
Comedian Josh Gondelman discuses his new comedy special, "Positive Reinforcement,"
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Alison Stewart
This is All OF It. I'm Alison Stewart live from the WNYC Studios in soho. Thank you for spending part of your day with us. I'm really grateful you're here and thanks to everyone who came out to our special all of it live show yesterday featuring the Buena Vista Social Club. It was so great. It was hot, but so worth it. Stay tuned for a re airing of that program. It's gonna be coming your way. On today's show, National Book Award winning author Susan Choi is here to talk about her new novel Flashlight. Then we'll get some suggestions for cheap dates from WR Danielle Kim. And we want to know your suggestions as well. So think about that. And we'll hear from writer Maris Kreitzman on her new book of essays titled I Want to Burn this Place Down. That's our plan. So let's get this started with a little positive reinforcement. Emmy winning writer, comedian and friend of the show, Josh Gondelman provides some much needed positive reinforcement in his latest comedy special, that's the Name of It, Positive Reinforcement. In the hour long Stand up, he reflects on the subtle shift in his perspective at the age of 39. Gonelan pokes fun at our need to know the political stances from corporations, revisits memories of his childhood friends, and contemplates what it means to get older as a man who was born before the turn of the century. The special is called Positive Reinforcement and it streams on YouTube this Friday, June 27th. It also has a new he also has a new comedy album out on Friday, July. Josh Goleman is with us today. He was the head writer and executive producer for Desus and Marrow, as well as a contributor to the final season of the Marvelous Mrs. Maisel. Josh, welcome back.
Josh Gondelman
Thank you so much for having me. It's so nice to see you.
Alison Stewart
In your new special, you open with a joke about how friendly you are and how when you've had a little bit to drink, you text your friends that you cherish them in your text.
Josh Gondelman
Yeah.
Alison Stewart
Why did you want to open up the special with this joke?
Josh Gondelman
That's such a good question. I guess part of it is it's too soft a joke to go later in the special. But the real Reason is, I think it's just a nice way to establish what it's gonna be for the hour. I am very friendly offstage, but I'm also very friendly on stage. I think there are a lot of really pleasant and wonderful comedians to talk to, people who are really gracious with fans and who do a lot of work in community, their communities. But for me, I think one of the things that is a little different is just, like, how gentle my onstage Persona is gonna be for the hour.
Alison Stewart
How important is that first joke when you're writing a special?
Josh Gondelman
Well, it doesn't always come first in the writing, you know, but it is helpful to introduce myself to the audience, because especially on YouTube, you know, when I'm doing a live show, it's many people who have come because they know what I'm gonna do, more or less, and they know my vibe, and that's really thrilling to be at that point in my career. But certainly, once those jokes escape containment and are on YouTube, it' do want to set the tone right away and set the expectation of, like, this is what it's going to be. So if you are. Look, if you are looking for something a little more abrasive, maybe if the joke gets you, you're still on board. But if you're looking, if you're afraid, maybe, or, like, you know, you go, I don't want something that's going to be as acerbic or relentless. It invites people in.
Alison Stewart
Positive reinforcement was recorded at the Bell House in Brooklyn. Why was this the right space for you to record your special?
Josh Gondelman
It's such a great room. I love the Bell House so much. I've lived in New York for 14 years as of next month. And the Bell House in Union hall and the Comedy Cellar have really started to feel like my comedic homes. And the Bell House is a big enough room that you get those big rolling laughs, but not so big that you stress out about selling tickets, you know, to get people in there and have it feel nice and full. And so we did two shows at the Bell House. It's walking distance from my apartment.
Alison Stewart
That's helpful.
Josh Gondelman
Yep. And it's just nice. It's nice to do. Our crew was mostly in the New York area, and so it's nice to do something that is not. We didn't have to bring a bunch of equipment somewhere or set up an encampment in a different city where we would have to fly out the director and the audio engineers and all that and kind of scramble to get people together. So it was Nice to play a home game.
Alison Stewart
You worked on the set. What aesthetic did you want for the special?
