Uber's leadership lessons, AI's disruption, and the power of solo founders with Josh Mohrer | E1911

0:00This whole thing is, I've done all of it. and I have a lot of pride in that. And part of this, of thinking that this is even feasible and really why I reached out is that you have talked about this of like era of the solopreneur and it could be, you know, there were always brilliant engineer types who would then dabble in the marketing side and put together their own thing. I don't think there's a lot of examples of a marketing or like business side exec. Growth exec. Yeah, doing the code. No, this is going to be the revolution. This Week in Startups is brought to you by LinkedIn Jobs. A business is only as strong as its people and every hire matters.

0:37Post your first job for free at linkedin.com slash twist. Squarespace. Turn your idea into a new website. Go to squarespace.com slash twist for a free trial. When you are ready to launch, use offer code twist to save 10 % off your first purchase of a website or domain. and northwest registered agent will form your company fast give you the documents you need to open a business bank account and more visit northwest registered agent.com slash twist to get a 60 discount on your next llc all right everybody welcome back to this week in startups we have an incredible show for you today i met josh more gosh 15 years ago maybe when he was the first, I believe, GM of Uber in New York City, which was in the first five cities, I think Travis launched and the team over there.

1:39He's moved on and become an angel investor, run a syndicate. And today we're going to talk about his new AI startup, which is inspired by this meme that's been going around. Who's going to build the first unicorn with one or two employees? Welcome to the program, Josh. Thank you so much. It's great to be here. Yeah. So you were the first GM of New York City, correct? Yeah. So Travis expanded outside of San Francisco. New York was the first spot. And how that would typically work when they were expanding is launchers would go to a city and sort of set up the basic thing there, get the first few drivers, get the first few riders, set up some infrastructure, and then hire a GM.

2:22I was actually, I was in there within the first year. there was a team of three who were brought on right before me and it didn't really work out and all three of them left and they hired a fresh group of three at the end of 2011 and I was the GM from that point on. And I heard I don't know if this is true so I'm not trying to take any credit here but at some point Travis had told me the Chicago LA and New York heads had all seen him on this week in startups that famous episode from 12 or 13 years ago

2:55startups episode and that's how you became aware my awareness of uber was actually so i used it when they when they really first launched here which was like you know spring summer 2011 i tried it out i thought it was cool at the time i was in an e-commerce marketing and ops role i had a bunch of those over the years and frankly i just tried uber and thought it was it was really neat and uh actually the the first time i tried using it was for an airport run at like 4 4 a.m or so and it actually didn't work. I tried to request a car. There were no vehicles available. I didn't think much of it. But later that day, I got a note from them saying, Hey, we saw you tried to use Uber and it didn't work.

3:33Here's 10 bucks for the next time. Even though that feels like a typical interaction now, at the time, it did not feel typical at all. It was amazing. I didn't even use Uber. I just opened the app. I looked. I didn't see any cars. I didn't use it. So that was cool. I was like, okay, there's something interesting here. And then a friend of mine, you know, five months later was like, hey, they're looking for a GM. The job listing was really exciting. It was like unlimited SUV rides. You'll ride around like a European diplomat. And it was just like, at that point, I think, um, like startup equity, you know, employee equity, all that stuff was really not on my radar.

4:12Like I wasn't really educated on that. I was more after something that I knew I would enjoy. I was very interested in an opportunity to sort of be the head of something of kind of like a startup within a startup. And it just sounded like something I would really love coming into work every day. And that is what it was. And so when I applied, I didn't know who Travis was. I knew who Ryan Graves was. When I got to San Francisco, I met Travis, of course. And that night, like in the, you know, like after that experience, I looked him up and tried to learn everything I could about him. And that is when I saw you do your due diligence.

4:49Got it. You know, what I found about Travis is that, you know, right away I got to know him. I I've, I've probably spoken to him on the phone. Um, you know, while I was in the role there, we probably had a hundred phone calls over the five years, maybe a little more zero of them were scheduled. This is a guy who is, who is so, uh, dialed in on the details of everything under him. You know, So there was that aspect of his leadership and also that he really encouraged me to be me and be myself and kind of lean into the way I am and kind of my intensity and the way I go about doing things. He made me feel really good about that.

