Pornhub has 90 million daily users and more pornographic videos than any other site in the history of the internet, and now it wants to be Playboy.

More specifically, what Playboy was in the ’90s. “A lifestyle brand, a fashion brand,” explains Alex Katz, co-founder of the Madrid-based creative agency Officer & Gentleman, which has been leading the brand strategy for Pornhub for the past four years.

Co-founder Javi Iñiguez jumps in: “The girls were wearing sweatshirts and purses with the Playboy bunny even though they might not have seen a Playboy magazine in their lives.”

Fair enough. Who doesn’t want the cultural clout of Hugh Hefner, literally everything else about Hugh Hefner aside?

It may be a small shock to discover that Pornhub even has a brand strategy, but it makes sense. The company has spent the past several years doing what anybody would do once they become superrich: buying their way to coolness. And, by extension, buying their way to women, whom the company has historically had a hard time appealing to.

I mean, who doesn’t see the connection between lifestyle brands and chicks?

Pornhub’s first website launched in 2007 and was acquired by the MindGeek conglomerate in 2010, at which time it merged with YouPorn, RedTube, and Xtube to become the Pornhub network. From there, it easily consolidated power to become the biggest porn distribution platform ever, but its new challenge was to become a brand that anyone would talk about out loud, and just maybe, someday, wear on a T-shirt.

In 2014, the network held a contest asking advertising and creative professionals to submit concepts for safe-for-work, PG-13 Pornhub ads that could run in traditional media spots. The move was a reaction to a year of mainstream misses and only two hits: In 2013, Pornhub finagled a centerpiece montage (with clips handpicked by VP Corey Price) in the heart of the porn-focused Joseph Gordon-Levitt rom-com Don Jon. It also nabbed dozens of headlines in outlets from BuzzFeed to SBNation when CBS refused to air a 20-second, completely innocuous ad spot during the Super Bowl. By the time anyone bothered to point out that Super Bowl ads are only sold in 30-second increments, the scam had done its work.

Thanks to the contest, Pornhub buddied up with both Officer & Gentleman and Vendetta Studios, an LA-based viral video production house headed by David Lehre — an anxiety-inducing internet personality best known for one of the first viral YouTube clips, “MySpace: the movie,” and more recently for an elaborate stunt in which he fashioned himself into “the first white American K-pop star.”

For Pornhub, Lehre made a litany of viral videos, mostly ads for Pornhub’s new product releases: a VPN service, a “BaDoink” VR headset, a $1,000 robotic twerking butt, and so on.

“Make the brand accessible to the world” was the brief, Lehre says. Make it PG-13; make it live on YouTube; make it shareable. “When we came in, it was all potential. Nobody had tapped the power of Pornhub.” He pauses. “Damn, that sounds epic.”

Officer & Gentleman’s first projects were also tech-related: videos for a cryptocurrency called Titcoin and a (real) piece of wearable tech that would recharge your phone while you masturbated. It was called Wankband. At Christmastime last year, noting the success of gift cards for streaming services like Spotify and Netflix, they started selling Pornhub Premium gift cards. “We thought it would be the perfect Secret Santa present at workplaces and stuff like that,” Iñiguez says.

(Please don’t give a Pornhub Premium gift card to anyone you work with.)

So, is Pornhub … a tech company? “Depends who you ask,” Katz says, though he seems uninterested in the proposition. “But I think the brand … it’s an entertainment company. You don’t see anyone wearing Facebook shirts because they’re cool.”

Right, right. Cool, we’re doing cool here.

“[In online porn], everyone has the same product, so the only way you can differentiate yourself is by building a brand,” Katz explains. “We only want to create advertising that can go viral.” That means safe-for-work content. “[Pornhub] has enough porn; they need content that’s shareable.”

“Everything has to go viral,” Iñiguez points out. So you throw a lot of shit at the wall to see what sticks. The list of what Pornhub has not been willing to try in the past four years would probably be more expedient, but here we are.