Josh Gondelman
Yeah. Oh, gosh, I felt so delighted to get to work on this. The backdrop is the. This kind of, like, gumdrop sunset or sunrise. Who can say? I think sunset. I'm not usually up at sunrise. Almost always awake during sunset. And I got to work with my friend Chris Werner, who directed this special, who's, like, just a really brilliant director. I worked with him when I was a writer at Last Week Tonight. He was a director and producer there, and now he's at snl and he put together this really wonderful team. On the production side, Mark Newell was the production designer, and I just thought, like, it was warm and a little whimsical. It felt kind of the Comedy Central half hour special sets from when I was.
Alison Stewart
Oh, those are so great.
Josh Gondelman
Yeah. Just like a touch of playfulness and a little less of, like, you know, I think a lot of stuff is shot in, like, a big, gorgeous theater, and it just looks big, beautiful theater, and I wanted it to feel, like, a little cozier. And Russ Swanson was the dp, the director of photography, and he just did such a great job. I'm, like, so honored that. And thrilled that, like, this great crew made themselves available to work on this project with me.
Alison Stewart
We're talking to writer and comedian Josh Gondelman. He's here to discuss his new comedy special, Positive Reinforcement, which is streaming on YouTube this Friday, June 27th. In the past, Jim Gaffigan has been on our show, and he's talked about how self awareness is really important in comedy. How essential is self awareness for you as a comic writer?
Josh Gondelman
I think it's really essential. It. It took me a while to kind of figure out how people see me. And not that you have to exactly reflect people's impressions when you're on stage or, you know, doing any kind of creative work, but it helps to know what the. What the impression you're giving off is so you can lean into it or play against it or manipulate it in some way or another. And I think, like, really knowing that people see me as kind of like a friendly guy is so helpful, because I can get away with a little more as long as I kind of keep my voice real gentle and smile when I say it. And I think other people, some comics go just sheer battering ram of energy. And with me, I feel it's more fun for me with my skill set and perspective to kind of draw them in and then kind of poke a little bit.
Alison Stewart
Are there Areas of your life that you think maybe I shouldn't go there.
Josh Gondelman
I'm pretty open about things. I'm not super confessional, but also, I don't have a lot to confess, but I try to be pretty open about the things I think and feel. And I guess the real line is I do try to, for the most part, represent the people in my life in a way that they think is fair when I talk about them. Or I try not to air people out. I've changed some names, I've left some names out. But, yeah, I do try to protect the innocent as much as possible.
Alison Stewart
Do your friends and family show up regularly in your material?
Josh Gondelman
Yeah, I mean, I have some stories. I mean, I talk a lot about my wife in my previous special, a little less in this one, I have some stories about childhood friends, a story about. One story about a high school teacher in there. And you know what? I'm gonna go on the record and say, I strongly suggest, I would say, I outright say it and accuse my former history teacher, basketball coach, of lying when he said he dunked a basketball one time. And I did that for comedy because I think it's very funny. And if he actually did dunk a basketball one time and lost the video so he never could show it to us, the basketball team he was coaching, I apologize. It was wrong of me not to be trusting, and I shouldn't have thrown you under the bus for comedic effect.
Alison Stewart
Is there a comic out there you really like these days?
Josh Gondelman
Oh, my gosh, there are so many. I just talked to. I just talked to Jeff Foxworthy for his radio show. Interesting about being a fan. And he was like, yeah, I'm always still a fan. And it was, like, so validating to hear someone who's achieved that status who, like, truly never, you know, if he sees comedy that he doesn't like on a tv, he can throw it out the window and then hire someone to replace the TV in the window. He's just, like, legendary and has been working forever and. And all that. But, yeah, there's so many people. Like, I co host a show at Union hall in Brooklyn with Alison Libby and Tyrone Thornhill and Jael Nicole Johnson. And, like, they're so wonderful to work with. They're just so funny. And I just did a show with a bunch of, you know, our booker Jordan. She produces the show and just brings in so many wonderful people. And the scene here is so rich right now and vibrant. You know, Benny Feldman has really been cracking me up. But then I go to the clubs And I'm just like, wow, there's so many powerhouses here. I get to work with Marina Franklin last week and it just like, I don't know, I'm just gonna name names for. It's gonna feel like. Liner notes.
