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Out of all of the things you’re doing – writing a book, launching White Girl Rosé, making appearances – what did you least expect to happen?

I think the thing I expected the least was the age of people that were going to be coming up to me. It used to be people in their 20s— younger weirdos, some goth people, runaways, stuff like that. Now 8-year-olds are like, “What up?” Some little Puerto Rican girl came up to me and goes, “Yo, you not even that fat.” [One time] I signed a baby. On the other side, there are 75-year-old women with bad plastic surgery sloshing white wine saying, “I love your stuff.” So I never really saw that coming. I figured it would be the turnt-up college types, but it’s turned out to be Hispanic children and older white women with rock-hard breast implants. It’s all I ever wanted, really. I’m trying to party with everybody.

You have 8 million Instagram followers, which is more than President Barack Obama and Oprah Winfrey. Who is someone you can’t believe follows you?

It was nice out in September and someone came up and put their hands over my eyes from behind, which is weird even if you know them. She said, “Guess who.” I really didn’t know. It was Brooke Shields, which was so weird. She was kind of day-drunk which was chill. She was rosé-drunk, which is what you should be at 3 p.m. on a Saturday. But I’m such a big fan of hers and now people ask me, “Do you ever get nervous when you post something on Instagram because there are so many people that look? Are you worried that they’re not going to think it’s funny?” I used to not really give a shit. It was kind of just for me and I pretended it was my friends and me. She said, “I love your Instagram. I look at it every day.” Now in my head I’m thinking, “Is Brooke gonna like this? What if Brooke doesn’t think this is funny? What if Brooke unfollows me?” That would be horrendous. Now she’s really upped the pressure of the situation.

Was writing your book, “Money Pizza Respect,” easier or harder than you thought it would be?

It was a nightmare. It was a complete nightmare. I don’t even understand how people write books. I definitely don’t understand how people write fiction. These were just stories from my life that I was retelling. I found out that my mom had sex with Shel Silverstein and stuff like that. You don’t even have to make it up, but what if you’re writing a story about a family on the frontier? I don’t even know how you make that shit up! It’s insane. I can barely recount stuff that actually happened.

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Where did you sit down to write the book?

I had this big, grand plan. I got a whole bunch of designer drugs and rented a hotel room out by JFK [International Airport] in New York. I thought, “I’m going to stay in here for a week and a half doing coke and when I emerge it’ll be done.” Then one day in I was like, “I feel sick. This isn’t working.” So that was supposed to be the plan, but then I ended up just writing it in my house.

Please tell me the chapter on how you thought you were the most famous kid in school because you were in one Hershey’s commercial is true.

Yes, completely true. I went from unknown to incredibly famous in my own school to a diva, fucking Mariah Carey nightmare to completely washed-up and out of the limelight— all within 45 days. It was a really quick meteoric rise to child fame and immediate downfall. It was done within about two calendar months. At the height of it, oh man, I was diva-ing out.

Pre-Instagram fame, is it also true that you were expelled a couple of times from college?

Totally.

You eventually ended up with a journalism degree. Why journalism?

I didn’t even know what I was doing. I guess I should’ve majored in something funnier because I didn’t need it and I didn’t even really want it. I did it because my Jewish parents would’ve not been happy [if I didn’t go to college].

What was the most awkward celebrity interview you’ve done?

The one that was the most awkward never actually aired. I was on E! and basically my whole angle was that they’d let me interview really bad celebrities. I’d interview “The Real Housewives of Tampa Bay,” or whatever. That was the whole angle— give me the worst possible thing— so it was sort of a funny dynamic. Then I guess people thought it was funny so they started upping the quality of the celebrity and that’s when things really derailed because I was trying to make a scene. The interview was more about me; it was about me doing something ridiculous. They let me interview John Mayer for his album a few years ago. I came in and I had a suit on, but I had it custom made so it was like a basketball warm-up outfit that you could tear off. So I tore the suit off. I had a used Versace Speedo on that I bought on eBay and I basically tried to force myself on him and give him a lap dance. I had actually heard he was funny and then he freaked out and said, “I don’t like this,” and left. Then I was back to the “Real Housewives of Orlando.”

So we can’t find this footage?

No, he was super pissed. I told the show, “What do you guys expect? This is your fault. Don’t put me in a room with a tear-away suit.” He didn’t even see it coming. It’s not like I came in in the Speedo; I came in with a full suit and tie— he felt comfortable with it. I was playing music out of a Blackberry. It was so soft you could barely hear it and then I tried to mount him. It was super awkward. I saw him a couple of years later and he pretended he was over it.

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Do you remember a specific moment when you took off on Instagram?

