Jason Stewart

That’s how most people start doing things—it’s how I started podcasting. You listen to a podcast and say, “I could do that” or, “There’s something going on here I think could do better, so I’m going to give it a try.” DJing was one of those things, and it worked out.

I was a professional DJ for about 10 years, from when I was like 24 to 34, with varying levels of success. Once I was able to quit my day job and DJ full time, that’s when I started taking it more seriously. I got into producing music and going on tour and DJing in a way where I could make a living doing it.

Luckily, digital DJing came along around when I started, so I didn’t have to spend decades collecting records and finding my craft. I was able to buy some software and get it going even though I did start DJing the old fashioned way. To me, DJing as a career definitely has a shelf life. You can be a DJ well into your older years, but it doesn’t happen very often. And then you have to be the old guy in the club, which is something that I wasn’t exactly down to do. It’s a young person’s game.

I got into podcasting maybe eight years ago, but it was always just a hobby, a side thing. I had two podcasts prior to How Long Gone: one about food, and one called Tall Tales, which was similar to what I’m doing now but more focused on interviewing people who were in the music industry. I used it to grow my profile in hopes of it translating to more DJ bookings. I had no plans to turn it into a business. But through the repetition of doing it for years and years, I got better at interviewing people, having conversations, and, hopefully, being funny. In the last few years, it’s become an actual profession. I now focus on podcasting full time.

How Long Gone started as a quarantine boredom, don’t-know-what-to-do kind of thing. My co-host Chris Black and I already had a rapport from podcasting together before, and working on some creative projects here and there. Our main goal was just to be entertaining. We weren’t trying to change the world. We weren’t trying to be political. We weren’t trying to do anything super intellectual. We were just trying to figure out what the hell was going on, and thought it would be nice to have a little way to turn the brain off and be entertained.

So that’s what we did. We found a hosting platform that doesn’t cost any money and we would just call each other on FaceTime three times a week to talk about whatever was going on in the world. When we first started, we literally just hit record, hit upload, and were done with it. If we were going to record three episodes a week, it had to be very streamlined and very easy for everyone involved. There’s no video. You don’t have to be camera-ready. You don’t have to have a glam squad. You don’t have to show up at a studio at a certain time. We didn’t want it to feel like homework, or really like work at all. And that worked. Now we’ve done over 300 episodes in less than two years, which is a shitload.

How Long Gone grew quickly because we were able to have a lot of conversations with guests who also had nothing else going on. Everyone had the time. We took advantage of an unfortunate situation in which a lot of people who are normally very busy suddenly had a whole lot of time.

Of all the people who we’ve tried to get, nobody has ever really shut us down. We’ve had people say, “I want to do it, but I just have to wait for the right timing.” And there are dream guests who we haven’t really tried to reach out to yet, like Paris Hilton, Liam Gallagher, Ina Garten. Hopefully one day we’ll get to the point where we can get the pick of the litter of whoever we want to talk to, but it just comes down to right place, right time.

I’m really fascinated by people who almost always give a bad interview because I want to see if I could get a good one out of them. Barack Obama’s an amazing speaker and anyone in the world could have an hour-long conversation with him that you’d want to listen to. But somebody who’s really difficult or annoying—like Kanye West, for example, is a very hard person to interview—that’s who I want to talk to. I’m not even a particularly big fan of Kanye West, but I like the idea of doing the Kanye West interview where he shows a side we didn’t know was there.

The higher the degree of difficulty, the more impressive something is. I model that after comedians who dig a hole for themselves for the sheer enjoyment of the difficulty of digging themselves out of that hole. I want to increase the level of difficulty to entertain myself, and because that’s also when people really start to pay attention. It’s like fishing. Nobody cares about pulling up a mackerel. We want to get a great white shark, because that’s going to be interesting.

The first year, I was doing a lot of podcast production work for other shows. I spent a lot of time editing and producing, telling people what works and what doesn’t. I saw the benefit of editing and post production, and how you can turn a truly awful podcast into something halfway listenable. Since I was already doing it for other people, I thought, What would happen if I took our podcast that I already think is good, and made it shiny and professional?

It is a lot of work, but when it’s work for myself and I’m holding myself accountable, it ends up being very rewarding. The hardest thing for me is self-editing. But I’ve learned the benefit of not just editing, but going back and listening to every conversation you’ve had. Kind of like how an athlete will watch their games with their coach and learn how they need to change what they’re doing.

It’s very difficult to do at first, to watch yourself fail. And the hardest thing for a lot of people is to listen to their own voice. It’s revolting for many—myself included. It was really difficult. But once you push through and you’re like, Okay, I fucked up here, hopefully next time you won’t make that mistake.

I noticed that the cadence of the way Chris and I spoke to each other changed. You almost start editing your conversation in real time. We developed a style where we can go back and forth. I know when he’s going to finish his thought and I can hop in right at that moment, kind of like double dutch jump rope. You begin to intuitively know when something is done and it’s time for something else to go in next.

Anything that happens outside of the podcast and on its own naturally is cool, but we’re not going to chase it down. But we do love making merch. We both love clothing, and we’ve been historians of band merchandise. It was a big part of our formative years. Now every time I smoke weed and come up with a fun design for a t-shirt, instead of me just making it in Photoshop, sending it to my friends and them being like, “That’s cool,” I send it to Chris, and he’ll be like, “That’s cool, let’s make 300 of these shirts and sell them on our website.”

