The Three Questions with Andy Richter - Josh Gondelman

Episode Date: November 26, 2019

Author and comedian Josh Gondelman chats with Andy Richter about giving the best apologies, laying the groundwork for a writing career, and the most important $40 he was ever given. Plus, Josh talks bridging the gap between stand-up and teaching, stone-sober breakfast dates, and his new book Nice Try: Stories of Best Intentions and Mixed Results.

Hello! You are listening to The Three Questions with Andy Richter, and I am delighted to have... It's almost ridiculous how nice this person is. It's almost like he's one of the nicest people in show business to the point where I think there's got to be bodies buried somewhere because he's just too nice. I'm talking about Josh Gondelman, the hilarious stand-up writer, now running a show, got a book coming out. Wow, you're everywhere. Thank you. Yeah. And thank you for calling me both nice and in show business. Well, what else are you? I guess I am. You have to admit it. I still, yeah. Does it feel, does it make you feel uncomfortable? Like, does it make you feel like, well, I feel like it,

I did comedy for so long and I, I wonder if you feel this way, but I was in comedy for so long, right. As a standup without feeling remotely in show business. Yes. And now I have to be like, oh, I do both of those things. Yes, yes. No, I mean, for me, it's been long enough. I mean, I have the embarrassment of riches of having had a television job very early in my life. I think I was 27.

Oh, wow. When the Conan show started and I had, and before that I had even, you know, I'd had a, I had been in the movie cabin boy and I'd been in another movie. Um, so yeah, no, I now being in show business to me is it's what I do. It's my, it's my profession. It's my craft. It's my industry. But I do not have, I do not, like I still am like, I'm always still a little bit taken aback when somebody, and this is a beautiful thing about my job, is that I was on a show that was as meaningful to young comedy people as the shows that were meaningful to me when I was a young comedy person. I'm thrilled that I'm on a formative show for a new generation of comedians. But it's weird when I meet them and they treat me like some sort of grand dame. Sure, sure, sure, sure, sure.

I just am like, no, listen, I'm just you plus time. I'm just old, but I'm you. I'm exactly you. Comedy equals tragedy plus time. Yes, yes. Show business equals comedy plus time. I'm just old, but I'm you. I'm exactly you. Comedy equals tragedy plus time and show business equals comedy. Yes. Yeah. Just being on stage and slinging hash, slinging comedy hash. Well, Josh, you know the deal here. There's three questions. I do. Where do you come from? Where are you going? What have you learned? Are you prepared? I am. To spill your guts guts i've thought about it yeah oh good yeah good you don't need to but i'm glad you did no i they're also imagine if i didn't have the answers

to at least two of those three right right just like where do you come from just like oh shit i was not ready i don't know i had a i had a head injury i don't remember i woke up in this studio i think i think maybe i'm like one of those guys that's going to be activated as a super spy. That's where I think I come from. I think I'm kind of a Jason Bourne. Yeah. Yeah.

Imagine if Jason Bourne, maybe this is the plot of one of them. I haven't seen them all. Just kind of like let himself go. And then when he activated, he just like pulled a hamstring. Yeah, exactly. Or if like when he was unactivated like he became a stand-up yeah yeah holy shit we just wrote a blockbuster yeah this is so good holy fuck that is a blockbuster right he's on stage stand-up comedian becomes activated from his previous life as a

and then now there's like a famous record another day because i need to write this yeah i gotta go they um right he hears like a snap of his fingers while he's on stage and all of a sudden it's famous comedian murders 11 audience yeah or it's just like yeah or like he sees someone in the audience that like holy shit it's you know yeah it's drago corinthian and i have to go kill him you know um you are from mass. I am from Massachusetts. You're one of those people. I'm one of those.

One of those New Englanders. Yeah, one of those salty townie types. From Stoneham, Massachusetts. Years and years and years. Stoneham? Yeah, yeah. Stoneham, Massachusetts. And your family's been there forever, yeah? My parents still live in the house that I grew up in.

Yeah. And they were from, not neighboring towns, but nearby towns. They grew up separately in nearby towns. So like very Massachusetts. My, my grandparents lived there and their parents, I believe some of them had come from other places. Yeah. Yeah.

Yeah. And where are the other places? The like Russia, Poland. Yeah. Yeah. Yeah. You're Jewish. Jewish.

Yeah. Yeah. And what, what is the family business? What are you, what are you all in up there? So I was in my mom's family business for a long time before and during the beginning of comedy. My mom was an educator for years. Yeah, and she was the director of a small private school that was like toddler through eighth grade, I think, kind of at its most expansive. was like toddler through eighth grade, I think kind of at its, at its most expansive.

Yeah. And I was an assistant there in the summers and I taught Spanish there for two, my last two years of college. Um, as I was still learning enough Spanish to like relay it to five-year-olds. To be old, just a little bit ahead. Yeah. Yeah. Yeah. Just with a Boston accent.

Cuatra. That's not how it sounds. Yeah. Yeah. The ace. That's actually more Chicago sounds. Yeah, yeah. The Ace. That's actually more Chicago. Still good. Yeah.

So I worked in education for years. That was like basically my entire non-comedy work experience. Until what age? Until, so I worked for my mom until I graduated college, basically. And then I taught preschool for another four years in the Boston suburbs in Arlington. And that was wonderful. And I was tutoring. And then I moved to New York and tutored for another three years until I was like full-time comedy TV stuff.

So I was 29. So I've been doing comedy full-time since I was 29. Wow. So you, I mean, that's a, in our gendered world, that's a pretty, that's a pretty nurturing man. Yeah. I think, I think I'm very maternal. Yeah. I also am.

I've said often, cause I didn't really have a, I didn't really have a constant present father role model. So when I started, when I became a father, I think I just mothered, I just did a, I just did a cis straight male version of mothering, you know? That's awesome. Yeah, no, honestly. Yeah, no, I have no, I have no qualms with it. I mean, I don't have, I've never had, you know, like afraid to discuss emotions or, or like, I want you, I, you know, I insist that you model your life after mine. Right.

Like I'm making a little, a little me, like I never really, I never really had that, which I think is probably a more, a more fatherly way to do things. Yeah. Generally speaking, it's not a healthy fatherly way. No, right. But it's that kind of like traditional masculine. Yeah. Yeah.

Yeah. I, I, it is, it felt very, it also was very professionally advantageous to be a man in that field. I bet. Because you just like, when you go to interview, it's like the exact opposite of when a woman interviews in a male dominated field where they're like skeptical and like, are you sure you know how to use the computer? And like when I showed up for preschool interviews, it was always just like, oh, thank goodness one of you is here. So it's just like, even in this female dominated space,

I was benefiting explicitly from sexism daily. Yes, yes. Yeah, no, I mean, it's sort of, and I mean, and this is meant in no way to diminish women in comedy, but women in comedy because of not so much now, but certainly when i started because of their scarcity they there was a higher value on them because you know and and there was frequently tokenism of course but definitely it's it's a similar it's the mirror image of that you

know and with women in comedy i think it also and not you know two guys we'll chop it up about women in comedy for a while but that you get the like, well, we have the one. Yes. Which is like, I think the pernicious way and that works. Precisely. In some places it would be like the first woman, oh, thank goodness you're here because now you cover our ass for not having women. Absolutely. And then the second woman is like, well, you need not apply.

