Podcasts soundtrack your road trips, liven up your commutes, and number in the unimaginable thousands. Each week, Podspotting brings you interviews, commentary and general gabbing on some of the best and most fascinating dispatches from the new audio frontier.

For Jimmy Pardo, the secret to success seems to be abandoning the concept of planning.

The Chicago-born comedian carved out a space for himself by eschewing the carefully practiced material that defines most stand-up comedy. Instead, Pardo specialized in acerbic improvisation and off-the-cuff banter with his audience.

That same freewheeling spirit defines Never Not Funny, the popular podcast Pardo started with producer Matt Belknap in 2006, long before the podcast big bang that gave rise to WTF with Marc Maron, The Nerdist, Comedy Bang Bang, and a few dozen others. Each episode is a low-key shoot-the-shitathon with Pardo, Belknap, and a series of guests that have included Jon Hamm, Conan O’Brien, and Patton Oswalt.

Blame it on the show’s spontaneity, the host’s unforced likeability, or simply that it was one of the first comedy podcasts out of the gate, but Never Not Funny helped jump-start Pardo’s career. It helped net him a regular gig serving as the warm-up comic for The Tonight Show with Conan O’Brien and its later TBS incarnation, Conan. Pardo also hosts The Writer’s Room, a regular show at the Upright Citizens Brigade (UCB) Theatre in Los Angeles, which will soon debut as a regular show on the Nerdist’s YouTube channel.

And perhaps most astonishingly, Pardo’s managed to successfully charge for his podcast—$20 a season, which ensures that Never Not Funny listeners will never have to sit through an ad for Audible or Stamps.com.

Pardo called up Podspotting shortly after a dispiriting Chicago White Sox loss to discuss the comedy podcast explosion, the radio DJs who inspired Never Not Funny, and why the gig of Conan O’Brien’s warm-up comedian is one of the sweetest jobs in show business.

The Daily Dot: When Never Not Funny started in 2006, the entire comedy podcast scene was still very nascent. Since then it’s grown by leaps and bounds. Do you find that explosion encouraging or threatening? Or both?

Boy, that’s an interesting question, because it’s all of that. People always credit me as the first comedy guy to do a podcast, but obviously Ricky Gervais was doing one sooner, and Keith and the Girl (Keith Malley and Chemda Kalili) were doing one on the East Coast. But I think might have been the first person from my West Coast comedy group. And I admit I was territorial for a while. When people started doing podcasts I was like, “Hey, this is my thing! Why are you guys encroaching on my thing?”

But it dawned on me that maybe that’s the same thing people thought when stand-up comedy first started taking off. In the ‘50s and ‘60s there were like nine guys doing it and you could conceivably name every standup comedian on the planet. When stand-up started to blow up, were those guys like “Hey, who are you to do standup comedy? Do your own thing!” That made it clearer in my head that it was OK. I said to myself, “OK, you’re not the only person doing standup comedy, and you’re not the only one doing a podcast either.”

DD: From your front-row seat, how do you think the podcast proliferation has changed the business of stand-up comedy? It seems like the old paradigm of stand-up tours and albums is totally upended now.

I think it’s kind of like what Dane Cook did with Myspace way back in the day. He kind of changed comedy a little bit and brought it back to the forefront. Here was this guy who grassrooted this whole career and industry just by adding all these friends on Myspace. And all of the sudden every comic was like “Oh, I’ll start a Myspace page and I’ll be famous.” Which is of course a ridiculous thing.

But it did bring a lot of attention back to stand-up, which podcasting has done too. And now of course every comic wants to start a podcast and get famous. But it’s also totally changed live shows. Take someplace like Atlanta, for instance. Ten years ago, if I was in Atlanta, nobody was there to see me. They were there because Bob was having a retirement party or it was Donna’s bachelorette party. Now, not everybody in the seats is there to see me specifically—I’m not at that Jim Gaffigan level—but at least half the room is there because they either listen to my podcast or they’ve heard me on the podcasts they do listen to.

DD: So the big change is just that podcasts are bringing more exposure to stand-up comedians in general? There’s more people out there who know those names now?

I think so. It’s crazy, just internally for me, here at Pardo Central, to think that way, because I fought Myspace for a long time. I’m still not on Twitter. I fought Facebook for a long time. So to expect this medium of the Internet to help me build this audience was weird for me. … But still, it’s hard to deny it. Even with people who don’t actually listen to my show! Which I think is insane, by the way. If you like me enough on Doug Loves Movies to come out to my stand-up and drop $25 on a ticket, why don’t you listen to my podcast?

DD: That actually happens a lot?

I get that more than you’d think I would. “We love you on Comedy Bang Bang!” And I’m like “That’s great! Thank you. So do you listen to Never Not Funny?” “Oh, no, but yeah, I’m definitely gonna start doing that.” I mean this sounds like I’m complaining. I of course appreciate anybody coming to see me live.