I don’t think the numbers ever specifically jumped, but the numbers were growing and it was big enough that I knew people were kind of into it. This was probably two years ago. Then this couple – this normal looking couple– came up to me in Times Square and wanted me to sign their baby with a permanent marker. I asked them, “Are you sure?” which is always a bad sign when I’m asking if it’s a good idea. That’s definitely a red flag. If I think it’s a bad idea, it’s definitely a bad idea. I signed the baby and I felt like it was a thing. It was happening. It had moved to another level— to signing babies with Sharpies.

What do you think it is about you that made you break away and garner such a large following?

I don’t know. That’s a good question. I honestly think that people are scared to try to relate to everybody. You feel like if you go too broad or too mainstream that it’ll dilute what you’re trying to do and that it’s impossible to connect with everyone. My feeling is, “This is a big orgy party. Why don’t we have everybody?” I can have 8-year-olds and 80-year-olds. I feel like I can connect with a Puerto Rican child or an old woman. I can do both of those things. People are scared to do that because it might get watered down if you try to go too broad, but that’s why people gravitated towards my stuff because it was for everybody. I wasn’t scared to try to do that. Get everyone to the party.

Is there a process before you post on Instagram?

I kind of just let it rip. I think sometimes people think I say, “We need a photo, we need a caption.” A lot of times it’s just me driving a car, smoking a cigarette, blasting Miley’s last album— which is really underrated by the way, her last album’s really good— and I’m just kind of like, “Oh shit, I should post this up.” I’m writing a caption trying to drive with my legs. I never wanted it to become more than it was when I had 100 followers. I just want to put out funny stuff. I like to say I can take you out of the day for a minute. If you’re at the DMV in a long line and it’s 10:30 in the morning and some guy’s eating chili and you’re thinking, “It’s way too early for chili. Where did you even get chili at this time? Is that from last night?” Maybe he’s a construction worker – they eat lunch really early – and you’re like, “There’s a baby crying, this is a fucking nightmare.” I’d like to think you look at my Instagram and forget about the chili smell for 10 seconds. So I like to get stuff out there all day and I definitely don’t sit and say, “It’s Instagram business time.”

Are there specific times you recommend posting?

No. There are a million guys named Jeff who work in Instagram social media analytics who will tell you so much information like, “Seven on Thursdays is a great time to hit Portuguese millennials.” I’m just like, “Jeff, relax.” I basically just see it and put it up. I don’t care. You know, at 4 in the morning you’re not necessarily going to get the most likes, but that’s when the savage weirdos are out… and the Europeans. If I post at 4 in the morning it’s drunk weirdos in the United States and British people eating breakfast, so that’s a cool time to do it. Jeff, the social media expert, is going to tell you that that’s not the optimal time and he’ll throw 50 buzz words at you, but I don’t believe in any of that. Fuck you, Jeff.

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How did your first collaboration go when you were paid to work with a brand?

The first brand stuff that I did was with people I knew or friends of mine. That’s the stuff I like doing the most. For me, it’s not about the money as much as it is about being able to do cool stuff. If you have a big social media following, a brand will pay you money, but they really just want you to hold up a can. I have these grand ideas about crazy stuff I want to do. A lot of times brands like to say that they’re crazy. “We’re YOLO out of control. We want to do crazy stuff.” Then the minute I suggest something they say it’s too crazy. They don’t want big ideas. They just want simple; they’re just trying to get it done. So I like working with the smaller brands. I have friends who own a beef jerky company and they didn’t have any money and I said it was fine, just make me a whole line of accessories out of beef jerky. I want a yamaka, a thong, a vest and some sandals. That’s the stuff that’s the most fun. Anybody that has a big social media following that wants to get paid big money by a brand to hold something up is chill, but I want beef jerky thongs. I’m looking for brands that are actually down to do cool stuff.

If you’re trying to build a social media following, at what point should you consider it a hobby versus a brand?

I think people focus too much on the numbers and not enough on who’s looking. If you have 37 followers and you’re getting 14 likes, you’re killing it. You’re nailing it, because you should have four likes. You should have so few likes that you can still see the names— it’s a weird place to be. If I see that, I take them out of that. Side note: a lot of people that I actually know in real life have asked me to stop liking their Instagram photos. I forget I have so many followers. I’ll comment on something my friend puts up and then 400 Ukrainian teens show up on his page. I have a friend who’s a nice looking girl who posted a picture of herself in a bikini and then 400 Eastern European teenagers showed up posting, “I want to be in you.” She goes, “I don’t want this, please stop liking my photos. Text me and tell me you like it, don’t actually like it.”

Is it easy for you to brush off negative comments you see online?

The comments are literally insane. Obviously they range. Some of them are like, “I want to bronze your penis and wear it because I’m so in love with you,” but then there’s a lot of, “I will kill you.” Don’t get stoned and read the comments. People are screaming at each other, screaming at me. I don’t take it personally.  If I was 15 and could have screamed at Britney Spears in 1998… I would’ve been saying wild shit that I didn’t even mean. They’re just trolling, being ridiculous.