5:28And so it was a really, really amazing experience. So even though he wasn't totally on my radar when I got there, he was my boss and we spoke all the time and it was a real pleasure. So a lot has been made about his management style and this distributed management style. So putting aside press nonsense, but just looking at from the inside, this distributed leadership architecture that he set up, which I think most people would probably think he's doing a cloud kitchens right now. Who knows, since he doesn't talk about it, and it's very much under the radar. But maybe you could talk about how the edges and individuals had a lot of autonomy.

6:06And then just generally, what was his management style like? Yeah, it was in some ways like remote before there was remote, because most of the employees at Uber were not in the San Francisco office. New York was like a hub. I mean, we had a big office by the end, but it grew more slowly than Uber globally. And so it always had a tight feel. And so I think maintaining the startup feeling on the city level was part of it. And really finding a GM in each place who can be like mini CEO is the way he would talk about it at the time and really represent him and represent Uber when he couldn't be there.

6:44So a big part of the job, particularly after the first little while, was dealing with regulators, dealing with the press, a lot of kind of local things. So I think it took a lot of trust. They spent a lot of time finding the right person. I would like to think that in New York, they probably had a lot of options. I think in Minneapolis, they probably have fewer. As we sort of went down to the smaller cities, it became harder and harder to find those people. But the GM crew, I think, because it was really the best they could find in every city, made for a pretty special group. And the folks that I'm still in touch with from Uber, many of them were GMs alongside me in those early days.

7:20Yeah. So we'll get to your new app in just a moment. one or two more questions uh new york was uh one of the most vibrant and challenging markets uh if my memory serves me correctly and i remember one day talking to travis because i see the headline uh de blasio is going to cap the number of ubers and i said hey dk what are we going to do here and uh he said i'll wait for it and he sent me like a screenshot of something and it was de blasio's phone number yeah the de blasio view right the de blasio view so explain and de blasio i think it turned out worst mayor in new york history since dinkins and that's a pretty low benchmark to hit i love talking to new yorkers well no i mean de blasio was an incompetent fool you know uh you know who you're talking to explain the de blasio relationship and explain your reaction and where did this idea come from and when travis says hey i'm assuming travis came up with this idea or whoever came up with it you are the gm did you come up with that idea and then how did this go over internally externally take us to that moment yeah so if i'm just gonna i just want to set the the scene i'll spend like less than a minute on this but what you have to know about about uber new york both in the beginning and still now is that it runs actually a a fundamentally different business than what uber does now everywhere else which i would call like ride sharing.

8:47Ride sharing being I have excess capacity in my car a few hours a day or a few hours a week or really whenever I want and I'll turn on the app and it'll be great. In New York, that system doesn't actually exist. It is the black car system set up by Ed Koch, who was mayor before Dickens. And this was in the 1980s where, you know, taxis were great for Manhattan, but they needed a system that would work both for kind of executives who wanted pickups at their office, but also folks like us who grew up in the boroughs. And so Uber has always operated within an infrastructure and a rule system that has existed for decades.

9:28It was not, it never tried to do the ride sharing, which was the true innovation of Uber. It never tried that in New York. So as a result, from the very beginning, we were kind of, at least from the regulator's standpoint, we were kind of like good little kids who filled out all the forms right and were kind of more responsive to them maybe than the average car base owner that was sort of operating in that system at the time so it was never the regulators that had a problem it was the politicians so there was a few different attempts de blasio's first attempt was in like early 2015 to try to pass rules that said the city had a right to review app updates right like that's a crazy one we definitely don't want them to look at code you know um eventually they sort of figured out the way to do it was to limit the growth of supply so not let any new drivers join the taxi limousine system uh that would then join uber and so it was sort of saying no more supply and the the challenge with this is that it's actually a death sentence but it's very hard to make people out in the world understand that.