Alison Stewart
Well, I'm wondering How has YouTube changed comedy? Yeah, it really has made a difference for a lot of people.
Josh Gondelman
Yeah. When I started out in comedy closer to the turn of the century, which is, it feels, you know, a little embarrassing to admit, but it was truly what YouTube did not exist. And there I grew up, I started comedy in Boston and there was this old school mentality of like, you don't record and release material until it's done, until you're ready to never say it again, or you tell it on TV or you record it onto a record and then it's over. And now so many people share like kind of work in progress stuff or jokes that was. That were never going to be part of a long term act. Like, you watch someone like Josh Johnson, who's really incredible and does these long sets that he like works up that it feels like over the course of a week and then puts it out and then just goes on to a new set of ideas. And it's really like a spectacular showcase for his dynamic and like rapid writing and performance. It's really incredible. But also there's just such a. It's. It opens people up to new voices that might not have had an outlet for like an hour long special in the past, but it is kind of a flood of stuff. So it's tough to, you know, get eyeballs on an individual thing because there's just like, there's so much.
Alison Stewart
My guest is Josh Gondelman. His new special is called Positive Reinforcement. It's streaming on YouTube this Friday, June 27th. We've talked about this a couple of times already. The turn of the century. That is really funny when you bring it up in the show because you realize we live through the turn of the century. When did this first come to you?
Josh Gondelman
You know, coming out of the isolation period of COVID and starting to perform live again, it like really hit me that I am on the older side of the most recent generational divide. Like before, you know, I'm like, oh, I'm one of the older, younger adults or younger, old guys. And it really felt like, oh, I'm from a different time. Not in a racism way, but just like there has been a lot of time since I was young. And so that's when I really started to feel it. Cause There are all these incredible working comics that are, like, in their. And writers that are like in their mid to late 20s. And I'm like, oh, that was so long ago for me. Like, there's a full. I turned 40 in January, so there's like a full day, decade chasm in between. And I think, like, being a fan of newer emerging comics is like a real service to yourself in terms of, like, staying in touch. But turn of the century, like, I don't know, last night I was watching TV and I was like, oh, I'm older than the next mayor of New York City. That's wild. That's like the first time I've ever been older than the mayor. Shout out to Zahran Mamdadi and his campaign and his, you know, fingers crossed for November. But it is. It just really hit me that it's like, oh, I'm not like a young up and comer anymore. I kind of am expected to be good and know what I'm doing.
Alison Stewart
You have experience, as I say.
Josh Gondelman
That's right. Elsa's pantomiming cigarette right now for listeners.
Alison Stewart
When you think about going forward in comedy and you think about the things that you have to deal with, things like AI and the creative field, are you frightened by it? Do you want to embrace it? How are you feeling about it?
Josh Gondelman
I'm such a hater.
Alison Stewart
You are a hater.
Josh Gondelman
I'm an incurable hater about that stuff. It leaves me cold. And I understand. I'll give people who are. I bet there are for smarter people than me that work in different fields, real concrete time saving, efficiency, applications, that kind of stuff. And I even will say, when you can type in, show me Peter Griffin, but with the body of Betty Boop and he's doing the Macarena. And then the computer kind of almost does that. You go, that's neat that a computer has that capacity. But when people start going, and this is gonna make movies, I'm like, no, it isn't. And the reason that I'm such a hater is because the people kind of jamming it down our throats are kind of foisting it upon us before it's even ready, if it will ever be ready. And that to me, is not the mark of a good product, right when it's integrated into functionality that you need and makes it worse. Like Google. AI. I was Googling myself humiliatingly because I couldn't remember how one of my old jokes went. And I was looking up a video and I Googled. I have an old joke about how my wife Maris, who will be on later, how she is a big fan of the recording artist Fiona Apple, and that because we're married, even before I'd ever listened to a Fiona Apple album front to back, I just absorbed her opinions. That's one of the beautiful things about being married is that you have opinions on stuff you don't know about. And I Googled Josh Gondelman, Fiona Apple, and the Google AI summary returned. The first sentence was, josh Gondelman and Fiona Apple are married. Oh, no, truly. So it's like, if that's what's coming up as, like, the top header result, it's like, well, that's not. This isn't ready yet. This hasn't faked all the. So stop putting it in my face. And it makes me additionally skeptical of it as a field of study because of they're going, how about now? Do you like it now? And I'm like, no, it's just telling me lies.
