Anna Wiener's Uncanny Valley

Anna Wiener talks to Verge editor-in-chief Nilay Patel about her book Uncanny Valley, a memoir about her time in Silicon Valley working for startups when they were new and flashy. Wiener also discusses the shift in tone to the reality of what technology and connection do to us and our culture. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Nilay Patel?

  Hey everybody, it's Anna from The Vergecast. We've got a special episode today. Anna Wiener, who wrote the new book Uncanny Valley, joins us on the interview show. The book is out today. Anna spent years working in Silicon Valley at a number of companies that she does not name in the book, they're pretty easy to guess, I definitely asked her about them in the interview. And the book is a memoir of that time, and a memoir of something we are always talking about. The moment in time when startups were new and exciting and could change the world, and the shift in tone to the reality of what all of this technology and all this connection is really doing to us and our culture. I really enjoyed talking to Anna. The book really made me think when I read it. It is extraordinarily well-written, and really challenges a lot of what I take to be foundational, conventional wisdom about technology companies, how they work, and the value they put in the world.

• 0:45Nilay Patel?

  This was a great conversation. It's kind of all over the place, but I think that, to me, is an enormous part of the charm. So check it out. It's Anna Wiener, author of Uncanny Valley, out now, and I highly recommend that everybody go read it.

• 1:02Nilay Patel?

  Anna Wiener, you're a contributing writer to The New Yorker, and you've just written a memoir called Uncanny Valley. Welcome to The Vergecast.

• 1:07Speaker 01

  Thank you. Thanks for having me.

• 1:09Nilay Patel?

  So your book touches on almost every theme that we cover regularly at The Verge, from how to start a company to how to scale a company and get really big, the problems that come with getting really big. You worked on terms of service agreements and enforcing them at a big company that had content moderation problems. But the book is actually, it's a memoir. It's not an instruction manual. But how did you tumble into this moment in the tech industry and then come out and decide to write a memoir?

• 1:36Speaker 01

  So I, after college, had a bunch of jobs. I wanted to be a music journalist, which was an incredibly ill-fated pursuit in 2009.

• 1:44Nilay Patel?

  Everybody wants to be a music journalist.

• 1:46Speaker 01

  I know. Every 22-year-old with a liberal arts degree who's listened to music wants to be a music journalist. So I eventually found myself in book publishing, and from there I went to an ebook startup, and from there I went to an analytics startup in San Francisco, and from there I went to work at a company that made open-source software, or a platform for open-source software development. And these were all jobs for me that I was pursuing for different reasons. I wanted to find meaning in work, I wanted to have some sense of momentum, I also wanted to make money. I heard this was the place to do that. But I never intended to to write about the work, although I did always like to write. I sort of assumed that I would write like a short story collection on the side about,

• 2:31Speaker 01

  you know, sisters or like sad teens growing up in Brooklyn who thinly resembled me, but hotter, I don't know. But I started to see that the way that people spoke to each other here was really interesting and the sort of pathos of the work environment. And you kind of have all of this stuff of of human tragedy and comedy and ambition. And I actually think that Silicon Valley is a strangely rich space for literary interrogation. So I sort of thought maybe someday, 10 or 20 years out, I would wind up writing about my experiences here as part of a major cultural shift. But after the presidential election in 2016, I started to feel that something had really ended.

• 3:15Speaker 01

  And I would actually be very curious what you think about that from your side of the table. And I wanted to kind of quickly document that as as as it seemed like an era had come to a close.

• 3:26Nilay Patel?

  I absolutely agree that an era came to a close at the election. I think we wrote a lot of stories at The Verge about the Obama campaign's use of technology and how they had these incredible incredibly detailed voter data sets and how they were just at such an advantage because they'd harnessed the the power of technology. And then the same sort of thing happened and it was the Trump campaign and Trump won. And it seemed like nobody had quite understood that it was going to happen in that way. And a major reckoning for particularly the social media platforms took place. I think everybody sees that. And I it's just very obvious that has spilled over into everything else. And I think your book chronicles that era of here's a heady rise, we're all going to

• 4:09Nilay Patel?

  talk about 25 year old CEOs changing the world, to a moment where it seems like, hey, this has to actually stop. And not stop in a negative way, but in a in a much more contemplative way about what the what giving everyone access to tools can actually do to a society without any sort of retrospection. But your book has sort of an enforced... When I first started reading it, I was like, this is written like a work of fiction because you have this sort of enforced distance. You don't name the companies you work for, you don't name a lot of the people that you worked with. And you were telling me earlier that you did that on purpose. Why that choice?

• 4:43Speaker 01

  I chose not to name companies or executives in the book because, to a certain extent, I don't think that it matters, the names of the companies that I worked for or these executives. I think that what I'm trying to point to are structural patterns and similarities among different startups, something that I think is sort of a product of a broader culture or broader system that is functioning. So the companies themselves, by describing them not by pseudonyms or by... When I was talking about this with my agent when I was crafting out the book, he was referring to them as epithets, but I, you know, just descriptors of what these companies do, I think, say more than the company names themselves, if that makes sense.

• 5:24Speaker 01

  And I'm hoping that it gets people thinking about what these corporations actually, you know, what their role is in our society, not just, you know, whether or not they're a household name.

• 5:34Nilay Patel?

  But it's pretty easy, I guess, if you've been in it for a while, it's pretty easy to guess what the companies are. So this wasn't... This is purely a stylistic choice. It's not a... You don't have like some NDA wall that you're trying to hide behind.

