After XOXO: Internet Art and Culture, Feelings, and Business Models
The XOXO Festival was an incredible community of people who love internet
Earlier this week, I returned to the Bay after attending the final XOXO Festival up in Portland. XOXO currently describes itself as “an experimental festival for artists who live and work online,” and I began attending in 2015 (note: there’s been no XOXO for the last few years, due to pandemic, so the previous event before this one was in 2019). Previous descriptions of XOXO highlighted discussions about money — more specifically, funding models — as making the festival what it is. I think a previous iteration of the XOXO website called it something like “a festival for artists who earn their living on the internet.”
XOXO has been with me through several career and life transitions. On the plane home, I found myself considering the “weird internet” zeitgeist, and what it’s meant to me at different points in time. While riding the train back from the airport I began writing this post as both a tribute to XOXO and a reflection on my own history.
At this year's event, one speaker opened by asking the audience about our “magic moment” — the moment we fell in love with the internet. For her, this was Neopets, a genre-defining virtual pet website that launched in 1999. For me, this moment was in 1996 when I first played an internet community text game called a multi-user dungeon (MUD). As soon as I got pulled into my first MUD, which was called GemStone III, I transitioned fast from spending ~zero time on the family computer to spending ~all my spare time on the family computer. I was eleven years old when I started.
My favorite character was a flashy wizard/warrior with spells, a sword, and a side business where she (I) sold virtual goods via online auctions. I never did anything “real” with my character’s money, which was in-game currency held in an in-game bank. Years later, when I quit GS3, I felt confused when people suggested that I sell my character and her coffers. Objectively, I understood that my character was an asset that I owned, that she was valuable in U.S. dollars due to her skills, gear, and the digital fortune I’d acquired over the years. Theoretically, I could have sold her easily, as easily as receiving money over PayPal in exchange for my username and password.
Her name was not mine. She was not me. Yet subjectively, this character was my avatar in this online community. And I… loved it. I loved that game, even if I was leaving. Maybe my character wasn’t me, but she wasn’t not-me, either, and the world where she lived didn’t not-exist. I was unable to fathom what it would mean to sell my character. So I just deactivated my account — eventually she probably got deleted in some data purge, but I haven’t kept track. Fun fact: The journalist Julian Dibbell made a splash in the nineties, as one of the first to cover the underground economies and emotional situations that arise within online games; more than a decade later, in 2012, Julian and I worked on a small anthology project about sexual assault in virtual worlds.
I could not have known in advance that my spellslinging warrior was the beginning of a career that’s been massively defined by internet media. When I was fifteen years old, I got an internship at another, smaller MUD; then my first writing job was at White Wolf Game Studio; and yet it took me a long time to understand that I gravitated to the “cutting edge.” I had no idea! I was just following my interests. When I first logged into GS3, a lot of people thought the internet didn’t matter and that digital media wouldn’t amount to anything. This seems incredible now, but it’s true. When I was a kid in the nineties, it was very hard to explain to my classmates and parents why I thought the internet was interesting.
Later, in the mid-oughts, I experimented with blogging for fun. I quickly became a semi-famous sex-positive blogger under a new pseudonym, Clarisse Thorn. In a way Clarisse was a character, too, but she was more me than my game character had been, and I used the Clarisse pseudonym to write about my own thoughts and experiences. I started my Clarisse blog in 2008 and by 2012, I was able to support myself — on an extremely slender budget — by writing and giving talks.
I did not earn much money. I was sensitive to the notion of “selling out” — this seems so quaint, now. So there was a lot of money I turned down. For example, I refused to run ads on my blog. I rejected sponsorships from sex-related companies, even companies I liked, because I worried about what would happen if I ever felt the need to publicly criticize a sponsor. I considered myself to be doing an essentially activist and intellectual project, and my independence from commercial interests mattered to me. Once I realized that I could potentially support myself doing this thing I loved, I became determined to crack the puzzle of earning a living doing it. Yet at the same time, I wanted to “make it” and work full-time on internet media only with my full integrity intact.
This sensitivity about commercializing creativity was widespread, back then. Every step towards transforming the internet into its current form, this highly monetized adscape, got hotly protested. For instance, when the MUD I used to play started selling virtual goods for real money, players were initially outraged, because players wanted in-game stuff to be earned via gameplay and creativity rather than purchased with U.S. dollars. And back then, when bloggers did product placement, readers were frequently outraged too. I felt this sensibility keenly. I cared enormously about maintaining my integrity in the face of these market forces.
