Since I was a kid, I always wanted to be a writer. It was never a soccer player or rock star—always a writer.

I’m from a town in Massachusetts called Sherborn. It’s near Wellesley, Framingham, and Natick. It’s in the middle of nowhere. All woods, no commercial stores, no sidewalks. The only thing people seem to know about it is that Shutter Island was filmed there because there was an abandoned insane asylum attached to my high school. It’s also where we’d often smoke weed.

So yeah, I’m from this bumblefuck town. There were 150 kids in my graduating class at my public high school, and in that, there were actually seven sets of twins, including myself. I have a fraternal twin brother. Ten percent of my grade were twins.

People are always like, “Must be something in the water,” but I looked into it once and it actually has to do with Massachusetts being a medical research hub. In the late ’80s and early ’90s, there were a lot of tech developments in IVF. The procedure also started getting covered by health insurance. If you look at the census data in that timeframe around Mass General, Harvard, and MIT, there are twin booms all throughout the suburbs around Boston, and it’s because IVF suddenly became more accessible.

Being a twin is one of the most defining factors of my life. My twin brother is like my Shakespearean foil, my bizarro. I’m very close with my parents, but he and I have a complicated relationship. He is my polar opposite. He has not been to New York in maybe 10-plus years, he is married, has two designer goldendoodles, works as a financial wealth manager CPA, owns a house, no tattoos, and doesn’t smoke weed. When you’re in a place where not only is it a small community, but there’s also seven sets of twins, all the twins get compared. The other twins were best friends whereas he and I were very different. We had totally different interests.

He was an athlete and it became clear by the time I was 15 that I was just doing sports because I thought that was how to fit in. Very quickly I became editor of the newspaper, the literary magazine, and started throwing battle of the bands shows. On top of all that, there were basically no Jewish kids in our community. We were the only Jews at our own bar mitzvah. I actually made out with a girl for the first time that night and she couldn’t have been WASPier. I think she ended up going to Princeton for swimming, if that says anything.

Before my time, my hometown had more of a punk and hardcore culture. But when I was a teenager, the skate park was always empty. There were no musicians except my small group of friends. Instead, I actively went to other towns and communities to find alternative culture. I started hanging out in Newton all the time, throwing shows. To this day, I’m still friends with some of the people I met back then. I was obsessed with getting out of my hometown. By the time I was a sophomore in high school, I was taking the bus to New York at least once a month for a weekend.

The fact that you can smoke a joint anywhere in New York City now is a fucking blessing. And I am just grateful for that.

No matter how fringe my life or lifestyle has gotten, my parents have always expressed curiosity. Not always acceptance, but curiosity—and that can then lead to acceptance or a deeper consideration of the topic. For instance, at one point during the pandemic I had moved in with married porn stars in Las Vegas. At the time, I was doing consulting work for some sex workers and my folks got freaked out because I hadn’t really filled them in on any of that. They googled the performers’ early work, which was definitely extreme, before talking to me about what I’d be doing with them in Las Vegas. I ended up having a long conversation with my mom and dad about who these people were, what work I was doing for them, and what our personal/working relationship was like. And now I feel like they’re not just interested, but actively supportive of sex worker rights and decriminalization.

I think because they were Jewish in a place where there were no Jews and my mom was the breadwinner in a town where a lot of moms did not necessarily work that they felt like outsiders, too. They noticed that I could fit in, but also that I felt like an outsider, and they nurtured that by trusting me to go to New York alone as a 16-year-old. This also translated down to my own personal substance use.

I moved to New York in 2010. My first month in New York, I got arrested for smoking weed in public. I was at a Janelle Monáe concert at Webster Hall, and—I still see the wall I had passed—I was smoking with a girl. Plainclothes cops came out of a car and I had to spend the night in a cell. I got my record expunged, but people of color, they obviously would have it way worse. There are so many things wrong with how legalization is rolled out and specifically the policing of cannabis and the legal market in general. But the fact that you can smoke a joint anywhere in New York City now is a fucking blessing. And I am just grateful for that.

I went to NYU, to Gallatin, which is the make-up-your-own-major thing. My attitude was, “This is a really fucking expensive private institution. If I’m gonna be in New York, I need to work constantly, nonstop.” And from day one, I did.

I interned at record labels, because I’ve always been a big music person. I booked shows and raves. I was working at True Panther, which was part of Four AD, XL, Rough Trade, Matador, that whole thing. I worked at NYU’s print newspaper, Washington Square News.

When a bunch of people created this thing called NYU Local, which was kinda NYU’s version of Gawker, I started there. To this day, all of my editors and mentors from NYU Local are still in media and absolutely killing it. That’s how I met Joe Coscarelli, who’s now the New York Times pop reporter. I consider him a big bro, actually.

While I’ve always been a writer, I think of myself more as both a writer and an editor. I’ve always had an editing day job, so to speak. I ran editorial at Merry Jane. I’ve done some stints here and there at other places. I’ve tried to crack it as a full-time freelance writer, but it burned me out every single time and made me hate writing. It’s always been nicer to have an editor position. I feel like I’m good at curating this photographer, this writer on this topic, trying to bring out the best of someone’s voice, and not getting in the way.

