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When did making plans get this complicated? It's time to streamline with WhatsApp, the secure messaging app that brings the whole group together. Use polls to settle dinner plans, send event invites and pin messages so no one forgets mom 60th and never miss a meme or milestone. All protected with end to end encryption. It's time for WhatsApp message privately with everyone. Learn more at WhatsApp.com welcome back to Infamous Everybody, a Sony Music Entertainment and Campside Media podcast. I'm Vanessa Grigoriadis.
B
I'm Natalie Ropamed.
A
And we are here today to discuss a company that has become synonymous with urban luxury, I would say, and also urban taking advantage of people who only can work as gig laborers. And that would be the company called Uber. Now, I probably started using Uber, I don't know, four years ago, I guess I would say. And at first, the idea of getting into a car with a strange person, often a man, was really foreign to me. I mean, I just couldn't believe I was doing this. Like I was putting myself in what felt to me a little bit like being in harm's way. But over time, obviously, the convenience just trumps any concern over danger. Or does this guy really have a license? Or is it actually the man driving the cab that I see on my photo here? Or did he somehow barter his license on the black market? I mean, there's so many things that go on in the underbelly of Uber, in addition to the company itself, which has had a rise and a fall and a rise again, and in a lot of ways still, I think, has a lot of the DNA of its original founder, Travis Kalanick, who is, you know, your typical Silicon Valley guy, once held the world's second highest score for the Nintendo Wii tennis video game. He paces so much that his dad once said that he wore a hole in the carpeting on the floor. If you've never heard this before, Amazon actually has these 14 principles for leadership, which is, you know, all curiosity and being open, having backbone, but at the same time accepting it when everybody in the boardroom says you're wrong. And Travis's values were things like always be hustling or super pumped. And that is actually the title of the book about Uber that Mike Isaac wrote. That is excellent. Everybody should go out and read it. It was the basis for a limited series on Showtime that was also called Super Pump, about this bizarre character.
C
How sticky is it really? If someone rides twice, we have him for life.
A
So today we're here to talk about Uber. Is it a good company? Is it a dangerous company? There's been a big news break about sexual assault in Ubers, which was very upsetting and destabilizing to me. I don't know if you guys have read that on the news recently, so we'll get into that as well. But we're going to start from the beginning and talk about who is this and what is this company that many of us have interacted with on a late night, at a dinner, whatever, in a different city and you just jump into somebody's car. So welcome, Mike. Thank you so much for being here.
C
Thank you. Thanks for having me.
A
So tell me how you got interested in Uber.
C
Yeah, so. Oh, gosh. Actually it probably goes back to my beginnings in tech journalism. I was out in the bay area in 2010, Uber was just taking off. They had called it Uber Cab, actually. And weirdly enough, one of the women I went to college with, we were both English majors, she joined this startup called Uber Cab and she's like, hey, this is blowing up. But I wrote it off and didn't really think about it until it really became this thing in San Francisco where people were just super into it. You know, we're not like New York out here. Basically, there's not cabs anywhere. And even if you call a cab to get somewhere, it's 50, 50 shot, it will show. So this was also around the time iPhone was out. And I think this idea of I can use my smartphone to call a cab from anywhere was a really big moment at the time.
A
And of course I was recently in California and saw the waymos the self driving taxis, which I couldn't believe. I was like, is that one? Oh my God, there's nobody inside there. And I still have to wrap my head around, okay, this is safer than a human being driving it. It would be fine if I called this and it came to pick me up, but I mean, I'm still grappling with the human being. I don't. But tell me more about Travis. So he grew up in la, right? And he was, I guess, relatively well to do. He ran track, he played football, he got good grades, but he famously was very bullied. Is that the case? Is that true? Is that where he got his poop listic nature?
C
Yeah, I think this is one of these things where I often see it a lot in these founder types who go on to create these huge companies is they have a chip on their shoulder. You know, they were a little bit different or they were not necessarily like falling in line with all their classmates or whatever. And Travis was very much that. He was definitely smart from people I spoke to, like, super sharp. He was super into math and in the weeds. This one story I had was he would sell, I don't know if you remember, like Cutco knives, like door to door knife salesmans, basically.
