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Educating the internet with Natalie Wynn: podcast and transcript

Chris Hayes speaks with YouTuber Natalie Wynn about her distinctive use of long form video essays as a way to discuss some of the thorniest topics.

You might think that nothing good happens on the internet anymore. It's just an algorithmically driven continuous feed of rage, disinformation, and subterfuge. Natalie Wynn, known for her YouTube channel ContraPoints, proves that good things are still happening on the internet. Part philosopher, part performance artist, and wholly genre-defying, Wynn crafts gorgeous and ethereal video essays on everything from TERFS and J.K Rowling to the rise of incels. There’s no one on the internet quite like Natalie Wynn, and she joins to tell us how she does it.

Note: This is a rough transcript — please excuse any typos.

NATALIE WYNN: A lot of people who watch my channel have reached out and told me that my videos in some way helped them not to fall into the far-right pipeline, because often, they'll say like, "Oh, I was watching all of these Ben Shapiro videos and I was really annoyed at feminists, but your videos, I didn't feel judged by, and it opened my eyes, and gave me this perspective that took some of the appeal out of Ben Shapiro."

That, to me, feels good, taking the appeal out of Ben Shapiro. That's good. If I did that for one person, that's a day's work.

CHRIS HAYES: Hello, and welcome to “Why Is This Happening?” with me, your host, Chris Hayes. I've found, recently, myself frustrated and increasingly disquieted, or just with unease about the state of the Discourse, capital D. Now, I mean, that's permanently true. If you spend all your day on the Internet and on social media, and arguing with people and reading stuff and reading people who are arguing with other people, you're constantly in this weird vortex of verbal battle and conflict that's probably completely unnatural. I mean, it's definitely completely unnatural.

There's something kind of satisfying about it, just because I like intellectual stimulation, and because I like argumentation. And I like debate. And I like public issues. And I like examining things. And I like back-and-forth. And I like learning new things, which is why I do what I do for a living, but there's a thing that's happened where I think that the technologies that we've been using to have our conversations have this flattening effect, where everything gets sledgehammered down into these slogans. I find that, even the case recently, I find myself with people I agree with, or views I agree with, being communicated in these very short, pithy slogans that, I get why they exist, and they might be effective for getting a message out, but there also seems increasingly this invitation for people not to think.

The way that social media functions is just to sloganeer or to pass on these memes, and examination or questioning or fighting or arguing about it or being curious about it, or... I was thinking about this because I saw this meme that was going around during the violence between the rockets being fired by Hamas and the Israeli bombardment of Gaza, which I found to be really awful and incredibly upsetting. 60-plus children were killed in that. Two Israeli children were killed. There were deaths on both sides, but massively, massively more on the Gazan side.

And there was this meme that was just like... The point of the meme was, it said something like, "It's not complicated." And I got what the meme was trying to communicate. What the meme was trying to communicate was like, "There's a moral simplicity to this that you shouldn't allow people to spin you away from." I get that, and I think that was actually probably an effective thing, but I also had this feeling of like, "Well, it's kind of complicated." Honestly, everything in life is pretty complicated, and the “it's not complicated” to me felt like this expression of an impulse and an ethos in social media discourse that I find myself increasingly just discomforted by, because I think learning things and asking questions and wrestling with hard questions can sit alongside moral clarity and clear principles.

Those two things don't have to be distinct. You can have clear views and clear principles and understand that some things are truly morally simple, but factually complex, and want to ask questions about the factually complex aspects, and maybe be open to the possibility of them being more morally complex than you thought going in. All this to say that the way that our discourse functions and the way that algorithms function, I think, particularly to produce the discourse we have, can be really flattening. And a great counter to that is today's guest, Natalie Wynn, who goes by ContraPoints on the internets.

She's a YouTuber who has a fascinating backstory as a philosophy grad student who basically started to get into YouTube, and found the algorithm to be pushing her in directions that she thought were really weird. I will get into her whole life story, but what I really, really like about Natalie's work is she is staking this claim. She's massively popular—millions and millions and millions of views—but she's trying to stake out this ground on the internet that is both morally clear and rigorous and also sophisticated and nuanced and curious and doesn't take herself too seriously, and produces these fascinating videos that are kind of genre-defying in their aesthetics. You should definitely check them out. We will definitely link to them, but I thought to talk about the state of the discourse or why our arguments sound like they do, the best person to talk to was Natalie Wynn, so thank you for coming on “Why Is This Happening?”

NATALIE WYNN: Thank you so much for having me on, and thank you for that intro.

CHRIS HAYES: I was trying to think of the best way to intro you for someone that is completely unfamiliar with your work.