Alison Stewart
I didn't like it before and I don't like it now.
Josh Gondelman
I like it less now, even.
Alison Stewart
Yeah, it's interesting. You just told me a story. It was very, very funny. And a lot of comedy is about telling stories.
Josh Gondelman
Sure.
Alison Stewart
When do you know you have something that is a good story? But maybe it wouldn't be a good joke.
Josh Gondelman
You have to. In my experience, I have to. Maybe other people know better that I have to try it and feel it flop. And if I do that, if I go on stage and I go, I have this story, I'm gonna tell it, and it just doesn't connect in any kind of meaningful way, or it just requires too much preamble and et cetera, But I still believe in it. I'll either try to rework it. I'm very stubborn and lazy. Once I've written something, I'm like, well, this has to work. I did it already. But if it doesn't, it's sometimes fun to reformat and see. Like, oh, is this a personal essay? Is this more of a newsletter item? Is this a. Like, can I figure out how to maybe stretch it out a little bit? And if it doesn't get huge laughs in the room, maybe I can make it like a richer reading experience and submit it to a New Yorker or McSweeney's as a piece of short humor that doesn't necessarily have the pacing for comedy club audiences.
Alison Stewart
How much does the audience impact the rhythm of your show?
Josh Gondelman
It's a give and take. Because I've said this all up and down, and this is A Mike Birbiglia quote that I'm paraphrasing. And it's really stuck with me. I heard him say this years ago, but it's. You do it your way, and then if the audience is like, mm, mm. If they're not feeling it, you take, like, a step towards them and you go, what if I, like, give you a little more of what you're expecting? Just like another. A touch more of what you thought you were gonna get, or a frame of reference that is more familiar to you? How about now? Now will you come meet me where I am? And that doing. Making art is about doing it as close to the way you feel like is your natural expression. And as you can get the. Especially with stand up, as you can get the audience on board with. So it's certainly like the audience influences it. But my goal isn't to come in doing just, like, the thing that will make audience members laugh if I don't like. Cause at that point, I might as well tickle people individually. And nobody's agreed to that.
Alison Stewart
Tell me about your comedy album.
Josh Gondelman
Oh, yeah. So the special and the album were produced with Blonde Medicine Records, who are Dominique Del Bene and Jess Moses. And they're based in the Bay Area in California, and I've known them forever. And they're just, like, so wonderful and such a joy to work with. And the album is, like, a little bit extended. There's, like, a few bits that didn't quite make it in the special. Just hard to get to work with the edit of the video or, like, there's one bit that I really love, but on the. It just takes a little longer to get going. And I think with the audio experience, you know, there's just a little more, like, patience with it than, like, someone on YouTube where they can just go next. And I think when you settle in for a comedy album, which is a medium I really love, you're kind of in for a penny, in for a pound. And so I think. So it's really. It's a lot of the same material, but there's a bunch of different stuff as well. A bunch of stuff added. And it was like, you know, I love comedy albums. Like, listening to comedy records was so big for me when I was a kid. And I still like to listen even when stuff is. Even when stuff sometimes is available as video. I would sometimes prefer to, like, listen and really, like, lock into it that way.
Alison Stewart
How do you hope people will feel after watching Positive reinforcement, Josh?
Josh Gondelman
I really want people to feel like they laughed I want that good soreness from laughing. That's the number one goal. And as I say in the special, if I can leave you with anything, which is not my responsibility, you don't have to leave better. But I do want anybody who listens to feeling like this was like I wasn't trying to keep them at arm's length, that I was welcoming everybody in. And I want everybody to kind of feel like they had just a warm, fun experience listening to someone who wanted them there. Because I think, I don't know, I think a lot of comedy lately has really felt like there are people that are being told, whether implicitly or explicitly, this isn't for you. Like, I don't want you here. This is about you. This is what I say when you're not around. And I want people to feel like, welcome at the live shows that I, you know, when I'm touring or at home in New York and watching this special, I don't want people watching to go like, oh, hey, that one was about me and it hurts my feelings again, especially apologies to my high school history teacher.