A
Oh, I don't like people who would come and say, 35 bucks, you can have this set.
C
Here's a suitcase of knives. Exactly. That feels like ancient history now, in the age of one click buying on my phone or whatever. But he was a great door to door salesman. He sold a bunch of knives because of his persistence. And I think this spoke to kind of the intensity of the guy from a real young age. And you know, his parents were like, oh my gosh, this. This kid is intense. But I think that, that and his sort of embrace of entrepreneurialism and growing up to be hyper competitive in everything he did, which, you know, includes what you said before, playing Wii tennis and getting to the top of that, that just kind of characterized him, I think, from a very young age and into startup land.
A
And he essentially has these two startups that don't really work for him. And then he moves in with his parents. And supposedly the origin story is he was trying to hail a cab with his friend one night in Paris and they couldn't find anything. And they said, we've got to fix this. We're Silicon Valley entrepreneurs. Is that true?
C
That was my favorite sort of apocryphal bit of storytelling backwards. You know, we were thinking on the Eiffel Tower, how we could build the next billion dollar unicorn or whatever. Like, I do, I really do love that. Like, these look, a lot of these guys love to do myth making and think about how can we look backwards and make a founding story more romantic? And the reality of it was, first of all, Travis was not the guy who actually founded the company. They brought him in a little bit later, But a guy named Garrett Camp, he was also going through this period where he's like, I can't get a cab anywhere. I'm having to hire private cars everywhere because he's a rich guy in San Francisco, so he could do that. And that was the spark. But he also didn't want to run the company, which is why he later brought in Travis. Basically, ever since the very beginning, from the first time I had the idea. Well, from. From when Garrett Camp and I had the idea, I bet we were in Paris at the top of the Eiffel Tower. And I remember it just Came to me in a burst. I saw a way to upend the wage slavery of the taxi business. You know, to democratize the entire industry for the good of those who hardworking drivers as well as for the passengers.
A
I got it. So it's a little like Elon with PayPal. Like he says it was all his idea, but it wasn't necessarily.
D
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A
I remember the time that he was having a huge fight with the New York City cab establishment, which, by the way, is not like, a really awesome group. I mean, these people sell the taxi medallions for, right? Like an inflated amount of money. Cabbies were not making that much. It's sort of a sad existence to be in New York City traffic all day. It's just really not fun.
C
Totally.
A
So he said we should have realized sooner that we are running a political. And the candidate is Uber and the opponent is named Taxi, and nobody likes him. He's not a nice character, but he's so woven into the political machinery and fabric that a lot of people owe him favors. So really, you did have a case of Uber, this Silicon Valley upstart coming in and unseating one of the most important urban New York institutions. Can you talk a little bit about that fight?
C
Yeah, 100%. When I joined the Times in 2014, I moved to New York from San Francisco. And this was right as Uber was really making its huge push into New York, as well as Lyft, the competitor basically, that they had that was small but growing. And I just remember thinking, like, there's no way, like, why would this work here? Everyone's got cabs. There's cabs everywhere. This is like an institution in this city. This is never going to work. I mean, look, I was wrong. Like, very clearly I was wrong as well as not just in New York expanding to basically every other market where cabs had been saturated. And I think it was this thing that kind of goes back to what we were talking about. First, let's take the sort of obvious, difficult positions that the laborers are in, because I do think that's a very valid point. But I think on the consumer side, there are things that people didn't like about cabs at the time. Could they hail them? Are they going to be rejected if they want to go to Brooklyn or something? Right. If they're in Manhattan, those were, like, things that I think bothered New Yorkers. And the idea that you could instantly click a button and have it show up or whatever resonated faster with people than I even suspected it would, basically. And so exactly where you said this fight with the taxi unions, which really did control New York, was knockdown, drag out, was one of these things where they were Tight with politicians, tight with the city. It was not an easy fight, and it was really a street fight, honestly.