I started smoking weed in my early twenties. I grew up straight edge. I never did drugs, never drank, never did anything. I never even smoked a cigarette until I was like, out of high school. I was not a party person. I was not cool. I related a lot more to people who were straight edge. Then my friends stopped being straight edge, and eventually peer-pressured me into weed use.

We would smoke weed in my car in front of my mom’s house, listen to music, and stay up all night having conversations. I had a shitty old Honda Accord that we called the “Dank Tank” because we would sit inside, play stoney music, and have the terrible, cliche, stoner conversations that you have when you are a late teen learning about the world. Like, “Oh my god, have you heard this band?” Having our Pink Floyd, blacklight poster moments. We would watch standup comedy and get super high, and then eventually make a bunch of food. All the things I love ended up being better with weed. Comedy is funnier, food tastes delicious, and music sounds better. So I enjoyed it.

Once I got older and life was not just a fun game and I had to actually do things, like pay rent and survive, weed was not a big part of my life. I actually took a break from it for a long time because I was getting paranoid and wasn’t enjoying it. This was during the time of my life that I was DJing and partying and drinking. Weed was not a social drug for me.

Then I started forcing myself to get back into it. I weighed the pros and cons of alcohol and weed and realized I didn’t get hungover on weed, and I only overate and ate poorly when I was drunk. I realized I was a better person with weed than with alcohol. So I forced myself to push through the paranoia and the existential dread and the freakouts that you have, and slowly started reintroducing it back into my life. That was about 10 years ago. Now I’m in a great place with it. It’s something I do pretty much every night. I still don’t smoke a lot of weed—I smoke every day, but a small amount. It doesn’t take much to get me where I want to be.

I’m definitely into the new weed world. I like all the options, I like the innovation. The more people work at it and invent new things and try to perfect it, the better it’s going to be. When you’re younger you’re like, “I’m going to make weed brownies, and I’m just going to eat them and cross my fingers,” and you end up crying and calling your mom and apologizing for the fact that you’re about to die. That’s really bad. But now you can control exactly how much THC is in each little gummy, take as much or as little as you want, and find out which strains and brands work the best for you. I think that’s amazing.

A lot of people in my life who are so not the type to smoke weed, who are prone to paranoia or negative thoughts, especially with drugs, are now able to be like, “Hey, I found this edible and I just eat a two and a half milligrams, and it helps me sleep at night.” That’s a lifesaver.

There’s a brand called Wyld that makes a marionberry-flavored edible that is just so delicious. The generally popular, cute hipster ones, like Rose Los Angeles and Pure Beauty, are always going to be some of my faves. I love Rose edibles, I love how they’re partnering with chefs and farmers to make new interesting flavors. And Pure Beauty has really cool packaging and does cool collaborations with brands. I like their little joints that look like cigarettes, those are really good.

Weed branding and packaging and products were never cool. It was always like a Sublime-inspired, stoner-looking bong with a dragon on it or something like that. There’s never been anything minimal about weed shit. It’s always been very specifically styled. Now enough people are like, “Hey, I’m into weed and I also care about design.” Coincidentally, my fiancée’s brother owns a bong company called Session Goods that approaches weed from the minimalist industrial design space.

Smoking weed and being vegan when I was younger were probably the two biggest catalysts for me getting into cooking. I had to learn how to cook vegan food because my mom was just like, “I don’t know what the fuck that is. Have fun. Go nuts. But I’m making this for dinner. If you want something vegan, you have to make it yourself.” And, like I said earlier, weed makes food taste really good.

Every night it was just, I have a refrigerator full of this stuff. What can I make out of it? It became a fun game to play. I have fun doing it from a creative point of view, but I get equal enjoyment out of feeding my friends and loved ones, just seeing the look on their faces, like, “Damn, this is fucking good.” It really made me happy. Same with the ability to have a home-cooked meal that’s also super stoney. You don’t have to go to Taco Bell to get that experience. You can have it in your house. And it’s made from real ingredients that aren’t going to make you feel terrible. That’s a feeling that hasn’t gotten old for me. I guess food is a love language of mine. That’s how I show my love, through the food that I cook.

The food industry has always been really archaic. The way people spoke and the things they said about others were kept behind closed doors. When I first started my food podcast, I wanted to be honest and talk about food the way I would with my friends. I had nothing to lose. I wasn’t a member of the food industry. I was like, I’m just going to talk shit and say whatever the fuck I want. The challenge of doing that is doing it in a way that doesn’t make you look like a complete asshole. That’s been the hardest part for me with How Long Gone, too. Once you grow in size and influence, you realize you have some responsibility for what it is that you’re doing and saying.

You have to have a come-to-Jesus moment if you achieve a certain level of success. As I get older and wiser, I’ve been trying to choose my words more carefully. Sometimes Joe Rogan will say, “Hey, don’t listen to me. I’m a comedian. I don’t know shit. These are just my jokes. I’m just having fun.” But if he says a restaurant is stupid and you shouldn’t go there, that could close a business.

Even though the podcast has grown a lot, we’re still not massive. So it’s not something that we’ve really had to sit down and consider. But hopefully we will get to that point one day. Cancel culture and being canceled—that’s been going on since the dawn of time. As time progresses, if you want to keep doing something, you have to be evolving. Everything is going to change. The rules of how the games are played change.

*This interview has been edited and condensed for clarity. Jason Stewart photographed by Maggie Shannon at his home in Los Angeles. 

If you like this Conversation, please feel free to share it with friends or enemies. You can also pick up a copy of the issue it originally appeared in—Gossamer Volume Eight: the Space issue—which is on newsstands and available to order now.