Stephanie Laing recalls the moment she started to think about doing more than just producing some of the most popular comedies on television—such as Eastbound and Down, the first four seasons of Veep, and Danny McBride's upcoming HBO series Vice Principals. Her daughter was four at the time, and they were rushing out the door to go somewhere. Suddenly her daughter stopped. "Hold on," she said, "I have to put my pretty on."
"I just paused for a moment," says Laing. "Because I have three kids. Two boys and one girl. It was definitely a moment. I realized, I have to help her define 'pretty.' What does that mean? What does it even mean to me?
"I watched her put Chapstick on—slightly horrified, but, like, okay, Chapstick's going on," Laing continues. "Because, you know, I'm not that person. I've been producing comedy for 20 years, and I'm on the set all the time. So I'm in jeans and sneakers. I'm not in lipstick, so she didn't get it from me. I wondered, where is this coming from?"
The Chapstick moment set in motion a series of events that ultimately led Laing to launch PYPO.com—for, you guessed it, Put Your Pretty On. The site, which is just coming out of a soft launch, is a kind of Funny or Die for women, with an element of feminist messaging all distilled through the prism of humor. There are comedic sketch videos, essays, and other editorial content aimed at women who want to see women, and women's issues, handled in a smart and funny way. "You'll never see a smoky-eye how-to," Laing jokes. PYPO's first digital series, The Crying Room, is about a new employee, Abi (played by Cassidy Freeman) who discovers that her new, Office Space-like workplace has a designated room for weeping, which people sign out the way you'd sign out a conference room. Another PYPO series, written by Veep scribe Georgia Pritchett, stars Rose Byrne as an online relationship guru who films a "Care-robics exercise" with her partner. And Paula Froelich, the former Page Six columnist and Yahoo Travel editor, takes to the streets of New York to talk to people about their comfort zones.
Indeed, many of Laing's high-profile colleagues are involved in PYPO—the advisory board reads like the Veep IMDB page and includes everyone from the show's creator Armando Iannucci to stars Tony Hale and Matt Walsh. But the mission behind the site isn't just to showcase familiar names, but to discover new female talent and help them get a leg up in a business that is famously unfriendly to the other sex—something Laing knows from experience. Despite her success in Hollywood, she says that all of her mentors have been men. Women, she says, "just always felt competitive in a weird way. That's my experience."
With PYPO, Laing hopes do her part to change this dynamic and become an encouraging role model to young upstarts. She and her network of creatives will lend expertise in producing, writing, and directing new digital productions that PYPO—which has raised an undisclosed amount of angel fundraising—will finance. Laing says she also hopes to develop and fund films through the company's film arm.
But if the site's origins are in humor, Laing says her goal is to take the conversations that begin on PYPO and expand them into the larger discourse surrounding the challenges that women face. Through a feature called PYPEin, PYPO asks viewers to film video responses to the site's biweekly themes—such as crying, saying you're sorry and not meaning it, and mistakes—and send them in. PYPO also collaborates with the SiriusXM show Wake Up With Taylor, where Laing and others have gone on to talk about PYPO themes and then asked listeners to call in.
"I think the main thing with PYPO is, yes, I started with a focus in comedy, that's my background, that's the change I can effect. But ultimately it's about women in tech, women in finance, women in general, and a two-way conversation. I never wanted PYPO to be, hey, I want to tell you all about this stuff and we don't care what you have to say. It has to be a two-way conversation. And that's what's interesting. Maybe if we can laugh so hard together, we can cry together, and everything will be different."
Laing recently spoke to Co.Create about the journey that led her to PYPO, and how she hopes it will inspire other women to push themselves creatively, tackle opportunities rather than wait for them, and toss aside fear.
PYPO actually originated as a blog, where Laing would recap life as a single mom with three kids, mining her experiences for humor. She says it was a pivotal moment in her career, when she also started to push herself in her work, moving into directing TV episodes as well as a short film.
"It really was a colliding of events. I had three shows on HBO. Veep, Eastbound and Down, and Banshee, which is on Cinemax. And I really had this moment of going, wait, something's going on here—you recognize that there are always these times in your career that are a pivotal moment. So I said, okay, I'll start writing this blog—I hate that word, but anyway—called PYPO to stretch myself creatively and see if I can even be consistent. I didn't publicize it. It really just was a production diary where I was talking about what was actually happening. I wasn't telling tales. I'm a single parent with three kids, there's humor there and there's also irony and it's hard.
