The Vergecast - Anna Wiener's Uncanny Valley

Episode Date: January 16, 2020

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

Hey everybody, it's now from the Vergecast. We've got a special episode today. Anna Weiner, 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 this technology and all this connection is, really doing to us in our culture. I really enjoy talking 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 kind of foundational, conventional, conventional wisdom about technology companies, how they work and the value they put in the world. 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 Weiner, author of Uncanny Valley Out Now, and I highly recommend that everybody go read it. Anna Weiner, you are a contributing writer to The New Yorker, and you've just read

a memoir called Uncanny Valley. Welcome to the Vergecast. Thank you. Thanks for having me. So your book touches on almost every theme that we cover regular here 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 sort of into this moment in the tech industry and then out and decide to write a memoir. 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. Everybody wants to be a music journalist. 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 e-book 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 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, 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 the stuff of human tragedy and comedy and ambition. And I actually think that Silicon Valley is a strangely rich space for literary interrogation. And 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. 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 it seemed like an era had come to a close. I absolutely agree that an era came to close 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 incredibly detailed voter data sets and how they were just such an advantage because they'd harness 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 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 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 much more contemplative way about what the, what giving everyone access. two tools can actually do to a society without any sort of retrospection. But your book has sort of an enforce, 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're telling you earlier that you did that on purpose. Why that choice? 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 company. 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 a 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. 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. But it's pretty easy, I guess, if you've been, 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. I don't know that I can answer that question. I don't have, no, I don't have an NDA wall. I did sign. I have paperwork. I'm not, 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,

you know, I also don't name companies I didn't work for. So I think that, you know, by referring to Facebook as a 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, in our culture. My favorite one of them was, one of your fortis, Isaac, is the Slovenian philosopher who introduced a generation of ways to Marxism. And I was like, that is, that's accurate. I went to Wesleyan, so, you know, I'm intimately familiar with that demographic. So as I was reading it, I was taking in the distance and sort of seeing how you employed it.

The first part that got to me is sort of the first third of the book, I would say, is almost a comedy, right? 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 as you were, obviously as you were experiencing it, but as you were writing it, but by the end of it, you were talking about venture capital. A, you're in arguments with venture capitalists and Twitter. You are talking about whether or not they should be invested in building cities.

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. 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.

I mean, when I first started working in tech in 2013, I was just swept away by the speed and the enthusiasm and the optimism and, 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 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 disillusion 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 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 writing the book in 2017, and it was based on a piece that I wrote for N++.

one, 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. You've got this line that I love about business books.

I had never seen it phrase 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 bloodless KPI metric. But just unpack that same element of it because it's one that really struck me. I would say that that came to me after I spent quite a bit of time reading posts on Medium.com. Oh, no. 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. And I actually do have a lot of sympathy for people who have committed themselves to endeavors that may not ever go anywhere. You've got this little vignette in the book where your boyfriend, who is a software engineer, you say 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? 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 the business.

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 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, 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 drag net, 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. And part of that is because everyone is approaching these, you know, these problems,

differently, and so 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 literary writer answer in the world? But I do think it has to do with time? 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 teacher self-drop scripts 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 teach Uber drivers in 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 happy customers are actually as valuable as everything else, 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-tumultuous way. Do you think that's changing now that this sort of 2016 break has happened? 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 compensation and equity, the actual value on the job market, or are we talking about a cultural value with 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 piece is uncognizant. We're 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 is essential. low level and essential and underpaid and 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 buy-in, if they have autonomy. 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 help inform what's happening now as you write about it in your journalism role? 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. 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 it. 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 who can write knowledgeably about it.

I don't mean that in like a business feelings writing way. I mean that more in just really synthesizing what's it like to be inside these companies, who has buy it. I mean, I don't know. One of my, like, if anyone wants to get me a Christmas present, which doesn't 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 leverage in that company?