Alison Stewart
Writer and comedian Josh Golluman's brand new comedy special Positive Reinforcement streams this Friday, June 27th on YouTube.
Progressive Insurance
Thanks, Josh.
Josh Gondelman
Thank you so much for having me. Josh.
Alison Stewart
I don't know if you've heard, but writer, critic and essayist Maris Kreisman. Her new book is titled I Want to Burn this Place Down. Kirkus described it as, quote, unexpectedly charming. Personal essays about disillusionment, diabetes and despair. You're about to go. Maris is coming in next.
Josh Gondelman
I would say. I expected how charming they are.
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Podcast Summary: All Of It with Alison Stewart Featuring Josh Gondelman
Episode Title: Josh Gondelman's New Comedy Special
Release Date: June 25, 2025
Host: Alison Stewart
Guest: Josh Gondelman, Emmy-winning writer and comedian
Introduction
In this episode of All Of It, Alison Stewart welcomes Josh Gondelman, a renowned writer and comedian, to discuss his latest work, Positive Reinforcement. Recorded live at the Bell House in Brooklyn, the conversation delves into the creation of his new comedy special, his experiences in the evolving landscape of comedy, and his perspectives on the future of the creative field.
Josh Gondelman’s New Comedy Special: Positive Reinforcement
Josh Gondelman introduces his new hour-long comedy special, Positive Reinforcement, which is set to stream on YouTube on Friday, June 27th. The special reflects on Gondelman's shift in perspective as he approaches 40, touching on themes such as aging, personal growth, and societal observations.
Key Highlights:
Opening Joke Strategy: Josh explains his choice to open the special with a seemingly soft joke about his friendliness and texting habits after drinking. He states, “I think it's just a nice way to establish what it's gonna be for the hour” (02:34).
Recording Venue: The Bell House was chosen for its intimate yet vibrant atmosphere. Josh shares his affinity for the venue, noting, “The Bell House in Union hall and the Comedy Cellar have really started to feel like my comedic homes” (04:04).
Aesthetic and Production: Collaborating with director Chris Werner and production designer Mark Newell, Josh aimed for a warm and whimsical set design. He describes the backdrop as “like, a touch of playfulness and a little less of, like, you know, a big, gorgeous theater” (05:00).
The Role of Self-Awareness in Comedy
Alison references Jim Gaffigan’s emphasis on self-awareness in comedy and probes Josh on its significance in his work.
Key Insights:
Essential for Relatability: Josh emphasizes the importance of understanding how the audience perceives him. “I think it's really essential... it helps to know what the impression you're giving off is so you can lean into it or play against it” (06:30).
Persona Management: Being seen as a friendly individual allows Josh to craft his humor in a gentle manner, contrasting with more abrasive comedic styles. “I can get away with a little more as long as I kind of keep my voice real gentle and smile when I say it” (07:24).
Personal Content and Ethical Comedy
The discussion moves to the balance between personal storytelling and respecting others' privacy in comedy.
Key Points:
Protection of Individuals: Josh strives to represent people fairly, often changing names or omitting details to avoid “airing people out.” “[I] try to protect the innocent as much as possible” (07:30).
Incorporating Personal Stories: While his material includes stories about his wife, childhood friends, and even a high school teacher, Josh ensures comedic intent doesn’t harm personal relationships. He humorously apologizes for “throwing [his] high school history teacher under the bus for comedic effect” (08:08).
Influence of YouTube and Digital Platforms on Comedy
Alison and Josh explore how platforms like YouTube have transformed the comedy landscape.
Key Observations:
Increased Accessibility: YouTube allows comedians to share work-in-progress material, fostering rapid idea sharing and showcasing dynamic performances. Josh remarks, “It opens people up to new voices that might not have had an outlet for like an hour-long special in the past” (10:07).