• 5:46Speaker 01

  I don't know that I can answer that question. I don't have a... No, I don't have an NDA wall. I did sign... I have paperwork. I'm not... I'm allowed to talk about where I worked. My name is also associated with these companies if you Google it. It's not...

• 5:59Nilay Patel?

  Yeah.

• 6:00Speaker 01

  You know, I also don't name companies I didn't work for. So I think that, you know, by referring to Facebook as the social network that everyone hated goes a little bit farther than just saying Facebook. I think what I'm trying to pull out is the relationship people have to these companies and the role that they play in our culture.

• 6:19Nilay Patel?

  My favorite one of them was when you referred to Isaac as the Slovenian philosopher who introduced a generation of boys to Marxism. And I was like, that is... That's accurate.

• 6:28Speaker 01

  I went to Wesleyan, so I'm intimately familiar with that demographic.

• 6:32Nilay Patel?

  So as I was reading it, I was taking in the distance and seeing how you employed it. The first part that got to me is that the first third of the book, I would say, is almost a comedy. Because you, as a character in your own memoir, are being swept along by startup culture. And you get to the end, and it feels like you've had a very sophisticated awakening to what the Valley is doing and how it works. And that distance, it's a lot closer for you as a person, but it's still there. Did you think about that shift, obviously as you were experiencing it, but as you were writing it? But by the end of it, you are talking about venture capitalists on Twitter. You are talking about whether or not they should be invested in building cities.

• 7:18Nilay Patel?

  There's just this huge expansion in your range of knowledge about how the tech industry works and what its goals are and how it operates. How did you think about that specific device of being disassociated from the actual companies and people as you were writing it? Because that's the thing that struck me the most as I was going through the book, is that the level of detail and sophistication increases even as that level of distance stayed the same.

• 7:39Speaker 01

  Thank you. I do think that the major arc of the book is one of disillusionment. And in maintaining that distance, the way that I thought about it was how would I explain this to friends or family members in 15 years? How would I explain what happened and what I saw and how I understood it at the time, but also how I grew to understand it with a little bit more reflection? And I think that Silicon Valley is incredibly seductive. When I first started working in tech in 2013, I was just swept away by the speed and the enthusiasm and the optimism and the sense of control that people had over not only their own Life decisions, but their products and that you really could make something and see

• 8:22Speaker 01

  people use it and get feedback like that. Like, that was amazing to me, especially coming from an industry where things move really slowly, as they do in book publishing. So, I think that, once you're sort of in tech, even if you are developing a sense of skepticism, or at least this was the case for me, I was maybe growing a little disillusioned with the work itself and with the environment, but I was increasingly interested in what I was actually a part of and what I was doing. And I think that the discourse around tech is also very seductive, right? There is something inherently interesting about this industry, whether you are, you know, fully bought in, or if you're just sort of criticizing it or scrutinizing it. So, this is material, to me, that has not gotten old, that I'm still really excited about, and obviously, I'm still writing about it. But I started

• 9:05Speaker 01

  writing the book in 2017, and it was based on a piece that I wrote for N+1, which was really just written as like a fun essay to entertain a friend of mine who worked there. And I didn't think anyone would read it. I definitely didn't think anyone in tech would read it. You know, it's published by this small print literary magazine in New York. But when I started writing the book, I was even less lighthearted, you know, than I was writing that piece in 2015. And it was really hard to summon that enthusiasm and the genuine excitement that I felt in 2013, because in 2017, it felt like everything was falling apart.

• 9:42Nilay Patel?

  You've got this line that I love about business books. I had never seen it phrased this way. I just want you to unpack a little bit. "Business is a way for men to talk about their feelings," which seems incredibly dangerous for an industry that has world-changing potential at almost every turn. But what made you see that? Because I see that almost everywhere we go, that it is so easy for, in particular, men in tech, to talk about their products, to talk about their revenue, and it's very hard for them to talk about the impact of those products. It's very hard to talk about how those products make people feel without reducing it to some, you know, bloodless KPI metric. But just unpack that segment a little bit, because it's one that really struck me.

• 10:23Speaker 01

  I would say that that came to me after I spent quite a bit of time reading posts on Medium.com.

• 10:29Nilay Patel?

  Oh, no.

• 10:31Speaker 01

  There's just so much, men just, so many men in tech giving each other advice. And so many men in tech who need advice. But the advice is all about like how to optimize your time, or how to email better, or how to like listen to your direct reports, or how to be a more empathetic leader, how to pivot, how to deal with disappointment if your company tanks. Things that I learned when I wasn't successful, things that I learned when I was successful. I guess to me, it seemed like a really rich psychoanalytic literature that hadn't yet acknowledged itself. I do think that in Silicon Valley and in startups in particular, there's so much emotional investment in these companies. There's so much ambition and so much risk and so much reputation that's on the line.

• 11:16Speaker 01

  And I actually do have a lot of sympathy for people who have committed themselves to endeavors that may not ever go anywhere.

• 11:24Nilay Patel?

  You have this little vignette in the book where your boyfriend, who's a software engineer, so he's his own safety net because he's a software engineer. His skills are always valued. But you are doing, in the book, extraordinarily valuable work. You're a frontline customer support representative. You're helping people debug the products that you're using. You're out, you're representing the company and its products. Why do you think there's that gap between actually building the stuff and then helping people use it to be valued in the same way? Why does that feel like such more of a commodity?

