our ability to launch uberX our ability to to ultimately drop the price and and you know this feeling of like there's no why why should the government be telling us we have to keep our prices high like that shouldn't be what what they're doing and um yeah he was totally right yeah I mean his his ability to sort of see around corners when it came to to those things was unbelievable what was your probably core learning of because you worked really closely with Travis again he was this was the this was the basically the main event of regulatory with Uber black so he was involved heavily what's your kind of core learning of working with him so closely in in the regular in the regulatory days I mean I think one is just like he was maniacal about preparation um in a really important way like we would you know he would he would have us write like this is what we want this is what they want this is why we're this is why we're right um you know and and and scenario plan down to exactly what the arguments were going to be with um you know in a very very sort of rigorous and detailed way meticulous and detailed way and then I think this concept of everything being precedent making is super important and just you know not being willing to compromise on things that didn't feel like comp that that again felt like they weren't really compromises at the time yeah um he he he he was truly you know to your point could see around corners just as well as anyone and then I think just from a more macro perspective like being willing to cannibalize yourself and not being afraid of that was is just an amazing reminder lesson something I repeat constantly when when talking to Founders cuz like you know he wasn't he wasn't willing to give an inch and when lft came even though it would been you know there's an it's an easy MBA case study to say like keep prices high and you know try and get the higher margin product and you know he immediately pushed every one of us to the point where it was like uncomfortable to say what is that what is that right price how do we continue to make this a ailable to more and more people and you know and then while saying you know how do we make sure drivers are also um you know able to to make this work for them yeah it's a very hard needle to thread particularly the marketplace and the fact that he had I mean I never knew him to have sort of these principles written out but he was so right on they can't control our pricing they can't control how we charge you know ultimately we're going to have to go more lowend and serve more people I mean the fact that he knew all those things was just wild and I and I remember at the same time think we went to the I was at the transportation regulatory conference if you remember that in DC and I remember you know multiple times throughout that where I even said to him hey you know we could couldn't we just relent on this thing or yeah do we really need to like do another presentation for another regulator but he was just you know you don't give on certain things that are that you believe in that you believe should be all right and then you always engage you know you always have the conversation and you talk until they get it till they get it yeah and he had you know despite all the you know obviously all of the press and everything else like actually one of the deepest convictions of like right and wrong um and and it was that it was that unwillingness to say that honestly sometimes got us in trouble right yes where he wasn't a compromiser um by Nature um when he felt like something was what he was compromising on wasn't the right thing right when it wasn't it didn't have a logical justification so I mean to that point we're going to maybe jump around now but like like tipping was one of those yeah and I mean you were I think on on the executive team when tipping actually then it was so like that's an example of like how do you how do you think about tipping cuz he was very against tipping he thought that it should be built in and had incorrect incentives and and whatever else yeah I mean I think I think the piece that where I think Uber got into trouble when it came to sort of the impressions of of uber was for a long time we were we were the upstart right we were the little guy and we were perceived as such and then we suddenly had this like monster valuations coming in and amazing growth and and won a bunch of the regulatory fights right but I think to the outside world like we became the 70 billion doll Behemoth and it all happened so fast um that that tip between sort of being the disrupt and being the big guy we like missed the boat a little bit on on when the public perception of that happened versus I think when the emotional internal reality of that happened which was later um and there are things you can get away with and do as the sort of you know petulant uh little kid that look that don't play well when you are the 70 billion doll company but was there ever a scenario in which we could have made because it did happen so quickly yeah that is there a scenario in which that could have played out differently or was it almost inevitable because of the speed I think I think the hard thing was like what got us there was going to be what made the next stage hard yeah and I don't know I don't know that you could have changed much you know um and that the the transition was so fast right I think Uber was like the biggest company ever on QuickBooks and then like the first company ever on whatever the sap Oracle right but it takes like nine months to implement that and like we literally in that nine months had grown so much that there were a lot of things take human time and even things like culturally and um talent development and other things that just like take real like human calendar time um versus like the warp speed at which things were happening at Uber that were very hard to reconcile I mean speaking