NATALIE WYNN: I think you did a good job. I usually try to avoid explaining what my channel is about if it comes up in conversation. People are like, "Oh, you have a YouTube channel. What's it about?" I'm like, "Oh, the internet." I'm evasive, because I don't want to say that, "Oh, I'm a leftist trans woman who talks about how the internet became fascist in 2017, and the consequences of..." Like, I don't want to have that conversation with an Uber driver. It's more than I can bear.

CHRIS HAYES: Well, that was a good one, a leftist trans woman who talks about how the internet essentially facilitated fascism in 2017 is actually, maybe that's a better button slogan for what I should have done as your intro.

NATALIE WYNN: No, I liked your intro. I thought it was new. I'm tired of the old intro about the fascism. I'm done with... I'm ready to move on from fascism.

CHRIS HAYES: Well, I don't think fascism is ready to move on from us.

NATALIE WYNN: Yeah, fascism is never ready to move on from us, so we'll keep an eye on it, but I do try to... I think it's good to talk about other things from time to time, instead of letting your entire life be run by these maniacs.

CHRIS HAYES: We're going to talk about the darkness of the fascist and proto-fascist and maybe fascist-sympathetic corners of the internet that you've explored in your work, but I wanted to start with telling me, you were a philosophy student, right?

NATALIE WYNN: That's right. Well, I was an undergraduate. I mean, I went through a few things. First, I was a music major, but I ended up double majoring in philosophy and psychology, and then I went to grad school. I was a PhD student in the philosophy department at Northwestern, where I made it two years, enough to get a master's degree, and realized academia is not for me. Nope. So, I dropped out. That's my background, but I would say that I have the instincts of an entertainer. I can remember going to an undergraduate philosophy conference and reading a paper to a full room, and at one point, some line in my philosophy paper got a laugh, and I was just like, "This is what I live for. This is what I want."

I was like, "Oh, I'm in the wrong career. Interesting."

CHRIS HAYES: By the way, I completely know that feeling, and 100% feel the same way about that.

NATALIE WYNN: It's intoxicating.

CHRIS HAYES: Oh my God. We did... Back in the before times, we were doing these live WITH Pod shows. We had the live podcast. If you come on a stage, and there's 1,000 people in the room or 1,500 people in the room, and you say something they all laugh at, I mean, that's really tough to beat.

NATALIE WYNN: Yeah, that'll sustain you through the next week, although I... I'm actually a very shy person offline, so I think that YouTube is actually the perfect stage for me because it caters to the exact contradiction of attention-starved and introversion that I think a lot of us who thrive on the internet have this combination of personality flaws.

CHRIS HAYES: So, you decided that philosophy is not for you, but what did you like about philosophy, or what had drawn you to it?

NATALIE WYNN: Well, I really liked being a philosophy major when I was an undergraduate. I think philosophy is more fun to study at the 101, 201, maybe even 301 level. It's fun to get this grand tour of intellectual history, and you're reading Plato one week, and the feminist philosophers the next week, and then postmodernism. It's very exciting to go through all this for the first time, and you feel the thrill of your mind expanding. But, by the time that you're considering writing a dissertation, and it's like, "Okay, which three paragraphs of Heidegger am I going to spend the rest of my 20s writing about?"


NATALIE WYNN: That's a different situation, and I don't have the patience for that, unfortunately.

CHRIS HAYES: Yeah, that's exactly how... I had flirted with the idea of philosophy grad school, and had the same feeling. I was also drawn to performance and theater, but yes, when things start to get super specialized and super recondite and super specific, it gets less fun.

NATALIE WYNN: I lose interest because it stops being about things. It becomes harder to make it about life. I think that is something that's a downer for me in academic philosophy and in the humanities in general. Obviously, there is incredible scholarship that still goes on in the humanities. I don't want to completely bash it, but I do find that a lot of people, once they really get up there to the higher echelons of academia, the stuff they're talking about is like, oh, it's so abstract and so detached from any actual problem that needs solving, that it's hard for me to sustain interest, for sure.

CHRIS HAYES: How did you first start both watching YouTube videos and then deciding you wanted to make them?

NATALIE WYNN: Well, I am a millennial. I was born in 1988. YouTube was invented in 2005. I was... How old? 17, something like that. I've been watching YouTube since the beginning. I think the first time I ever uploaded a video of myself was in 2007 and it was a video of me playing the piano. I started out in a very amateurish way, just uploading little piano videos, later vlogs.

I guess my first real sense that YouTube could be a place where discourse happens—it could be an actual public forum, it could be a place where people are getting news or getting information, where conversations are happening—is, there was this phenomenon in 2008, 2009, what later became called “YouTube skepticism” or the “YouTube skeptic community,” that was kind of like... I mean, it was almost a fan community that started with the New Atheists, people like Richard Dawkins, Sam Harris, Christopher Hitchens. I don't know why this was the one topic that took off on YouTube, but there was a real community around it. There were meetups. There were debates. People were making a primeval, what we now call video essay, about why creationism is wrong, and “here's my argument against Anselm's ontological argument for the existence of God,” and this kind of thing. This was interesting to me when I was 19 years old. I guess by the time I was 22, I had decided this was cringe.