10:35So at this point, we're getting 25 ,000 new riders every week. We're loading a thousand new drivers every week. We are really going for it. And this law comes out, this is roughly a proposed law in July of 2015 saying no more new cars. And I think to the casual observer that was like, okay, well, what's the big deal about that? You have a great business already. It's already quite large. You'll just stop adding cars for a bit, the sort of nuanced people didn't get, and I'll get to the thing that you asked about in a second, is that actually, if you reduce supply, the system becomes unreliable, and no one will want to use it anymore.

11:13We have to add supply to keep up with demand. So the winning, and we did a bunch of things. We tried to explain it in all different ways. The winning idea came from someone on the comms team who was stationed in New York, and her idea was to have a de Blasio view. So at this point in the app, you'd sort of have a little slider at the bottom that you would choose UberX, Uber black, whatever. And there was one for de Blasio and you would go to the de Blasio view and it would be all the cars on the map would disappear. And it would say ETA 15 minutes. Because we sort of just thought, you know, the ETAs at that point were like two minutes.

11:46And that is actually what would happen. It would make a lot of surge pricing, the price would go up, ETAs would go down, it would make the system unreliable. And the whole premise of Uber is a a reliable ride, you know, at that. Right. And so it was a big deal. And it was like, you know, 21 days in July that were probably the most intense of my, of my working life. And it was like going on CNBC every day, talking to the like newspapers every day, getting them on board. And it was not just me. There was like 50 people who worked really hard to get this done. And I think we just made the case and we won.

12:21Like they pulled it back. They would end up returning in 2018 under a different type of Uber with no Travis, with no me, with no a lot of people. And then they would actually get through some version of those rules. But in the three years between those, I mean, it's a game changer. I think they probably 10x in those three years. So, you know. Okay, let me cut to the chase right now because I know you're busy and everyone is hiring right now. And, you know, it's a lot of competition for the best candidates, right? Every position counts. market's starting to come back, you need to get the perfect person.

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13:56They just roll in. And guess what? First one's on us. Call to action. Very simple. LinkedIn.com slash T-W-I-S-T. LinkedIn.com slash twist. That'll get you your first job posting for free on your boy, J-Cal. Terms and conditions do apply. When you look at the recent performance, the question was always, uh can uber ever be profitable is it always going to be unprofitable and you're smiling i'm smiling because in the beginning people don't know the lincoln town car business was wildly profitable yeah uber x well we're going down market we're trying to get more people to download the app yeah so there were some incentives and yeah you're in a dog fight to get drivers so yeah you want to give them an extra hundred bucks if they hit x number of rides but it was very clear that once the habit was formed it didn't matter if an uber was eight nine ten or eleven dollars to ninety whatever percent of consumers yeah i think that's right i mean i'm obviously so happy for the folks there now and for dara and for anyone smart enough to still be holding shares which uh admittedly i am not but yeah i mean i think they kind of worked it out um and it's really wonderful to see.

15:08And I use Uber a lot here and it's great. It works great. And I don't notice the few bucks. And a lot of, you know, here, the unit economics, even though we call it UberX because it's that licensed scheme that I talked about earlier and not ride share and Uber is not doing their like excess insurance umbrella because it's not ride share and the drivers are by and large full-time guys. The unit economics are very different in New York. And like New York has always been a pretty good business, just like structurally. But in the ride share places where the competition with Lyft and others was particularly aggressive, it wasn't making much money.