• 11:52Speaker 01

  Thank you for saying that work is valuable. I don't feel that it is valued as much as the building. And I think that's because, I think that a lot of people get into this industry because they're excited about systems and about scale. And they're not so excited about working with the individual user on the other end of the product. I think that it's an engineering culture. It's not what I would call engineering culture writ large, but it's pretty specific to the valley. Part of it, it has to do with the job market, right? Engineers are harder to hire, so they get put on a pedestal. At the same time, you have this sort of like reluctance to demystify that profession because it helps concentrate a certain amount of power. Then you have the Soft Skills employees, who I think, like me,

• 12:36Speaker 01

  who enjoys maybe the cultural side of the work or the descriptive side of the work. I think that in many cases, if we could be automated out of a job, we would be. I don't think that we are seen as essential. And I think a part of that is just a sort of disdain for anything that acts as a dragnet, right? So the values of a startup are speed and growth and growth or scale and saturation. And soft skilled work tends to be on the human level and it just is slower for the most part. It's really hard to scale customer support for a technical product, for example. You can write the most thorough help documentation in the world and you will still have people emailing you, asking you to repeat what you've already published online.

• 13:21Speaker 01

  So, and part of that is because everyone is approaching these, you know, these, these problems differently and so they, they need something different from that documentation. I think it's just, I think it has to do with time. Is that the most like, like literary writer answer in the world? But I do think it has to do with time.

• 13:38Nilay Patel?

  Yeah, it could be. I mean, do you think it also has something to do with the fact that, like you said, the job market for engineers is pretty hot? It stays pretty overheated. At the same time, how many coding workshops get pitched? How many teach yourself JavaScript in four days books have been written? There is some push towards making that easier to jump into. One of my favorite startups in New York is called Pursuit and they just, they teach like Uber drivers and like underprivileged kids how to code and then place them in jobs at startups over time. There is that side of it, but at the same time, it doesn't seem like any company realizes that like happy customers are actually as valuable as everything else.

• 14:20Nilay Patel?

  Or clear content moderation policies where you don't have committees at Facebook making up First Amendment rules might actually help you scale your business in a non-timorous way. Do you think that's changing now that this sort of 2016 break has happened?

• 14:35Speaker 01

  That's interesting. I mean, I think that when we're talking about valuing a certain skill set, I don't, I think we need to tease out whether we mean like as a, just salary and, you know, compensation and equity, the actual value on the job market? Or are we talking about a cultural value, a sort of understanding of the importance of these jobs? Because I haven't been in the industry since early 2018, so I don't know what it feels like inside of these companies. I don't know, maybe I'm misunderstanding your question, but a lot of these companies outsource this work, as you guys have documented amazingly. Casey Newton's pieces on Cognizant were incredible, and I think there is an increasing attentiveness to the human cost of these platforms and the people doing that low-level work that

• 15:17Speaker 01

  is essential, low-level and essential and underpaid and, you know, without benefits. And I don't know internally at these companies, I mean, I think I would be surprised, I feel like there's a lot of lip service being paid, but I don't know if these teams inside of these companies have much leverage, you know, if they have, if they have buy-in, if they have autonomy.

• 15:37Nilay Patel?

  Yeah, I mean, there's an entire worker organization movement in and around Google right at this second. As you think about it from your other perspective, writing about it at The New Yorker, do you think that your time in the industry serves to, to help inform what's happening now, as you write about it from, in your journalism role?

• 15:56Speaker 01

  I hope so. I'm usually much more interested in what's happening on the employee level than what's happening at the executive level. So I was writing a little bit about tech culture when I was still in my last tech job, and I do think it's just really valuable to be in the mix, and I think that there's a certain distance, especially, it's changing, it's changed a lot since 2016, but I do think that there should be more writing from people who've had experience inside of these companies, and I don't mean that in the like, people who can think critically about what they've, that they're doing, and also knowledge, who can write knowledgeably about it. I don't mean that in like a business, business feelings writing way. I mean that more in just really synthesizing what's, what's it like to be inside these companies, who has buy-in. I mean, I don't know, one of my like, if anyone wants to

• 16:39Speaker 01

  get me a Christmas present, which does make sense because I think this podcast is airing in January, but something I would love is just the Facebook org chart, like who has... Who has leverage in that company? Have you seen a Facebook org chart?

• 16:51Nilay Patel?

  I think the information publish publishes one. I think the information publishes a lot of org charts, but it's very, it's very hard to tell how rooted they are in the on the ground reality of a company.

• 17:00Speaker 01

  But that's again, I think it's usually the executive level, right?

• 17:03Nilay Patel?

  Yeah.

• 17:03Speaker 01

  Or the C suite. Yeah, I want to know like how quickly, you know, a piece of flagged content moves up the ranks and gets, you know, made into a policy.

• 17:13Nilay Patel?

  Yeah, I interviewed the, um, the chief legal officer of Microsoft, Brad Smith, who also has a book out. We interviewed him right after Azure took Gab off its cloud for like a couple of weeks. And he was like, yeah, my pager went off. And I was like, does that happen all the time? And he was like, no, it happened this time. And that to me is one of those, you can't run a company where like the president of your company gets, literally has like the war room meeting because some Nazi used to Azure. Right? Like that seems unworkable, but also in practice, the way these, these companies are structured, where the, the C suite is the face of the company, it's what everyone wants. And I think unless you empower some of those employees and put them out in front and say,

• 17:54Nilay Patel?

  these are the people who make the decisions, you're always in the trap of Mark Zuckerberg is personally responsible for what the Trump campaign is doing on Facebook, even though he very clearly does not, would like not to be. Do you think that's just a problem of scale? One of the chapters of your book is entirely, sections, I should say, of your book is entirely called scale. And it seems, it's such a powerful word in our industry, but I think we rarely talk about the downsides of it. Maybe we are doing a little bit more now, but it seems like no company can run at the, at the scale of our current companies without collapsing everything onto a founder or like some godlike CEO figure that is, just cannot be capable of making all the decisions necessary.