Since we’re in Richard Branson’s flat, if you were to have rosé with him what would you want to talk about?

Richard Branson is straight up from the future. I’m not serious about anything, but I am serious about Richard Branson. He’s straight up on a whole other level. I met this girl and I was trying to be with her and I asked her what she does. She told me she sold tickets to space. I was like, “Whaaat? You sell tickets to space?” She basically sold tickets to space for Richard Branson. Richard Branson has people in the world whose job it is to sell tickets to space. That is so killer. No one is doing that. Obviously I knew that he could do anything. I feel like Richard is cliff-diving naked with the ghost of Steve Jobs. That’s what I imagine he’s doing right now at this exact moment in a country where it’s two days from now at 10 in the morning.

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Would you go to space?

Definitely. So down for space. A lot of people are not down for space. But this girl sold tickets to space. That is the most future job. Imagine you had told that to my grandfather.

You’ve built your brand with new media and non-traditional marketing. What old-school marketing techniques do you see sticking around?

I think people want to kill everything and I don’t like that. For the rosé, we’re doing billboards all over New York. The way we consume is definitely different, but that’s part of the reason we wrote the book. One, I wanted to get turnt-up Millennials to read, which seems like the world’s hardest thing to do because they’re not reading. [That said,] I’m not some nerd in a record store saying he likes the feel of an album cover. Don’t put a Jewel case in my face ever again. Certain things needed to go, but some things should not die. I feel like real books are cool. That’s something I don’t want to get away from. Things are changing really fast, but a lot of it is that kids were born out of the Internet. If you were born out of a hard drive, you’re over it before it happens. You’ve heard a Drake album that hasn’t even been recorded yet. “I heard it, I hated it.” I’m like, “He hasn’t recorded it, it’s not out.” Everyone’s just over everything so quickly, so the question is, how do you capture people’s attention? The other thing is that there’s so much noise on the Internet; the Internet is so loud, everyone is basically screaming at you at all times. How do you sift through the noise? Everything is so disposable. You’re seeing so much in a day that you’re forgetting it; you end up knowing nothing. So, how do I stay with you and get people to talk over dinner? Whether it’s positive or negative, whether you hate a beef jerky thong or you think a beef jerky thong is amazing. The fact that you’re going to be talking about it, that impact is the goal for marketing.

Are you a Justin Bieber fan?

I actually interviewed him on my radio show. I’ve known him for a long time. He’s super weird and awesome and he really is great. Obviously there’s a lot of stuff you can’t put on Instagram because Zuckerberg is like a Jew Pharaoh. So I have a massive text list that I send to people of really crazy stuff, crazy photos, and a lot of people definitely want to get off it, but once you’re on it you can never get off. [Bieber’s] manager was on it and Justin saw it and really wanted to be on it. He’s a 21-year-old kid. He’s into really weird shit. He’s super cool and down. He’s super fun. I would have a sleepover with him.

Thoughts on the name Saint West?

I love Saint, but it doesn’t really go with West. Right? I don’t know. I don’t love the pairing. I would’ve gone the complete opposite direction and named the kid “Kevin.” That would’ve been hot. Everyone was like, “What’s it gonna be? Arugula? Balmain? Turban West?” There were all these theories floating around of how crazy it was going to get. It would’ve been hot if it was “Bruce West.”  “Dave.” People would’ve been shocked. “Saint” came out and people were like, “Okay, that makes sense.” They consistently take so long. People were freaking out because they wouldn’t release it for four or five days. I couldn’t sleep. I was definitely freaking out. I texted some wild, gay hairstylists who just know everything asking, “Do you have a beat on this?” They had no word. I was just in bed thinking, “What is the deal? Is it Kevin or is it Turban?” I couldn’t really get on with my life.

If you could have a drink with anyone, who would it be?

I would be in a bathing suit with my legs wrapped around Richard Branson while we’re parasailing through an ocean we’ve never heard of two days from now. I’d have the rosé bottle around his shoulder and he’d be drinking out of it with a straw. And I’d be kissing his back. I’m trying to sleep with Richard Branson, that’s kind of what I’m getting at. Has that not been made clear? That’s what I’ve been intimating. You said, “Have a drink with?” or “Have sex with?” They’re both Richard Branson.

I could start asking that in my interviews, too.

Yeah, not a bad question. So, Richard Branson. And not even because we’re in his flat. We could be anywhere right now and I would’ve said the same. You gotta have a drink with a guy like that. He’s like, “I’ll make your airline and your cell phone and your hotel.” Totally. And his hair? What does that guy use for conditioner? How do you get that kind of volume and body? So voluminous… it’s probably something so crazy. It’s probably falcon saliva.

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