Absolutely. I mean, I work on a show and now we have women writers, but I will say we don't have enough women writers. And for years we didn't have any women writers. And that was not good. And we didn't have any writers of color. And that was not good. And I think especially someone of my age who doesn't kind of get out into the world enough. And believe me, there's a lot of men my age who don't, who don't interface as much as say, like I do, like I'm on Twitter. One of the reasons I'm on

Twitter is to know what the zeitgeist is basically. And I don't mean that in like a calculated way. I mean it in like a polite way. Yes. Like I'd like to be in step with the world. Precisely. I want to know that, like, I want to know to know that that that attitude that I hold is now widely panned and that I should reexamine it. For sure. Yeah. I think it's so helpful. And I like, I get on my high horse about this all the time. But like when New York Times columnists or whoever get the thing about like people are saying that I'm stupid on Twitter and that just makes me more sure that I'm smart. Yeah.

It's like that's the stupidest thing I've ever heard. Precisely. Yeah. Maybe everyone's yelling at you because you're wrong. Is that something you'd entertained for one moment? Everybody likes democracy, except for when it comes to their own opinions. Yeah, for sure. Yeah.

Oh, in comedy, I just think that we felt, and I say we as a general thing, you know, And we felt, and I say we as a general thing, you know, when people started to really talk about representation in a serious way, there's a sense of a white male, like I've made jokes about, like when you tell a white male that he's wrong about something, it's like murdering him. And in those days, when you get notes about representation, you say, well, who wants tokenism? And it's like, yeah, that's true. But also, how else is anything going to change? You have to start. Unless you take a flyer, you take a leap of faith

on somebody that doesn't look like you. Yeah, I think it's so important to have different perspectives represented. Right. And like, even for the sake of that. Sure, sure. I think it's really wonderful. And this is something we should save till later

to talk about your current job. Because you certainly, you know, you're a white man running a black show. I'm, so fortunately there's people above me. I'm a supervising producer, which is very exciting. And it's like more influence than I've ever had. And, and it's,

but it is like, it is a space where I am very mindful of being deferential and open to opinions that are not in perspectives that are not mine. Absolutely. More than, more than anywhere I've ever worked because I, I don't want to be pushing things that are either false or like distasteful. Certainly.

Or out of step with the people that I work with and the people that I work for. And as understanding as you can be, and I say you, I mean, as understanding as one in your position can be. Yeah. You will never understand. Of course. What it's like to be black. never understand of course what it's like to be black and there's there are there are points at which with things i am like oh i think of things this way but i trust the the expertise and the experience of the people around me and i defer to your judgment and perspective sure and

it's not right or wrong it's just like what we want to say yeah the perspective we want to present for sure um yeah i think like there's so i was talking with somebody recently about like apologize because you said like when a when a white man's opinion is questioned it's like murder which is like that and people act like that right like celebrities sometimes or even non-celebrities who people are criticizing publicly and there's such a a tendency to dig in and be defensive which i understand yes but once you get to the point of like okay i i understand that i have to deliver an apology of some sort yeah and ideally like change my behavior like why not just give the best apology? Why like continue to be defensive?

Like when, why give the like, well, I'm sorry you felt that way. Because like once you're at that, it doesn't hurt more to be like, you know what? I messed up and I'm really sorry. And what I understand that what I did was hurtful and I, I will do, I'm going to try to do better. Yeah. Like it doesn't, you lose nothing by doing that and you gain so much by like exhibiting like a little more contrition. Right.

It's, it's situational because there are times when I think people, I mean, not necessarily in sort of political correctness, but like there have been times within just within our show where because one of my jobs is to give notes, basically, and is to sort of Conan and I are the end, the end of the quality control. Like everything that goes out the door, the last place it passes is me and him. So and there are times and I and I have a tendency sometimes to be, one could say brusque. Sure. I would think of it as just efficient. And like, I don't, I don't need a lot of, if I have an idea that people go like, nah, it's not good. I, I don't, I'm like, okay, I'll make more. But there are other people that aren't built like me and that need a little bit more sort of gentleness when you reject their ideas. And there have been times when people have had issue with that.

And I definitely want to show contrition, but I also want to let them know, you know, this is a workplace. We're all making donuts here. Yes. And the point is the donuts. And I certainly, I'm sorry if I was neglectful of your feelings, but I will continue to put the quality of the product. Totally. A little bit ahead of, not of like real feelings,

but of just like, come on, you got to get a little thicker skin. For sure. Yeah. But there again, that's a work thing. And that's like a work style issue. Yeah. Yeah.

It's not, you know, you're not going like, you fucking imbecile. Yeah. Yeah. Yeah. Out of my sight with that garbage. Typical broad. Right. And in that case, you're like, oh boy.

Right. Right. Sorry. Yeah. Yeah. Well, let's get back to the young Josh. Sure. What kind of kid were you?

I was, I think, like a sweet little dweeb. Yeah. And I was, I read a lot. And I played sports for like an unexpectedly long time. Why do you say unexpectedly? Because I wasn't good at them then. Yeah. And to see me now, you would be like, you weren't good at them then.

But I played the last kind of like organized sport I stopped playing was I played basketball on the JV team sophomore year in high school. Yeah. And then I just kind of, I saw that I'd reached the end of the line. And there was also, I'd started getting really into theater at school. And so by the time the next basketball season rolled around, it was like I could either participate in the competitive drama festival. Oh, I see. Yeah. Or I could try out for the basketball team, probably not make it, maybe kind of make it as like, well, he hustles, but like even then he's not that fast.

Right, right, right. So I, I gave up with organized sports, like junior and high school, and then was like all kind of academics, arts, that kind of stuff. Yeah, yeah. Do you have siblings? I do. I have one sister. Older, younger?

Younger. She's three years younger, but we were two grades apart because she was kind of like a smart pushy toddler yeah and so when she was in preschool she would be like no i want to be in that class yeah yeah you know she knows the letters so what's the harm and so she just so we progressed in school two years apart so we uh went to we were in college together for two years as well yeah which was cool we both went to to Brandeis. Do you think that being a big brother was somewhat informed, the sort of nurturing nature of yourself? I think so.

I think it, like, fed both ways. Like, I think because I'm kind of a nurturing person, I was a better brother, especially as I got older. And because of doing that, I think I was a little more nurturing. And because of doing that, I think I was a little more nurturing. But like, I don't think I, I think I got more big brothery, like, and it's such a, I think a standard thing that happens to people sometimes. But when we were both in high school together, because I would drive her places. Yeah. We, you know, my parents kind of, there were times where they would go, they would defer to me of like, is this party okay for her to go to?

Like, is this going to be a bad scene? I'm like, that's fine. And so I felt like I was a little more supervisory of my sister. Yeah, yeah, yeah. And did she have good judgment anyway? Yeah, she's like a super good kid. She was a super good kid. I mean, she's a pediatric physical therapist.