Perhaps another way to put it is that I had a strong sense of purity about my work. I wanted that purity to ripple out into every element of the work, including the business model. In a way, it’s exactly the same question many sincere artists have dealt with through the ages: How to create the most beauty we can, given the constraints of this fallen world. But the internet provided new approaches.
When I was Clarisse Thorn, one method of earning money that seemed probably okay was self-publishing books for my online audience. Back in the 20teens, this was a very new thing. I figured it out step-by-step by sifting online information sources. I didn’t have any mentors to show me how to do it, and a lot of the tools that make it easier now did not exist yet. I spent dozens of hours in cafés, hand-coding my ebooks; nobody does this now. I remember launching one book right before SXSW 2012, because I was going to speak at the event, and I worked fourteen-hour days and didn’t change out of my pajamas for at least a week before I went to the conference. (It was worth it; I convinced everyone in my SXSW audience to buy that book, and the book hit #1 in both of its Amazon categories that day.) The people who taught me how to self-publish were mostly romance novelists and pickup artists, because those were the people self-publishing back then. I also made friends with employees at the Electronic Frontier Foundation. The EFF’s mission was to protect free speech on the internet, and their employees — particularly my friend Peter, RIP — kept me abreast of relevant tech and policy ideas. I thought of the EFF kind of like my “guild.”
I earned enough to support me as a thrifty, healthy girl in my twenties living in Chicago (where my rent was $450). But then I had a terrible bicycle accident. I survived, but I got scared. I decided to “get a real job” to build a rainy day fund. I allowed my friends in the tech industry to convince me to move to San Francisco, where the tech industry was entering a frothy, bubblicious phase.
But there was another reason I burned out on blogging and went into the tech industry. It wasn’t just the money. When I was a sex-positive blogger, I was deep in the social justice sphere, especially Internet Feminism. And I cared so much. Oh, how I cared. I wanted to Do The Right Thing, and I got drawn into the feminist movement because I believed feminism had strong moral grounding. I still believe this — but I was very naive about the movement’s blind spots, as well as my own. So, when I was Clarisse Thorn, I went through a cancellation in 2012 that made me question my allegiances. Basically, the short version of the story is this: I had a male feminist mentor who turned out to be a narcissist, and I tried to stand up for him when he got canceled, so I got canceled too. (There’s a long version of the story, but it tends to bore anyone who isn’t obsessively fascinated by these sorts of things, so I’m trying to be brief.)
In 2012 the thing we currently call “cancel culture” was a subculture thing. It only happened to people within the social justice world and the impact didn’t typically spread beyond that. It was a different phenomenon with different stakes. Those stakes felt high at the time. Getting canceled hurt, it broke my heart and made me question myself and whether I was an okay person. It also made me see feminism differently. However, I still believed in social justice principles — and at the time, I thought that if I left the social justice movement and became an “aligned outsider” rather than an “activist,” then I could move on without needing to tackle the problem head-on. I did not yet realize that social justice culture was about to go mainstream and that its problems would, too.
I struggled with the feeling that I was “giving up” and “selling out” as I moved to the Bay Area to work in tech. But after I got here, I found that tech contains multitudes. My first full-time Silicon Valley job was at a startup called Tugboat Yards. The company is gone now, but today Tugboat might be described as a combination of Substack + Patreon, though it came and went years before Substack. Tugboat hired me because I was an example of someone who could have used their product when I was earning my living as a blogger, and Tugboat gave me a customer-facing role, so I met a lot of internet heavyweights. It was my job to help people figure out how to support themselves on the internet with their blogs or newsletters or podcasts or whatever, and I poured my heart into it. Sadly, the job didn’t last long, and the company not much longer than my job, but the people were awesome.
This was when I heard about XOXO — from people I was following after Tugboat Yards. I vaguely remembered reading a blog by one of the XOXO founders, Andy Baio, years before. It was a great blog, but that wasn’t why I went. It wasn’t because of the topic, either, because no one on Twitter was terribly specific about what XOXO was about. I just looked at who was attending and I concluded some of them might know about jobs where I could work on interesting stuff. Later, I came to understand that Andy was an early supporter of the company Kickstarter, and his connections there, among others, put XOXO at the center of the conversation about making tools for digital creators to earn an independent living.