Have you seen a Facebook org chart? I think the information publishes one. I think the information publishes a lot of org charts, but it's very hard to tell how rooted they are on the ground reality of a company. But that's, again, I think it's usually the executive level, right? 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. Yeah, I interviewed the chief legal officer of Microsoft, Bradsmith, who also has a bookout. We interviewed him right after Azure took Gab off its cloud for like a couple 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 companies are structured where 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 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 your book is entirely, sections, I should say, of your book is entirely called scale. And it seems like 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 scale of our current companies without collapsing everything onto a founder or like some godlike CEO figure that just cannot be capable of making all the decisions necessary.

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 is happening on Amazon. I mean, it does raise the question. Do we, should we have companies that are this big? Like, should scale be the objective? And you sort of need scale to have a monopoly and to really effectively disrupt an industry.

But, I mean, 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 musing in one place, right? What a gift I've discovered so much music through Spotify, but I don't know that the trade-off there is actually is worth it. Maybe this is my, you know, 22-year-old music writer's self creeping out of the woodwork, but people can't make money 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, 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 feel like finally, as a society, we're starting to weigh the tradeoffs, and people are finding that maybe some things are too good to be true, and maybe it's time to do something about that. This is the conversation we're all having.

You've got, I'm just going to 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 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 it 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? 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 among employees. I think that people are starting to think more critically about 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.

to society or to the damage that it's already done. I think that that would look like effectively decimating its profits, right? 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. I wonder in the case of it, 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 to YouTube and maybe you can get famous and then maybe you 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. have to be the gatekeepers? Like, you're actually responsible? 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 unlike, you know, the venture capital universe, the entrepreneurial community, as you might say. But personally, I don't really want to listen to music that Spotify has contracted.

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 so successfully pandered to. I feel like I am watching a live animation of my, of my, like, data preferences. 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 it is,

if you really loved books, I don't know that you would make an e-book app because it sort of undercuts the whole enterprise. I do find it hard to stomach that the people that work at these companies that are sort of disrupting books or whatever you want to say at Netflix for e-books 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. So obviously I got a little in my feelings about this. But I just so know that the values align with values of cultural production, I guess? Unpack the values of cultural production for me. I think I have a little sense, but I'm

curious what you actually mean by that. 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 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, oh, 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. And that's not universal.

It's just what I've experienced. And the first job that I had actually, before I 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 alike. 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 and tech feels to me, right? Like it's, or a cultural production from tech companies tends to feel. Everything is almost Bittersweet Symphony. I just want to listen to Bitter's Sweet Symphony. Can I live? Well, so you're touching on something that you also write about. And I think we have maybe danced around this conversation.

You just said explicitly, which is gaykeepers, 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 inclusion specialists,

and it gets sold like enterprise software, which I have seen all over the place. place, right? The person comes in, they give the speech about how having the more inclusive team is actually more productive or we'll make you more revenue or we'll 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, people are disrupting the gatekeepers, I'll have it. But it doesn't seem to be solved at all.

Yeah, in my experience, I do think it worked. I think that the consultant who came in, who then came on board 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 complicated. 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. 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 inclusion. But again, it's this question of buy-in. Do they have a budget? Do they have the time? Is it a full-time job or is it a sort of side gig for people who already have full-in?

time roles. I also just think that like the structure, the incentives of this industry make it very hard for people to do diversity and 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, 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 in tech who, you know, when I talk to them about hiring or recruiting, they're like, we are here. 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. 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. And now we're demanding sort of as a larger culture to see the change in how these companies, 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? 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, Cheryl Sandberg routinely refers to YouTube as a music service. Like, that seems very confusing to me. Oh, that's stressful. Yeah.

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... 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 that the, 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? Oh, I absolutely think that makes sense. And I think I see it just in the shift in our coverage and then the reaction on that coverage. Even a light criticism of 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 totology 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 did it. And now it exists. It was hard and it happened, but it's good, but it's good.

And we're like trying to do a good job. There's a lot of musicians that would not have come up, if not for the SoundCloud's for 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. 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 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 bad things that happen. And I think that check is very, really necessary. I agree. So where do you think it comes from if not? Is it just where do you think comes from most effectively? I guess is my question. 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 boot camps earlier and I've been thinking a little bit about that

Recently, and part of what might be exciting to investors or to executives about coding boot camps is that it will let a little air in in terms of the market. And it will be cheaper and easier to employ engineers. And also, they can rest a little power away from engineers, right? So I think right now employees have a ton of power. Engineers have tremendous amount of power internally. But I think that any expectation that that will always be the case is misguided. Support for this show comes from Shopify.