In retrospect, I guess a lot of the New Atheist stuff had the seeds of some very toxic things that later became alt-right YouTube, or maybe alt-lite YouTube, we can say. This fixation on the “unique barbarism of Islam,” for example, I think, was something that I look back on and I'm like, "Oh, God." You can see the ugliness. There is also the fact that this is a... I mean, I knew a lot of women in this community. The gender balance was... There were a lot of women involved, but, much like gaming around the same time, the community was fairly misogynistic. That ended up being the issue that tore the community apart was the question of feminism.

A lot of men in STEM or who had STEM degrees and that... I mean, again, I'm not trying to bash an entire family of fields. I'm just saying culturally, well, let's just say that the idea of some women coming forward as feminists was so threatening to them that it tore the community apart.

CHRIS HAYES: My understanding is part of your desire and decision to make your own videos was in a dialogue with this part of the internet, and you've continued it up. What is it about a certain kind of youngish man on the internet, and the subcultures they create that become, I don't know, toxic, authoritarian, fascist sympathetic? What is that dynamic?

NATALIE WYNN: Well, I think a lot of young men in the last couple of decades feel very threatened by the advancement of, in particular, people who are not white men. I think the reason for that is, culturally, I think this is still a generation of men that was raised to think that the world was theirs. Obviously, it's more complicated than just that, but I think in subtle ways, there's a sense of entitlement that is cultivated in the upbringing of a lot of boys, especially white boys, and so the very real gains of women, for example, I think, to the point where it's like women are now the majority in a lot of universities, is kind of threatening and makes boys insecure, young men insecure about what their place in the world is exactly.

I think there's a crisis of masculinity, where men aren't sure how to be men in the 21st century. What is it that they're supposed to do now? They're being told that it's toxic to engage in some of the traditional expressions of masculinity, sexual aggression, Don Juanism aggression against other men that... And so, here's this anxiety that is pretty legible to me. Things like the soy boys and cucks and all this vocabulary that we got in 2015 was an expression of this, I don't know, quarter-life identity crisis of a lot of men.

CHRIS HAYES: I think that that crisis and the way that it feeds itself online, I mean, a lot of those instincts and cultural pathologies feel both very distinct to the moment, but also across time. I think I've said this before the program—

NATALIE WYNN: It's not new.

CHRIS HAYES: Yeah. A bunch of young men together hopped up in any setting—

NATALIE WYNN: It's been known to cause trouble.

CHRIS HAYES: Exactly. In any setting... I think about this violence all the time when you look at both historical, but also cross-country violence studies. Men between 16 and 30 are doing the bulk of violence basically everywhere.

NATALIE WYNN: It's not some special thing about American culture, no. It's a combination of high testosterone levels and too much time on one's hand.

CHRIS HAYES: Right, but I also wonder how much the algorithms facilitate it, which gets to this medium question. I can never... I go back and forth on this as someone who spends a lot of time on the internet. How much of it is just the way things are, and how much of it is the way that the algorithms are functioning, or the way the platforms, or what they're incentivizing? What do you think about that?

NATALIE WYNN: Well, I think that the way people talk about the algorithm is so vague. I think one issue here is that it's, for the most part, very opaque. There's a few things we know. We know that in 2012, the algorithm began to consider watch time over raw clicks. That clearly played a role in the success of video essays as a genre, where, suddenly, it was never in your interest before to... I mean, I've been on YouTube long enough that I remember when the advice to aspiring creators was keep it under five minutes. No one's going to watch a video that's so long, it’s 10 minutes. That started changing, though, I think as a result of the algorithm.

It actually made long-form political videos a much more viable thing on the medium. A lot of attention on the media has been given to what was termed the “alt-right pipeline,” where people watching gamers on YouTube would eventually be recommended gaming commentators. The gaming commentators were also talking about politics. “Gamergate” is an event that is, I think, correctly seen as pivotal, where gamer as an identity was politicized as a millennial male identity politics almost.

CHRIS HAYES: In a very reactionary fashion.

NATALIE WYNN: Very reactionary, absolutely, because it's backlash politics against feminism, against women, against people of color, against LGBT people. This moment launched the careers of people who became infamous in the following years, Milo Yiannopoulos being the most prominent one. That was all a result of the increasing reactionary thread in gaming culture on YouTube. I think that we talk about the algorithm like we're talking about some kind of Sumerian god that's motivations are mysterious and possibly sinister, but I think it's just a simple...