I used to want to be a profile writer when I was younger. I was super into everyone from Calvin Tomkins and Mike Sager to Jonah Weiner, who’s now a friend. But it always felt like both the subject and I were taking an L. There were always so many compromises that, even when it went well, it still was a failure.

When I was editor at Merry Jane, I found that weed and sex work and psychedelics all go hand-in-hand.

My favorite thing is interviews. If you look at my portfolio, I’ve done over 500 published interviews in the last 13 years. I find people infinitely interesting. I’m a big talker, but I also remember I have two ears and one mouth.

When I was editor at Merry Jane, I found that weed and sex work and psychedelics all go hand-in-hand. They’re multibillion dollar, marginalized industries that people discredit. No one actually listens to the participants who make those industries what they are. Moral scare stories, left and right. I interviewed a very prominent producer-filmmaker who then introduced me to performers who started writing regularly for Merry Jane about the intersection of cannabis and sex work, and other things as well. This led to me helping a pretty prominent porn star on a memoir project. I was essentially somewhere between ghostwriter, ghost editor, and therapist. That was my foray into actually collaborating with sex workers. But I feel like if you're a civ—an outsider—who can be trusted, word-of-mouth travels quickly in that community.

I PA’d a couple of porn shoots, and I was awful at it.

I believe at one point Merry Jane was the first media company putting content on PornHub. We did “Janice Griffith Teaches Us How to Roll a Blunt, Nude,” stuff like that. And it just snowballed. The more people I collaborated with, the more I met. I started doing low-key media management for people's platforms or, in other instances, just shooting content for their OnlyFans and things like that. I find that, for the most part, sex workers are amazing people who have fascinating stories. Most people just want to talk about how crazy it is that you’re a sex worker. But to me, they’re artists like anyone else.

I PA’d a couple of porn shoots, and I was awful at it. I can do a lot in film, but Jesus Christ. I’m a bit athletic, but clumsy, too, and I’m a shaky person generally. I remember someone being like, “Zach, will you hold the ring light over their assholes?” And I was literally shaking and just getting in the way. I wasn’t nervous about the sex component, but that my lack of skills as a PA would fuck up the shoot. Which ended up becoming a self-fulfilling prophecy. But to this day, I still feature sex workers constantly on Cash Only.

I got hired at Vice when I was still a student, actually. I made next to no money, all the exploitative shit. But I was young and my rent was $700 and I had two or three roommates, so it was the time I could afford to do that. And I learned so much. I was doing a bunch of stories about cannabis and policy reform. I think this was around 2015 when Stop and Frisk ended and minor decriminalization measures were put into place by de Blasio. It was also, in my opinion, when New York’s underground legacy market almost got more formalized in certain ways.

When I first moved to New York, you were buying the glass cubes and plastic bags, and then all of a sudden everyone had Pelican cases and were using Wickr to message things. It felt like a moment of change. Other places like Colorado and Washington had legalized and California was on the precipice of legalization. I found it a really interesting time, especially to be talking to dealers who were running the scene in New York.

Many of my friends would sell weed to support whatever creative thing they were doing, so I had a lot of dealers in my Rolodex who were personal friends. They had the craziest stories. The ones I was most interested in were like, how do you move a pack from California to South Williamsburg and what happens when UPS takes your package? Things like that. I’ve always said my beats are arts and culture, so to speak, but more so fringe arts and culture, and fringe businesses in general. And I feel like, at the time, cannabis culture in New York spoke to all those things. I’ve interviewed dozens and dozens and dozens of dealers over the years.

With Cash Only, I wanted to interview people about their relationship with cannabis who aren’t necessarily industry people. Everyone from Chloe Cherry to Odd Future to Parquet Courts. Interviews that have some sort of through-line, but could easily veer off and have nothing to do with weed at the same time. On top of that, I like talking with sober people, or people who don't like weed. I appreciate people with convictions in general. I’m not necessarily someone who believes everyone should smoke. I do not think that “you just haven’t found the right strain yet, bro.” I’m not gonna try and proselytize or change their mind.

I’m not necessarily someone who believes everyone should smoke. I do not think that “you just haven’t found the right strain yet, bro.”

I published 60 or 70 interviews in the first three months. We were doing video interviews during the early days of the pandemic. At first, I was very hesitant to put my face or name on it. I saw how being anonymous was good for people and I was still insecure about putting my face forward. But as soon as I did and took ownership of it, that’s when it started working better. It’s a lesson I will keep with me going forward, in that if you’re going to do something, commit to it. Don’t half ass or doubt yourself. It’s either lean in and own it or don’t do it.

Originally, I wanted to make it about the subjects I interview. They’re more interesting than me, anyway. But in truth, there’s so much happening in New York that you actually need someone there asking questions in order to tell the story. I still struggle with this though. New York Nico and Sidetalk are really great because they stay out of the way and let the characters and subjects do the talking. But that doesn’t work for what I’m doing. Because the truth is that a lot of people are confused about what’s going on with weed in New York right now, and it helps that I really understand what's going on with policy, what is legal, what is not. I’m a talker, I can’t help myself, but when I’m interviewing someone on camera, I know to shut my mouth ... for the most part.

This interview has been edited and condensed for clarity. Zach Sokol photographed by Ryan Duffin at his home in Brooklyn. If you like this Conversation, please feel free to share it with friends or enemies. Subscribe to our newsletter here.