She's like a very sweet, wonderful adult person. Yeah, yeah. I have an 18-year-old son, and when he – what people don't realize, and your parents knew it about you, is that the first kid is the first time you've done everything. And so, like, when he started to get to be the age where he was going to be going to parties. I mean, A, we're not really restrictive. And I was raised, I mean, our house was the house when I was a kid that everybody drank at. Sure. You know, and my parents were kind of like,

give me your car keys or don't, you know, that kind of thing. And so, because they were just realistic. And, you know, like, and my mother, when she was young, she said they didn't, it wasn't beer. It was like cocktails. They'd come home from high school and have like Manhhattans that is a sophisticated underage drinking situation well i also just think that that was the time it was you know the 50s and i think people just drank cocktails and uh and she she remembered there was one time where her mother came home and you know

these are kids sitting around drinking manhattans and rob roy's it's so funny at 4 30 and her mom came home and they all dumped their drinks in the fish tank and murdered all the fish and like her mom was like why are all the fish dead it's like uh i guess we should have just told you we were drinking death by old-fashioned uh so but um when my son started to to go to parties and we're like, we had no idea, like, what are, are we, like, are we going to have him in rehab in six months? And one of the first parties that he went to that was a friend of his, his friend and like a big house party that was crazy and overrun, but the parents were there. Some kid in the backyard brought a taser to tase girls. Oh my God. And when that happened, my son was on the front porch and it was North Ventura Boulevard. And I just got this call from him on a pay phone because he didn't have a cell phone yet. On a pay phone going,

Sean, at the party, I think they pulled a knife. Everyone ran. And I just ran down the hill to Ventura. And he took off, left his friends, left his friends. And from that point on, I was like, I think it's going to be fine. Because at the first sign of trouble, he bolted as fast as he could. That's a good impulse at that age. He's always been very cautious. His friends call him Dad. To tase girls. That's always been very cautious. His friends call him dad. To tase girls.

Oh, I just. That's like so fucked up. It's, yeah, like, because that's what girls want. Yeah. To get tased. Oof. But anyway, I think actually the parents got like in legal trouble for that. That seems.

As in reasonable. Not wrong. Yeah. Exactly. I can't go too hard against that. Was your dad the nurturing type both both of my parents are there what does your dad do my dad uh was a he's retired now he was a glazer so he installed glass and aluminum mostly storefronts yeah and so even to to this

day if we're driving through boston he'll go oh yeah that hotel i did is still still the same yeah which is really cool it like really i have so much admiration for like the physical imprint he has on like the city and the environment. It's so cool. Yeah. I, there, there, I, there's tradesmen in my family too. And it's the same sort of thing. Like my mom is in the kitchen business and she'll be like, I, I did all the cabinets

in that house 25 years ago. Yeah. Yeah. And like for that stuff to stand up, I mean, you know, everything gets replaced eventually, but like to, to go, Oh, that 25 years ago, I have this connection with this space, even if the cabinets or whatever are different or the cabinets are still here. Like what a legacy to have, even if only you think about it. It's a useful contribution to society and to a family. So when you started, when you transitioned into being artsy, you know, what was your goal then? What did you think you were going to end up doing at that point? Or did you just, were you still like, I'm going to be a teacher?

I think so. I think there were, the goal was some kind of writing. Yeah. Um, my, my grandmother used to say when she would see me and when she would see me in plays, she would say, you know, you're a really good writer. Thanks grandma. Which is, I always, I said for years when people would people read things that i write you know if i wrote a freelance piece they would go hey that's that's pretty good i would like for

you to write for us and when people see me do stand up they're gonna pretty good you should write for us so it's like i it was always kind of what i i gravitate towards i always liked doing it i like i've always liked writing and so I started performing and that was fun too. Yeah. But I didn't, I don't think I ever was like, oh, I'm going to be a stage actor. Right. As like a, as a job. Yeah.

And I went, when I applied to colleges, I had kind of the unexpected foresight, I guess, to look at schools, to only apply to schools where I could do a creative writing thesis of some kind. And I thought going in, it was going to be playwriting. That's because I'd written a play when I was like 17 that had in the like Massachusetts competitive drama festival gotten some recognition. And I was like, oh, maybe this is a kind of writing I could do as a job. And, and not realizing, I mean, like, you know, I was like, oh, maybe this is the kind of writing I could do as a job. And not realizing, I mean, like, you know, I started doing stand-up a couple years later when I was still in college. And numerically, there are just so many more comedians than playwrights. And I had no perspective of that then.

Yeah, yeah. Where, like, you don't know anything before you go in. For sure. It all seems like magic. Yeah, you just, like, go in and then you come out an adult. And my sister had even more foresight because when she was finishing high school, and she was always a good student who I think visibly would care more about some subjects than others. And my parents were always a little bit like, well, you got to try at all of them.

And she was like, do I? That's me. Yeah. Yeah. Math? Why do I need fucking math? Yeah. little bit like well you gotta try at all of them and she was like do i and that's that's me yeah yeah math why do i need fucking math yeah it's like we have the calculator's right there i can see it yeah yeah and and if it's not there i'll find one right i'll hire someone to do the math and so she when she they my parents kind of they they said what do you what are you interested in what field of discipline and my sister just like very immediately, very surprisingly to them was like,

I'm going to be a physical therapist. And they were like, you've never mentioned that before. And she's like, yeah, but that's what I'm going to do. How old was she? She must've been like 16.

Oh wow. Yeah. And then she just did it. And so she, we both went to Brandeis, but they don't have a real, they kind of pride themselves on not being a pre-professional school, which just means like,

if you want to have a career in something that takes more schooling, you have to like take classes outside too. Yeah. So we're going to teach you to be unemployable. Yeah, exactly. Like, yeah, we'll, we'll teach you everything you need to know about literature. Yeah. We're not into practical. Yeah. If you want to study the law, you can do that on your own time. Yeah. Degenerate. So she had to take like summer, She like planned it out from a very young age. Like, I guess I'll have to take these anatomy courses over the summers. And she just like plotted a course.

So I went into college. That's incredible. And that's what, and she just like called her shot as a mid teenager. I just it's on, I just wish I still am not quite sure what the hell I'm supposed to do on this planet. You know, it's just amazing when people know that. Yeah. You know, I just wish, I still am not quite sure what the hell I'm supposed to do on this planet. You know, it's just amazing when people know that stuff, you know?

Yeah, it's so impressive. So I came into college thinking I was going to write plays. And then I just didn't have the, like, desire to do the kind of backstage practicum stuff. Like the, well, you wear all black and then you move this to here and then you move that to there. And it's every night for this whole semester. And I was like, I don't think so. Yeah. So I transitioned into, um, fiction writing. So I wrote a short fiction thesis. So that's, that's like what I built towards in college, but really like I was doing improv from freshman year on after freshman year, I started stand up like in the city of Boston. And then I was doing sketch,

like a bunch of friends and I had like a weekly late night sketch show that we just decided we would do. And no one told us to stop. So, so I was doing a lot of comedy stuff in school. That's I've talked on this show frequently about finding your tribe. And that sounds like, yeah, like it was great. We had these roommates, like it was almost all guys that were just plunked into the same freshman dorm and then kept living together for the ensuing years. And so we had this off-campus house and we would do comedy stuff together. And then my friend Ethan would, once or twice a semester, we would throw a big party and charge at the door and then donate all the money to a charity that he kind of spearheaded looking for that. Like, this is like a very specific, but we did like

hurricane Katrina relief one time. And so it was like kind of, it wasn't a big party school. So, and people would come and it was generally not like that wild because it was just a bunch of, uh, you know, it was just kind of a bunch of Jews that were like, well, we have to study tomorrow morning. Yeah, yeah, yeah. It never got too, too out of hand. And that was just kind of like what we did. It was like, and it was the same guys. We would rehearse for sketch and then Ethan would go, we're having a party next weekend.

