Gather 'round, children, and let Jesse Thorn tell you about the dark ages of podcasting.

"I know there are a lot of people who probably don't remember when podcasts weren't in iTunes," says the 37-year-old host of the interview show Bullseye With Jesse Thorn. "It was so long ago now, but there was quite a length of time when podcasts existed but were not available in any software anyone actually had."

It was during those lean days of the early 2000s when Thorn first stepped into the podcast arena, which was then less an arena than a cramped, lonely basement. At the time, it was mostly just a means of disseminating his college radio show, then called The Sound of Young America, to an audience beyond the campus of UC Santa Cruz.

But as the years went on, and podcasts moved out of basements into real studios and finally onto iTunes, Thorn emerged as one of the pioneers of the form. He started his own podcast network, Maximum Fun, while honing his insightful, deeply informed interview style. Today, Thorn is something of a rap-loving, comedy-geek Terry Gross—National Public Radio broadcasts a terrestrial version of Bullseye—and podcasting now passes what one of his friends terms "the dentist test," as in, "Does your dentist know what a podcast is?"

"We're finally at the point," Thorn says, "where if I have to take a Lyft to the airport and the driver asks, 'What do you do for a living?' and I say, 'I own a podcasting company,' they don't say, 'Podcasting? What's that?'"

Another mile marker: There are now entire festivals dedicated to podcasts.

This week, Thorn joins several other popular podcasters in Portland for Listen Up, a multiday, multivenue celebration of the medium—think of it as the MusicfestNW of talking, essentially. (See our festival picks below.) WW spoke to Thorn ahead of the festival about his interviewing philosophy, being made fun of by Neil deGrasse Tyson and the future of podcasting—which, he warns, might already be doomed.

WW: You were really a first-wave podcaster. Did you immediately recognize podcasting would eventually get this big?

Jesse Thorn: I think I almost immediately recognized it was its own medium and art form. I don't think I was confident it would be a mass medium. I thought there was a chance it would always be like ham radio, that only the most technology-obsessed 5 percent of the world were interested in. I sort of got lucky in that, even in the booms that happened in social media and blogging in the years since podcasting was invented, it never really happened for podcasting. Instead, what we got was many years of slow growth that, for my purposes, matched the slow growth of my capacity. When the medium was a thing where you were lucky if you could get 50 people to listen, I was making a product that should only have been listened to by 50 people.

Your career has straddled both radio and podcasting, which I sense is becoming increasingly rare. Is that a good thing? 

I absolutely, unquestionably think it's a good thing, without even a moment's hesitation. I think it's a good thing for radio, even, because the economic structure of the radio industry in the United States was really not conducive to almost any creative programming. The consolidation of music radio and the way that talk radio distribution works meant that it was a rare and miraculous event when someone with talent went into radio and stayed in radio. Howard Stern, who's brilliantly talented, whether or not you enjoy his show, was like a shooting star.

Do you think that if you had gone to collage a couple years later, would you have skipped radio altogether and just gone straight to podcasting? 

Well, I was lucky to go to a college, the University of California at Santa Cruz, that had a radio station with a pretty powerful transmitter in a very community-minded area with real committed listeners. It wasn't just, you know, yelling into a storm sewer, which is what most college radio stations are. So I think that, were I in those circumstances today, I would probably still go into radio just because there were really people listening. But I also think that certainly, whatever we were doing in the studio at the college radio station would have been directed toward a podcast audience, perhaps even above and beyond the live radio audience. Back then we were already posting RealAudio files of our shows on the internet, yso we would have taken any opportunity to get people to listen to us.

Honestly, I think technologically, if I were a few years younger than I am, I might just be a filmmaker, because I'm like three years too old to have been able to afford a movie camera that you could actually make a decent movie with. Those nice pro-am quality movie cameras were like $8,000 and $12,000 when I was in college, and by the mid-2000s they were $1,200. I mostly went into radio because that was like, there.

Comedy is your wheelhouse. What effect has the growth of podcasting had on it?

Some of my oldest friends I made through comedy nerdery, both in real life and on the internet. That world had just started to open up in the late 90s and 2000s. The idea that you could bring the same kind of connoisseurship and passion to comedy that you could bring to say, punk rock—like, it was new to say that there would be a place on the internet for people to get together to talk about Larry Sanders or Mr. Show. And when we started The Sound of Young America, we partly wanted to make media about this thing that we cared about so passionately and about which there was so little media. Comedy was really just ignored in—I was going to say in mainstream media, but there was no alternative media really supporting it, either. This was right at the time when David Cross started touring rock clubs instead of comedy clubs. And all these things were kind of growing simultaneously.

For comics, I think the rise of podcasting gave them a way to connect with audiences besides the two previous venues, one of which was relentless touring, which is a very slow and difficult way to build an audience because you're only talking to 50 people at a time, or getting on television. There was a time when the comedy world was basically a hierarchy of what kind of television you had done. Like, an arena comic was one who had his own sitcom that was successful, a theater comic was one who had a sitcom that wasn't successful, and a road comic was somebody who the booker had their phone number. It gave comics a way to build a fan base they previously had not had access to.

