Thanks for grabbing a drink while you’re in town. Are you happy to be home?

Yeah, I love it in Chicago. I love it when it’s not the winter, too. So this is a nice time to be in Chicago.

After all of your BuzzFeed “Whine About It” videos and now your new “TBH” video series where you get drunk by yourself and tell people how to live their life, do you have any rules for drinking on camera?

I went to my doctor in New York — not because there was anything wrong – but I feel like someone should tell me this is a bad idea. A medical professional should tell me that this is not what I should make my career out of. He was shockingly unfazed that I chug a bottle of wine, every week. He was like, “You’re not going to do that forever. You’re young, it’ll be fine.” Now I feel like I got the medical industry’s clearance to go all out.

What happens when you finish filming? Do you go out? Take a nap?

I have my tips for being a functioning alcoholic. I learned to be very proficient while under the influence. I never drove a car. I’m not breaking the law. We filmed the very first episode at 5:30 p.m. and I said, “I’ll get drunk and take a cab home afterwards.” I’m secretly a diva —not secretly, I guess I’m pretty openly a diva — and we did it [at 5:30 p.m.] and I hated the lighting so we had to redo it at 1 p.m. instead. So I drank a full bottle of wine at 1 p.m. [on Modays]. I was a writer for BuzzFeed full-time, but “Whine About It” became my full-time job. It took the full week to prepare the topics, gather props and get all of those things together. I very quickly learned how to get my shit together after drinking. My routine was always to chug a full glass of water. Then I would chug a small black coffee and then two boxes of coconut water, which is the secret to hydration even though it’s not good at all. But, it helped; it hydrated me very well. I would let [the fluids] battle one another inside of me.

Would you be hungover the next day?

Normally when you get drunk you reach that point of being drunk where you’re kind of sad and want to lie down. Usually that happens at 3 a.m. or 4 a.m. if you’re drinking at a normal hour. For me, because I got wasted at 1 p.m., I would hit that point at like 7 p.m. So, every Monday night I would be depressed on my couch watching “MasterChef Junior” and eating a bowl of penne alla vodka. This was my Monday routine. I would always cry during that show. It’s one of the most touching shows on television. It’s very earnest children doing something they love and being nice to one another even though it’s a competition.

How much prep goes into your videos?

“Whine About It” was very produced and the intention was for it to feel very fun and laidback. It’s not like suddenly I go home and I’m a Harvard professor. I’m a drunk guy at work. But there was a lot of preparation. I wrote a lot of it beforehand, I crowdsourced with everybody at work to get ideas. We’d plan ahead in terms of getting props and making sure everything was there. In general, BuzzFeed is a place where you experiment a lot and then you read comments and you look at the data on how well something performed. A lot of the job was seeing how people respond to things and then reacting for the next week.

What’s your key to producing great content?

The backstory to “Whine About It” was that about a year ago BuzzFeed started an effort called BuzzFeed Distributed. The idea was to make content that just went directly onto people’s feeds so you don’t have to click away, you just see it there. As part of that effort, we started my Facebook page, which was called “BuzzFeed Matt”. At first I had this blog called “Literally Matt” – awful blog – but every day I’d write about a different topic. Every Tuesday was “Tipsy Tuesday” where I’d get drunk and give advice. Wednesday was “Whine Wednesday” where I’d complain about stuff. The blog didn’t do very well and I just felt like I wanted to make videos for Facebook– similar to what a YouTuber would do, but on Facebook instead. So we combined a couple of ideas from the blog and turned it into “Whine About It.” I never thought it would be a huge success so it’s hard to say all the things that made it successful.

Would you say there is an element of luck when something goes viral?

Definitely. The story about how “Whine About It” was born from a failed blog that combined elements is [an example] of the success of stuff online. [You have to] recognize when it’s not working and either adapt or react or shut it down and try something new.

Did a lot of sleepless nights go into your decision to break away from BuzzFeed and fly solo?