B
Yeah, I mean, you mentioned Lyft. We should talk about Lyft for a second. So Lyft was the Uber competitor. I think at one point, Travis called Lyft an Uber clone on Twitter or something like that. But I remember taking Lyfts back in San Francisco, I think in 2014. They had these pink mustaches on the front. They were the cute, cuddly competitor, and they were fun and friendly and the drivers were really nice. But Uber was really fighting the cabs on both of their behalfs, is how I see it. And Uber was the very cutthroat business, almost black car exec, kind of luxury brand, I guess.
C
Yeah, no, 100%. You know, it's kind of hard to remember now, but at the time, Uber was the dominant player. Lyft was coming up, but they were smaller. Uber was the bigger company, the one willing to fight really dirty and kind of doing a lot of the fighting on behalf of both of the companies. And so because Uber was so deep pocketed, they hired political operatives. They hired Obama's former top political digital guy, David Plouffe. So it was weird. Like they were kind of frenemies with Lyft, mostly enemies, but also aligned in the sense that they both wanted regulations overturned to break into this market.
B
And it's a pretty similar story to Airbnb, which went through a similar fight with regulators in various cities, New York being one of them. So what ended up happening with that fight with the cabbies in New York?
C
Really, you can track it through the medallion system and the value of them. I mean, basically you have to get a medallion to drive a cab. It's sort of like a version of a license to drive a cab. But medallions are very, very expensive. And there's a reason for that. They limit the amount of cabs on the road. It's sort of like traditional market dynamics, right? You want to not flood the market with too many cabs because then not enough people will be able to make a living being a cab driver. So they only many medallions they hand out. Some people go into debt buying a medallion. They could at one point, they cost a million dollars or more. It was a system of scarcity. And it was a great thing to have a medallion because you could really make money. By the time Uber and Lyft started entering the scene, we saw over a period of years, the price of medallions basically plummet from a million dollars to you know, half a million dollars to $200,000 to even lower than that. And it was really brutal for a lot of cabbies who have taken out tons of debt or, you know, had these huge payments on a medallion that they were paying off over time that suddenly essentially became worthless.
A
And what happened to those guys? They're probably Uber drivers now. Or, like, what happened?
C
I mean, Uber drivers, at best, at worst, some. Some literally committed suicide because of financial.
A
Oh, my God.
C
Yeah, it was. It was very serious stuff. It wasn't a smooth transition is what I was.
A
And this is. This is sort of what the bad story is about Uber is they moved fast, they broke things, but they really disintermediated not only those people's lives, but a ton of other people's lives. Because I sort of think of them as the prime movers of the gig economy, which has left so many people without employee sponsored healthcare and 401k plans and all the stuff that freelancers grapple with every day. Do you agree with that?
C
Oh, a hundred percent. What I would say is, like, to some degree, there's always been a sort of gig economy in different professions. In writing, for instance, or in nail salons, everything. But I do think as far as technology making that an obvious choice for companies and how they deal with labor at a massive scale, 100%. Uber and Airbnb really popularized the whole idea of these need to be 1099 workers. And they fought a bunch of regulations where some companies in different states or countries would have had to employ certain people after a while. So, like, they didn't break the ground of creating it, but they definitely pioneered it. And a wave of other companies. Gig economy companies were sort of spurred from the success of Uber and Airbnb for sure.
A
And you have this guy who's sort of in his red pants yelling at everybody, like, just being not nice to people, right? I mean, is that the. I mean, and also, unfortunately, his. His parents get into a serious boating accident randomly, his mom dies, you know, but you have the sense of this is a person who is just emotionally not holding it together.
C
I mean, the way a lot of these entrepreneurs operate, I think, is that they think there's going to be, look, broken eggs on the way to making an omelet sort of thing, right? And, like, the amount of change and tumult in technological advancement is just a side effect on the way to a greater good. And you can look at that in the lens of Facebook, you can look at that in the lens of Twitter or any number of different companies that can really dramat upset how the economy works, how the labor force works, how just the fabric of how we interact with each other works. But I think in their mind, aside from Travis's other sort of, let's say, quirks, they do often find it as this kind of inexorable march towards an abstract idea of progress.