And we go, okay. So we do that too. Yeah, yeah. It was really, it was very lovely. No, that's, you know, when I started doing improv in Chicago, it wasn't even so much. That's, you know, when I started doing improv in Chicago, it wasn't even so much. And I still, to this day, I am fine with an audience, but they're not who I'm there for. Yeah. You know, I'm there for, I've said it before, too.

Like, I want to make the cameramen laugh. Absolutely. And when our band, when we used to have a band on the show, like, if I made the band laugh, I'd be like, all right, I earned my check today. Oh yeah, that's so fun. Because the audience, they're strangers. I want to make my family laugh because I know that they're used to my bullshit. Yes.

They know like my standard issue stuff. So if I can surprise them, I feel like I'm surprising me. And I'm always trying to make me happy. Like that's my showbiz ethos is like, I'm, I'm here being me and enjoying myself. And that's especially, you know, that doesn't work when you're making a movie. No. Does still kind of, you know, because I've worked on fun sets and I've worked on not

fun sets and you increase your odds of making a good movie. If the set is fun, just, and I don't care what kind of movie you're making. That's so intuitive. Yeah. But, but you would think, but there's a lot of people that seem very heavily invested in not having fun. Sure. So I, you know, but that's like such a fun and thoughtful way to do it. Right. Like the job is to make the audience laugh. Yeah. But like the reason that you get into that job is to make your friends laugh and the people that you respect and enjoy laugh. Yeah. Well, and also too, because it will come.

Yeah. You have to have faith that this is, if this is your focus in sort of like, it's, it's, it's just such a simple thing of If you make yourself happy in a way that is in good faith and in a way that is loving and caring and not intrusive on other people's happiness. Not at the expense of the audience. Precisely. But I also mean in your life and in your family. If you make yourself happy, you are going to be a lot more successful at making the people around you happy. Yeah. Because happiness is a, is a, it's a gas

that everyone breathes in when it starts to really flow. Totally. So what happens? How do you become, when you started teaching, is that just a day job then? And you're still kind of like really in your head or you're like, I'm going to make this work, this writing and comedy. That is kind of what I thought. I thought I was going to be like a writer of funny books.

That's like, you know, kind of like a, George Saunders is like the apex of what I was shooting for at that time. And so I was doing standup already and neglecting other writing at the expense of that or at the, for the benefit of my standup. So that was like this period where I kind of had this impression of myself as like a writer that hadn't published yet, but really what I was was like a comedic performer and writer who was like laying that kind of groundwork. Like I did, I just didn't have the patience for like submitting to literary magazines.

And my parents who are so supportive would always say, or my dad took me aside one day and was like, hey, you talk a lot about writing. You know, that's still something you're interested in, right? And I said, yeah. And he said, well, here, give me 40 bucks. And it was like, you always talk about needing to find like the places to submit writing that, that fit your style. So take 40 bucks, go buy a bunch of literary magazines and like, see where you want to submit, which was so generous and specific. And it wasn't like, oh, I'm going to pay your rent for six months so you can

be an artist. But it was like, look, you keep talking about this thing, like put it into action. And it like, I think doing that, I did some submitting, but I just liked getting on stage. I liked writing short, funny things. And it just, I didn't have like a lot of, a lot to say in a literary voice. So I was teaching and I got my teaching job right after I graduated college. And I stayed at the same place for about four years, which was it was really great. I had an awesome experience. And I had before I got this teaching job, I was on the phone with my mom and I just

been looking for like jobs like I truly like if you stock image search like guy at job, that's like what I pictured myself doing while I was working on this creative stuff on the side. And so I was like looking at banks and like insurance companies and I was on the phone with my mom being like, yeah, I'm just looking at like jobs. And she's like,

well, why don't you get a teaching job? You like that and you're good at it and you will never have to work nights if you're teaching preschool. And I was like, Oh yeah. And also it's performing. Yes, for sure. It's preschool. Right. And I was like, oh, yeah. Yeah. And also, it's performing. Yes, for sure.

It's performing. It is a lot of performing, especially with kids that age, because so much of it is like holding their attention, communicating things in a way that grabs the imagination of people who are like so easily distractible. There are teachers in my family, and I've always, and it's my brother's a high school teacher and he actually ran for Congress

in Illinois and it was it was, you know, when he said I'm going to run for Congress, I was thrilled and excited but also kind of surprised. Oh no, he talks every day. Yeah. But he's talking to fucking high school kids. Yeah, that tough crowd hostile audience that's a really tough crowd and i've always thought there's there's showbiz around you that you don't notice and that's teachers

and ministers they're they are performing every day you know who else gives underratedly excellent performances are like baristas and restaurant servers like it is so i was bartenders bartenders for sure i was at a restaurant and the service was so warm and friendly that i was like i was like this is such a pleasure and it must take so much for the like this is their job that they're that's part of the job. They're not just like exceptionally nice people. I mean, they probably are. They're putting on a show.

And it's like, that is, that should not go unnoticed and unappreciated. Yeah. Like, and so I had so much like gratitude for that part of the experience. Yeah. So I was teaching, I taught for four years and it was like, and I tutored all that time as well. And it was like a day job, but it was a day job that I liked. And I brought at first, I kind of felt like I was, um, fiddling with the margins of the job. Cause there was stuff I would do where like we had four-year-olds and we would do like little Spanish lessons and we would, uh, do like improv games, like that you could kind of scale down for

four-year-olds. Yeah. And I would write like, I was like, Oh, do you guys do like improv games, like that you could kind of scale down for four-year-olds. Yeah. And I would write, like, I was like, oh, do you guys do like a, is there a performance at the big holiday party? And they were like, well, kind of, but not really. And so I like wrote them a little play. And I, at first it felt like, oh, this is, I'm like skating by. And then I was like, no, this is what I bring to the table.

I'm not like the arts and crafts person, but I can have these kind of dramatic and performative things and the little Spanish stuff around the sides. And, and the other thing I brought to the table was I worked with almost exclusively women and I had, for whatever reason, more patience than they did for when little girls would just throw a horrific tantrums. I have from being a parent, I have, there is an intra gender intolerance. Like there was shit that my son would do when he was, yeah, it's usually in the 13, 14 year old range where I was like, yeah, that's bullshit. That's, you know, like,

come on, snap out of it. And my wife would be a lot more tolerant of it. I have a 13 year old daughter. It's the same thing where there's stuff that my wife is like, I know exactly what she's doing. It's calculate. And, and I'm like, oh, you know, it doesn't, it doesn't, it doesn't hit my button. Yeah. That's exactly what it it was because when there would be a little boy who would pick up a block look at another kid four feet away take a running start and just mush him in the face I would be like you little prick I saw that

in your eyes and I couldn't get there in time and they would be like look let's take it down let's make sure he's okay and I would be like oh this kid he's gonna grow up to boil a cat. Which I'd be so. And then when it was just a little girl who, for whatever reason, had a different kind of emotional outpouring.

Yeah. I was the one that would, you know, sit on the floor with him for like 20 minutes and go, hey, I know it's a really hard time. Like, you want this green crayon, but you had to have that green crayon. Yeah. And like, we don't always get what we want in life and that's really it's so frustrating and and they would be like how do you do that and the only answer i could muster was like when you are a straight male in your 20s people female people women and then in this case girls, but women are just going to cry because you're not good enough at not making people cry yet.

