Flash forward to today, and ContraPoints has been celebrated as everything from “the Oscar Wilde of Youtube” to a vital antidote against the digital Alt-Right. To further explore the powerful platform Wynn's built, Writer Kae Goode spoke with the Youtube creator about everything from social justice, to trans identities, to (self) love and dating while internet famous.

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Interview by Kae Goode.

Photos by Signe Pierce. Hair + MUA: Arpita Brahmbhatt Style: Sionan Murtagh Assistant: Riv Begas

In 2016, Natalie Wynn found inspiration for her career in the unlikeliest of places: the scary corners of extremist YouTube.

Wynn — or ContraPoints, as over 700K subscribers now know her — was a self-described “underemployed PHD dropout” at the time, who spent her newly-freed up schedule working odd-jobs and scrolling through Youtube. “YouTube’s algorithm was recommending me a lot of antifeminist content, and anti-progressive and anti-Black-Lives-Matter content, and it was just showing up in my ‘recommended’ section,” she explains. “So I got the idea that I could do political content on YouTube that was a voice against all the antifeminist, anti-progressive stuff, because it seemed like that was a niche that wasn’t being filled.”

Flash forward to today, and ContraPoints has been celebrated as everything from “the Oscar Wilde of Youtube” to a vital antidote against the digital Alt-Right. To further explore the powerful platform Wynn’s built, Writer Kae Goode spoke with the Youtube creator about everything from social justice, to trans identities, to (self) love and dating while internet famous.

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Kae: Tell me about your YouTuber origin story.

Natalie: I’m someone who’s been watching YouTube videos since YouTube started in 2005, and I dabbled with making videos since 2007 — but just like little piano videos and things and later vlogs when I was in college. But I never really took it seriously or treated it as more than a very casual hobby until 2016 when I started my current channel. And what made me start was that YouTube’s algorithm was recommending me a lot of antifeminist content, and anti-progressive and anti-Black-Lives-Matter content, and it was just showing up in my ‘recommended’ section. And a lot of them were very, very popular. They were getting hundreds of thousands and even millions of views. And at the time I was a philosophy PhD dropout, I was underemployed and working the gig economy teaching piano lessons, copywriting, uber driving — that kind of thing. I was kind of failing as a writer of fiction, which was what I wanted to do at the time. So I got the idea that I could do political content on YouTube that was a voice against all the antifeminist, anti-progressive stuff, because it seemed like that was a niche that wasn’t being filled. I was at such a low point in my life that I wasn’t afraid of any backlash, I was like: bring it on.



Kae: What are some of the accomplishments that you’re most proud of?

Natalie: I’m really proud of the way my videos are sometimes able to reach people who start watching from a place of strong disagreement or ignorance. And in particular, I’m proud of videos I’ve done on transsexuality, for example, ⁠and men who are attracted to trans women and the stigma around that. I did a video called “Are Traps Gay?” which is about this transphobic meme. I used that as a jumping-off point to discuss men who are attracted to trans women — that video is getting close to two million views now. And I’ve heard from numerous trans women that they have boyfriends who were encouraged to date trans women in part by that video. So, to me that’s a real-life effect of a YouTube video I made, and that’s something I’m very proud of.

I’m really proud of the way my videos are sometimes able to reach people who start watching from a place of strong disagreement or ignorance. Natalie Wynn

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Kae: What are the goals of your content?

Natalie: My content is educational, it’s persuasive, it’s informative. But at my core, I am an entertainer. And the number one thing I think of is “How can I be entertaining? How can I make visuals that are striking? How can I write jokes that are funny? How can I make a 30 – 40 minute video on a difficult topic that will engage people and make them feel not like they’re being lectured or sitting through a sermon, but more like they’re sitting at a nightclub being entertained by a performer?” And so that’s, I would say, my biggest goal. Now of course I do also want to be accurate when I’m presenting information, and I want to be a good advocate for the causes I believe in. These are also my goals, but I am first an entertainer.

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Kae: I love the way you use storytelling as a tool to create a more digestible and in-depth conversation for your audience. Would you mind briefly talking more about what that process looks like?

Natalie: A couple of years ago I first started doing videos that were not just monologues but were actually dialogues between two or three characters. And my first reason for doing that was that there were some topics where I was kind of mixed on opinions myself. I found that when it comes to a topic like that, a monologue where I say “I’m not sure what I think about this. On one hand, x, but on the other hand y,” seemed kind of boring to me. I thought it would be much more interesting if I wrote fictional characters that represent advocates of those different views.

The first time I did that was in a video about street violence against Nazis, like ‘Is it okay to punch a Nazi?’ I guess I had mixed feelings about that, so I created an enthusiastic Nazi-punching character and a more reserved character. And then I had them have the argument that was going on in my head. And then later I had the idea to expand on that and do more than just characters that represent different ideas.

I did some videos where it’s supposed to be a debate show, and I was parodying the way a political debate goes down on YouTube where it’s just this big spectacle, almost like professional wrestling or something. And I used the fictional debate format to show rather than tell how disingenuousness can win in those situations. And then the third stage of using characters and storytelling was when I decided to create characters that have more depth to them. So it’s not just about ideas, it’s also about people. That’s what really interests me. It’s not just about what people believe, but why they believe it ⁠— what experiences lead people to believe those things. For example, I created this character called Tiffany Tumbles who is a self-loathing, Trump-supporting trans woman. And I used her to tell a story about the way a person from a hated minority can come to hate themselves and identify with their oppressors.