How do you prep for interviews?

The first thing is that my show is my show, and it always has been. It was never to reflect a broad survey of entertainment in America. It was always to curate a selection of things that I recommend. And so in that sense, I am always at least somewhat prepared ahead of time because I get to pick it. Like, if I was the host of All Things Considered, one morning I'd be interviewing Steny Hoyer and the next day I'd be interviewing Ani Difranco and the next day I'd be interviewing somebody who has a snake with two heads. For me, one week I'm interviewing the creator of Archer, the next week I'm interviewing one of the stars of Archer and the week after that I'm interviewing one of the other stars of Archer. So it's things that I already care about.

I don't write questions. I will sometimes take a few notes just so that I don't forget to ask about something crazy that I read about, but generally speaking, when I go into the studio, I don't even have notes. What I'm really trying to do is have a human conversation with the person and get them to treat me like a human being, but also get some insight into their work. I really care most about people's work and why and how they make it, and less about personal anecdoteS, which tends to be the center of a lot of interviews with creative people: "What's a funny thing that happened on set?" That kind of question is what I'm less interested in relative to, "Why did you use this palette?"

How do you gauge success as an interviewer?

I feel like there's a connection you get with somebody where they are giving you sort of truer answers, and they are kind of surprised and passionate and in some way almost off-balance. You can tell when that is happening, and often I find I'll sit there in the studio and be asking questions, and it'll take 10 minutes for them to believe I'm for real. Generally speaking, these are people who have been interviewed about their work many times, and they have a show they can put on that's perfectly fine. I know when they're giving me the pat stuff, but, um, but you also can tell when somebody's, when there's something real happening.

Like, I know how many people Big Boi from Outkast has been interviewed by in his career, and when he hung up the phone on our interview, they were still running tape in his studio in Atlanta where he was recording from, and when they sent us the tape, he turned to his engineer and said, "That was a fucking great interview." You couldn't pick an artist who's had a deeper emotional effect on my life than Outkast, so to know he felt like he got some insight into his own work from the way he talked about it with me, it meant a lot.

What interviews have you done that stand out to you as failures?

There are times I had been profoundly challenged by interview subjects. [Funk singer] Betty Davis comes to mind. In certain circles, she is a legend, but she is also a genuine recluse. She answered mostly with one word, and then I had to stay quiet for 10 seconds before she would add anything. She was very nice woman but she didn't want to talk to people.

If I was going to give an example of an interview where I was mad and disappointed and I felt like I failed—I've had John Waters on the show a couple of times, and John Waters may literally be the most charming human being in the world. And in the past, I had some really great conversations with John Waters. But the last time he was here a couple of years ago, he was feeling sick, and he sat down and he kind of gave me his act. And I think if you listened to that interview and you didn't know that \ was his act, you'd be like, "Wow, John Waters is the greatest." Because he is, he's so fun. Even the most pat version of a John Waters interview is fucking delightful. But I was like, "Man, you know, I never got to that place where he was really listening to me and we were really interacting." It was really just me setting him up for his shtick. And it's great, it's really great shtick, but it's still a disappointment to me.

I've had so, so few people over the years be rude or like, pick on me. Neil deGrasse Tyson once made fun of me, and I got actually kind of mad at him. I basically asked him if he was ever discomfited by the infinite nature of space. And he made fun of me. I was like, "Dude, I have big feelings about this that I'm trying to share with you." But like even that was such a little thing and it's so, so, so rare. Many, many years ago, we had Dustin Diamond on the show when we were still in college and he was such an asshole that we kind of decided, then and there, no more assholes. Like, we're not inviting anyone on our show for any reason other than we like them, because what a waste. We only get an hour a week, right? I don't need to have Steve King on my show so that I can yell at him. I'd rather just not give them the oxygen.

Speaking of Neil deGrasse Tyson, with all these recent revelations about the misdeeds of certain celebrities—some of whom I know you've had on your show and admire—has that changed your approach at all? 

I think it has underscored for me that people are complicated. It's been driven home for me that just because I have a pleasant hour in a recording studio with someone a few times, it doesn't mean they haven't done terrible things to others in their lives. I think the lesson for everybody is how important it is to listen and think about those experiences other than yours, because if you had asked me what kind of guy Louis C.K. was before all of the news broke about him—I had no fucking clue about this shit, and I thought he was a fucking great guy.

I get really mad at people who react to that kind of news with like, "Gee, I never thought that guy was funny," or whatever. And I'm like, "You didn't fucking know. I didn't fucking know, and I knew the person!" This doesn't get to reinforce your omniscience. This should reinforce your need to ask and listen instead of telling, especially for people with a lot of economic and cultural power, like an upper middle class, cisgendered straight white dude like myself.

If someone like Louis C.K. wanted to come back on your show, would you have them?