I haven’t slept in like three months. I go on pure cycles of caffeine and alcohol. It was definitely a hard decision. I was at BuzzFeed for three and a half years. I joined right when I was out of college, so they gave me my start, really. It kind of came down to this moment where I had to decide if I wanted to stay under the umbrella of BuzzFeed, which is a great umbrella, or take a big risk and not only be able to make videos on my own but also do live shows, write a book, have a TV show and a podcast and all of those other things. And not only have the freedom to do it, but then to own all of that. It felt like the right time to do it, not the least of which is that I’m still on my parents’ insurance, which helps a little bit.

When you have so many opportunities for ways to make and release content, how do you prioritize?

I have no idea. I’m still trying to figure it out. I’m someone who started on the Internet so that [platform] is still important to me and I want to make sure I’m putting out stuff there. Even though I’m not doing “Whine About It” now, I’m doing a new video series that I’m starting to film out of my apartment called “TBH” [“To Be Honest”], which is basically the same concept. I get drunk and share advice on things.

What went into the decision to choose Facebook over YouTube?

I didn’t think of myself as a video personality before I started my Facebook page. I was just a person on the Internet. [The choice] was born more out of wanting to put content onto a page that was my personality instead of a YouTube channel.

When your videos get about 1 million views, what is your relationship like with Facebook?

They have people just like YouTube that do outreach and help to inform you in terms of best practices. They have some great live videos happening now so they’ll reach out and say, “Hey, you should do more of this,” but I don’t have someone who calls me every day. Facebook is great and super supportive. They’re a platform, but they benefit from funny, smart people doing awesome stuff. It’s a nice symbiotic relationship.

Are there more nerves doing a live show since there’s a crowd in front of you?

Yes. It’s different. A lot of stand-up comedians talk about stand-up as a great way to practice your craft because you get immediate feedback from people– they’re either glaring at you or laughing. I always thought about the Internet in similar ways. Either people are liking it and sharing it and commenting on it, or they’re not. Making that transition was not as scary as it might have been if I came into this two years ago.

You went to school for journalism. How has your degree helped your career?

I do think it was valuable. Maybe this is me trying to jab a justification onto the amount of student loans that I have right now, but I always thought I’d be a magazine writer and move to New York and work for Anna Wintour. Clearly I’m about to walk into Vogue right now. My senior year I really started to get into Tumblr, Twitter, Facebook and Internet culture, so I went through a brief transition period where I wanted to be a writer. I also loved the Internet and entertainment on the Internet. I do think good comedy takes good observations and good reporting. You have to know your shit and know what you’re talking about. People don’t believe it unless it’s based in some truth, so that’s my justification for all of my years of learning reporting. Even if your topic is something dumb like why people on airplanes are the worst, you have to experience that, you have to do your reporting.

Where do you see yourself if ten years?

I’d love to have a couple of books that are successful and have a successful TV show. To me, the platform isn’t necessarily as important. It’s about making people laugh and being an entertainer that people feel like they can relate to.

Who are some comedians you look up to?

There are so many people. I’m a huge Tina Fey and Amy Poehler fan. I also love Second City-Chicago people. I’m not from Second City, but I’m a Chicago person. I love that they also stand for something. I feel like my focus is very Seinfeld-ian, if that’s a word. It’s just everyday stuff that I talk about, everyday observations. Then I think my humor is a little darker, like Louis C.K. I’m a little mix of everybody.

What advice do you have for people trying to start their own personal brand online?

I was always terrified of posting anything in college. You put something out there and it’s not ready and then you publish it on the Internet and it’s there forever, it’s searchable. It was always intimidating to me so I never wanted to write or post anything. I was never someone who could keep a diary or a journal– it felt weird to write knowing that there’s no audience reading on the other end. “Who am I writing this for?” But, you can’t get to a point where you have an audience unless you take the risk and put some stuff out there. Ideally the garbage that you write will be replaced with better stuff because you’ll learn from the garbage you put out there and get feedback from people. The good thing is having people you know you can trust for feedback. The Internet is terrifying– everyone has an opinion, whether it’s good or bad. You have to have your people that you know are going to give you honest feedback.

Who do you turn to for feedback?

I’m still friends with a lot of people at BuzzFeed. They’re all smart, funny people who I know will give me some real talk if I need it. There are a lot of people like them who I ask, “Is this really funny? Or was I just really drunk when I wrote it?”

What piece of advice has stuck with you over the years?