The fact that, like I said, popular gaming content funneled people into commentary. A lot of that commentary was reactionary, and it became a snowball effect where you had increasing radicalism. People found that... People who had far right beliefs found that this was actually a pretty good area to do recruitment, and more and more people started doing that.

CHRIS HAYES: How would you compare the vibrancy of that alt-right nexus of young male interests, gaming content, reactionary resistance to what's viewed as political correctness, that, I'm dating myself now, “wokeness?” I put in quotes, because it's such an annoying...

NATALIE WYNN: That's exactly the same concept.

CHRIS HAYES: It's literally the same thing. Yes. What is the status of that in 2021 as opposed to 2015

NATALIE WYNN: Well, I think in 2015, there was this really intense sense of being embattled and aggrieved. I mean, there still is that, of course, but I think it was actually more intense in 2015 when we'd had eight years of Obama. It seemed like Hillary was likely to be president next. I think Trump changed some things. I think that... Well, there's part of me that's hoping that this nightmarish four years will inoculate this country and inoculate the internet against some of this far-right populist stuff, but maybe that's too optimistic.

CHRIS HAYES: Talk about your form, because you made mention of it now. What I really like about what you do is they’re these long, very well produced, fascinatingly produced—

NATALIE WYNN: Thank you.

CHRIS HAYES: —visual essays that are, like, 30 minutes long. Do people watch them?

NATALIE WYNN: People certainly do, and my videos keep getting longer. The last one I did was, I think, 90 minutes. It's gotten watched as much as anything. It has three million views in a few months, so people are watching very long-form content. The increasing length of the videos is something that's... I think it's a combination of things. One is, as I get more experienced, I'm better able to execute a really ambitious project like that. I know how to pace it so that it doesn't get boring. I think, as I said, the algorithm now encourages stuff where people are watching for a long time. People are used to... I mean, people listen to hour-long podcasts, of course. People will—

CHRIS HAYES: Shout out to the people listening right now. Don't turn us off.

NATALIE WYNN: Of course. I know that some people will watch a political or commentary YouTube video. They'll kind of use it as a podcast. I mean, my videos are so visual. I like to think that people are just watching and starry eyed the whole time. I think the reality is, though, people are doing their laundry, and that's fine. I mean, that's how I watch YouTube. I'm making dinner or whatever, and I'll put a video on. I think this is a good development, quite honestly, because people read less, which is a little bit concerning, because you worry that... I mean, there's always a panic going on about how media is going to destroy the minds of the young, right? I think that's overblown, but I think people are willing to listen to 90 minutes to two hours. It may as well be a lecture or reading an essay. It's just that it's done in an audio-video form on YouTube. I think that probably this is a medium that's only going to be taken more seriously as time goes on.

CHRIS HAYES: I want to talk to you about what you're trying to do in these conversations, what your approach is, and trying to talk to people where they are, bring them in and persuade them, right after we take this quick break. Natalie, for people that are not familiar with your work, can you just give an example of what a topic would be and what your goal is, and what the visual essay is trying to do, who you're trying to talk to?

NATALIE WYNN: My most popular video I've ever done was one I did about three years ago called “Incels.” It's about... I assume most people know what incels are at this point. It's about this community of men who feel that they, because of whatever unfortunate genetic defects, simply are unable to find a girlfriend. It becomes this spiral of self-defeating doom. It's not only, "Oh, I'm unlovable." It's also, "I'll never be happy," and then that pretty much quickly turns to, "It's feminism's fault, and it's the fault of..." A person in pain always wants someone to blame, so that starts, and at this point, the incel movement has inspired so many mass murderers. There's an entire timeline on Wikipedia devoted to charting them.

CHRIS HAYES: It's really, really grizzly.

NATALIE WYNN: It's extremely grizzly. I became fascinated by this community because of the violence that it was producing, and so I made a video. I wanted it to serve two functions. One is that it's supposed to educate a general audience about what this group of people is—why are they like this, and what are they like? Is there anything we can do about it? And then the other is, I'm aware that people who are, if not obsessive members of these incel forums, people who are at risk for falling into this way of thinking, I want those people to watch.

I want to try to make content in a way so that someone who's not with me from the beginning might actually listen to at least a little bit of what I have to say. I try to be very inviting in my videos. No one likes to be lectured and no one likes a sermon. That's the tone that I always try to avoid having. I want to produce content in a way that is a little more seductive than that. It's not hectoring, and doesn't make you feel like you're being judged.

That also just naturally suits my personality. I think that some people think that I actually am a moral fanatic at heart, and I'm just adopting this ironic persona as some strategy. No, I think that it just suits my personality. I think for me, I feel a little bit an arm's length from morality. I'm just more of an aesthetic person than a moral person. That's not a popular personality type on the far left, but I think it's-

CHRIS HAYES: No, in a nice, sublimated Kierkegaard either-or reference there.

NATALIE WYNN: That's exactly where I got that from.