"And I started directing at the same time. Thankfully, when I was on Veep I started directing second unit because every guy around me raised their hand and said they were going to do the second unit in D.C.—this was on the pilot. And I, for some reason, said, 'No. I will.' I never wanted to direct. It was never anything I wanted to do. I love producing. But in that moment I stepped up and I just kept doing it on the show because, frankly, no one told me to stop, and because Armando was really supportive. I mean, really supportive. I started to realize, in my life I hadn't had a lot of female mentors.
"So I started writing this blog and directing, and I got a call from Yahoo Travel and Refinery29 and a few other people, saying, 'Will you write for us?' And one of the articles was, literally, name your female mentors. And I said, 'I actually don't really have any.' Actually, it's kind of quite the opposite. I haven't had a great experience with women, and I thought, why is that? Why don't we help each other? It's on us to help each other. It's also on the men to help us as well. But what are we doing to perpetuate this amongst ourselves?"
Directing TV episodes gave Laing the courage to think about directing a film, despite having very little experience. Thanks to some encouragement from male colleagues, she went for it, feeling that as a woman no one was going to hand her the opportunity.
"I was really stretching" creatively, she says. "You know, once you step into that arena [of directing], you really kind of get a little, not bolder, but, you're afraid, but the fear is good. It's like, I'm really nervous about what I'm doing, but I'm just gonna keep stretching my wings. And what happened was, I decided to do a short film. There were two short stories—I optioned both of them, and then David Gordon Green, who's a prolific filmmaker, was like, 'I'm going to support you in this process. You should do a narrative short film.' And I remember asking Tony Hale to be in it, and he responded that he would do it without even reading it. And in that moment I literally thought I was going to throw up. I burst into tears and then I thought I was going to vomit. Because, now I have to do it! Thankfully we landed at 13 festivals and opened two of them.
"It's called Trouble and the Shadowy Deathblow. It's a dark comedy. It was a great experience for me. At the end of the day, I thought, I'm going to direct this. If I suck, I suck. But at the end of the day, at least I'll be a better producer out of it. And as it turns out, I didn't suck as a director. So that sort of shifted my career. And I realized, there is a comfort level, like, you're in a box, but then you're like, but I just did [this new thing]. I think with women, we're constantly asked to show, don't tell. And show again and again and again that we can do something."
PYPO transformed from blog to multimedia site one day when Laing was "sitting in an agency and someone there asked me if I wanted to sell the name [PYPO] to campaigns. Companies looking to get to woman in a really organic way. The person threw out four different brands and said, 'Do you want to sell this?' So I knew I better do something with PYPO. I called my business partner Susan Paley [the former Beats by Dre CEO]. I've known her for 20 years, and you know I stayed in film and TV and she went tech. And I said, 'Look, I think we need to do something with PYPO,' and so we trademarked it.
"That was easily a year and a half ago. Then we went about figuring out what it was, what it would mean, what it would mean to women in terms of a platform. It was another colliding of events. I reached out to all these women, saying, 'Hey, I'm going to do this thing called PYPO. I'm not exactly sure what it is yet, would you . . . ?' And across the board they would say, 'I'm in, I'm in.' And I suddenly realized, if you watch Game of Thrones, it felt like Mother Dragon, we're freeing the slaves. Suddenly all these women, they're engaged. They were in.
"Susan and I said, we're going to do a comedy platform. Really multilayering it in so we can actually help people be their own producers and their own directors. You know, Greg Yaitanes—he's an advisor on PYPO—he used to say all the time on Banshee, 'Be your own producer.' I thought, if I can help someone execute something—because execution is hard—that's a big part of PYPO. Trying to level the playing field from the point of view that I can, as a producer, because that's my background."
Although PYPO is aimed at women, Laing says it's crucial to have men be a part of the project in order to truly be effective. Whether as an advisor or sketch writer, PYPO seeks out male voices to join in the mission.
"We have a lot of men, guys, who write for us. Tony Roche. That's really important to us. Because I think what we're up against is, it's so interesting to me—I've only had one, I won't say it was a bad meeting, but it was just an interesting meeting with a company, where literally someone said, 'We do really broad comedy, and next we're going to branch out into niche comedy. First we're going to do sports, then pets, then women. But by women we mean mainly moms.' I was like, you just wiped out over half the population!
"I think, if we don't invite men to the table, we're not going to be very successful in effecting change. They have to be a part of it. We have to come together, which is why it has to be funny. There's nothing wrong with having a man's funny perspective on crying."