How can I make a video on a difficult topic that will engage people and make them feel not like they’re being lectured or sitting through a sermon, but more like they’re sitting at a nightclub being entertained by a performer? Natalie Wynn

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Kae: How do you feel about online social justice discourse communities?

Natalie: I am honestly very disillusioned with online social justice communities. I find them to be places where anger and drama are vented without much reflection, and places where infighting becomes the main activity and we lose sight of all of our major goals. I personally have checked out of a lot of these spaces because I get so exhausted by the infighting and by the callouts, and by just the meanness that people have for each other, that it’s distracting to me. If I spend too much time in these spaces, I would just make videos about other leftist activists and about other queer activist that I’m annoyed by. Well that’s not a good topic for videos that are watched by a mainstream audience. Because making videos about how other people in my community are doing things in ways I don’t agree with ⁠— that doesn’t really help the community as a whole. It’s much better for me to keep my eye on the big picture. Who are our real enemies here? What is the real source of oppression? It’s not whatever people are saying on Twitter.

Kae: Being a public figure, what does it look like to acknowledge your privilege?

Natalie: It means, to me, being honest with my audience about the fact that my experiences are limited to my social position in terms of all kinds of things like, not just gender and sexual orientation, but also race and class. I am a white middle-class binary trans woman. That means there’s a whole lot of oppression in this country and in this world that I simply don’t experience. And checking my privilege to me means that I don’t try to speak overly confidently about those other axes of experience. I have to be deferential to the viewpoints of people of color when it comes to issues of race. I have to be deferential to people who come from working-class backgrounds when it comes to those kinds of issues. I can’t speak for them, and to me, checking my privilege means not losing sight of that and acknowledging it.

I am honestly very disillusioned with online social justice communities… Making videos about how other people in my community are doing things in ways I don’t agree with ⁠— that doesn’t really help the community as a whole. It’s much better for me to keep my eye on the big picture. Who are our real enemies here? What is the real source of oppression? It’s not whatever people are saying on Twitter. Natalie Wynn aka Contrapoints



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Kae: What are some of your self-care practices as a public figure?

Natalie: The best self-care is logging off. If I ever find myself getting heated or upset, really the best thing I can do for myself is logging off until I’m feeling better. Because there really is no advantage to continuing to hurt yourself by looking at comments, looking at tweets, looking at posts wherever that are causing hurt. I think there’s a place for reading what people are saying about you and engaging with criticism, but in my experience, that’s only ever effective when it’s done from a place of calm and not of defensiveness, and from a genuine desire to learn, and not from a place of digital self-harm. And so knowing when to log out and knowing what mindset I need to be in when I’m going to do that turns out not just to be a matter of self-care, but it’s also the best way I can be a good ally to others and the best way I can learn.



Kae: Does being a public figure affect your dating experiences at all?

Natalie: It’s very hard for me to date, especially as a high-profile trans woman, because being trans really restricts your dating pool. And what dating pool is left is disproportionately people who already know who I am because they’re aware of trans media, in which I’m a big figure. So, there is this challenge of dating people who are open to dating a trans person but who are also not fans. You don’t want to date a fan. That’s not a good dynamic.

White silk skirt (worn as top) by @kinkshame_heathcliff | Mathuson Anthony

Pink ruffle pants by @lidoarchive | Lido Archive

Kae: Speaking of dating, do you mind talking about how your intersections may affect how you navigate dating?

Natalie: Well, I’ve had two kinds of dating experiences: dating trans people and dating cis people. Dating trans people is in a lot of ways more simple, because they’ve often been with a trans person before, they understand dysphoria, and they just intuitively get what I’m experiencing. Now dating cis people is a little harder. The experiences I’ve had with cis men have always been with men who’ve never dated or often have never met a trans person before me. So, they are finding themselves attracted to a trans person for more or less the first time. And I kind of have to talk them through my needs and desires at a more basic level than I think a cis woman would have to. Because there’s a kind of standard heterosexual script that everyone basically knows and adults with sexual experience usually assume how things go. Well when you’re with someone who’s dating or hooking up with a trans person for the first time, you’re doing a lot of what is essentially educating.

If you find one person who loves you, that’s enough. Natalie Wynn

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Kae: Are there any words of inspiration you want to give to our Salty Babes before you leave today?

Natalie: If you find one person who loves you, that’s enough. If you find three people who love you and you’re into that, that’s enough. Not everyone has to be attracted to you, not everyone has to be perfect for you. So, rejection, the small dating pool, the obstacles that come with being queer or trans and dating ⁠— these things can be discouraging. But ultimately, you just need to find someone who’s compatible. And there’s gonna be someone out there. So even if 99% of dating experiences you have are bad, there will be that 1 in a 100 or 1 in a 1,000 that’s the one for you. So don’t lose hope!

Kae Goode is an interdisciplinary artist, activist and organizer. Kae is a New Jersey native who moved to Atlanta to further her education and build community in QTPOC spaces. She found her passion for activism during her time navigating her undergraduate career where she battled with sexism, racism, misogynoir and transphobia. Kae currently centers her art and activism around gender, sexuality, fatness, blackness, and class.

Photos by Signe Pierce. Hair + MUA: Arpita Brahmbhatt Style: Sionan Murtagh Assistant: Riv Begas

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