Challenges with Oversaturation: The abundance of content makes it difficult for individual comedians to stand out amidst the “flood of stuff” (10:07).
Navigating Generational Shifts in Comedy
Josh reflects on feeling part of an older generation within the comedy scene, especially post-COVID.
Insights:
Generational Divide: Approaching 40, Josh feels a noticeable gap between himself and younger comedians, leading to a sense of being from “a different time” (11:35).
Responsibility and Expectations: With age comes the expectation of expertise and reliability in his craft. “I kind of am expected to be good and know what I'm doing” (12:17).
Concerns About Artificial Intelligence in the Creative Field
Alison probes into Josh’s thoughts on the rise of AI and its impact on creative industries.
Key Points:
Skepticism and Disdain: Josh expresses strong reservations about AI’s role in creativity, labeling himself “an incurable hater” of AI advancements that he feels are prematurely integrated without readiness (13:48).
Misinformation Issues: He shares a personal anecdote where AI incorrectly linked him with Fiona Apple, highlighting inaccuracies and the potential harm of AI-generated content (14:24).
Crafting and Refining Comedy Material
The conversation touches on the creative process behind developing stand-up material.
Key Strategies:
Trial and Error: Josh acknowledges the importance of testing material live and being willing to adapt or discard jokes that don’t resonate. “If it doesn't connect... I might as well tickle people individually” (16:12).
Versatility in Formats: He considers reformatting jokes that don’t work on stage for other mediums like personal essays for publications such as The New Yorker or McSweeney's (16:12).
Audience Interaction and Show Rhythm
Alison inquires about how audience reactions influence Josh’s performance.
Key Insights:
Balancing Authenticity and Adaptation: Josh strives to maintain his natural comedic expression while reading the room and sometimes adjusting to better connect with the audience. “[...] making art is about doing it as close to the way you feel like is your natural expression” (17:17).
Avoiding Forced Content: He resists altering his material solely for laughs, aiming instead for genuine engagement. “My goal isn't to come in doing just, like, the thing that will make audience members laugh if I don't like” (17:17).
Promotion of Josh Gondelman’s Comedy Album
Josh discusses his new comedy album produced alongside his special.
Details:
Extended Content: The album includes additional bits not featured in the special, offering a richer listening experience. “There's a bunch of different stuff as well. A bunch of stuff added” (18:24).
Nostalgia for Comedy Albums: He shares his love for the medium, reminiscing about listening to comedy records as a child and preferring audio experiences for their intimacy. “I would sometimes prefer to, like, listen and really, like, lock into it that way” (18:24).
Goals for Audience Experience
Concluding the discussion, Josh outlines his aspirations for how audiences will feel after engaging with his work.
Key Objectives:
Elicit Genuine Laughter: His primary aim is for listeners to “feel like they laughed” with a lasting sense of joy (19:44).
Create an Inclusive Atmosphere: Josh wants his performances to be welcoming, ensuring that audiences feel included rather than alienated. “I wanted everybody to kind of feel like they had just a warm, fun experience” (19:44).
Upcoming Segments
Following the interview with Josh, Alison Stewart introduces the next guest, writer and comedian Maris Kreitzman, who will discuss her new book I Want to Burn this Place Down. The episode concludes with a brief promotional segment for Progressive Insurance and NYC Now.
Notable Quotes
“I am very friendly offstage, but I'm also very friendly on stage.” – Josh Gondelman (02:34)
“It opens people up to new voices that might not have had an outlet for like an hour long special in the past.” – Josh Gondelman (10:07)
“I'm an incurable hater about that stuff.” – Josh Gondelman on AI (13:48)
“I want people to feel like they laughed I want that good soreness from laughing.” – Josh Gondelman (19:44)
Conclusion
This episode of All Of It offers an insightful look into Josh Gondelman’s creative process, the nuances of modern comedy, and his personal reflections on navigating an ever-changing cultural landscape. Listeners gain a deeper understanding of what it takes to produce a meaningful and engaging comedy special in today’s digital age.