CHRIS HAYES: No, I think you're right, and I think there's something interesting, which is that, I actually think that the valence of both moral relativism versus moral absolutism and moral certainty versus aesthetic investment, the valence of that has switched a little bit in my lifetime. 20 years ago, I would say that moral relativism was a little bit of the domain of the left and moral absolutism was kind of the puritanical right. I think there's been a little bit of an inversion between those two.


CHRIS HAYES: I think the right wing has gotten increasingly morally relativistic, even nihilistic, and the left has gotten more moral absolutist in good... I'm not saying that in a judgmental way, just observing that. I think it actually is, that transposition accounts for some of the weirdness in our politics at this moment.

NATALIE WYNN: I completely agree with that analysis. It's fascinating to have watched this. I remember being in high school. This was the early 2000s and even back then, I understood myself as a progressive. What that meant was much more of this, I don't know, free love, anti-censorship, almost like looking back to the ‘60s idea of what leftism was, whereas it has become this more Soviet atmosphere of moral fanaticism in the meantime. And I, well, you can probably glean from the way that I'm describing this, I don't love the development, but I also think that there are good things about it.

CHRIS HAYES: Yeah. The thing I wrestle with is moral fanaticism has its place. As someone who spends a lot of time reading history of the run-up to the Civil War and the aftermath, the abolitionists were constantly being called moral fanaticists, and they absolutely were moral fanaticists.

NATALIE WYNN: Yes. Well, John Brown, that guy at the time would have been considered a maniac, but in retrospect, he looks like he is the only rational one there.

CHRIS HAYES: Right, yeah. That becomes the tricky part, which is what to be morally clear about and what not to be, which I think ends up being the distinction that we all make informally, and then becomes the battleground for a lot of the fights we're having.

NATALIE WYNN: I think that's right. You have to choose moments where you're going to be a moral fanatic in your own time, right? You choose moments where you're like, "Oh, I'm putting my foot down on this," but you have to choose those moments selectively because it's actually a destructive thing to be really committed. I mean, you sort of have to be, right? If you're going to change the world, that doesn't happen without disorder and disruption.

CHRIS HAYES: What is your... Can I... If it's okay with you, I want to just ask some personal questions just about what your life is like because you're such a, I don't know, for lack of a better word, ethereal presence on YouTube, and partly because of the aesthetics of your production. To me, you exist in this digital universe, but you're a person. You wake up. You get coffee. Where do you live? What's your day like?

NATALIE WYNN: I'm different from a lot of YouTubers. I mean, conventionally on YouTube, authenticity is the ultimate virtue. People tend to watch YouTubers, especially more traditional vloggers because it's like, oh, you feel like you know this person. They're like, "Hey, what's up you, guys? I'm showing you around my apartment, and we're doing things today." That's kind of the vibe of the video, whereas I have created this aestheticized alternate universe that I exist in. Well, I am a person. I guess I consider myself some kind of artist, and I create these videos, but I'm not literally... I'm not an aesthetic creation.

I'm just a person who eats at Subway sometimes when I'm at the airport, and I'm late like everyone else. I live in Baltimore. I live alone. I've been quarantined alone for a year. It's been very horrible. I don't know. What do you want me to say? I'm a trans woman, so that comes up a lot.

CHRIS HAYES: Yeah, I'm going to get to that in a second, but also, do you... This is a prying question, but you make a living off YouTube, right?


CHRIS HAYES: I mean, I feel like a such an old man asking you this, and I apologize, but—


CHRIS HAYES: I'm just like, "Well, what's the deal?" How's it work? Again, this is one of these things where YouTubers and the culture around YouTubers and Instagram influencers, all these things, I know about them, because I read Style pieces in the New York Times. I remember the cringe-inducing nature of conversations with baby boomers back in 2003 about bloggers, because they had read a New York Times Magazine piece about blogs. I, as a native to that universe, had to explain it in this annoying way. Now, I am that person asking you. Explain to me. Well, how does the business model work?

NATALIE WYNN: From a business perspective, I'll tell you exactly how it works. In my case, most of the money that I make comes from Patreon. Patreon is subscription-based fan funding. People who like my videos go to my Patreon page. It's separate from YouTube, and they pledge a monthly amount in the way that people use to pledge to support, I don't know, classical music radio stations or something like that. And they get little rewards for that, such as their name goes in the credits of my videos. I will do “ask me anything” live streams where people can ask me a question. That's honestly the only reason why I was able to make a career out of this.

Traditionally, the way YouTubers make money is through ad revenue, and that incentivizes a very different structure of video making to Patreon. If you're treating this as a business and you want to make money with ad revenue, your job is to get as many clicks, as many eyeballs on ads, by whatever means necessary, which tends to mean churning out content that... I mean, I hesitate to call it garbage, but sometimes, it's garbage. I don't know. A lot of stuff—

CHRIS HAYES: It's disposable.