of warp speed you go from probably not managing very few people at Clorox or whatever you know pre Uber to a couple of people to then massive teams really really quickly and I think one of the things about you that I you know look up to and and admire is that everyone to a person says the best things about working underneath you and you you scaled these teams and you had all these groups and you worked on a lot of things I mean speaking about all these regulatory issues it's not like you had a a deep expertise and you know no offense but in a lot of these things but you scaled and you took on more and more what do you sort of attribute your ability to do that your ability to succeed your ability to tackle a lot of these different issues or projects or work streams that you probably didn't have much experience in and then also just scale these teams which you ended up doing you know really numerous times yeah I mean I think I mean I think it almost all comes down to like hiring the right people around you and and being willing you know finding the right like systems and processes where it's like trust but verify constantly um where you have to think about not where is the business today but like where is the business going to be in six months and like how do I how do I I'm not going to have the same level of you know knowing every single possible number as you know we knew when we manag one city when I'm managing um you know 15 or 50 or or more um but like what is the you know what is the Business Review processor how do I find like a strategy and planning person to help pull together you know the red yellow green stoplight version of this that can allow me to figure out what do I need to zero in on um but fundamentally like we had great people we were very you know I think very fortunate with the people we hired and then I think you know I think we did a good job of like not just rewarding and reward is even the wrong word here um outcomes but like thinking about what we could control right like sometimes the regulatory thing wouldn't go right um but like were we prepared did we have that Playbook had we done the the work the work um and you know you can I think there's a a an element of sort of confidence people can have in knowing like what they're going to be judged on is a lot of things that they control rather than a lot of things they don't and I think a lot of people get that wrong and that creates like a tremendous amount of stress because you know you don't you don't feel like you can control whether or not you're doing a good job for sure and I think that helped a lot and then I think the other thing was like being able to like one of the things I think was like a hack I Learned was you know Travis's mind moved so fast right like faster basically than almost anyone else I've ever been around and sometimes he would jump from like Aid acsy right and I think just saying like okay I got it we're doing right and we're going to do Q on the way but like walk me through how you got there and trying to kind of un unwrap like how he thought about things in a way where you started to understand like what are the building blocks not just like what do I need to do and like when you start understanding the building blocks of how someone thinks like you start being able to it's not even think like them cuz so it's not about doing what they what they would do but it it is about saying okay if we're not going to do that here's why right and I know this is where that building block is going and and then I think really as a as a manager also explaining that to the people you work with right like here's how I'm thinking about this problem and like let me scale my brain to as many people as possible really helps you have a lot more mini use around the organization um I think in a way that like we got a lot done yeah you need to decipher something from your boss and then also understand how they think about it and then figure out how to disseminate that information to your people yeah and you do serve that you need to be there because that message from that person to everybody else probably is not going to work so how do you sort of you know shift that and sometimes it's like you know as a manager particularly if you're not the CEO it's like it's a question of like you're a Civ and it's like how wide should the Civ be right versus how tight it should be and you know accolades should fall right through the Civ and criticism should be a lot tighter um and you know sometimes those criticisms are important but like let me then figure out how I'm going to communicate them um but like keep that Civ as wide as possible when like it's Kudos that are coming down totally and and we had I mean to your point on control you can control Uber also the metrics were clear we were so tight on leaderboards from the beginning it really was you had a good understanding in real time of what was happening with the business that's exactly right I mean I found it I found it like a deeply particularly on the Ops side like meritocratic organization because you literally had a a daily weekly hourly in some cases you know leaderboard of performance and of course there were sometimes there were things that you couldn't control about that you'd be like rain rain rain you know or like we can't have rain because I'm GNA get you know killed on on surge right or you know you I suddenly became a DC Sports Fan even though I'm actually not I'm a New York sports fan but like the impact of of you know the you know exactly was huge so it wasn't as though everything was it but but if you started to look at it over you know month monthly Trends you really could start to see who was doing a great job managing cities and who wasn't and um and that was you know there's so many jobs and you know it's now I'm in Venture it's like now I got to adjust to like a 10-year time frame just totally different from