A lot of things made me uncomfortable once I got to XOXO. It was an extremely leftist space, and in some ways I loved that. But also, I felt like it contained many of the same dynamics that bothered me about the internet social justice world. I remembered having been canceled within internet feminism, and I never quite felt safe after that, in any strongly leftist space — even though by any normal measure I was strongly leftist myself.
Still, I agreed with the XOXO crowd about many social problems. And the crowd was reliably clever in an internet culture kind of way. I remember a particular situation that came up around the time I started to attend. The conference that year invited Anita Sarkeesian, a feminist game critic, who, from what I understand, frequently receives death threats from trolls who hate feminists. Since Anita was attending, some of these folks found out about XOXO and made a giant scene online. A brigade started dumping ludicrously awful tweets into the #xoxofest hashtag that we were using to post about the conference on Twitter. This made it hard for us to communicate on Twitter, which was a big part of the event; following the hashtag on Twitter became nearly impossible because there was so much crap mixed in.
Then the two men named Andy who run XOXO (colloquially, “the Andys”) came up with a clever approach. XOXO has a Slack chat room where attendees hang out; the Andys made a list of Twitter handles for everyone attending the event, and then they made a dedicated channel in our Slack to import all the tweets using the #xoxofest hashtag, if and only if the tweeter was an XOXO attendee. This created a kind of chat bunker. We could still post externally on Twitter about the conference, so our followers would see the tweets, and we also had an option to retreat from the BS by monitoring the Slack channel instead of Twitter itself. It wasn’t a perfect solution, because the hashtag was still publicly a mess, but it helped, a lot.
I remember one other thing about XOXO that struck me early on: Many people there were willing to be honest about how cancel culture is an actual problem.
This was incredibly rare in leftist spaces. Seemingly nobody wanted to admit that cancel culture existed, much less that it was a problem. For years, I had an obsessive side project of collecting essays that describe the issue, though I rarely met people who wanted to discuss it. Here are some examples of essays I collected over the years. In “Exiting The Vampire Castle” from 2013, Mark Fisher, author of Capitalist Realism, pointed out that “In theory [cancel culture] claims to be in favour of structural critique, in practice it never focuses on anything except individual behaviour.” In 2012, the blogger Ariel Meadows Stallings wrote about it in a post called “Liberal Bullying,” calling it “the biggest challenge [her independent publishing company] deals with on a daily basis.” She ended with: “We're fighting for the same team, here. I wish we didn't have to spend so much time fighting with each other.” And in 1976, before I was born, activist Jo Freeman described it in a detailed article for Ms. Magazine called “Trashing,” which attracted an enormous amount of fan mail from Ms. readers. I have more of these links. Ask me anytime! But of course, there are hundreds of these now, covering every corner of society now affected by the problem.
In those years, it was rare in my experience for leftists to talk honestly about cancel culture. But it wasn’t rare at XOXO. For example, at one XOXO, the Youtuber Natalie Wynn went on stage about cancel culture, in which she directly called it harassment. She later published a popular video on the subject, but her XOXO talk came first.
XOXO, generally, was like that: Way ahead of the curve. On the surface, it was just folks chatting about tech, policy, internet art, and how to make small business work using the internet. Underneath, it was a sparkling gestalt of weird creative minds, a lot of us doing professional stuff that wasn’t even a job when we were kids, coming together over our sincere love of this internet thing, always dreaming of making things better. Often at XOXO, I saw previews of upcoming trends. Yet that wasn’t what felt important about the event. There was a purity to it, a beautiful shared idealism — an idea that we don’t have to settle. And there are multiple ways we don’t have to settle. We don’t have to settle for gross internet media infested with scammy nonsense; we can build it better. We don’t have to settle for zero-sum political conversation where well-meaning people get bullied and shunned for saying the wrong thing; we can have a better community than that.
Even so, for years I felt unsure I could trust the XOXO community, although I benefited from it. I heard about amazing digital tools and I met great people. Not everyone was a niche internet indie. One year I met the fantasy author Patrick Rothfuss and spent an hour discussing representations of sex work in literature. I met government employees from departments like the U.S. Digital Service, as well as writers from the so-called “legacy” media companies on the East Coast. Over the years, my “sellout” career became a surprisingly awesome career, specializing in media and technology. I received tons of helpful professional advice from XOXO attendees, and as I became older and wiser I gave advice, too. Eventually, I began to see my way clear towards trying again to develop my own independent media projects. I launched my own magazine on Kickstarter, and I got help from lots of people, including people from XOXO. (I sold copies at XOXO 2024!) In an odd way, the XOXO world has more “colleagues” for me than any other community ever has.