NATALIE WYNN: It's disposable content that is never made to be rewatched. It doesn't particularly need to be life-changing or loved by people. It just needs to be watched. That's the bar, and so there's no reason really to devote more time and effort than the minimum needed to achieve that. Whereas, on Patreon, the goal is to make content that people love so much that they will pay you to make it. That's a very different bar, and it incentivizes a very different kind of structure. I'm working on a huge project right now. It's a video that's going to be more than an hour long, once again. I've been working on it for months. That would be a disaster if I was only making money from ads, but because of Patreon, I can do this.

CHRIS HAYES: I had that thought when I was watching your videos of like, "Man, this seems like a lot of work."

NATALIE WYNN: It's an immense amount of work. I often have no life when I'm working on these projects because of how much work it is.

CHRIS HAYES: Yeah, it’s like the lightings and costumes and the cutaways, I mean, these are extremely produced things, so that makes sense. That speaks to something broader to me, where I am really excited about the subscription versus ad-based, which are basically the two models. I mean, cable news has a hunter-gatherer hybrid, which is that, the reason cable news is successful is that it has both. So there's subscription fees, the sub fees that come in, and then there's the advertising, and between those two, you have two different models.

It sounds like what you're describing is kind of the same. There's some advertising revenue that comes in from YouTube. Most of what provides stability are these subscribers through Patreon.

NATALIE WYNN: That's exactly right. I mean, at this point, my videos are getting views in the millions. That's enough... That's significant ad revenue, but still, most of the funding that I have comes from Patreon. You don't need to have millions of people to make it as a living. I made this my full-time job when I was at a much smaller level, because before this, I mean, after I dropped out of grad school, I was basically in the gig economy. I was teaching piano lessons. I was driving Uber. I was being a copywriter and that kind of gig work.

CHRIS HAYES: Contract work.

NATALIE WYNN: Exactly. So the second that I was able to switch to YouTube full time, I did. At the time, I think I only had 40,000 subscribers on YouTube, and probably, I don't know, just probably a few hundred patrons, but that was enough.

CHRIS HAYES: How many patrons do you have now?

NATALIE WYNN: It just fluctuates between 12,000 and 13,000.

CHRIS HAYES: Wow, that's cool.

NATALIE WYNN: I'm in the top 20 on Patreon, which, I'm very fortunate.

CHRIS HAYES: Have you built out a business around this, or do you just do this all yourself?

NATALIE WYNN: I mostly do it myself. To the point that it's actually a little bit insane, I have a half-time personal assistant who helps get me on to podcasts, and schedule things and helps me be an organized human being. I also have a lot of people who do contract work, so composers, music... It’s two people who regularly will be writing and recording music for my videos. I also use a lot of stock music. I will pay voice actors to read voiceover for some things. In my last video, actually, for the first time, I had a contractor to do visual effects.

But a shocking amount of it, I say... Well, I'm not shocked, but a lot of people I tell about it are shocked. I just do it myself. I write the video. I do the research. A lot of times, it's me moving the lights and camera around before I sit down to film. I'm alone. I'm editing the video by myself. It's madness, actually. Most people who are at the level I'm at will hire an editor and hire other people to do these things. I'm not quite sure why I weirdly insist on doing it all myself still. I think it's hard to let go of control of your own project when you're used to doing it all yourself, but I think probably in the future. It's a little bit unsustainable that I'm doing all of this, because, like I said, I have no life apart from this a lot of the time.

CHRIS HAYES: You mentioned that you're a trans woman, and you have had the experience of transitioning in the public eye. You started making videos before you transitioned. You've talked about this a bit, about the ways cis folks, trans folks, anyone who is in front of a camera is going to develop. I speak from personal experience, all sorts of insanity about how you look. I'm saying this with a lot of privilege in my personal subjective bearing and also as someone who had a not intense relationship to how I appear to the world, or any kind of feelings that those didn't match how I felt inside.

I could just imagine that that's got to be really magnified for putting yourself in front of a camera all the time.

NATALIE WYNN: Yes. You're imagining correctly. It is nightmarish. I mean, honestly, for a lot of trans women, how you look is often the determining factor between are you socially legible? Are you able to function in a given social space? Are you even allowed into certain spaces, like bathrooms and things? How you look is of extreme importance. It's like the difference between being seen as a functioning member of society and some kind of, I don't know, liminal—


NATALIE WYNN: —freak or threat. Yes, exactly. So that, obviously, is something that has been... I'm at a point in my transition now, where offline, this does not create a problem for me. Well, I shouldn't say it never creates a problem for me, because I'm vaccinated now, so I went out to a club two weeks ago. A man will just grope you if you're a woman at a club. There's a fear that comes with, okay, what happens when the man who basically assaults you finds anatomy he wasn't expecting? That stuff is still a concern offline. But online, I mean, God, the microscopic analysis of every single physical feature that you have, assessing whether it's passable or whether you look male or female, it's hard not to go insane.