B
Also at this time, this. Just to place this in the context, we're talking this boom time of sort of 2014 through 2017, where this was the heyday of startups in a lot of ways. Startups were raising so much money and venture capital was just flowing. And at least from where I was sitting, like, Uber seems to have been one of the really big winners. They were a unicorn. They were raising funding round after funding round. There was that party in Vegas where they had Beyonce perform, I think reportedly for $6 million in stock. Can you tell me about the culture at Uber at this time?
C
Absolutely. The idea of like crazy excess is definitely epitomized by how Uber was operating at the time. I think you're right in that it was like a lot of different companies, but Uber seemed to be the one, particularly because they had so much success and ease fundraising. You know, I talked to some folks who would tell me about this system they had. It was Travis and his colleague Emil Michael, who was the chief business officer at the time. And they would basically go into a room and have all the financial backers come to them and basically beg to get into the round. So, like this dynamic of everyone's throwing money at us, we're growing like a weed and we can't be stopped, so why not Live large was exactly how they did it.
A
Isn't there a famous story that Jay Z wired the money and they returned it because they were like, no, you can't put more money money in. We're not open for business.
C
Yeah, it was funny, actually. Later, Beyonce, I believe, makes a sort of subtle reference to her equity in this company in a song at one point. But yes, there was a way where I believe they paid her in shares for performing in this Vegas party that you referenced, which is just sort of like the pinnacle of the opulence of this era.
B
I mean, I think one of the most interesting things is that some of this VC funding was going to playing very dirty. As you reported, there was this Operation Uber Gray Ball. Can you explain to me what that was?
C
Yeah. Gray Ball was this fascinating thing. And I think this gets into Travis's sort of mentality of we need to do whatever we can to fight against the unfair taxi industry and the unfair sort of politicians in the pocket of taxi industry, as they put it. At the time Uber rushed into Portland, they were operating illegally, or at least the regulations did not allow them to operate, and so they did it anyway. And what transportation officials would do was call an Uber, have the Uber come to them, and then ticket them or impound the car, basically. So in order to get around that and continue operating, Uber would basically pinpoint who these transportation officials were, give them a sort of fake, quote, unquote, gray ball version of the app, and make them unable to call cars so they can come in or impound them or ticket them.
B
And this kind of willingness to do whatever it takes to make it is not uncommon for Silicon Valley entrepreneurs. But, you know, I think in recent years, we're being much more critical of it than we used to be in a sort of post Theranos world. And Travis wound up being accused of sexual harassment. And there were a series of scandals at Uber, quite frankly, about a lot of the behavior of some of these top executives, including Travis. So what happened there?
C
So this is ultimately the thing that did Travis in as a CEO, Basically, under Travis's watch, there was, you know, we talked about the huge parties and stuff. There was just a host of really crazy behavior, bad behavior that was tolerated for a long time internally that I think.
B
Like what?
C
So in particular, the thing that sort of broke the dam open was one employee, Susan Fowler, who said she suffered, you know, sexual harassment from colleagues from male peers and reported it to folks up the chain, and it went ignored. Women on the teams were treated differently than their male peers. They were not getting the same sort of perks and promotions. A number of women inside described it as essentially discrimination. And as Fowler spoke out, it became very clear that it was not just one person. It was a bunch of people. And then slowly but surely, there were other different examples across the world of inappropriate behavior across Uber's offices. And it was never really reined in. The HR department that they had also was very, let's say, disempowered, if not completely chaotic. And so if people did try to report things to hr, they were. Were never taken care of at the time. And I think this idea that Uber was a place where toxic behavior was not only tolerated in the workplace, but even encouraged if you were a top performer, became unavoidable. And I want to say the other thing too, that you have to remember is this was 2017, right around the MeToo movement and the Harvey Weinstein Scandal breaking and kind of a reckoning throughout corporate America around bad behavior, particularly from men. That I think, compounded how gnarly this was for Uber and Travis at the time. Yeah.