Yeah, yeah, yeah. Like I was just like enough, even though I tried, I was just like enough of like a shithead that like women would cry at me or to me and I would go, yeah, I deserve this. Yeah, yeah, yeah. And you learn to be patient and not just be like, knock it off. Well, I also think it's a very garden variety neurosis that the things that you do that are sort of gendered, you know, like behaviors that are sort of gendered, that you work to not do them in a way that is intolerant of your own like sort of primal, ugly urges. So when you see it mirrored in someone else.

Oh, yeah, totally. It's like you are yelling at yourself. Yes. You're like, stop doing that. And it's the way you're socialized too, right? Like man to boy of like um and it's also with stuff like that it's like oh i wish that these boys weren't this way because right because i see this like the way that that we were socialized to play when i was a kid of just like smashing each other

up and it's like it doesn't have to be like that yes but i know i also too i'm not entirely sure if a kid smashing a boy smashing a block into another boy's face, which is a better way to deal with that calm or a short, sharp shock. I mean, I don't mean hitting them, but saying like, Hey, no, you know, because certainly in parenting, you learn, there are times to explain and there are times to, like I said, the only kind of real corporal punishment my children got was on their eardrums because and you and as a dad you learn like that's that's in your arsenal in your in your toolbox you save that one because you got to learn you know like your kids know like oh shit dad's mad you are in this was dangerous yes this is yes someone was at risk here and this cannot happen

yes and it's not like there's a threat of violence but there certainly is just a sort of like like i'm serious listen to me now because part of being a parent too is getting used to not being listened to at all most of the time so um when did you go to new York? I mean, that was probably, I imagine, certainly a step forward in your professional life. So I moved to New York in 2011 in the summer, and I had had some like a little more success with standup at doing festivals outside of Boston. And I had seen from the outside looking back in like, oh, and from the inside looking out, like if I want to keep progressing in comedy and writing, I should go where there are more opportunities. Yeah, yeah. That just, I mean, coming from Chicago, it's the same thing.

You got to go, if you're a coal miner, you got to go where the coal is. Where the coal is, for sure. And like, there's also in, I think Chicago and Boston are similar. Very similar. In that you can, you can go, I'm going to stay and work this local circuit at the highest level or aspire to the highest level of this local show business and entertainment. Or I could try for a different thing that maybe has a larger scope. Right. And I think I was ready at that time.

I'd had enough success to encourage me that like, Oh, maybe this will, this could work out. And I was dating someone who lived in New York and just everything kind of lined up of like, Oh, this is a good move for my life and my career. So I moved in 2011 and I, my tutoring office transferred me and I stopped teaching full-time. So I was tutoring several hours a week. Oh, that's great. Yeah. It was really nice. It was so fortunate. Yeah. And they, I got called in, like, maybe eight months into being in New York, maybe a year. They called me into the office, and I was like, oh, I am, I'm in trouble. They, like, never want, because you would, it was mostly in-home visits. And so I was like, why would they call me in the office? And they were like, we really like the way you communicate to, like, why would they call me in the office? And they were like,

we really like the way you communicate to like the younger kids on the spectrum, like the 12 and 13, 11, 12, 13 year olds, as opposed to the 15, 16, 17 year olds preparing for college. And they were like, do you have any like tips on this? We want to like move you to like a senior level tutoring position. And I was like, oh, that's, this is awesome. And so the, the hourly rate was good enough tutoring. And I was on the road a little bit doing standup and I would like Skype session with some of my kids, which was like very fortunate that that technology existed by then. Yeah. Yeah. And was doing a little freelance writing for like mostly women's magazines and other magazines as well, but like internet stuff, you know, a couple hundred bucks here, a couple hundred bucks there and was kind of piecing together a living where the tutoring made sure my rent was paid and my bills were paid.

And then the other stuff was like, was like growing enough that it felt like several side jobs as opposed to like, oh, these are my fun, creative hobbies. Yeah, yeah. And so that was kind of 2011, the last half of 2011, 2012, 2013 was a lot of that. Yeah. And it was great. And so the thing that kind of pivoted into like from side job to career was in late 2012, my friend Jack Moore and I co-created this very popular viral Twitter account. Yeah. The Modern Seinfeld Twitter account. Which was just the premises like, what if Seinfeld, but now.

It continued, yeah. And it was, you know, it was just like a fun hobbyish thing that we were doing. Yeah. And people, it seemed to click with a lot of people. And that kind of gave me, it was the first time I was ever like, Oh, you're that guy. You're that guy who did this thing that I liked instead of like, Oh, your standup was funny. Like, good to meet you. See you around. And so it gave me all these opportunities and I'd started applying for jobs mostly in late night. Um, and I did that for like

a year, 2013 was just like packet after packet, submission materials for different late night shows, got hired or did a little tiny bit of work for Billy on the Street, which was like very encouraging and fun. Yeah, and whoa, boy. He's so funny. Oh, just the best.

He had like, his fastball is faster than just about anybody. You know, he's just like, he has a gear that people don't have. And he's just delightful. Wonderful. He just isn't, he's magical like, he has a gear that people don't have. And he's just delightful. Wonderful. He's magical. He's so great. And so I did a little of that. And that was kind of like in the summer doldrum when I was like, oh, maybe my height, the height of where I get is like, gets to apply to jobs. And then I did that and I was like, ooh, maybe he gets jobs is in my

repertoire as well. And then the beginning of 2014, I started working at Last Week Tonight doing their like web, social, digital stuff. And I did that for a year. How long a day is that? So they were pretty, the days on the show are pretty humane. Yeah. It was, but it was weekends too, was part of it. So we were like 10 to 6 in the office. And then if you were working on a long script or a script that you got assigned late in the day for that week's show, you might have to work into the evening.

I see. Especially early on, I think it took a little while for the – to figure out, like, how long these long scripts took to write or, like, how long they were even going to be. Yeah. Because I think they – over the first several months, like, the main stories that they do on the show are, you know, 16, 18, 20 minutes. And it's a lot of writing. And I think as that expanded, they recalibrated like, oh, this is the amount of lead time we need. So people aren't staying at the office super late.

That's so nice. It's really nice. A lot of places, they don't give a shit. Yeah. They go, well, it's more convenient for us to assign it to you at 3 p.m. And then you stay till 3 a.m. I always think that the secret ingredient to a show with, as you put it, humane hours

is someone in charge who has a happy home life. Because people with unhappy home lives, they're going to keep you there till two o'clock in the morning because they don't want to go home. Oh yeah. And all three of the EPs had like families and children that they like.

Yeah. And so it was like, it was very nice because you knew that they had things they wanted to do. Yeah, yeah. And it's lovely. And it makes them considerate of other people. It's very nice. And so I did the digital and web stuff there for a year

and then moved over and wrote for the show for four. Are you a topically minded comedian? I think my standup isn't super topical. Yeah, that's why, that's why I asked, but I like it. Standup is more just sort of existential. Yeah.

