I started Jannuzzi’s Cookies while I was still at GQ. I was on vacation in New Mexico and we found this chocolate place there called Kakawa Chocolates. They sold Mesoamerican hot chocolate elixirs. It was like crack. I just got hooked on the flavors. When I came back to the city, I was like, okay, I'm going to try and make this myself. I would make Duncan Hines Chocolate Cake and pour sriracha in it and see what would happen. It was disgusting.

I kept trying to work with that and eventually it became way too complicated with the kitchen setup that I had. So I switched to cookies and decided that instead of trying to do the spices thing, I'd just to try to make a chocolate chip cookie that was really good. It snowballed from there. When I was testing recipes, I would bring a box to work once or twice a week. People kept asking, "Are you starting something?"

When I got laid off, a really good friend of mine was like, "You should do the cookies full time." I didn't. But it's still something I would really like to do, especially because a lot of my peers have their own things. Whether they're a huge success or not, it’s something that's their own—something they can make a living at and totally control. I'm so envious of that. Not that I don't love the jobs that I've had.

I'm a very big victim of this thing called magical thinking, which is where you constantly focus on the end game of a dream as opposed to thinking about the work that goes into it. My girlfriend and I joke about it and we're like, yeah, it could be America's favorite cookie! Why not? I mean, it's delicious. There’s no drugs in them, but they give you crazy vivid dreams if you have them right before you go to sleep. It's just really fun to think about.

I get asked a lot about making weed cookies, and it's definitely something that's been on my mind. I have some family members who are pretty savvy when it comes to the legality and future of it all, but that's all I can say about that right now.

People will reach out to me occasionally on Instagram and ask for a box and I’ll do that. Other people have come to me and said that they'd be interested in investing, which is great, but I don't have a business plan. I don't know how any of that works. But I think I would be a real crazy CEO. I'd just be like, everyone take the rest of the day off because I'm tired. We’d have a four-day work week. America needs cookies? Too bad, I'm going to the beach. And then the company would get run into the ground.

I'm a very big victim of this thing called magical thinking.

I started sketching when I was three or four years old. I started by drawing characters from movies and TV and continued doing it all through high school. I loved it so much. I just kept doing it and when I graduated college I figured, okay, I'll be a graphic designer. I remember my parents asking me what the goal was. I told them, "I'm going to be a graphic designer at GQ."

I came to the city and took some classes at Parsons. I had some friends who worked in magazines and I went on some informational interviews, but they were all like, "You need internships."

So I started interning and working in a restaurant. I was the maître d' at Craftsteak—one of Tom Colicchio's restaurants. I met so many crazy people. All the head waiters there had been in the city since the '80s. There were drag queens who worked there—in waiter uniforms—that would just tell you the craziest stories. It was awesome.

I was never a writer. I never thought I would be, but while I was working at Kate Spade, I started a blog on Tumblr called Textbook. It's still up. I would take a character from a movie or history or anything really, and style them. I cut out runway photos of individual pieces, a coat from this person, pants from that person, whatever. Each character would get three looks and I'd write up a little thing about them. It got really popular, which was an extreme stroke of luck—this was in the days of Tumblarity and Tumblr Tuesday and all that crazy stuff. I think it still has, like, over half a million followers.

You don't want to admit that people treat you better because it means the world is an extremely superficial place, but I was a fashion editor. Who am I to judge superficial people?

I have such a love-hate relationship with where I grew up. I had a solid group of high school friends, but I was very much like, I just want to get the fuck out of here. There were people there that I really detested. I didn't play sports; I was an art kid. I was really fat. It was just miserable. There is a small part of me that thinks everything I do in my adult life is just a response to hating high school.

My senior year, I started walk-running around town, and I lost some weight. I remember when I did that, my high school experience—though there wasn't very much left of it—completely changed. All these popular kids started talking to me. But when I went to college, between alcohol and food, my weight went up and down very crazily.

When I was 26, I did a big freelance project one summer and I got paid a ridiculous amount of money. I was like, I can do what I would normally do with this kind of freelance windfall, which is to go buy, like, six coats and call it a day. But instead I ended up buying only two coats and spending the rest of the money on a membership at Equinox. I remember the guy at the membership desk was such a dick. I paid him so much money and he was like, "We get a lot of people like you." I was just like, "I am going to come every day. Just to spite you. Even if I get no benefit out of this, I will come every day for the rest of my life because you are disgusting." I glared at him every time I came in. I think he's since been fired because I kept very close tabs on his behavior after that.