CHRIS HAYES: Yeah, and I think you had a great video essay about this, about beauty and about wrestling through all these questions and the ways... and how it's bound up in identity, in personhood, in trans-ness altogether. I just found it really brilliant, and got at this stuff in ways I hadn't thought about before.

NATALIE WYNN: Thank you.

CHRIS HAYES: Well, but partly because also, what I like about the videos is, there’s such an industry of... It's funny. So much of what's new is just old. When you go to the “recommended for you” part of social media, or things that have tons of subscribers... Again, I'm generationally out of touch with this, but it's all like, "Oh, these are conventionally attractive women doing conventionally suggestive dances." It's like, "Oh, this is the new frontier of media," and it's like, "Right. Well, this is just what's been going on forever."

NATALIE WYNN: It's the same exact thing. What was once called “selfie feminism” has turned out to be a disappointment, in my view. It turns out that when you give women the camera, I mean, in some ways, it improves things, but also, in some ways, things are not as different as one might have hoped. I think that it's tough. It is a question that you ask yourself as a woman who's in media. Your face is on camera all the time. At what point am I going to hit my expiration date? Well, I am pretty determined to resist that. I think that... I don't know, do men worry about their expiration date?

Maybe they do, but I don't think it's to the same extent. I'm determined not to allow myself to be forced off for that reason. I think that there's more to my videos than looking at me. My hope is that people... I don't think that's the only reason people are watching.

CHRIS HAYES: Well, the expiration date. I totally hear that, but I also feel like, if I were in your... How old are you, Natalie?


CHRIS HAYES: To me, the scarier thing from an expiration date is there's going to be... In three years, there's going to be like, all the kids are into this new app that's like a brain chip and they do some... Again, I remember when I was on the cutting edge of media and blogging, and now, I have to read New York Times articles about what people are doing—

NATALIE WYNN: What TikTok is.

CHRIS HAYES: TikTok, exactly.

NATALIE WYNN: I'm even there too. I'm not even on TikTok. I'm losing it.

CHRIS HAYES: It all moves so quickly. I wonder how quickly the waters are rushing around you.

NATALIE WYNN: Well, that's a question I ask myself frequently. I do think I need to get on TikTok. I don't use it. My judgment is that YouTube is going to be here for the foreseeable future. I don't claim to be able to foresee very far into the future. By the foreseeable future, I mean, three years, let's say. I think that it's going to be around for that long, but I do think it is the height of hubris to imagine that the current technology and this current state of social media, "That's just what the reality is going to be for the next 50 years." That seems highly unlikely if you compare us to where we were 50 years ago.

I do think for anyone to have long-term career success that spans decades in this industry, meaning media, you have to keep in mind that you need to be agile. You need to be spotting the next trend.

CHRIS HAYES: It’s exhausting.

NATALIE WYNN: I know it’s exhausting, but you have to do it. “There's this weird new app that kids are using. God, do we really have to learn this?” Yes, you do. You have to learn it. Find a 20-year-old, buy them lunch and have them show you how to do it.

CHRIS HAYES: My wife, she has a legal podcast called “Strict Scrutiny,” which is fantastic, which I recommend. One of her co-hosts did that and just started doing legal TikToks, and they've been hugely successful.

NATALIE WYNN: That's cool.

CHRIS HAYES: I was like, "Wow, that's awesome." It was exactly just like, "Alright, I'm going to figure this out." I think she may have recruited a young to give her a tutorial.

NATALIE WYNN: It's good to get a youth spy. I think, that's from “1984,” the youth spies.

CHRIS HAYES: Youth spy. You are engaged in this different kind of discourse, these long-form videos. You talk about wanting to bring people in. I wonder if you have... You must have interactions with your viewers and your patrons, surely. I wonder if you hear from people that you change the mind of, or who got into politics through you, or that you introduced into a different worldview.

NATALIE WYNN: Yeah. I've heard from many people like that in the last few years. I mean, there’s been different eras of my channel, but a lot of people who watch my channel have reached out and told me that my videos in some way helped them not to fall into the far-right pipeline, because often, they'll say like, "Oh, I was watching all of these Ben Shapiro videos and I was really annoyed at feminists, but your videos, I didn't feel judged by, and it opened my eyes, and gave me this perspective that took some of the appeal out of Ben Shapiro."

That, to me, feels good, taking the appeal out of Ben Shapiro. That's good. If I did that for one person, that's a day's work.