like the hourly time frame scoreboard we used to have but um that it Uber was very unique um in in regard to that that feedback loop um and how quick that cycle time was so you end up scaling all the way what was the peak number of markets that you ran I mean it was the whole US and Canada business so sometimes we call it a lot and sometimes exactly it was it was almost half the the revenue um of uber at the time wild you scale all the way to the leadership team you're on the leadership team during a tumultuous time yep how do you sort of think about that time looking back yeah no it was it was pretty brutal um you know I I often will describe it as like the best the best summer of learning that I never ever want to have happen again because you know we were it was both trying to figure out you know literally the exact level you know kind of who was going to be CEO of uber but also just how do you function um as a 15 person exec team as like a headless you know 15 person exec team like that was like the worst budget meeting I've ever been part of because like especially in a budget meeting like someone needs to be like you're cutting you're cool right and like instead we just went round and round I still remember where I was during that meeting but it was um you know just an amazing it was an amazing learning moment for me um and of course you know you go back and you rewind and you think about you know what could have been different or what if what if what if what if but um but ultimately obviously the company today is in a is in a great spot and um you know Dar deserves a ton of credit for that for sure and and the team um but it was it was very stressful what you're one of the unique people that worked closely with Travis and dar so little DK versus DK yeah what uh I mean they are so different um there even any like how do you think of like what are the similarities I mean they both have been CEO of uber um but and it stops there exactly no they're both they both have just completely different strengths You Know Travis is such a Bottoms Up thinker right like he sort of thinks from like from the most the smallest detail up to the big picture like d thinks the other way right he thinks big picture down and um D couldn't have built Uber to where it is I don't know if Travis would have scaled Uber who knows I mean in some ways I think I would love to see that play out um just because but you know but at this point I would love to be on the sidelines of that of that playing out but you know they both have such different strengths and I think like there is almost no one better at get building from nothing to something than Travis and it's because he can go so deep on things it's because he can get in the details it's because you know he can break apart a really complex problem into the smallest piece like almost instantly in any Arena but like D's ability to get a big group of people excited about a vision to you know to kind of be able now to have these kind of conversations at the like presidents of country level that that Uber is doing now like he is masterful and I just think the I mean the company is very very different I joined Uber because I wanted to work at a startup right at some point you wake up and I'm like I'm working at a 25,000 person public company not a startup that's not that wasn't you know and and you had I had gone on this learning kick like almost unlike any other I don't think I could have picked any other startup at that point and had this the learning trajectory I had so it's hard when that starts plateauing um and uh for me right and and and um you know that's ultimately why I was like I want a new challenge um and you know when you go from sort of like the adrenaline highs that we had it's hard to readjust um to a much more sane probably for everyone involved for many reasons existence but it's really we had you know I think we had something so special um and I think it's it's very hard to imagine being able to recreate that absolutely I I do want to get into that but before we do you ended up also running Uber's Mobility business what how do you think about Uber Eats so the ride business is obviously in one of the most successful core businesses ever yeah Uber Eats ends up being successful but there was a path it was Rocky y Mobility probably not so much or you know do you end up leading the acquisition of jump which was a big deal at the time how do you think about Mobility yeah now lime bird and then how do you think about secondary business lines you're you're you know you're deep in VC and all a successful company that's trying to launch it's not easy and we thought early days oh we'll be able to launch deliver anything and this and that and then it plays out and it it's harder than it seems totally so so Uber had just acquired jump um um I wasn't involved in the acquisition itself but but um sort of quickly um I think a couple things one um and you know another credit to DAR like I was like I just I want to turn back the clock like I had I I was running the US and Canada business I've been doing it for a while I was like I'll do this for you know six eight months more you know if if that's what makes sense for the business um I was coming back from attorney leave but like I just I I want to get closer to product and like I just I would love to turn back the clock and I remember as like a happen stance comment I made I was like like I would I would run jump you know like that would be fun bring it back and yeah roll back the clock I had done big I checked the Box on big what I hadn't done I hadn't done product related so that was kind of one one area I was interested in and um and I I wanted you know the beauty of being in the US and Canada role is like don't say this to Mac and Pierre but like it is the critical region um at least at the time and um so everyone's involved in everything you're doing and because it's in the