15:44I think it was always sort of like, structurally, this can make money, we are choosing not to now. So I never really believed like, it'll never be profitable. It's like there's profit on every ride. It is how Uber chooses to spend that, that will change the direction. Yeah, it was just so weird to see journalists pile on and just even CNBC talking as I remember was on with deirdre bosa or something at some point i just i said to her deirdre they did a billion rides this is when like we're at a billion rides a year or something i said i did a billion rides lost a billion dollars whatever it is or you know lost four billion dollars uh you rate you do two billion rides next year you raise the price is two dollars all of a sudden you know this thing is going to be a money printing machine and of course here we are they raise the prices you know whatever 20 30 percent you get the economies of scale and here we are and then lift of course you know being incompetent um you know it was always the greatest gift i think uber ever had yeah i mean they weren't always incompetent and i don't pay attention that much but i read like headlines about a misspeak on an earnings call like that sent the stock soaring and then back down to it like that's like pretty much and perhaps indicative of general things going on there but i really have no idea yeah no i just i and then finally surge pricing you see it's coming to wendy's finally you can get a chicken sandwich for twice as much but not wait in line i mean i don't know i don't know if you've seen this but they're like in buses in new york on the side of buses it'll be like this bus never has search pricing and like in taxis the taxi screens will say never have search pricing it like became such a flashpoint um and i think like you know i think we probably could have done a better job explaining it i think what someone said to me the problem with you uber people is you think everyone has a degree in math and economics and i think like there is some degree of fair to that we were talking to people the way we wanted to be spoken to and i think particularly in those very early years you know new year's eve we would do like a math equation on the thing and people are drunk and they're like you uber guys i don't know what you're talking about but i'm going to do it and then get charged a couple hundred bucks or something they thought would cost 20 bucks like you can understand why people were pissed And I think it took a couple of years of iterating, but I do think particularly when we just show you the rate in the beginning, this ride will cost$80.

17:59Do you want it? That's probably the end point. That's the best way to do it. But it's a thing that people just weren't used to, but are used to it, whether they realize it or not. And things like airfare and hotels and restaurants on Valentine's Day and all these sorts of things. And Taylor Swift tickets. And StubHub generally. I don't think I've bought a ticket at face value despite my best efforts in years. I mean, it's perma. Right now, we're on perma surge pricing for tickets. That cartel has just destroyed it all. Are your kids into Olivia Rodrigo? No. They're not particularly into any specific artists.

18:35I mean, it was impossible to get tickets for that. Yeah. My 14-year-old's really into Billy Joel. So, it was like my favorite artist growing up or one of them, Dire Straits, Billy Joel, Bob Dylan. Every month, he's doing a gig at the Garden. I know. and he's going to end his thing in july i think so i'm going to try to take her to one of the final shows and definitely should if anybody in my audience knows billy joe or his like non-profit or something i got to do like a couple of donations a year anyway somebody put me in touch with that i would just love to introduce him to my daughter and be a hero and just say thank you to him for 30 seconds take a quick selfie and get the hell out of there but maybe i could you know donate to his he's got to have a charity for something i thought you've gotten good dad stuff over the years like for the kids they probably think you're all right you know my daughter my daughters think i'm cool yeah they also make fun of me because of the podcast they're like oh you're doing your podcast right and so i started doing a daddy daughter podcast with my two eight-year-olds um yeah it's pretty funny if you can find the daddy daughter podcast there's one episode out on spotify right now but i haven't tweeted it or anything i just put it out there just to i'll tell my kids that or i'll be buying a second and third you know microphone pretty soon you know what my philosophy of the debt for the daddy daughter podcast was to just take out my phone put on the voice recorder and then ask them about one topic school being twins food whatever and then i just hold the iphone towards whoever's talking and i'm like training them to not over talk over each other and it's great all right listen you are watching this ai uh craziness happen you've worked at one of the great startups uh in history and you decide i want to create my own startup but i want to do it with this i want to actually write the code or be the developer and you emailed me and I was like, well, that's rad.

20:15Yeah, build the product yourself. Cool. So why don't you tell us a little bit about your philosophy of building this startup wave and AI note-taking app and then just show it to us. Yeah, sure. I mean, I've always been developer adjacent. No one's ever paid me to code before, but working at startups, particularly in like e-commerce, not like a little bit at Uber, but mostly the other jobs that I've kind of done over the years, I've been near engineers. years. And I think I've always had a bit of a, like, envy. And the reason for that is, I always felt like they are the ones with their hands on the thing doing the thing.