DD: Where was your career at when you first started doing Never Not Funny?

I was between television gigs. The truth is I had nothing going on. I was doing live shows at the UCB Theatre, which people seemed to like. And [Never Not Funny producer] Matt Belknap came to me and said, “Why don’t we start doing this as a podcast? It’d fit your stream-of-consciousness, incessantly-talking-off-the-top-of-your-head thing.” And it was counterintuitive for me, given what I’ve said about not wanting to embrace Facebook. I like to say I started podcasting because I wanted to follow by leading. I didn’t want it to get to be 2010 or for there to be a thousand comedy podcasts and be like, “Damnit, I could have done this in 2006!” So I was like, “This time, let’s do it. Let’s give it a try. I’ve got nothing going on; why not use this format?”

DD: Was it always your intent that Never Not Funny be so conversational and free-form? There are other comedy interview shows now, obviously, but yours, like your stand-up, is a lot less regimented.

I grew up on the south side of Chicago listening to these radio DJs by the name of Steve Dahl and Gerry Meier. They were Howard Stern before Howard Stern was Howard Stern. They pushed the envelope; they took chances. They were always loose and off-the-cuff. And I was like, “Boy, if I ever got into radio I’d want to emulate what these guys did.” So when I started this podcast I knew I was gonna do it that way. I was never gonna have a plan, I was just gonna show up. And the show went from 20 minutes to 30 minutes to 45 minutes to an hour and a half.

It just kept growing, because we realized we didn’t like shutting up.

DD: You started charging for Never Not Funny starting in Season 3. It’s not a model that a lot of other comedy podcasts have found success with—or even tried. Why do you think you can pull it off when so few others can?

I think I just did it in the perfect window. I waited just long enough to build up an audience of devoted Never Not Funny listeners but before the boom happened. Since comedy podcasting wasn’t this huge thing yet, I kind of felt like a bit of a loser doing cable access radio. I felt like… almost embarrassed.

So one day I said to Matt, “Let’s start charging for this and do a really professional show. If they come along, great. And if they don’t, let’s stop doing this.” I maybe even said that podcasting wasn’t going anywhere, which is hilariously wrong in retrospect. I never liked the donation model. I always felt uncomfortable begging for money, almost like a homeless person on the street doing a tap dance with a hat in front of him. Luckily—I cannot stress the word “luckily” enough—a lot of people came with us.

DD: It seems like it would be a harder sell now, with such a deep bench of comedy podcasts out there.

If I’d waited three more months I think people might have said, “You know what? There’s enough free podcasts out there. I love Jimmy Pardo, but I don’t want to give him 20 bucks every six months.” I feel like a drug dealer in that I hooked them with a couple of years for free.

DD: How do you squeeze recording the podcast in with being the warm-up comedian for Conan, and anything else you might do for the show? That seems like it would be a demanding gig.

That is honestly the greatest gig in the world, and not just because I’m there for no more than an hour and a half a day. I show up, by my choice, at 3:30 in the afternoon. I choose to get there that early so that I’m not panicked about being late. I go on at 4:08 and I’m on stage until 4:26, unless I need to go longer because of tech problems or whatever. Then I introduce the band and the show starts and I can go home. But nine times out of 10 I stay for the whole show. I’m basically in my car more than I’m at work. Again, I’m really lucky, but it came after years of spinning in circles: 22 years of doing stand-up and getting on a plane every Tuesday to travel someplace new, or driving 10 hours to do horrible gigs all over the country to make little to no money. That was hard work. Now I’ve got all this, and man I’m grateful.

DD: Earlier this year, Steve Heisler of The Onion’s A.V. Club posted a piece that asked if we’d hit comedy podcast overload. With so many shows and so much overlap in guests and hosts, do you think there’s something to that?

I’m quoted in that piece as saying podcasts are incestuous, and I think that’s the only thing attributed to me in there, that negative quote. But I do stand by it. In this world it’s often the same 20 of us that keep going on each other’s shows, although I work pretty hard on that not being the case. But I really only think it’s an overload for a very small portion of the world. Yeah, the Onion A.V. Club guy who writes about podcasts might be bored by listening to Jimmy Pardo on five different podcasts in a month or whatever. But my dad’s never even listened to a podcast. Every time he talks to me he asks me, “How’s your iPod show going?” Some guy in the stand-up audience in Atlanta may have never listened to my show.

I think saying there’s a podcast overload is jumping the gun by a few years. It’s so premature. I meet people every day who don’t know what the hell a podcast is. So I think it’s a stretch to say we’re hitting overload when it’s still a pretty niche thing at the end of the day. It’s like throwing a wet blanket on what might be the future of comedy. I mean it had better be the future of comedy, because I’m charging for it.

Photo by  Mandee Johnson via Jimmy Pardo