It's a little personal. It's a little just like, what is fascinating me at the time? Yeah. Um, especially topical standup. I feel like unless you can get it on TV really fast with the pace that the news moves now,

it's like, it's not durable. And I am trying to, especially those years in Boston where I was only doing stand-up and not writing other stuff, it kind of taught me, oh, but to make something that holds a script that you can have, and whenever someone says, do you have a script that you like? You're like, oh, I have this one that I'm really proud of. Like something durable that you can take place to place. And topical stuff, I think, just doesn't always have that like lasting power because the news. You go, hey, Rick Perry is the secretary of energy.

And people are like, what? There's a hundred other things. I don't care. Yeah, yeah. And so, but I'm newsy minded and like kind of the social issues of the day minded. And that's like what I think about more. So I, I, I liked working on it and I learned a lot about like who these people, like, I didn't know. Cause I read most of my news. I don't like watch, but it like, that's what it took. Like working there for five years, I was like, Oh, that's who does the news now. Cause you would watch the footage and go,

five years, I was like, oh, that's who does the news now. Yeah. Because you would watch the footage and go, oh, yeah, all right. Yeah, yeah. It's all showbiz. Yeah. Yeah. Now, you are married to a very talented writer, too.

I am, yeah. And tell me how you guys met. So we met. Maris Kreisman. Yes, Maris Kreisman. Yeah. So we knew of each other. She's a brilliant person and a brilliant writer. And we met.

We were acquainted lightly over the internet. And then a mutual friend brought me to a party she was throwing. She was like, she had this long running blog that had a lot of followers and like specifically, I think all over the place, but like it was, she was very plugged in and is very plugged into the like literary scene.

Yeah. And especially in New York, there were a lot of friends and peers and fans. Yeah. And so she, because she worked in publishing for a long time. So she was having a five-year anniversary party for this blog, Slaughterhouse90210, that she ran for years. a picture, a screen grab from a pop culture event or moment or institution, and then a quote from literature. And that's like exactly her sensibility as a consumer of things.

Like she just wants to think. The sublime and the ridiculous. She just wants to know like, what would Toni Morrison have to say about Jane the Virgin? Right. And like, can we put these two things in conversation? would Tony Morrison have to say about Jane the Virgin, right? And like, can we put these two things in conversation? And I think that that's, so we met at this party and we made a date for, we got along immediately, made a date for the following.

It was like a stone cold, sober 9am breakfast date that weekend because I was about to leave town and I had said, so the only cool thing I've ever done in my life got me married, which was we met at this party. And she said, what's new with you? Because we knew of each other enough that we weren't like, who are you? What do you do? And she goes, what's new? And I go, I just got booked for this standup gig in Sweden and I'm very excited. And she goes, I want to go to Sweden. We had a couple of drinks and she goes, I want to go to Sweden. And I said, well, give me your phone number. We'll hang out once in America first to make sure we don't hate each other. So I had her phone number

from that moment. And, uh, we parted ways after the party and I texted her the next day and I said, Hey, I had a really good time talking with you last night. Let's hang out before enough time passes that it's weird that we haven't hung out yet. And so we like two days later or three days later, we had like a stone cold, sober second date or first date breakfast. Yeah. And then we've just been dating since then. Yeah. And she go to Sweden with you.

She did not go to Sweden. Okay. Because I was like, wow, that's incredible. Wow. But also to like, that's a big swing. Yeah. No. Because like, wow, that's incredible. Wow. But also too, like that's a big swing. A big commitment. Yeah. Yeah. No.

And also my family, my immediate family, my parents had, I think, never been to Europe. I also had not at that point. And so I was like, I'm going for work. You guys should come because you never take trips this big. And you, I think, had just retired or about to. And I was like, just come. It's like, everybody's going to speak English. It'll be easy was it just Sweden we went to London for two days afterwards or three days afterwards which was

awesome and we and that was I think like even more their speed because it was like a cool different cultural experience but without um kind of the stress of like what are those letters and punctuations yeah yeah which me too yeah I like, I get so nervous about international travel where I'm like, but I don't know Italian. And it's like, and I feel so self-conscious of the idea of like going from a phrase book or an app. Yeah, yeah. Buongiorno. Yeah, yeah. It's, yeah, the first time, because I never traveled.

And then shortly after, it was probably like 1994 or so, and my sister-in-law was working in an au pair in France, and we flew to Paris to meet her. And when we landed, I had like a panic attack of like, I don't speak the language here. What happens if I get separated from everyone? And I was like, well, what happens? And I was like, you have a credit card.

Yes. You get on a plane and go home. Yeah, for sure. Like it's not – you don't have to – but there definitely was that fear of you go to a foreign land. But now, I mean, now it's kind of like, you know, every time we went to Italy last summer and I signed up for some app because it's like, I'm going to, I know a little bit of restaurant Italian, but I was like, I'm going to do more. And I didn't do anything. Yeah. Fine.

You know, we went to Greece for our honeymoon and I truly this, I've talked about it on stage, but truly was blown away because I did no preparation. I didn't even really consider it till I got on the plane. because I did no preparation. I didn't even really consider it until I got on the plane. And like from the airplane Wi-Fi, I downloaded a translation app and I punched in one word and I was like, I don't even know what these letters sound like. Like, how do you say pie? Like, is it pi?

Yeah, yeah, yeah. And I was just like, I fully punted. Yeah. I was just like, I'll point at things for a week. Yeah. I'm not prepared for this. Well, we've covered a lot of where you come from. Yeah.

Now let's go to, where do you, what's next for you? I mean, do you have, are you a set goals kind of person? I tried to set goals, but I also try to be more open to like going with the flow. Yeah. Because I think, I set short-term goals. That's what I'm pretty good at. I'm good at setting short-term goals and generally achieving them. So like I'm pretty good at going, I want to write this project and get it done in roughly this period of time.

I'm less, I don't have like a true five-year plan where it's like in five years I want to be doing this kind of thing and I'll just make my way and manifest it into the world. But I'm a lot better at being like, well, I need a new five minute tape so I can send it out to television bookers and I can do another set on television. And that's like something that, that feels very manageable to me. Right. Exactly. It's, it's like, instead of, uh, yeah, you're, you're laying tracks for a train. That's one rail at a time, you know, so that makes sense. And then I go, oh, there's a mountain there. I guess my track goes this way now. Or up and over, however. Yeah, right.

That's true. But I'm like not – I don't have that kind of like vision and confidence to like look towards the mountains and be like, this is going to be a train through you, motherfucker. Yeah, yeah. like this is gonna be a train through you motherfucker yeah yeah no i i i still am one of the things that i struggle with is is the goals that i would have and the things because forever i mean i i have a attention deficit issues and there's nothing sort of more daunting to me than a blank page yeah and or the question and this is a sort of a more deeper philosophical thing. What do you want?