• 18:32Speaker 01

  Scale is sort of at the root of most problems that we're seeing right now. And moderation, obviously you're seeing it. I think Amazon is fascinating and I think it'll be like 30 years until we understand what's happening on Amazon. I mean, it does raise the question, do we, do, should we have companies that are this big? Like, should scale be the objective? And you sort of need scale to, to have a monopoly and to really effectively disrupt an industry. But, I mean, to, to take this to like a more, it's not lower stakes. It's actually pretty high stakes for a lot of people, but a less divisive example maybe is Spotify. I don't know that I need all of the world's music in one place, right? Like it's what a gift. I've discovered so much music through Spotify, but I don't know

• 19:15Speaker 01

  that the trade off there is actually is worth it. Maybe this is my, you know, 22 year old music writer self creeping out of the woodwork, but people can't make money in that in that field anymore unless they're touring or selling merch. And I just don't know that I need to be able to access like compressed music throughout for the last 40 years in one place. And maybe we shouldn't have these platforms. I mean, I maybe we shouldn't have them at the scale that they are. I don't want to sound like a crank about it. I just, I just feel like finally, as a society, we're starting to weigh the trade offs and people are finding that that like, maybe some things are too good to be true. And maybe it's time to to make to do something about that.

• 19:55Nilay Patel?

  This is the conversation we're all having. You've got, I'm just gonna keep quoting your book at you because it's pretty fun to do. You've got this line that I love, which is disruptors at the end, they dominate. And then you were talking about the end of the idea, the end of the disruption idea, which I think is the moment we're in. For so long, it just seems like every startup was predicated on the existence of a market that they were going to disrupt. So you can't disrupt books unless a book industry exists and is like large and validates your notion that you should disrupt it and somehow move value up and down the chain somehow. You can't disrupt music unless a music industry exists. But at some point, those companies succeed, they disrupt the entrenched industry,

• 20:36Nilay Patel?

  and then they become that industry. And that seems like the moment we're in. If I had to zoom out of the political implication of 2016, I would say the moment we're in is those companies actually became big. Uber just became taxis. Spotify just became music. Amazon just became books. And I'm wondering if you see the next turn. Do you see more responsibility on that side of those platforms? Do you see a different level of attitude where those companies recognize that they're now dominant?

• 21:04Speaker 01

  Generally, I try not to do like future forecasting. I just think it's a losing game and I definitely a game that I will lose. I do think that there is a shift in among employees. I think that people are starting to think more critically about what they're What they're working on and what they're helping push forward. I don't know how to talk about a company or about accountability. I don't, because like what in our current economic structure, like what would it look like for a company like Facebook to be responsible or to be accountable to society or to the damage that it's already done? I think that that would look like effectively decimating its profits, right?

• 21:45Speaker 01

  It would mean having throttled content, you know, not being able to post everything instantaneously. It would mean hiring more moderators with ethical benefit and compensation packages. It would mean, whatever, it would be extremely expensive and it would mean, you know, surrendering their dominance.

• 22:06Nilay Patel?

  I wonder in the case of, in particular, the consumer-facing social startups. You worked in publishing. Publishing is famously built upon layer, on layer of gatekeepers. At some point, like Facebook and Amazon, they try to remove those gatekeepers, right? You can publish a video on YouTube and maybe you can get famous and then you maybe can get an ad deal and you don't need any, no suits are necessarily involved, right? Amazon will just let you publish a book, for better or worse, that's a thing that can happen. At some point, do you think that the switch needs to be, hey, you have to be the gatekeepers? Like, you're actually responsible?

• 22:38Speaker 01

  Well, it's tough. When we talk about gatekeepers, usually what we're also talking about is exclusion, right? And I think it's actually more about tastemakers and about having some skin in the game, really caring about the product or the culture around the product. It feels weird even to talk about books as products, even though most of them are. Like, I'm not trying to be precious about that or precious about gatekeeping. I think that there's a lot of problems with the industry, with the publishing industry or with the music industry or any of these creative industries that are built on relationships, not on like, you know, the venture capital universe, entrepreneurial community, as you might say. But personally, I don't really want to listen to music that Spotify has contracted.

• 23:22Speaker 01

  I don't really want to read books that are sort of algorithmically determined. I find it incredibly uncanny to watch Netflix originals. I think that's where we're already sort of seeing this, right, is in film and television, because I feel, I feel so successfully pandered to. I feel like I am watching a live animation of my, of my like data preferences.

• 23:46Speaker 01

  I guess I feel like, having been inside some of these companies, and admittedly, I only worked at one consumer-facing company. The other two were like, pretty serious technology companies. But my general feeling is that people are getting into this business for different reasons than a love of the product. And if you, if you really loved books, I don't know that you would make an ebook app because it sort of undercuts the whole enterprise. I do find it hard to stomach that the, the people that work at these, at companies that are sort of disrupting books, or whatever you want to say, Netflix for ebooks, are probably going to come out on the other end, having made more money off books than anyone I know who's committed a career to writing or publishing books. That's tough.

• 24:30Speaker 01

  So obviously, I got, I got a little in my feelings about this. But I just don't know that the values align with values of cultural production, I guess.