B
And Travis had said and done a lot of things sort of on the record before that happened. I mean, he talks about how Uber had kind of boosted his desirability with women calling the company boober. And then you had an anecdote in your book of kind of him going to this strip club in San Francisco called Gold Club.
C
Gold Club actually became a sort of meme in San Francisco where the tech guys sort of go on their lunch breaks or something to go see exotic dancers and then go back to work or whatever. Travis would, I guess, take his, like, laptop there and do coding and be like, less interested in what was going on there than working. It was a very sort of like, strange culture of work back then.
A
It's like Sopranos like, it's like, do your work at the strip club. Why not bring your laptop? Hey, it's just like a coffee shop.
C
That's exact. I mean, literally. Yes, that's exactly.
B
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C
I mean, yeah, this is like a really important point, like bad behavior and sort of talks behavior across corporate America is not anything new. I think, if anything, such a flagrant example of it in one particular company that sort of epitomized everything people didn't like about tech bros and transformative technology that ends up hurting a lot of people. It really called a lot of attention to it in a way that I think there was a reckoning for a number of years. You could argue that that reckoning is now swinging back the other way. But I think there was definitely a moment where this company, I think, epitomized that and people recognized that it shouldn't be at least not such an, an epidemic in, in corporate America.
B
And as far as the sexual assaults happening in Ubers, I mean, that's been sort of reported over the years. Little bits have come out here and there. And I actually remember myself, I think this would have been probably 2017. I wasn't sexually assaulted, but I was sort of hit on in a very uncomfortable situation by my Uber driver.
C
Yes.
B
And this was the days of Uber Pool, when Uber pool was incredibly cheap. And if I remember correctly, it was something ridiculous like I took an Uber pool from West Hollywood to Silver Lake, which if people know la, that's quite a ride. It probably took an hour. This was the magic early days when I guess the rides were subsidized by funding or something because it was $3.50 and various people get in and out the car. Whatever, it's fine. I'm making polite conversation with my Uber driver. We get to my street at the end of this ride and my Uber driver says, oh, you know, I really enjoyed talking to you. I would love to, to take you out to dinner. And at this point, all the other people have gotten out the car. It's just me and him. We're at my street where I live at the time was a very quiet street in Silverlake. And I sort of said, oh, sorry, you know, I have a boyfriend. And then just kind of was deadly silent and uncomfortable for the rest of the ride because, you know, in my mind I'm like, well, now this guy knows where I live. And nothing nefarious happened. I was sober, it was deeply uncomfortable and definitely Unnerving. But you can also see how a situation like that could have gone much worse, especially when you have people drinking, like, in a city like la. It's like people are getting Ubers home late at night because they don't want to drive and stuff like that. So what ended up being reported in Emily Steele's story for the New York Times was that there is this incredibly festering sexual assault problem at Uber. And that according to her reporting, Uber received a report of sexual assault or sexual misconduct in the United states almost every eight minutes on average between 2017 and 2022, according to sealed court documents showing that this sort of misbehavior and potentially criminal behavior is happening far, far more than the company has ever disclosed.
A
But, Mike, what do you think they can do about this? I mean, we have the sense that, like, you know, there's some brain company that can just twiddle some knobs and fix this problem. But is it actually that easy? Could they change the way they're routing people or the drivers or what do they do?
C
So exactly what you were talking about, Natalie, that 100%, honestly, like, that's been happening since these companies began. I do think part of it is inherent in how this stuff works. If you're just allowing people to get into cars, you know, anyone can sort of work for this. This is going to happen. And, like, look, could you get asked out by your cab driver or something? Yes. Could you get asked by, like, there are versions of this that exist across different industries or whatever, but can they stop this? Can they prohibit it or whatever? I do think it's. They're limited. You know, what they would say is, look, unlike cabs, we can track these people. You can report them. There's functions in the app if you feel unsafe, but it's still one of those things where it's like, okay, maybe this helps me, like, after the fact, but in the moment, this can be very scary, you know, so it's an ongoing safety issue that the company continues to reckon with. And what. What they said in. In response to my colleague Emily's story is like, look, the vast majority of rides are safe. Da, da, da, da. Which is accurate.