I think that's not the show I'm doing. Some of our journalistic ethics have been ad hoc. I never went to J school and I never worked as a journalist other than doing this show, which I didn't even think of as journalism until NPR informed me it was a few years ago. Four or five years ago, we kinda, maybe, sorta had the chance of having R. Kelly on [Bullseye]. And it was like, "No, man." I'm not trying to say I'm special for it, but it's just like, there are so many people in the world who do great stuff. I don't need the assholes.

Now that you've been pretty successful doing radio and podcasts for 15 years, do you have any aspirations to move into different media?

I might be too bald to be on camera these days. The list of bald on-camera talent is so short, and so fucking handsome. But I wouldn't ever say never about that. As a creator, I'm pretty medium-agnostic. The reason that I got into audio was largely because I could afford the equipment after I sold my car—I had a '65 Dart that I sold for $2,500. That's how I bought my equipment. But there are also special things about audio, just as there are special things about any medium, that can't be replicated elsewhere.

I think in the future I'll probably do some new things, but this thing is also going great. I certainly never expected to be a member of the middle-class. I had never been before. It's still exciting to me to have health insurance. Like, my parents never owned a house, and I own a house and a cabin. It seems like a genuine miracle. You know, my dad was a professional antiwar organizer!

Are we in the golden age of podcasts?

There's plenty of room for growth. That said, I think we also are looking at a real challenge in terms of the way platforms shape media. Podcasts still mostly live on platforms that are very friendly to independent creators. And that could change. We've seen the way social media has come close to eliminating independent publishing on the web over the past 10 years or so, and that could happen for podcasts. The venues could be pay-to-play. The venues could be controlled by big corporations that only want you to watch whatever the podcasting equivalent of The Ranch with Ashton Kutcher is. When there's one pipe coming into your house that influences what content you have, or even when it's as subtle as the algorithms Facebook creates, it's very dangerous. One of the reasons I think podcasting has been so vibrant as a community and as a medium has been that the platforms have been neutral and open. But there are certainly people trying to make them otherwise, and they might win.

SEE IT: Bullseye With Jesse Thorn is at Revolution Hall, 1300 SE Stark St., on Friday, Feb. 15, as part of the Listen Up Podcast Festival. 7 pm. $10-$25. All ages. Get tickets here.

SIX OTHER LISTEN UP PICKS by Tiara Darnell

Guys We F@%#ed

Genre: Comedy

After her boyfriend dumped her in a Panera Bread, Corinne Fischer rebounded with her comedic better half, Krystyna Hutchinson, to create Guys We F@%#ed. The comedic duo riff on the salacious to the serious—everything from relationships gone wild to porn, masturbation, slut-shaming and rape culture–alongside a lineup of show including comedians, activists, sex workers, celebrities and, naturally, guys they've fucked.

SEE IT: Guys We F@%#ed is at Revolution Hall on Thursday, Feb. 14. Get tickets here.

Side Hustle School

Genre: Careers

It's all about the Benjamins and how to make a little extra income without quitting your day job. Hosted by bestselling author and globetrotter Chris Guillebeau, each episode highlights a different, industrious hustler and the challenges and successes they have faced getting their side-gig rolling.

SEE IT: Side Hustle School is at Dossier on Saturday, Feb. 16. Get tickets here.

White Wine True Crime

Genre: True crime fandom.

Hosts Kari Martin and Caitlin Cutt slay in this comedic pod that brings true crime fandom out of the dark. From throwbacks like Unsolved Mysteries to the recent Making A Murder series, these two LA-based partners wine down and dish on everything from crime shows to relationships.

Recommended Episode: "Son of Sam, A Real POS."

SEE IT: White Wine True Crime is at Coopers Hall on Saturday, Feb. 16. Get tickets here.

Yo, Is This Racist?

Genre: Comedy

Based on the popular blog of the same name, hosts Andrew Ti and Tawny Newsome, along with rotating guests, answer fan-submitted voicemail questions and emails about whether or something is, in fact, racist or not.

SEE IT: Yo, Is This Racist? is at Revolution Hall on Saturday, Feb. 16. Get tickets here.

Alright Mary

Genre: TV & Film

Since 2016, Colin and Johnny have been putting in werk on this podcast dedicated to all things RuPaul's Drag Race. Come for commentary on the hit television series, stay for the larger, paradigm-shifting conversations around misogyny, gender, homophobia, trans and queer rights, and drag as art.

SEE IT: Alright Mary is at Hotel Deluxe on Sunday, Feb. 17. Get tickets here.

Potterless

Genre: Comedy

Revisit the wizarding world of Harry Potter with this equally binge-worthy show hosted by Mike Schubert, a millennial reading the series for the first time. Chapter by chapter, Schubert brings humor and wit as he rants to show guests and Potter fanatics about how Quidditch is the worst sport ever invented, makes painfully incorrect predictions and pokes fun at the books' plot holes.

SEE IT: Potterless is at the Sentinel on Sunday, Feb. 17. Get tickets here.