• 24:37Nilay Patel?

  Unpack the values of cultural production for me. I think, I have a little sense, but I'm, I'm curious what you actually mean by that.

• 24:43Speaker 01

  Yeah, I don't exactly know what I mean by that either, because, you know, the values of cultural production are inextricably linked to all sorts of sexist, racist, cultural values that I think are, are still being dragged into the 21st century. I can talk about the values of startup culture, and I guess I see them as just sort of, it's content for content's sake in a lot of ways, right? It's not about making people feel joy, or more in touch with, ugh, I just sound like such an asshole. But I think, like, you know, good art moves you, right? In one direction or another. And a lot of the, sort of algorithmically, if not generated, then certainly motivated, content that I see is, it feels more like content than like art.

• 25:26Speaker 01

  And that's not universal, it's just what I've experienced. And the first job that I had, actually, before I even went into book publishing, was as a receptionist at a production music company. And they had their own recording studio, and so they would make these CDs of sound-alikes, so songs that sounded like top 40, or whatever. And so you would listen to these songs, you could look them up by data tags, right? So you could see like, oh, songs that sound inspirational, songs that sound like Bittersweet Symphony. And it sounded so close, and so fake, but almost there, like, it almost made you feel something. And maybe if you were like, looking at a video of a car going quickly through- You know, down through Big Sur, like, maybe you would feel something. But that's sort of how cultural production in tech feels to me, right?

• 26:11Speaker 01

  Like, it's... Or cultural production from tech companies tends to feel.

• 26:15Nilay Patel?

  Everything is almost Bittersweet Symphony.

• 26:16Speaker 01

  I just want to listen to Bittersweet Symphony. Can I live?

• 26:21Nilay Patel?

  Well, so you're touching on something that you also write about, and I think we have maybe danced around this conversation, and you just explicitly, which is, gatekeepers traditionally have been white men, and just the way it goes. The tech industry right now has historically been white men. One of the companies you worked at in the book is GitHub. It's not hard to deduce. GitHub went through a sort of massive, earth-shaking, cultural break when its first female engineer leveled some very serious charges of sexism in the workplace. And then you have this line where it says, okay, and they're bringing diversity and inclusion specialists, and it gets sold like enterprise software, which I've seen all over the place, right? The person comes in, they give the speech about how having the more inclusive team is

• 27:06Nilay Patel?

  actually more productive, or will make you more revenue, or will capture more market share. Do you think that's working? Like, honestly, like, I've seen exactly what you described there so many times, and I always wonder, like, is this working? Is the case to be made just a financial case, or a worker productivity case? Or is there some other case or method that needs to be used in this situation? Because it is, even the gatekeepers all had it, and now the people who are disrupting the gatekeepers all have it, but it doesn't seem to be solved at all.

• 27:34Speaker 01

  Yeah. In my experience, I do think it worked. I think that the consultant who came in, who then came on board as our, as a VP at GitHub, was incredibly talented and really, really good at getting people invested. And I mean that, again, at the employee level. I think she was also good at getting executives invested to a certain extent. I can't really speak to what happened there because I think it's complicat... I don't know what I can say on the record about that. But I generally think that people in tech are very receptive to an argument that is made clearly, it has some data to back it up, it's logical, you know, it isn't disrupting their vision of the world exactly, it's sort of enhancing it rather than making them feel crummy about it. I think there are a lot of people doing really important work around diversity and

• 28:19Speaker 01

  inclusion, but again, it's this question of buy-in, you know, do they have a budget? Do they have the time? Do they, is it a full-time job or is it a sort of side gig for people who already have full-time roles? I also just think that like the structure, the incentives of this industry make it very hard for people to do diversity inclusion work that can be sustained at the level that it needs to be. This is again, sort of speculative because I didn't myself do any of this work, I just was watching it. And, you know, I think that every industry, right, is inheriting decades of its own damage. So to start to undo that, there are people who are going to want results in a year, and that's going to be really, really hard. At the same time, you know, whenever I talk to people who are underrepresented minorities

• 29:04Speaker 01

  in tech, who, you know, when I talk to them about hiring or recruiting, they're like, "We are here, we are, we are available to be hired and we keep hitting the same wall." So it's thorny. I think it gets people on, in terms of getting executives on board, I guess I think that the enterprise software approach probably does work to an extent, but then people want to see results because they have, you know, they have to report back to their board or they want to show something for it.

• 29:28Nilay Patel?

  At some level, it's something they have to buy, right? Whether they're buying it for money and they're going to hire the people to do it, or they're going to buy into it emotionally, I guess. You do have to sell it, you have to make the case for it, I suppose. It just, that line struck me because I'd never, never quite seen it phrased that sharply. And it's one of those things, you know, I think a lot of what we've talked about so far is there's the period of your book, 2012 to 2016, when it seemed like no one could really do any wrong, and then there's this moment now where it seems like there's just a reckoning. And I keep asking you like, "Hey, did that, what changed?" As the reckoning had results, and you keep saying, "I don't know, I'm not there." But I can't get away from the notion that you wrote about a perfect bubble in time.

• 30:11Nilay Patel?

  And now we're demanding, sort of as a larger culture, to see the change in how these, these companies, and in particular, these leaders act, and I just don't know that it's there. I see more lawyers come to talk to us about their Terms of Service policies. Right, like, but I don't see any massive shift in how YouTube really conceives of itself. Right? You brought up the, does Mark Zuckerberg really know what Facebook is? Like, Sheryl Sandberg routinely refers to YouTube as a music service. Like, that seems very confusing to me.