CHRIS HAYES: We started by... You were saying that fascism always looms in the background. You said an interesting thing, which is that it felt less intense in some ways than 2015, that 2015 felt like a peak of a certain kind of political formation online, and maybe it's less that way now. I wonder with this rise of this counter-woke internet community, which, to me, feels very much like the New Atheists, very, very similar, in some ways is sometimes the same people, the same impulses, what you make of that and whether that feels different or similar to some of the things you've seen happen before in these internet spaces.

NATALIE WYNN: Well, I guess the reason to me that 2016 and 2015 were scarier than now is that back then, I felt like I was one of very few people who were noticing. Gamergate was written about, but when the alt-right was gaining traction on YouTube and on social media, there was an early period where this was not being taken seriously at all, before Trump was elected. That I can remember being, in some ways, the scariest. Nazi-adjacent ideology was gaining incredible traction, and that to me was like Ionesco’s play, “Rhinoceros,” where, although it's a metaphor for the coming of fascism, everyone around you is turning into a rhino, it felt like that.

That's when I started making these videos, against that trend, but then, obviously, the Trump era, in some ways got less scary for me, because I felt less alone. It's like, "Oh, everyone else is now paying attention, too." It's like, "I'm not crazy, and I'm not alone." Now, I would say that one major change, and this actually affects the way I work and think, is that when I started doing my YouTube videos, leftist YouTube was not really a thing. There was feminist YouTube, which was mostly vloggers who would talk about feminist issues and then get ruthlessly dunked on by these skeptic people, but there wasn't an economy of leftist video essays in the way that there is now.

There are just hundreds of these creators who are making “LeftTube” videos, and that has changed me. For one thing, I don't have the sense that I used to have that I'm surrounded by the encroaching victory of the far right. I have, instead, the sense that I'm surrounded by leftists feuding with each other, which changes the kind of topic that you're prone to discuss.

CHRIS HAYES: Those internecine battles can be the... They can take it out of you even more in some ways, because—


CHRIS HAYES: It wounds, it cuts so much more deeply when you're critiqued by a comrade than a foe.

NATALIE WYNN: In some ways, it was more fun in 2017 when the people sending you death threats were Nazis, because there's a sense of righteous victimhood that comes with that, whereas now when it's just, I don't know, an angry 20-year-old anarchist harassing me, I don't know, it just doesn't have the same thrill to it.

CHRIS HAYES: I also wonder, too, if we're in a moment now, where what was a kind of internet subculture and vanguard is incredibly mainstream now. You know what I mean?

NATALIE WYNN: Yes. No, I think that's right.

CHRIS HAYES: The insurrection on January 6 was basically a normie insurrection. It's like-

NATALIE WYNN: Yes, a normie insurrection.

CHRIS HAYES: It was not like online edgelords.

NATALIE WYNN: This was not 8chan.

CHRIS HAYES: No, it was not an 8chan. It was people with boats and mortgages...

NATALIE WYNN: People with boats, yeah, 100%.

CHRIS HAYES: ... who stormed the Capitol, and it's like but that is now-

NATALIE WYNN: That boat owners’ uprising.

CHRIS HAYES: Exactly. That is now... What was on the edges, and in these forums, is now part and parcel of a mainstream American political faction formation tendency that is an existential threat to American democracy, but also takes up so much space in daylight, that it's not this creepy thing at the edges anymore.

NATALIE WYNN: I agree with that. In some sense, I feel like it is so mainstream that I feel like, as a YouTuber, it's not quite my domain in the way that it used to be. Maybe that's what I'm feeling as this becomes what conservatism in America is. It's like, "Well, everyone's already talking about this, so I have to find something that..." I'm always looking. What can I do that other people aren't doing? Because I feel other people are working on this. Of course, who knows how to solve this problem. As you say, it's a threat to democracy. It's, in some ways, would have been an unimaginably awful outcome like eight years ago, that this is where we would be. But yeah, it's out of my league now.

CHRIS HAYES: Natalie Wynn goes by ContraPoints on YouTube. You can find her there. You can find her on Patreon as well. I really, really suggest after you listen to this podcast, if you haven't seen any of her work or heard any of her work, you should head over to her YouTube page and watch a bunch. Natalie, thank you so much.

NATALIE WYNN: Thank you for having me on.

CHRIS HAYES: Once again, great thanks to Natalie Wynn. You can check her out at ContraPoints, C-O-N-T-R-A-P-O-I-N-T-S, ContraPoints on YouTube. Search for her, you’ll find her videos. Start with any of them. You can start with the famous incel one, the one on beauty is fantastic and I’m looking forward to the new, super-mega-opus that she’s working on now.

Tweet us with the hashtag #WITHpod, email We really do love to hear your feedback, so send it along. “Why Is This Happening?” is presented by MSNBC and NBC News, produced by the “All In” team and features music by Eddie Cooper. You can see more of our work, including links to things we mentioned here, by going to

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