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which leads you into a friendship with a startup. CEO. I think I can get to this, but I won't say this. But his first name is Patrick, which would be pretty easy to guess. And he asks you this question, would you prefer to have two Silicon Valley's 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 have been thinking nonstop about that question, because I don't think I know the answer. What was his answer? Because he says, I know the where you'd never actually say what it was.

And what is yours? Oh, I think he would love to have two Silicon Valley. I think he'd love to have seven. I think that he's doing what he can to have a Silicon Valley all over the world. And I mean that in a – I think he would agree with me. I don't mean that as a criticism. I think that this is someone who's committed his life to supporting entrepreneurship. So, among other things.

But my answer to that question – well, if we'd been in the moment at Foreign Cinema, I probably would have downed an entire glass of one. wine and then, you know, sat sulking for 20 minutes. One of 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 sixth tech reference. Now do it. 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 capitalizing

on institutional erosion or social breakdown? And with that question about two Silicon Valley's or none, I just feel like even inside of that question, there is a failure of imagination because I would have multiple Silicon valleys. 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 U.S. 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. 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 Wisconsin. They're calling it the Wisconsin Valley because Foxcon's, it's like. Oh, that's adorable. It's truly adorable.

That's pretty cute. 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 to 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. 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 Roos in 2019 or the lack of seriousness or the like seduction of like honestly very embarrassing rhetoric when I think about WeWork. Yeah. Like, really? We felt for this. This is very embarrassing for all of us. Even if WeWork's product is great, you know, the corporate rhetoric.

And I don't know if it is great. I can't comment on that. But I don't know. I mean, I think technology can be amazing. 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. 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. It was just a thing that we needed.

And we looked around and someone I worked for just very good. bluntly, and he'd been in the media for a long time, was like all those people are gone. They all got light off in the financial crisis and they're 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 and 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 why they didn't exist. They built these companies and 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. 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. 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 to employees. He's like, this is the generation of people that will have lived through solving them. Will that sort of necessarily improve it? This is also the generation of people that created those problems.

Yeah. 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. Is there going to 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 going to improve. Yeah, I think you're already seeing there. 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 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. 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'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 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? 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 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. Like, Google has become the fixed market for search that you would hear about in a pitch deck 10 years.

ago. Like 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 that it's a rumble. It's not very loud. No one's going to say it out loud because they'll 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. I have no idea if that maps to a generation of people solved this problem once and they're going to solve it again.

I just, 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. I hope they stay, right? I mean, that's not a certainty. Yeah. I think that if there is 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. 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. I think tech industry is more nihilistic than it gives itself credit for. Who's cynical and who's optimistic in your view? Something I'm constantly struggling with. I think what we are beginning to see is that companies are all cynical. And so if you'd ask me that question three years ago, I would have said Facebook is the most cynical company I've ever met my entire life. I would categorize it is. The people at Facebook I see the most are like ad salespeople, right?

Like, they're, that even if they're engineers, they like talk like ad salespeople. And like, that's, that was just that company. And 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. 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 just 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 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. 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. Yeah, I think I would have, again, several years ago, I told you, Microsoft used to be the most cynical company in the world. And their new CEO has made them an idolistic company. I like him. He's fun to talk to you.

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 all right. 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. 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 as tasteful. Or we have to sacrifice one set of ideals for growth somewhere else. And 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? They turned out to be a big corporation, just like the rest of them. Yeah, against sometimes, in some cases, maybe against even their own ambitions initially. Yeah. All right.

Well, I've held you for a very long time. Tell people where to buy a book and when it comes out. 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 an ad for Amazon. Thank you so much for having me. This really was a delight.

Thank you, Anna. We'll talk to you soon. Okay, my thanks to Anna Weiner, author of Uncanny Valley. It's at night. You can go check it out. We'll be back tomorrow with the 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 Sue, 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.