• 30:38Speaker 01

  Oh, that's stressful.

• 30:39Nilay Patel?

  Yeah.

• 30:40Speaker 01

  Yeah, no, so when I talk about the era being over, the one that I hope I captured in my book, I don't actually think that there's been a massive change. I think we're seeing smaller shifts. The two things that I'm seeing are, A, obviously increased scrutiny on these companies and their labor practices and their cultural values and their impact. And then B is that you're seeing a shifting attitude in the tech industry that I find actually very interesting and sort of alarming. And I would be curious if you have also witnessed this, where people who are really not used to being criticized are suddenly being hammered with criticism. And some of that criticism is being seen as an attack rather than like sort of an overdue, perhaps slightly overcompensating recognition

• 31:24Speaker 01

  that this is a huge power center that kind of went unchecked for a long time. And the response that I'm seeing inside the industry from a lot of people is one that is so defensive and sort of has a sense of victimhood around it that it's coalescing, I think, into sort of a political reaction, which I think could potentially characterize the next phase of Silicon Valley, where you see people coming from that position of defensiveness rather than being a sort of exuberant underdog. Does that make sense?

• 31:54Nilay Patel?

  Oh, I absolutely think that makes sense. And I think I see it just in the shift in our coverage and then the reaction to that coverage. Even a light criticism of a big company's power is usually met with, well, if they didn't act that way, they wouldn't have built a company of that size, which is a mythology in its way. But it also, I think, fails to, it fails to reckon with something that I'm still grappling with, which is this industry has inspired a lot of people to build a lot of things, to try really hard to have world-changing dreams. I think that's, on balance, a pretty good thing. It has democratized a lot of access. I don't know that I would have my career if I'd had to go through some set of gatekeepers to start a tech blog, right? We just, like, did it, and now it exists. And like, it was hard, and it happened, but it's good, and we're, like, trying to do a job.

• 32:38Nilay Patel?

  There's a lot of musicians that would not have come up if not for the SoundClouds of the world, even if SoundCloud was an extremely messy company, remains an extremely messy company. So that's the balance that I'm trying to make sure that we get right, to be perfectly honest, which is, yep, a lot of good things have happened. We should not forget them, but they're not insulation from criticism for the bad things, right? They're part and parcel of the same moment, and I think particularly now, when you have these companies that kind of don't actually compete with each other, like Apple doesn't compete with YouTube, Facebook does not compete with Google, right? Like, maybe for ad dollars, but not directly in terms of what they do. There isn't any check, except for angry people and journalists pointing out the obvious

• 33:22Nilay Patel?

  bad things that happen, and I think that check is really necessary.

• 33:25Speaker 01

  I agree.

• 33:26Nilay Patel?

  So where do you think it comes from if not? If, is it just, where do you think it comes from most effectively? I guess is my question.

• 33:31Speaker 01

  I think that the most significant potential check on power will come from employees. I think employees right now have tremendous leverage inside of their own companies. I don't know that that will always be the case, right? And you mentioned coding bootcamps earlier, and I've been thinking a little bit about that recently, and I, part of what might be exciting to investors or to executives about coding bootcamps is that it'll let a little, little air in, in terms of the market, and it will be, be cheaper and easier to employ engineers, and also, they can wrest a little power away from engineers, right? So I think, I think right now, employees have a ton of power, engineers have tremendous

• 34:12Speaker 01

  amount of power internally, but I think that any expectation that that will always be the case is, is misguided.

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• 35:25Nilay Patel?

  So I want to end with this question that you, that somebody asked you in the book. So you tweet, "Tech needs to stop ruining everything I love," which leads you into a friendship with a startup CEO. I think I can guess who it is, but I won't say who it is. But you name, his first name is Patrick, which should be pretty easy to guess. And he asks you this question, "Would you prefer to have two Silicon Valleys or none?" Right? And he says, "Why?" So the question is, is Silicon Valley like special, world historical special? Is it unique? Can it be replicated elsewhere? And would you rather have two of them or none? And I, I've been thinking nonstop about that question, uh, cause I don't think I know the answer. What was his answer? Cause he says, "I know the answer," but you never actually said what it was. And what is yours?

• 36:05Speaker 01

  Oh, I think he would love to have two Silicon Valleys. I think he'd love to have seven. I think that, um, he's doing what he can to, to have a Silicon Valley all over the world. And I mean that in a, I think he would agree with me. It's not, I don't mean that as a criticism. I think that, um, this is someone who's committed his life to supporting entrepreneurship. So, among other things. But my answer to that question, well, if, if we'd been in the moment at Foreign Cinema, I probably would have like downed an entire glass of wine and then, you know, sat sulking for 20 minutes. One of the, the biggest things that I come up against with Silicon Valley as it is right now, is that it seems like we are experiencing a failure of imagination at scale, if you'll forgive me for my six tech reference.

• 36:49Nilay Patel?

  Now do it.

• 36:50Speaker 01

  For me, one of the things that I am constantly struggling with is like, who's cynical and who's optimistic? And is what we right now understand as optimistic actually hugely cynical when it comes to what companies are being built and what problems they're solving? And are they, um, capitalizing on institutional erosion or social breakdown?

• 37:09Speaker 01

  And with that question about two Silicon Valleys or none, I just feel like even inside of that question, there is a failure of imagination because I would have multiple Silicon Valleys, you know, I think the question, the decision that one can make there is not allowing space for an alternative structure for how we could have entrepreneurship in the US or across the world, or in Northern California, sorry, if we're going to keep it local. I think I wrote in the book that I would prefer a Silicon Valley that was organized alongside different values, but I also acknowledge in the book, that's a contradiction in terms.