I had this professor at Northwestern in the journalism school. It was my senior year and I had completely given up. “You’re a senior, who cares anymore?” We had a final project that I had clearly given no thought to, and this professor really liked me. I turned it in and the next day I had a conference with her. I got there and she threw my project across the room. I was like, “I’m not picking that up, first of all.” I hate disappointing people and even though I didn’t care about that project, it reminded me to always put in the effort. That was the lesson.

If you could have any other career, what would it be?

When I was applying to colleges, I loved writing but I was a huge nerd in high school. I was a Mathletes MVP and Science Club president. I’ve always been right brain and left brain– I liked being creative, but liked math and science. I remember everybody telling me, “Don’t study journalism, because you don’t learn journalism in the classroom. You learn it by going out and writing.” In my head, I was going to be in school for four years– I had to study something. For a little while I wanted to study biology and be a doctor. I remember having a conversation with my high school teacher saying, “I want to be the next Sanjay Gupta.” He’s the CNN doctor who gets to touch Anderson Cooper. So for a bit I wanted to be a doctor or write about science and medicine. Look at me; I’m not a doctor by any means. I’ve always had a really weak stomach; in fact, a lot of my live shows are about my worst vomit stories. When I was a kid I had an especially weak stomach and one of my cousins was like, “You know, nobody goes to the doctor for a normal foot. They go to the doctor because something is seriously wrong with their foot.” I thought that was a good point. Being a doctor is not just putting a Band-Aid on someone. That’s all it took.

Are there any celebrities you can’t believe follow you on Twitter?

When I was at BuzzFeed I started writing a lot about One Direction, in part because I thought it was funny that I was this grown man who loved a boy band. At first it was kind of a joke, but then I got deep into it and really started enjoying it. So I started this campaign to get Harry Styles to follow me on Twitter. It took like a year and a half, but at some point I tweeted that I would buy everyone at work an ice cream cake if he followed me, expecting them all to join the effort. No one took the bait, but six months later he followed me on Twitter and someone at BuzzFeed pulled up the old tweet and told me I owed everyone an ice cream cake. I went to Dairy Queen and got a giant cake.

Where were you when you got the notification Harry Styles had followed you?

It happened overnight, so I woke up and saw it. Immediately I screencapped it and tweeted it. I knew I’d go into the office and everyone would be so excited. Then I had to get an ice cream cake.

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

I’m fascinated by Oprah, even more than Beyoncé. Oprah birthed Beyoncé. I love that Oprah’s thing now is dragging chairs out into the forest and interviewing President Jimmy Carter in the middle of a forest clearing. That man is like 100 years old. I would love to know what happens inside of her brain. I also love that Oprah is really into gardening. She’s always harvesting crops. Only Oprah is harvesting crops all year round. There’s never an off season. I was on “CBS This Morning” a month ago with Gayle King and I had to contain myself. She knew I was Oprah-crazy; I was trying to get some secrets. She didn’t break.

Were you nervous for that interview?

Yeah. I’m getting used to being on camera more. Before “Whine About It” I had never done stuff on camera. Part of it was me just getting comfortable seeing myself on tape. I did a lot of personal growing in that time. I also edited all of the videos. I didn’t know how to edit video before that. If you look at the first episode, which is awful, you can tell that I had no idea what I was doing. In part, it was me being able to control what face I was making, but I also got more comfortable seeing myself on camera. Knowing the behind-the-camera work made me more comfortable in front of the camera.

Did you go through any training since the first episode?

I’ve been shockingly undertrained for being in public. I’m shocked when people let me go outside and trust me to behave. I think the great thing about who I am on the Internet is that it’s very much who I am in person. I like to say that based on the person I am on the Internet that people have very low expectations of who I’m going to be in person. That’s a good thing; there’s nothing worse that I could do than what they’ve already seen. I have nowhere to go but up and impress them. Every little bit has been a learning experience. I did my first red carpet for the People’s Choice Awards. That was the weirdest thing. I thought, “I absolutely don’t belong here.” You have to switch off the part of your brain that’s aware of what’s going on. Whatever is immediately in front of you is what you react to. It’s a million people in one room that have no idea what’s happening around them. Or maybe that was just me.