A
It.
C
But it doesn't account for how this is something they've not been able to completely eliminate. And it's unclear if they can completely eliminate it at all.
A
But do you think they'll have to respond? Like, I thought one thing that was really interesting was this idea that women could be paired with female drivers, like, if they're willing to Wait a little longer. And it's late at night and they say, I want to click a button. Can I have a, a female driver? It's 1am that's what I want. You know, will consumers like me and Natalie see something like that pop up?
C
So it's funny because I think even the startup market has responded and some have existed, some have not. But there have been different versions of a startup that does Uber for women, by women. You know, that has actually existed at one point. I'm not sure if it lasted just because of how difficult it can be to break Uber's stranglehold on the market. But Uber I think has dabbled. I'm not sure if they're going to release it. They might have said they may be releasing it pretty soon, but they have dabbled with the idea of, you know, you can request a woman if you are a woman, you know, this is how you feel safer driving with them. Like I imagine as you, as you both are talking like this would be a popular enough function, you know, this is something that women have to think about on any ride, much less in the middle of the night, you know.
B
Yeah, I mean it's also, it's also so depressing to me. I'm like, I wish this wasn't a thing. But yeah, just to kind of wrap, I mean, what do you think is the future of Uber? I mean are we going to be in self driving Ubers in 100 years or in 10 years or what's next for Uber?
C
No, and this is the sort of fascinating thing about technology, about these companies is that one solution to one problem kind of brings up other problems. You know, like to your point, you know, if we go into a self driving future and there are companies like Google which owns Waymo, and they're pioneering this self driving tech out here in San Francisco and down in la there's tons of that. The cars now that are self driving people I think are wary of self driving tech, but once they get in a Waymo, are pretty blown away. That's a potential solution to this idea of like, oh, you have a predatory driver or someone you can't trust, but also then you have to deal with labor implications there. Oh, now you want to take away every job of someone who you are telling that they need to create their livelihood as a gig worker on Uber, know, so it's this game of whack a mole that tech in general can create sometimes that can change the world for better and sometimes it can really change it in profound ways. We didn't even expect.
A
So wait, but are we going to see self driving cars in like Dallas and Chicago and New York? What's your crystal ball? Three years.
C
That's the plan.
A
That's three years.
C
I would say next three to five years. Elon had a test of his self driving Teslas down there. Waymo has way better relationships with, with local governments, I would say, than Uber has in the past. And so they've done it kind of slowly but surely and said, hey, we're doing this as a test. We're going to do this the right way. And like, because people are really responding positively, I think it's happening faster than even Waymo would have suspected.
A
So, I mean, yeah, so maybe that is the death knell for Uber. I mean it's so totally impossible.
C
It really could be.
A
Well, thank you so much, Michael, guys. I so appreciate this interview. It's a wonderful book, super pumped. And you can of course read Mike in the New York Times all the time on tech, on Facebook. Anything you want to learn about that. Thanks so much.
C
Oh, no, thank you for having me. This was great.
A
All right, that's it this week for infamous. Thanks for tuning in to our episode about Uber. I know it's a little drier than we usually do, but we thought maybe some people could really. And it's just a fascinating company. No matter what. I sort of look forward to a future where we are all in self driving cars three to five years. Put it on your calendar. So next week we're going to be back and we're going to be rolling out one of our narrative series and it is really pretty salacious because it is about Jeffrey Epstein and his secrets.
C
The woman accused of helping alleged sex trafficker Jeffrey Epstein recruit and abuse underage girls is in jail this morning.
A
I believe that he was murdered.
C
Yo, I'd like to answer that question at least today. I'm going to have to restrict my 5th, 6th and 14th amendment right, sir. And so the biggest misconception of you.