20:50And particularly in startups, and there's not that many people, and everyone is rather self driven, there's decision making there about what to build, how to build it that I always have kind of envy, like I can weigh in, I can write a memo, whatever. But actually doing it, you know, is a different thing. And so I've taken a bunch of like, you know, Udemy classes, like YouTube things over the years. And I've had little like little increments of getting somewhere, but really never actually getting there. It's a cliche, but when chat GPT, the very first one, the sort of original in like November, 2022 came out.

21:24The first thing I started doing is asking questions about about the code, like, hey, I'm trying to make a website in Next.js. How does this work and found that it was a very, it really worked well for me as like a question and answer. How does this work? How do I do it? and it'll answer right away. A bunch of questions I was probably asking to engineers that I worked with, maybe one a day or one a week. Now I can do like one a minute and just start like really mainlining information. And not only that, but I also found that it actually could help me write the code itself. Like not just teach me, but actually pair with me and I can kind of guide it.

21:58Engineering is taking a problem and breaking it up into the tiniest increments and solving each increment and putting it together. And so it was sort of like, okay, this thing can help me like build magical things. And so I'll put a pin in that, you know, for, for one second, like around this time, you know, AI, it's a big AI moment. I was kind of like into deep learning and learning about that five or 10 years ago. It's, and I always sort of thought it would, like, they'll never actually call this AI it's deeper. But anyway, like AI is the thing in this AI era. I found there's sort of all these demos coming out all the time, very cool demos, but there's many of them or most of them are either web-based or they're sort of demo-ish in nature like install this docker container and then run this like python script and then it'll do the magic thing there's like all these ways to like very sort of artificially generate the like magic in an environment but like i i believe that life's most important moments happen away from your desk and that most normals are not at a computer all day and they're not on twitter and reading about AI and trying the demos.

23:06And it's like, what is the AI that my 70 year old dad is going to use, you know? And so there is no, and similarly, there's no shortage of ways, even then, but especially now, there's no shortage of ways to record your zoom and record your meet and record your, your, you know, hangout and teams and all this, but like just very little for the real world. That's more than just a demo, a proof of concept. I'm like, what, what would it look like if I made an audio recording app and just got feedback and just started adding features that people say and sort of intuiting things like, huh, it seems like if I do all the transcription on the phone, it'll take too long.

23:46What do I do? Oh, servers. I didn't really know about that. I knew the word, but I didn't really know how it worked. Oh, cloud functions. I'll learn how to do that. So it's sort of been like a walkabout of trying to figure stuff out with brute force. I have two kids. I have a semi-busy life with them. I love working remotely. And so the idea was like, okay, wouldn't it be fun to just see how far can I get this on my own? Without hiring, I could easily drive this off the rails, hire a bunch of people, maybe raise money, maybe not, do a whole thing. But what about just tying my hands and just saying, I'll only do what I can do personally.

24:25And so I made a few different little mini apps. And this is the one that people were interested in. I think the real clicking point for me was when my dad brought it to a doctor's appointment and recorded it, and then got a summary of what was discussed. And that was much deeper, just in the moment, things happen, and it's good to record. And so yeah, it was like, okay, let me do audio recording. And then I added phone calls. So you can make a phone call through the app, and it records the phone call. Or maybe I'll import podcast. I can import you into the app and get a summary there. Like, okay, people want to share out of the app.

24:58How should we do it? We'll share it in Notion and we'll share it like a web URL. And it just sort of like, really just kind of having a good time. And I like to say like, skyscrapers look like holes in the ground for a very long time. And then suddenly they start to shoot up. And not that this will be a skyscraper, but I have found like, it started really small. And people in my life were like, oh, it's Josh's little like retirement project. I was like, well, actually, like I'm taking this really seriously and I'm working full time on it. And people who live with me know that I'm like going Josh Moore style on this.

25:29Like I'm just turning it up to 12 and like hammering on this until it's good enough. And found some friends who would humor me and like try it and just sort of polish and polish and, you know, rebuild and rebuild and rebuild until it kind of, it kind of works. And now it's the subscriber volume is like roughly doubling every month. It's really kind of insane and the most exciting thing I think I've ever done, even more than Uber, because it's like it's just me. It's like me versus the world. And I have all these customers. And if they chat in the app, it goes to my phone. It's just like a very there is for the first time nothing standing between me and consumers of the thing that I'm building.