It launched its own lube brand, then the world’s largest lube slide. (One of Lehre’s projects, of which he says, “They didn’t come to set, they just said ‘Oh, we have these 5-gallon drums of lube we can send over.’ We got this huge slide. They sent all these porn stars to hang out and slide down it. That was a magic day.”)

“[In online porn], everyone has the same product, so the only way you can differentiate yourself is by building a brand”

At one point, the company started a record label and hosted music video premieres for California rapper Mykki Blanco and Michigan metal band King 810. It hosted a porn film festival in New York, featuring soft-core entries from Miley Cyrus and James Franco. It made an “adult adult coloring book” featuring X-rated sketches from Instagram and Tumblr artists, which it then sold exclusively at the Think Tank Gallery in LA, Verso Books in Milan, and the menswear boutique Off the Hook in Montreal. It launched a line of sex toys, then commissioned Spanish electro-pop band Perlita to create a song from sex toy noises.

The high-end Italian denim company Diesel became the first fashion brand to advertise on a porn site in January 2016, kicking off a much-covered official partnership with Pornhub. Creative director Nicola Formichetti told Dazed, “We all go on websites like Pornhub, you know? So before you start jerking off maybe you can stop and look at our new pants.” For New York Fashion Week in 2017, Hood by Air sent a Pornhub-inspired line down the runway (models wore their hair stylized as if it were coated in semen, and jackets reading “HUSTLER” and “NEVER TRUST A CHURCH GIRL”).

In September that year, the New York streetwear brand Richardson announced a capsule collection featuring Pornhub-branded hoodies, hats, swimsuits, jackets, and T-shirts — one featuring porn actress, poet, and Pornhub spokesperson Asa Akira, and another featuring the flags of countries in which Pornhub is banned. Two months later, the Montreal outerwear brand Moose Knuckles debuted a limited-edition Pornhub bomber jacket that was sold through the Rihanna-blessed SoHo streetwear staple VFILES.

VFILES is also beloved by Pornhub’s most important woman: Kim Kardashian.

Last summer, the team stopped by the De Re Gallery in Los Angeles for “Make Me Famous,” the first exhibition by “professionally provocative” Instagram-famous twins Allie and Lexi Kaplan — just to pick up a painting of the Kim Kardashian–Ray J sex tape, which is now prominently displayed in the company’s LA office.

Pornhub loves Kim. When she was robbed at gunpoint later that year, Pornhub offered $50,000 “in exchange for information leading to [the] arrest and conviction of criminals who robbed Kim Kardashian.” The press release said that everyone at Pornhub was “deeply saddened” by the “horrible incident,” and reminded the world that Kim Kardashian’s sex tape with Ray J “remains the most viewed video on Pornhub with 110,198,725 views and counting.”

“We consider her to be a member of the Pornhub family,” Pornhub VP Corey Price tells Vox. “As such, we wanted to extend a helping hand and do all that we could to help bring the wrongdoers to justice.” Ultimately, the police didn’t need Pornhub’s help, but it’s a nice gesture. The video now has more than 143 million views!

This June, the company sponsored an elaborate sci-fi art installation at the LA nightclub Union — handing the reins over to LA photographer and activist Maggie West (best known for her “Fluid” series, containing abstract images of blood, saliva, and semen) and New York artist Ryder Ripps (best known for creating the branding for Soylent and using the Ace Hotel’s artist residency to hire two Craigslist sex workers for a widely-reviled project called “ART WHORE”).

Then it partnered with the editorial arm of luxury fashion seller SSENSE to produce an avant-garde photo shoot and literary companion essay called “The Data of Desire,” using Pornhub analytics to figure out which sneaker brands are most fetishized in porn. (Converse, Nike, Adidas, Vans, and Yeezy, in that order.)

Then last month, Kanye West told Jimmy Kimmel he “still looks at Pornhub” and the company reached out via Twitter to offer him a lifetime subscription to Pornhub Premium. Two weeks later, he was serving as creative director for the first annual Pornhub Awards in Los Angeles, which were reportedly a disaster but came off, anyway, as a major coup.