I lost a ton of weight really fast, but I also gained a lot of muscle, and people I knew in the industry would talk about it. I felt so great. Everyone was just nicer and friendlier. I was just like oh, okay. This is what people are talking about. You don't want to admit that people treat you better because it means the world is an extremely superficial place, but I was a fashion editor. Who am I to judge superficial people?

I find working out extremely stress-relieving. It's one of the only times of day where I don't have to worry about anything else. The only thing you can have on your mind is lifting this thing up and down.

Working at GQ was a dream of mine for so long. It was an incredible experience. I remember being very high on myself when I went there, but that whole mentality was quickly shattered. I was definitely put in my place. I like to think that the best thing I learned at GQ was how to work with people. I could lose my temper very easily, but if you're an asshole in the workplace, it's not good. Live and learn. But I got to meet some really incredible people, many that I'm still really close with today.

The opportunities that you get working at a place like that are insane. I interviewed Common while he was getting ready for the Met Ball and that was a really surreal experience. He’s not the run-of-the-mill famous person. He's a very interesting human and a very good person. You could tell—he was super humble the whole time.

I had tea with Valentino and Andre Leon Talley and I remember just being like, what the fuck is happening right now? I was smiling the whole time. I remember them almost not knowing what to make of me because I was so happy. They were like, “Do you think we're joking?” I was like, “No, it’s just that I’m sitting in front of the two of you.” They are both legends and to be able to converse with or even just listen to them in that setting was wild.

I know so many people who work in the fashion industry that in high school were ostracized, were freaks, and then we all kind of find each other in our 20s and 30s.

Twitter was difficult work. Especially trying to cover all the news. It's funny, the hours weren't actually that bad, but you can't really check out of that job, ever. I worked on Moments, so it was an editorial team operating within a tech platform. It's unlike any other editorial job you could have. Twitter is the only place that does editorial that way because it's Twitter. It was really insane.

It was one of the best job learning experiences I had, but ultimately it was a pace I couldn't sustain. One, because of the actual speed at which things were happening and two, the nature of the things that my team and I had to cover. I mean, school shootings, terrorist attacks—just everything with the political climate in the U.S. right now. Covering something like Charlottesville, that was one of the hardest. I did some stuff around the Women's March. I thought that was so incredible. That was such a powerful day in so many ways. It had a very optimistic feeling about it.

There are really incredible things that happen only on Twitter. But ultimately it just wasn't something I could really keep up with. I missed the creativity of the fashion industry and writing. I'm not a news guy. Although now I'm addicted to it.

Working at Bonobos is cool. They make great pants that fit my weird legs, so that's a huge plus. The main thing we're doing now is trying to tell stories about guys we look up to, guys who are making a difference. We did some stuff with the astronaut Leland Melvin, who's been doing a lot of amazing work with STEM education for girls. And we just had Parker Molloy profile Chris Mosier, who's a leading activist for LGBTQ+ athletes. All good stuff, all good people. Plus, again, the pants.

The funny thing about fashion is that people always say it's so exclusive. And it certainly is. But if you were to take a cross section of the people in it, you'd see it's an extremely inclusive and welcoming environment. I know so many people who work in the industry who in high school were ostracized, were freaks, and we all kind of found each other in our 20s and 30s. When you're surrounded by like-minded people, it's really incredible. The one thing I loved about working at Condé Nast was that there were just floors and floors of my kind of people. It was so fun.

My dad's a pediatrician and he's had his job my entire life, which is such a foreign concept to me. I think it’s ADD, to some degree. But we have access to so much more than previous generations, which is such a cliché thing to say, but it's so true. You can learn so many different things on your own now. So many people are self-taught. I remember watching the movie Renaissance Man and learning what that meant. Not that I am one, but I love the idea of doing a million different things. I think everyone wants that now.

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John Jannuzzi photographed by Laura Wilson at his apartment in New York City. This conversation has been edited and condensed for clarity.