• 37:45Nilay Patel?

  I've been knocking it around ever since I read it in the book, and I agree with you, that there's a sort of failure of imagination built into it, but at the same time, I think it really hits at the heart of, you know, there is a fake Silicon Alley in New York, that's what they call it. And like, in my home state of Wisconsin, they're calling it the Wiscon Valley, because Fox Cotton, it's like-

• 38:08Speaker 01

  Oh, that's adorable.

• 38:10Nilay Patel?

  It's truly adorable.

• 38:11Speaker 01

  That's pretty cute.

• 38:12Nilay Patel?

  But everyone is naming it the same thing because they want to capture what is there, right? And just in that, there's a failure of imagination. But it's kind of like you don't know what you want two of. Do you want two of a massive, sort of like landed venture capital base, and then like a Stanford to feed up a network of startups that I'll sell to Google, or do you just want a bunch of kids starting companies? And I actually, I don't know, I think the difference is we went from one to the other.

• 38:38Speaker 01

  Yeah, that's really interesting. I mean, I think, and in Patrick's defense, in this conversation, I think we both are interested in experimentation and what that actually looks like, probably we have different ideas, right? But his whole thing is, you know, I would prefer for it to be, I'm trying to remember what's in the book, more inclusive and more serious. I mean, I think that the seriousness is something that is maybe coming home to roost in 2019, or the lack of seriousness, or the like, seduction of like, honestly very embarrassing rhetoric, when I think about WeWork. Like, really? We fell for this? This is very embarrassing for all of us. Even if WeWorks product is great, you know, the corporate rhetoric. And I don't know if it is great, can't comment on that. But, I don't know, I mean, I think technology can be amazing.

• 39:22Speaker 01

  I just think that right now, what people are focusing on is either like really quick fixes to huge social problems, or unnecessary companies that take advantage of huge social problems.

• 39:36Nilay Patel?

  Last big question I'll ask you. So, a thing that happened when we were starting The Verge was, I wanted to hire some people with experience, which is the thing that we needed. And we looked around, and someone I worked for, just very bluntly, and he'd been in media for a long time, was like, "All those people are gone. They all got laid off in the financial crisis and are not coming back." And there was just this absolute gap of people who had like more than five years of experience in the industry that we were trying to enter, right? Like, we just couldn't find them. They were gone. They'd been pushed out by this huge financial crisis. And so, we had to like figure it out, and like, hopefully we were successful in whatever happened. But, I just think about it all the time, because for the tech industry in particular, those people never existed. There wasn't even a story of like why they didn't exist, right?

• 40:21Nilay Patel?

  They built these companies, and like, this is the first set of people that's ever had to deal with content moderation at scale. They're literally inventing it on the fly, that there's no one with experience. This is the first set of people that has had to decide whether the map should respect the Russian laws about recognizing the boundaries of the Ukraine or Crimea. Like, it's such an enormous set of novel problems, and no one has ever tried to solve them before. And I'm wondering, you keep talking about employees, like, this is the generation of people that will have lived through solving them. Will that sort of necessarily improve it?

• 40:53Speaker 01

  This is also the generation of people that created those problems.

• 40:57Nilay Patel?

  Yeah, fair.

• 40:58Speaker 01

  So, I feel like, yes, we are dealing with world historical problems, and coming up with the solutions to them now, but they're only world historical because we created them.

• 41:07Nilay Patel?

  Is there gonna be an entire generation of executives, or managers, or employees who are like, "I did this once, I know all the mistakes. The next time around, we're gonna improve"?

• 41:15Speaker 01

  Yeah, I think you're already seeing, there are already people I can think of who have some of that experience, who come from Facebook. We'll know that we've solved that issue when we start seeing like two-person consulting shops set up, you know, down in Cupertino. And it'll feel like the way when you see a server migration company, something like that. Like solutions consulting, whatever. It'll be like, ah, this belongs to the older era. I'm optimistic. I mean, I think you have to be optimistic about change if you, if you are like a general depressive who is nervous about everything. I think there's a lot of damage that people need to, there's a huge mess to clean up. I hope that we see people who have been there and done that, figured out how to solve these issues.

• 41:58Speaker 01

  I don't think we will solve them again at the scale that we have for these platforms. I think that that's the biggest issue and I, I'm not making a case for antitrust exactly. I think I'm making a case for technology that is slower, smaller scale and has a different set of incentives that like possibly aren't feasible under our economic structure. So it's a non-answer. What do you think? I'm curious because it's sort of an unusual question. What are you getting at?

• 42:27Nilay Patel?

  I think what I'm getting at is, I agree with you completely that this is the generation of companies that created these problems. I think this moment of intense criticism is, in some cases, being taken the wrong way. I also think that I'm privileged to be able to talk to a bunch of CEOs all the time, like on the show in particular, and some of them are very candid that, hey, our markets are broken, or hey, it's really hard to build a startup company that can compete with one of the big companies without just losing and getting swallowed. They see that as a problem because that is their story, right? And they see that as, hey, who, like necessarily someone should be trying to disrupt a Google, but they never will try, right?

• 43:11Nilay Patel?

