You’re in charge of [advertising agency] Rooster’s branded entertainment, among other creative duties. It sounds like you’ve retained the voice you had at Vice magazine. Rooster hasn’t restricted you?
I haven’t changed at all. It’s the opposite. I’ve always been telling stories. I do it more with video now than I did in the past, but I’m still writing the exact same things I’ve always written. After I left Vice I thought, “What the fuck am I going to do with my life?” I box at Church Street Boxing Gym and I highly recommend that if you’re ever at a crossroads. And it just hit me one day when I was hitting the heavy bag: “I know what I’m going to do—what I’ve always done.” It was shortly after that I started at Rooster, and started doing sketch comedy. We’re trying to get a show on the air—and we’ve done a lot of pilots—but it’s a really quick way to do some sketch comedy.
You came from a company that once entered a partnership with Viacom to launch VBS.TV. In your job as creative director at Rooster, is authenticity still important?
That’s what I’m saying about comedy. It doesn’t give you a choice. The joke has to be a certain way. Even if you delay it just a little bit . . . I mean, look at stand-up comedy. If somebody stutters or if they pronounce Cleveland wrong, the whole joke is ruined. And that’s what I like about this. You can try to sell out with a joke, but it’ll bomb.
Have you always had a curiosity about the advertising industry, even before Rooster?
Yeah, no. When I was at Vice, the construct was “editorial and marketing have to be at odds,” and they were literally at the opposite ends of the room. If editorial was happy, marketing was unhappy—and vice versa. That conflict is what magazines are about. I’ve never been interested in advertising, and I think Rooster is an evolution of that.
Then why did you take a job in the advertising industry?
I’m thinking about making this into a banner and hanging it in the office: There was a comment on a YouTube video when it got a million hits, and it said, “This better not be a fucking Vans ad.” And I thought, “That’s exactly what we’re doing.” I think young people today . . . it’s a cliché, but they’re savvier than my generation because they’ve been drowning in the Internet. To do this Don Draper shit, where you say “smoking is cool,” and you have James Dean with a cigarette, you just can’t do that anymore.
At the risk of sounding cynical, do you ever worry that no matter what you do—no matter how brilliant your content, or how ingenious the idea—young consumers are still just going to be skeptical about everything you do in the advertising industry?
Yeah, but can you blame them? I mean, they’ve been abused. They’re like orphans who’ve been abandoned one too many times. So I think the way to pin ‘em back is to deliver good jokes. With these cynical kids, if you give them something that’s useful or genuinely funny, they appreciate it. Don’t bullshit kids. Don’t bullshit anyone.
Your soon-to-be-released memoir  was originally titled The Death of Cool. Why did you change the name to How to Piss in Public?
The rationale, at first, was that the book is all about the partiers, and then you have kids, and then you’re not cool anymore, and that’s the end of that. Which is good—because there’s nothing sadder than an aging hipster. But it didn’t convey what the book was, which is an over-the-top, balls-out, unapologetic series of crazy stories. And the original name was too macabre. The cover is me and a bear getting wasted.