West debuted a new music video featuring the currently incarcerated Lil Pump at the awards and brought G.O.O.D. Music signee Teyana Taylor along to perform. He dressed porn stars in the latest Yeezy collection (when he bothered to dress them at all) and arranged them onstage to accept futuristic-dildo-shaped award statues he also supposedly designed. The next day, he announced a line of Yeezy sweatshirts featuring the night’s winners, including “Nicest Tits” honoree Kendra Sunderland and “Hottest Female Ass” honoree Mia Malkova.

“Where do these [partnership] decisions come from?” Katz parrots back to me. “Well, we can’t be in mainstream spaces, so we become this outsider brand that’s doing out-there things. That’s what attracts these other brands like Richardson and Yeezy. Pornhub has an outsider quality that draws people to them.”

Here’s the rub (sorry): Per Pornhub’s own data, as of December 2017, just 26 percent of the site’s users are women.

This is not really a problem, as what Iñiguez pointed out is true: Girls didn’t have to read Playboy to buy the clothes. But it is kind of a problem, mostly because women make up a large share of the people on earth, and Pornhub has basically nowhere to go within the demographic it already serves.

So far, Pornhub has tried selling Mother’s Day–specific cardboard VR headsets, publishing site traffic insights from the day of the 2017 Women’s March, and weighing in on International Women’s Day to announce that it would change the “female-friendly” tag on its site to “popular with women.” It also pointed out that searches for Amy Schumer rose 513 percent in tandem with her Instagram post about the holiday.

“More than ever before, women are coming forward to express their desires more openly,” Price says. “And we want to provide resources to support that.”

So, this January, Pornhub debuted “F*ck Your Period.”

“There are two types of women: women who have sex on their period and women who don’t,” Katz tells me. “It’s 49 [percent] to 51,” (based on an informal Pornhub survey of its female users). With that, uh, fact in mind, Pornhub launched a campaign with the goal of explaining the health benefits of having an orgasm during your period. It made its own period calendar app and encouraged women to fill it out so that each month, they would receive a free login code for Pornhub Premium for the duration of their period. “[The goal was] to get girls to experiment with Pornhub for the first time in case they hadn’t,” Katz says. “Pornhub is a sex-friendly, female-friendly company.”

Yet the campaigns aimed at women are rarely the ones that blow up. In March, the site started accepting cryptocurrency as payment and had models stroll through the Financial District in Pornhub-branded ski masks, tossing plastic coins and licking the Wall Street bull’s balls. This worked: It got press.

The following month, Pornhub launched a program called “The Visionaries Director’s Club” with the aim of “[diversifying] porn production” and gave rapper Young M.A. a budget to write and produce her own pornographic short film. The company described the film in a press release, writing that it would appeal to “our progressive generation,” and adding, “While high production level lesbian content is often clearly created with the male gaze in mind, M.A’s debut film is authentic and genuine to her taste profile.”

Last month, it gave a similar budget to pansexual singer and rapper Brooke Candy, who wrote of her film, “We had the most next level crew of fine artists from all over the world and the cast of actors that I chose really had an inner beauty which they unleashed on film. It’s queer, it’s sex-positive and it’s super-hot.” This didn’t work — it got no press. But the data says that female usership of Pornhub grows every year, Price points out. So it’s fine.

As a woman who menstruates, did I know that orgasms make period cramps less painful and bleeding cycles shorter? I mean, as a woman who drinks water, did I know it keeps my organs running?

Pornhub’s brand strategy is elaborate, multifaceted, funny, and cool. It’s also as simple as a bunch of straight boys chasing what straight boys so often chase: a projection of ease and edge that makes them appealing to other boys like them, and a veneer of caring that they hope will grant them an in with women.

Correction: Moose Knuckles is based in Montreal, not New York as previously stated.