US everyone's involved in everything you're doing and I was kind of like I wna you know I want ownership more ownership and I want I'm totally happy starting with something that is Tiny um so when Uber acquired jump I mean it was there was almost very little um they had had a very small business San Francisco very small business in DC and um but a very good uh Hardware product um and and Uber took um you know I think and we built out what I think was the right strategy um to win in this space and ultimately to make the unit Economics work which is actually investing in Hardware where uh it's not disposable Hardware um it's not off-the-shelf um you know off-the-shelf scooters um and and the beauty of kind of the whole model that we had built was the swappable battery and this concept that the battery could be swapped rather than the the bike or the scooter needing to come off the you know kind of come off the streets while it was charged um and you know after so I I had left and then the lime acquisition and then and then Co happened got it which killed the mobility business and then the the acquisition to Lime happened but lime has kept um you know really the hardware is the jump Hardware um that has kind of and lime's done pretty well um since then and uh and has kept you know more really has kept the iterating on the jump Hardware um and I think that strategy was the right strategy so I still would do that again I think one of the challenges we had that I don't think would would would have been as big a challenge today is remember the Uber app was like not designed to be a platform right and that was a constant tension uh we had actually I went with with d and and and some other folks Jason drogie and others um over to Singapore and um and Indonesia to see how grab cuz grab had actually done a much better job of really early on building out that full super app the super app concept um and Uber today has really much more of that that super app concept which makes the potential of new products possible but I was like arguing with like why should you know it' be like Uber X Uber black and I'm like no you should put my like bike or sco as you only could see three choices and um and it's really hard to justify that when that was the the concept and so I think um I think Uber's done a great job since in terms of like rethinking the app redesigning the app in a way that enables other products because otherwise it was the you know it really was a painful cannibalization argument you were making where you could have Uber black you could have Uber X and then you couldn't have Excel you couldn't have and it wasn't Dynamic right today it's Dynamic based on um what you use frequently yeah I mean Uber Eats starts as its own app like it's not even in the core Uber app you have to reacquire all those users exactly and at that time that was what it was like um and and you know when you're thinking about Transportation you're not like oh what I want to do is stay at home and eat you know so it's just a very different consideration set and even in the side there's a little bit of that but you're usually not like okay am I taking an XL or am I like hopping on a scooter um and and uh and so that transition I think needed to was was tough without that because we were we were fighting a lot up against the Core Business yeah I was just in Indonesia and I was using grab and you put in a destination and then it starts to try and sell you food from there you're like no I'm trying to go there I now Uber's done a great job of how it's designed it's clean yeah but it took a while so you end up having uh one of the best second acts I think of a lot of us I mean it's hard you kind of touched on it you're on this rocket ship it's one in a billion it's once in a generation whatever you want to call it it's hard to reinvent yourself and find success and also just feel good about what you're doing next and happy every day so tell us more about you know what you've been doing since Uber and and everything you know that you've been doing in the VC space yeah no um it really is hard and I think I was pretty keenly aware of that when I was leaving and and I think um if for me I really wanted to change the metrics of success because I think had I been comparing it you know my next startup to um the valuation did was the valuation going to increase as much it would have been a everything would have been a flop basically you know there's sure if I had picked like in hindsight we could have crypto Jerry yeah Jerry rigged right into the the those opportunities but um or if it had been like the growth in my role and and I think one of the things I learned from the jump experience as well is it's really tough to come in take over somebody else's baby um and so even coming in at a startup that had been established like with me coming in as a CEO or coo um I was like a little weary of um and so I really wanted to just completely change what is what is success looked like I want to use my brain in a totally different way um and you know kind of started to poke around a little bit on kind of what investing would look like um with just a you know really initially from this kind of belief of like you know eight and a half nine years at Uber is like 85 or 90 years of like any other startup experience and so how could I take that experience and like try and push it down to the next generation of companies that are trying to do what U did um and so that was really and I I really found those moments of of you know little moments of advising companies or working with companies like really rewarding because partially and it's like it was an chance for me to reflect on everything I had learned at Uber because it's really hard when you're going through those moments to to like actually sit back and reflect and be like God I've like learned so much in this um and I loved those those little opportunities when