What do you want to say? I'm like, uh, I don't know. I've been busy worrying about what other people want. Um, and so there, something that I struggle with is that I, I have these, you know, like I should be more of an author. I should be writing things. I should be good. And, and there's, and I've had this pressure that I put on myself over that. And I don't know, like,

maybe that's not who I am. Maybe I'm an actor. Maybe I'm just, maybe I am just an improviser act. And I don't mean just, I mean. Right. These are the, these are my lanes that I like to work in. Exactly. And I, and I think sometimes too, and I don't, I think it's a fairly normal thing, I tend to discount the things that come easily to me. I think creative people do that a lot. And there's – I was just talking to a friend of mine who's working on like a – she's like finishing grad school and working on a thesis. And she was like kind of lamenting that she doesn't write a certain way or doesn't easily write a certain way and it's like it doing the thing that is natural to you like doing the thing that like if you have to really stress and strain to make something work and like oh i wish i could write magical realism maybe it's like an interesting exercise to try

yeah but like if what you write is like really umulsive crime drama and that feels stupid to you because it's easy, it's like it's not stupid because it's easy. It is a gift that you can do that in a natural way and make something really compelling for people in a way that doesn't feel like laboring or like, you know, making your muscles move in an unnatural way. And I also think, too, you have to listen to other people. You know, there's a lot, there tends to be a sort of an opinion that, you know, you can't define yourself based on other people's opinion of you. But it certainly is helpful. You know, like there's things that I do and I'm,

plenty of things that I do that I'm like, I don't know, is this good? Is this not good? And people tell me it's good. I mean, the reason I'm in show business is because there was enough people told me, Oh no, you're, you're good at this. And so I could believe, I believed them because I had no sense of, of whether or not I could believe myself in terms of it. Yeah. So I'm, I'm in goal in terms of goal setting.

It's like, there are certain things that I've been kind of working, trying to work towards for a little while that I'm like, I still have this goal and it just feels like I'm maybe inching closer to it. Like I'd love to do a longer form standup special and sell that to a network. That's like something that is like a big goal that's been looming for a while that I'm kind of hopefully closing in on little by little. And then the next thing, and not to be too pluggy, is I have a book coming out this fall. I wanted to, I certainly wanted to talk about it. Thank you.

And that was something where it really felt like I had co-written a book before that was more of like a straight humor book. Like it was like an etiquette guide to like, you've already screwed this up. Here's how you fix it. etiquette guide to like, you've already screwed this up. Here's how you fix it. And this, so, and that was, it came out in 2015, 20, 2014. Look it up folks. What does it mean? It doesn't matter. It came out in 2014. And then I waited a little while because I, I'm also, I like, don't sit down at a blank page and go like, here are the five brilliant ideas that I have. And like, get ready world, because I'm about to set you on fire. And so it took me a little while to go, okay, this is what I want. Like, because a book takes, it's almost in the way like a film does.

From the time you're like, here's the idea for it, it's years until it reaches completion. So I had the, having done a book in the past with my, I co-wrote with my friend, Joe Berkowitz, who's an excellent writer as well, or as well. I'm also excellent. Go right ahead. There we go. Yeah. It's a safe space. Thank you. So I had the experience and the, the wisdom of like, oh, I'm going to have to sit with this for a long time. So I better be really sure that if I'm doing this while I have a day job and while I'm performing, that it's something that I'm going to be motivated to work on on the weekends or work on at night. And so I worked, I spent probably a long time

relatively just refining the proposal into something that my agent, my literary agent, Noah, who's awesome, was like, yeah, this is a thing that people will be interested in and you can sell it and it'll be like worth the time of going out with it and writing it and putting it into the world. So we tweaked that for a long time. And then I went and then we so it sold the proposal sold in late September, early October 2017. And then I took 11 months to write the first draft. And then there's been various stages of edits. And then I recorded the audio book. And now I'm working on just writing essays to support the book to publish places.

Like, oh, pitch an op-ed to the Times or something. to publish places like oh pitch uh pitch an op-ed to the times or something and it's like well i just i wrote all my ideas they're in the they're in the book yeah yeah and so like working on that and but it's been i think because of the the time that that i spent refining the idea and then my editor's like expert eye and notes and guidance that it's been a really cool, rewarding process. And it's a book of comedic personal essays. Okay. And what's it called?

It's called Nice Try, Stories of Best Intentions and Mixed Results. Nice. So I'm like really psyched about it. And I'm trying to, my agent had said to me a couple months ago, like, are you, would you like to try to sell another book before this comes out? Kind of like riding the wave of like pre-publication goodwill. And I just wasn't, I didn't have the idea that I was like, I'm ready to jump in and sit with any idea that I have in my head for another two years right now. So like,

I'm trying to stay really present and, and not go like, well, this, well, I wrote this book, so it's done and I have to do the next thing. I'm trying to really sit with it and like be enthusiastic because sometimes it's hard to cheerlead for your own work because you're like, is it grotesque? Is it, is it grading on people? But I really worked hard on it and I'm trying to give myself the like permission to tell people that and that I think they would like it and that I'm proud of it. Yeah. Yeah. Yeah. And also just sit with it for a while. Don't like, you know, it's still your baby and it's getting out into the world before you start thinking about the next kid. Yeah. And I also like the, I like doing the live

events, like the tour events and the launch events. that's like part of the, the joy of like creating something to me. And I know I have author friends who that's something they do because it's part of the job, but I'm like very much looking forward to like, okay, I'm going to go book tour. Yeah. Book tour. I'm going to go up to Boston on a Tuesday night and do an event there. And it'll be like a real fun hometown thing. And then I'm going to do, uh, uh, Philly, a different Tuesday and do a standup show and sell books after that. And I have live events in New York that people are going to come to. And I'm like pretty extroverted. So I'm pretty energized by that possibility. Like I don't, I don't have that dread that I think some people who are like primarily

authors or even TV writers who don't perform as much, the dread of like, oh, I have to talk to all these people, which will like kind of slowly deplete my energy level. Like I get tired to be looked at. Yes. Yeah. Yeah. Yeah. And just like everyone's gaze takes one 10th of a percent out of me. And I understand that. And I think that's so valid, but I, I'm, this is a fortunate part of the process for me where I'm like, cool. My other favorite work thing to do is just to go out. And like, I I'm from doing standup, I'm like a pretty capable live performer. And I have a pretty good sense of like what audiences want

from a live event and how to tailor that. Because sometimes you see people who don't do a lot of like live talking and they read 20 minutes of a very dry section of a – like I went to a reading in college, I remember, and I like – it was this poet. And I loved his work on the page. And I was so psyched that he was coming to campus. Loved his work on the page. And I was so psyched that he was coming to campus. And I fell asleep in the archives room of the library listening to him because I was like, oh, man, you are bringing no – there is nothing that I'm getting from hearing you.

Yeah. It's taking away from the beauty of the words on the page. It's showbiz, buddy. Yeah, yeah, yeah. It's showbiz. Yeah. Something that you do that is a lovely thing is that you give pep talks on Twitter. Tell me how that started and tell me the thought behind it. And I also am curious if like there has been nice outcomes of

that that you've heard, whereas where that were just those that exchange of words has manifested itself in a good way. Sure. So I so so it started, I was in kind of like a, a career slump. It felt like it was a few months before I got hired at last week tonight. And I'd had that, that kind of like explosive viral Twitter success. And then I was like, I, just like a couple things fell apart on me at this time. Like, you know, I was having these meetings that came from that, that I was not super well equipped for or prepared for in terms of like, I wish I had had like a killer feature script to show people or a killer pilot that I was like, this, let's make it. And I just like that kind of writing, I was lagging behind on that. Yeah. So I'd kind of had a bunch of pleasant meetings where people are like, cool, well, let us know when you got something.

And I was like, well, I don't got something. And then a couple of little things that I thought I had lined up kind of fell away. And then so one day I had this gig that I was supposed to do in New Haven and I was getting ready to get in my car and drive the hour and 40 minutes. And I was getting ready to get in my car and drive the hour and 40 minutes. And the guy that booked me was like, hey, the venue's doors are like deadbolted shut. And there's not like enough tickets sold that we should like move it to somewhere else. It's like we're just going to call it because I can't get into this building. And I was just like, well, fuck me then.