Yet there was always a question in the back of my mind about whether I would fit in, ever, in a thoroughly leftist space. (Who knows if I’ll fit in anywhere ever… but that’s a separate question, I guess.) This question got thrown into high relief as I started researching political polarization and then became genuinely interested in right-wing ideas. In 2022, I was highlighted in a viral Vanity Fair article as part of the so-called “dissident right” or “New Right” (this group overlaps with the groups who harass people like Anita, which is behavior I obviously do not support). When that article was published, I was engaged to a famous right-wing writer, but we broke up soon afterwards. So, to be clear: I have friends in the dissident right world, and I believe there are many right-wing people who are good; but I do not endorse my ex-fiancé in any way, I want nothing to do with him anymore, and I am now ashamed to be linked to him. So uh yeah, that was rough.
Why did I get engaged to a right-wing intellectual? It was primarily because I fell in love with that particular person, also partly because I have a few right-wing opinions… and additionally, I was idealistic about the depolarization of civil society and I had a story in my head about our marital union setting a positive example. These ideals, it turned out, are not broadly shared. Upon publication of that Vanity Fair article, a lot of my former friends stopped talking to me. And to this day, I still get hate comments about my past involvement with my ex-fiancé.
I thought I might get excluded from XOXO 2024 due to my association with the right wing. I almost didn’t fill out the survey to attend because I was so afraid I’d be rejected. My heart is so raw from the last few years. To my relief, I was able to go. And when I made it to XOXO this year, I was moved. I didn’t know in advance what people might say to me, but it turned out that people sincerely checked in, and not in a fake or sarcastic way, not a way that seemed like snideness or novelty-seeking. People were like: Oh hey Lydia. You had a rough few years. Are you okay? I saw what happened. I don’t know the whole story, but it looked awful and I’m so sorry. Your pain was clear. But you have a special place in my heart, Lydia. Glad to see you. Glad you’re okay.
I’m still processing that.
My favorite presentation at XOXO 2024 was by Darius Kazemi, who uses the handle “Tiny Subversions” in various internet places. What I loved about Darius’s talk was (a) the talk made fun of what he called “The XOXO Dream,” which is to move to Portland and earn a full-time living creating idiosyncratic internet art — and yet, (b) the talk was also totally serious about that dream — totally serious about these questions of how creative people compromise with capital to make our dreams happen. (The talk will get posted online eventually, and I’ll come back and drop the link here when it’s posted; right now you can find Darius’s previous XOXO talk from 2014, but not the 2024 talk.) I felt like Darius’s talk encapsulated the artistic longing for purity, so common on the old-school internet, which sometimes feels like it’s almost gone.
A lot of core questions about making great media boil down to questions about business models. Not all, but a lot. Every time I think about quitting media I am reminded that few people get as far as I have, that I still believe there is a unique contribution I can make, and that the money aspects don’t have to be cynical but can instead be meaningful and beautiful in themselves. At XOXO this year I had side conversations about business models with two badass middle-aged women who’ve both succeeded in different ways, one by selling her VC-funded startup, and the other by working twenty years at her bootstrapped one. I felt warmed by those conversations — by the kinship of them, really — and also by the moment I tried Danielle Baskin’s latest tongue-in-cheek internet toy, LinkedIn Tarot, and got The Star representing my career. Lydia Laurenson embodies the archetype of The Star, a card that symbolizes hope, inspiration, and the promise of a brighter future.
Good omens, I hope. I hope so, because there’s so much work to do.
Sidenote: This year I also found out that XOXO had childcare! There is no way this was financially viable given the ticket price, so they did it because it made the event accessible to parents, and especially single parents low on cash, which is incredible. This speaks to their community commitment and I love them for it.
So… XOXO. Oh XOXO. RIP. Goodbye, you excellent little festival. You served us well.
XOXO — RIP — was political, in a sense. Yet it had its own identity, separate from the mainstream. Perhaps, ultimately, that identity was less political than it might appear. XOXO lit the way on so many elements of internet creativity, even the aspects many dismiss as impossibly compromised, like the business aspect. XOXO did extraordinary work empowering independent creators with unique voices, which is something everyone says they want, but few people get how hard it really is. In the nineties, this attitude was almost the entire internet. Now the internet is, uh, well, let’s just say it’s different. But we still have each other.