I had them and um my partner and co-founder at construct Dana graceon was a partner at at Nea and um you know and she had she and I had known each other pretty well um you know just kind of in a professional context for for a number of years and so you know she she was like hey would you ever think about joining you know co-founding a fund with me um um and she's like I'm thinking about doing this I think I'm going to do it like come on you know let's go uh let's go and I remember it's funny I remember a conversation I had with Austin um when I was like should I do this should I not should I do this and and she was like Rachel if you think back on the tenure of the time we've both had at at Uber like there are very few moments where you can leave and you're neither like leaving everyone on the field abandoning everyone on the field nor people seeming like you're getting pushed out and like you've got one of those moments like just go you know and um and of course in hind like in hindsight it really was cuz like eight weeks later was Co which then would have been like aband you know abandonment or like what are we going to do with the jump business that totally dried up and um and so you know in many ways there was kind of that that short window um she was right on um but you know for for me it was really I was excited about trying to kind of like think very differently about companies see startups in a totally different way and you know I had gotten glimpses of the investor side at Uber in in small pieces I'd gotten glimpses of the board side and kind of being on the exact team um as the company mature really saw that evolution and of course but had been at a company where I joined a seriesa company and I left a you know an IPO a company that iped and that's of course like every startup school um and so really having had that journey and being able to say okay how can I find like the next generation of Ubers um is is really exciting and then from a fun thesis perspective like everything we do is is like Tech meets the real world we call it foundational Industries we think of that as supply chain manufacturing you know Mobility being these areas but for all the reasons in 2011 you know people were like you're crazy to go join a taxi company I'm sure you heard the same thing right you're never going to get a venture breakout in these spaces it's slow moving it's high capex it's heavily regulated that's not where tech companies succeed and of course Uber broke that model and and for all those same reasons like there are still huge opportunities in these you know historically low Tech areas that frankly have missed mobile and cl you know Cloud not to mention like Ai and Next Generation tech and and I think especially now like these spaces have an opportunity like Leap Frog um ahead and and we spent we spent so much time um as a country like Outsourcing everything and thinking about compa you know comparative advantage that we like neglected um these huge areas of of of innovation at home and so you know it's been it's been really fun to also like see that kind of next set of of startups you also quickly realize like most most startups are not Uber um but um to get to kind of like work with Founders like from the beginning is is has been awesome and so we're um you know investing out of our second fund right now um about to about to close Fun three and um off the races yeah exactly fingers crossed they can't knock on wood yeah well it's so so cool to see and we'll make sure we Link in the notes to to your firm and for people that are looking for interesting things they want to do in the real world you're the perfect person to beol them and one of the most fun things is like there were so many awesome people at Uber yeah that are doing like we have a whole bunch of EX Uber um ex u f F who understand these spaces who have been part of scaling something who have had that really distributed model and um like that's the best part amazing well you were the best thank you so much for doing this thank you Max and uh excited to get this live love it all right thanks see you
How Rachel Holt Helped Fight for Ridesharing in DC and beyond | Early Podcast Ep. 7 Recorded in person, in New York City! In this episode of Early, Max Crowley sits down with Rachel Holt — one of the earliest and most impactful operators at Uber and one of the company's first General Managers. Rachel shares never-before-heard stories from the company’s early days, including regulatory showdowns in D.C., the launch playbook, hiring her first team, and what it was like working directly with Travis Kalanick during Uber’s most high-stakes moments. 👀 What you’ll hear: • The viral tweet that triggered a taxi war in Washington D.C. • The 83-year-old cab commissioner who ordered an Uber… and had it impounded on the spot • Rachel’s journey from Stanford MBA to General Manager of the U.S. and Canada • How Uber scaled with humans first—and product second • Lessons from Travis and Dara on leadership, pressure, and building generational companies • Why Rachel left Uber and co-founded Construct Capital to back the next wave of real-world tech founders If you’ve ever wondered what it really looked like inside Uber during hyper-growth, this is the episode for you. #EarlyPodcast #Startups #Entrepreneurship #Uber #Founders #TechStartups #StartupStories #Podcast #EarlyPod -- 🎧 Listen to the full episode: 🔹 Spotify: https://open.spotify.com/show/13dcsmz27cQ4LZUHxJY1n4 🔹 Apple Podcasts: https://earlypod.com/apple 🚀 New episodes drop every Tuesday. Let’s build this together. 👉 Like, subscribe, and drop a comment — we want to hear from you!! 📩 Thoughts or guest ideas? Email me: max@earlypod.com 📱 Follow for daily updates: • 🐦 X (Twitter): https://earlypod.com/x • ✨ TikTok: https://www.earlypod/tt • 📸 Instagram: https://www.earlypod/ig • 💼 LinkedIn: https://www.earlypod/li • 📩 Newsletter: https://earlypod.com/subscribe