Like I can't even do this $200 gig that I was like, well, at least I know how to do this. And I was feeling kind of like low and needy. And I thought like, I have enough of a presence and a following online that I could have asked for someone to do something nice for me. Just like, Hey man, I'm not, I'm not feeling great. Can you, is there somebody that can reassure me that things are probably fine? Yeah. And I, I thought about doing that, but I was like, if 5,000 people or whatever, 15,000 people at the time followed me on Twitter, I didn't need to ask 15,000 people for something nice because like, I didn't need that kind of influx of like, yeah, buddy, it's fine. And it might've been late at night enough too, that I was like, I couldn't just call a friend, you know, a college friend or something. And so instead of asking for it,

I was like, what if I did that for someone else? I bet there's other people that, that are feeling the way I'm feeling right now. And if I, I intellectually know that many things are fine, that don't feel fine or many things that aren't fine can get better. So I was like, if I can offer that kind of encouragement to someone else, maybe that'll feel good in the same way. So I tried it and I probably got like a couple dozen requests and kind of handled those. And it felt really good. And it's especially something that I can do. Like if I met a, if I'm on the road and, and by myself, it's like a really nice way to feel connected to people. Or like if I've just had a long day and by the time I get home from doing a standup set,

Or like if I've just had a long day and by the time I get home from doing a standup set, Maris is asleep and Busy or Fat Pug is asleep. And so it's just like a nice way to feel connected to people without like the intrusive thing of like, who can I text at midnight that it's not going to seem like it's either urgent or like I'm trying to have an affair. You know what I mean? And so it's like a nice way to reach out to like, hey, who's around? What can I, can I do something for you? And so the, and the outcomes have been, there've been really lovely ones,

just that like nothing huge. Like I don't think I've changed anyone's life, but usually there's some follow-up or often there's follow-up where someone will go, Hey, I had this job interview and you had, you had told me like, just go in, like, you're not there by accident. This is, they want to see you. So just like go in and do you. And they're like, and I got the job. And it meant a lot that you like were encouraging about that. And just like little things, like I didn't get them the job, but it's nice to say a nice thing and have someone like, like instill someone with that feeling.

Yeah. Or like, I mean, a thing that I tell people a lot, cause I, you get a lot of kind of the same requests when people have specifics or just like the news feels really bad and the world feels really bad. And,

and one thing that I tell people a lot is like, it, it is bad. Good night. It people a lot is like, it is bad. Good night. It is bad. But like you can be one of the people who makes it better. Like we all can. Yeah, yeah.

And there are people that can make that will help you make it better for yourself and for others. Yeah. And like that is so when I'm talking about where am I going? talking about where am I going? I think one of the things that I am trying to like really center in the work that I'm doing is like, what am I doing to make things better? And like, how am I helping people? And how am I making work with intention rather than just like, does this get a laugh? Then I will do it.

And so that's like a way that I'm trying to orient myself, big picture. That's great. Thank you. That's really, I mean, it's a lovely thing to do. And also it's one of those examples of, you know, everybody shits on Twitter. Everybody, you know, everybody shits on Twitter, but here you sit with, you are a going concern.

You are, you know, your career is growing. Well, thank you. You have so many great things ahead of you. And you can credit some of that to this silly Twitter thing you did. Even like the ability and the familiarity when I met my now wife for the first time that we were familiar with each other enough that we could talk and she wasn't like, who's this weirdo? And I wasn't like, why would I go to this party? So I, the way I say it in the book too, but I say like, Twitter is like really harsh on a lot of people. And as like, you know, a straight cisgendered white man, I don't get the

worst of it by a long shot. And so I don't want to discount that. But like, so Twitter is kind of like, I fell into an open sewer and found a hundred dollars and that's my career. And then I fell into the same sewer again and found a diamond ring. And I was like, look, I get that this is a sewer, but I've had like a lot of luck falling into the sewer. And I have, it has enriched my life. I have friends, like real serious in real life friends that I've made through this. And I know so many people, especially women, who are now comedy professionals because they got on Twitter. Yeah. And somebody could see.

Everybody saw this is a funny person. And then somebody takes a risk on them, hires them, and now they have comedy careers. Yeah, it's very cool. And I also think for a particular kind of person, a joke thinking, joke writing person, I know, like there are people on Twitter I've never met, but I know them because I have a mind that thinks of jokes. They have a mind that thinks of jokes. Yep. And it's like a blood test or it's like a, like it's just, you sense. I know who that person is just from their jokes, you know, because it's a language that I understand.

Yeah. So, all right. Well, we're, we're getting towards the end here. We're to the, what have you learned part? I mean, you, you know, I think it's fairly, fairly safe to say you've learned that kindness is a good thing. Yeah. And so I've learned, um, that's one of the things, I mean, like the, the prep, the overarching narrative of the, of the book is

that like, I was a nice kid and like niceness and kindness and goodness are not always synonymous. Yeah. And so I'm trying to like move in my life and work from like, just niceness of like, Hey, good to see you, buddy. To like kindness of like, Hey, um, is there anything I can do for you? Yeah. And goodness of like, what am I doing for the world? And like, and especially now that I have a little more in terms of resources of like a platform and a little more financial stability in my own life and like career stability, where I don't feel like I have to constantly be clamoring to make things happen for myself. Like how can I do for others? And I think like, I'm trying to be

better about being like assertive or like righteously indignant and like calling bullshit on things that are bullshit as opposed to being like, I don't know, they're probably having a hard day. And like, which is also an important impulse. Sure. But like to not just like let people being an asshole slide. But to do that with like tenderness and gentleness, I think is like what I'm, that's like my human being brain project. Yeah. Well, I mean, you are definitely somebody that puts a lot of goodness into the world. Thank you. That's a wonderful thing.

And I mean, when you, you know, like when you talk about that, you're going to Sweden and you ask your, you tell your parents to come with you. Like that's, that's a pretty one.

Like you obviously are very well loved. Oh, thank you. And, and I, and that is much credit to your parents and to your family. And, and I mean,

and it's, it's really wonderful that that's what you put out into the world. Thank you. And because, you know, I mean, comedy can be very navel gazey and it can and people can sort of create their own feedback loop of what they do with their comedy. And yours is so expansive and so kind of outward reaching and, and it's about doing goodness. And I think that that's great. Thank you. You're welcome. And thank you for coming on the podcast. Oh, this was such a pleasure. I'm glad. And I, I urge people to go out and get your book. Tell me the name one more time. Nice try stories of best intentions and mixed results.

Thank you so much for coming. My pleasure. Thank you for having me. And thank you listeners for listening. And we will see you next time on The Three Questions. Bye-bye. The Three Questions with Andy Richter is a Team Coco and Earwolf production. It's produced by me, Kevin Bartelt,

executive produced by Adam Sachs and Jeff Ross at Team Coco, and Chris Bannon and Colin Anderson at Earwolf. Our supervising producer is Aaron Blair, associate produced by Jen Samples and Galit Sahayek, and engineered by Will Becton. And if you haven't already, make sure to rate and review the three questions with Andy Richter on Apple Podcasts. This has been a Team Coco production in association with Earwolf.