26:07And that is for me at this point in my life, a very good feeling and something that I'm really enjoying. Martin Scorsese makes gorgeous movies. Squarespace makes gorgeous websites. So it's not really a shocker that Squarespace convinced Scorsese to direct their recent Super Bowl ad, which you can see on the video right now, or you can go ahead and Google it or look for it on YouTube. Squarespace is known for helping people build beautiful websites, but it's become so much more than that. Now you can build or sell anything and your Squarespace experience is powered by AI. Squarespace AI can instantly generate content for website text, email campaigns, and more.

26:45Think about how much time that's going to save you. Squarespace also recently extended its bio sites platform, you know, those Lincoln bio sites, they've always been pretty boring. But now you can build them beautifully with Squarespace. Yes, bio sites. So here's your call to action. Check out squarespace.com slash twist to get a free trial. And when you're ready to launch, go to squarespace.com slash twist to get 10 % off your first website or domain purchase. That's squarespace.com slash twist. Let's demo it. Let's take a look at what you built here. Yeah. And if you're listening at home and not seeing the video, basically, you're looking at a screen that says all recordings, all waves, and each row is sort of like in a traditional Apple style with summary.

27:24So I'll just start to record. And this could be I am doing a brain dump, or I'm in a meeting, I actually in preparation for this podcast, I was taking a walk somewhere and I recorded about 10 minutes of myself giving my bio. And then at the end, got a summary of that and sent it over to you guys. So I've been speaking for about, it'll be almost about 30 seconds. If you're watching the video, you see like an indicator or wave that there is sound coming out. And when I'm done, I'll just press stop and it'll transcribe this in the cloud rather quickly. And then it will summarize it. And so there is the transcription right there.

28:04And then we'll probably have a summary in about 10 or 15 seconds. This will be like GPT-4 style. So it's up. the speaker discusses their use of recording feature, possibly within an app or device, or capture their thoughts or conduct a brain dump. The summary goes on a bit. It's on the screen now if you want to check out the video. But that was a 20 second, then I can listen to it. I can share it either in a URL or a notion, or I can do some changes to the format, or I could even change the language. Let's say I want to send this to someone in Italian. It'll reprocess the summary and transcription in a you know in italian so uh you know um what are people using this for uh it is a lot of meetings meetings not on zoom but sort of in their office i have a guy recording all his sermons at church so here is the summary that i just did a second ago in uh it's in italian now if that's useful so um that's it and basically just to give you uh some call idea seems like the killer one is that what people are buying it for because i know sometimes you want to record a call and you know you just want to make a quick phone call record it and share it um and then obviously depending on the state you're in could be two-party consent could be one-party consent i remember in new york as a journalist i believe it was one-party consent so we could record calls without a problem yeah i mean we're talking to people yeah and look it should go without saying that anyone using this anywhere should be be aware of the local laws and it is not intended to be a secret.

29:38So for recording phone calls, you know, you can't actually, like in the phone app, if you're using the phone app on your iPhone, there isn't actually a way to record a phone call. So what this does is it's a redirect. First, you basically verify your phone number, so that we know that it's you and then you make a call through the app. And what that does is it calls you first, you pick up and it says now connecting, and it called the other recipient with your phone number as the ID. So to them, it feels like a normal phone call. And to you, they redirect. The phone feature is a big one. It's not most of the action.

30:16I think it's poorly marketed and frankly, a bit clunky. People will make a phone call and then press the red button. And why not? The red button is right there. So there's like... And then they'll stop the call by hitting the red button. That's right. They'll kind of screwed up. So I'm doing roughly at this point about 15 ,000 minutes a day. And I'd say, you know, 500 of them are phone minutes. And that's so it's still pretty small, but it is growing as a segment faster than the than the overall thing. So it's sort of like when we started Uber X, like, you know, we're still we still love the main Uber, but we introduced something new because people might want to try that.