B
Is I ended crazy, meanest, horriblest person.
C
Who'S done committed crimes.
A
Okay, that's it for this week. Thanks so much and please tune in next week.
C
Martha listens to her favorite band all the time in the car, gym, even sleeping. So when they finally went on tour, Martha bundled her flight and hotel on Expedia to see them live. She saved so much, she got a seat close enough to actually see and hear them, sort of. You were made to scream from the front row. We were made to quietly save you more. Expedia made to travel. Savings vary and subject to availability. Flight inclusive packages are atoll protected.
Hosts: Vanessa Grigoriadis, Natalie Robehmed
Guest: Mike Isaac (New York Times tech journalist, author of Super Pumped)
Date: September 4, 2025
This episode of Infamous takes listeners on a deep dive into the explosive, controversial history of Uber, one of Silicon Valley’s most notorious disruptors. Through the lens of journalist Mike Isaac (author of the acclaimed book Super Pumped), hosts Vanessa Grigoriadis and Natalie Robehmed examine Uber’s origin tale, its ferocious culture under Travis Kalanick, the company’s impact on taxi medallion owners and labor, allegations of toxic behavior and sexual harassment, and the persistent issue of rider safety. The episode also explores the broader context of gig economy evolution and what the future of ride-sharing might look like.
"He was a great door to door salesman... this spoke to the intensity of the guy from a real young age." — Mike Isaac (06:01)
"At best, [former cabbies became] Uber drivers. At worst, some literally committed suicide because of financial (ruin)." — Mike Isaac (16:00)
"They would basically pinpoint who these transportation officials were, give them a sort of fake, quote, unquote, gray ball version of the app, and make them unable to call cars..." — Mike Isaac (20:44)
"Women on the teams were treated differently than their male peers... as Fowler spoke out, it became very clear that it was not just one person." — Mike Isaac (22:27)
"Travis would, I guess, take his laptop there and do coding and be like, less interested in what was going on there than working." — Mike Isaac (24:21)
"Uber received a report of sexual assault or sexual misconduct... almost every eight minutes on average between 2017 and 2022..." — Natalie Robehmed citing Emily Steele, NYT (29:00)
"This would be a popular enough function... this is something that women have to think about on any ride, much less in the middle of the night." — Mike Isaac (32:06)
"It’s this game of whack a mole that tech in general can create sometimes that can change the world for better and sometimes... in profound ways we didn’t expect." — Mike Isaac (33:10)
The Value of Myth
"They love to do myth making and think about how can we look backwards and make a founding story more romantic?" — Mike Isaac (07:07)
On ‘Boober’ and Tech Bro Chauvinism
"He talks about how Uber had kind of boosted his desirability with women, calling the company 'Boober.'" — Natalie Robehmed (24:01)
On Labor Displacement and Personal Tragedy
"Some [former taxi drivers] literally committed suicide because of financial [ruin]." — Mike Isaac (16:00)
On Uber’s Tactics Against Regulators
"They would basically... give [transportation officials] a fake app and make them unable to call cars so they can’t impound them or ticket them." — Mike Isaac (20:44)
On the Challenge of Fixing Uber’s Safety Crisis
"They can track these people... report them... But in the moment, this can be very scary." — Mike Isaac (30:24)
On Automation Replacing Human Drivers
"If we go into a self-driving future... oh, now you want to take away every job of someone who you are telling that they need to create their livelihood as a gig worker on Uber." — Mike Isaac (33:10)
The episode paints a richly detailed, unflinching portrait of Uber—from the idealistic veneer on its founding myth to the moral crises and systemic challenges it now faces. Uber is shown as both a pioneer and a cautionary tale of Silicon Valley’s breakneck disruption: a company that reshaped cities and labor, but also one whose “move fast and break things” attitude has left unresolved questions of exploitation, safety, and the human cost of progress. The conversation offers no neat answers, but gives listeners plenty to ponder about the future of work, technology, and urban life.
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