  Like, Google has become the fixed market for search that you would hear about in a pitch deck 10 years ago. Like, the, the total market for grapefruits is a $5 billion market and grapefruit distribution has never been disrupted. Like, Google is that product now, right? And no one's trying. And I think, I hear, I hear that it's a rumble. It's not very loud. No one's going to say it out loud because they don't depend on Google to fund them or pay them or... Send traffic to their websites or whatever, but you hear it. And not just about Google, about Facebook, about Apple, about everybody. And I think that that is what actually gives me a sense of optimism, is everybody kind of recognizes that the big players have become the industries that actually need to be disrupted. And it's really hard to do that now, and maybe some change needs to occur.

• 43:56Nilay Patel?

  I have no idea if that maps to a generation of people solve this problem once, and they're going to solve it again. I just, that's the, that's the specific thing that I think about is, for the first time in a while, you have one generation of managers, executives, employees who have stayed in the industry, whereas I think so many people got wiped out of the previous industries during the financial crisis.

• 44:17Speaker 01

  I hope they stay, right? I mean, that's not a certainty.

• 44:21Nilay Patel?

  Yeah.

• 44:22Speaker 01

  I think that if there's another financial crisis or collapse, or the first people to go, just to hark back to our last conversation, the first people to go will be non-technical employees. And I think policy, moderation, content, whatever, all of that's going to, going to fall into that category. I don't think that there's a company prioritizing content moderation, because we would know.

• 44:46Nilay Patel?

  Yeah.

• 44:47Speaker 01

  But I will say, just to maybe end on a more optimistic note, to dovetail with what you were saying, I do think that in terms of these large tech corporations being the establishment, being the industries that can be disrupted, I do think that they'll likely be disrupted by other tech companies, right? And the technology is getting cheaper, it's getting faster. I think I have a quote, a friend in the book saying something to this effect, but the barriers to entry are lower than they ever have been, and they will continue to get lower. And while I think that this is sort of a solutionist perspective, or a techno-solutionist perspective, that I don't really love to espouse, I do think that the industry has sort of created the tools for its own destruction, which is compelling, if slightly nihilistic.

• 45:34Nilay Patel?

  I think tech industry is more nihilistic than it gives itself credit for.

• 45:38Speaker 01

  Who's cynical and who's optimistic in your view? Something I'm constantly struggling with.

• 45:42Nilay Patel?

  I think what we are beginning to see is that companies are all cynical. And so, if you'd asked me that question three years ago, I would have said Facebook is the most cynical company I've ever met in my entire life. I would categorize it as the people at Facebook that I like see the most are like ad salespeople. Right, like they're, even if they're engineers, they're like, talk like ad salespeople. And like, that's, that was just that company. It had that vibe. And maybe that's because I'm in New York and most of the Facebook people I see are in New York and whatever. And that's where ad sales happens. I would have told you that Google is a super idealistic company, regardless of its many, many, many problems. Like, this is a company that like generally has a high sense of idealism that wants to be optimistic.

• 46:28Nilay Patel?

  And I would have told you that Apple holds itself out as an idealistic company is in fact very cynical. And now I would tell you they're all cynical. Right, and like, there are people in those companies who are trying really hard to be idealists. And they want to be idealists. And they, they, they talk the talk. And when they have the opportunity to shape the products directly, they will walk the walk. But now these companies are so big, they have no choice but to be cynicist.

• 46:52Speaker 01

  It makes me think about GitHub and how that corporate culture was so idealistic. And now they're inside of Microsoft and it seems like there's a reckoning. That's really, that your answer is really interesting.

• 47:03Nilay Patel?

  Yeah, I think I would have, again, several years ago, I would have told you Microsoft used to be the most cynical company in the world. And their new CEO has made them an idealistic company. You know, I like him. He's fun to talk to. He gave me the best advice anyone has ever given me about managing my time, which is he sternly looked at me and said, it's your time. And I was like, oh, I should just do it.

• 47:23Nilay Patel?

  But it was like, you know, like, he's that kind of figure. At the same time, Microsoft is like, they just won the Jedi contract from the Department of Defense, like. And they're very clear, like, we're doing this. This is who we are. This is what we do. They have a contract with ICE. And so I think it's just very hard for any company, regardless of its consumer-facing idealism, to not have that internal cynicism of, in order to grow, we have to do things that we find distasteful. Or we have to sacrifice one set of ideals for growth somewhere else. That's just going to keep happening and happening and happening as they get bigger. So, yeah, maybe that's a downer, and maybe that's a downer place to end on, but I think it's an awakening that most people are having about companies that were once held out as like the future great hope of America. Right?

• 48:08Nilay Patel?

  They turned out to be big corporations, just like the rest of them.

• 48:10Speaker 01

  Yeah, against sometime, in some cases, maybe against even their own ambitions initially.

• 48:15Nilay Patel?

  Yeah. All right. Well, I've held you for a very long time. Tell people where to buy your book and when it comes out.

• 48:21Speaker 01

  My book, Uncanny Valley, comes out January 14th. I'd love it if you bought it at an independent bookstore, but it is also available on Amazon. I can't believe I just did a, an ad for Amazon. Thank you so much for having me. This really was a delight.

• 48:34Nilay Patel?

  Thank you, Anna. We'll talk to you soon. Okay. My thanks to Anna Wiener, author of Uncanny Valley. It's at night. You can go check it out. We'll be back tomorrow with a chat show, wrapping up all the stuff that's happened at CES and beyond. And then we actually taped a bunch of interviews at CES. You'll see those coming out on Tuesday. We'll have Lisa Su, CEO of AMD. And then we'll be rolling out more interviews that we did at CES as the weeks go on. It's good to be back. It's good to be starting here with you. We'll talk to you soon.

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