Mike Birbiglia's Working It Out - 111. Gary Simons: A New Comedian Asks Mike 10 Key Questions About Starting Out in Comedy

Episode Date: October 16, 2023

25 years ago, Mike won Georgetown University‘s funniest person on campus contest. This week's guest Gary Simons won it three years ago. Now, Gary has been opening for Mike’s new tour and has a lot of questions: How do I get an agent? How do I go from doing 5 minutes to doing an hour? Any relationship advice for comedians in love? Plus, Pete Holmes calls in and offers his own advice.Please Consider Donating To: Connecticut Foodshare

You use the term laugh quotient. It's like once you can start turning this into math in a way where you're like, okay, no, that's like a five-level joke. That's a seven-level joke. That's a ten-level joke. And then be like, all your jokes need to be, or approach tens. You're at seven right now. So cut down these words or rethink that joke

and start breaking it down and then put it all together like it's some type of Lego that I've just made. And now it's like, this sets now so much better than it ever could be. Yeah, the math of it in some ways is a trick. You're tricking yourself into doing artistic work that is hard. It's actually harder than math homework. Yeah, it's harder than math homework. Math homework is easy.

Math homework's a breeze compared to sitting down and being like, how do I feel about my dad? Yeah. That is the voice of the great Gary Simons. I am so excited

about this episode. We have been talking about doing this for a while. Gary Simons is a comedian who started at Georgetown, like I did, won the funniest person on campus contest, like I did, except 20 years later, and reached out to me a few years ago and said, hey, I do comedy, you do comedy, maybe we should talk. And now he works on the podcast. In the last six months at my club shows, he's been opening up the shows.

And he's been great, killing, so good. But we decided, like, why don't we do an episode where literally he just asks all the questions that a new comedian who moved to New York two years ago would ask a comedian who's been working in New York for 20 years. What would those questions be? And maybe that's helpful for you. And we just thought that would be a really fun thing to do.

So that is what this episode is today. I love how it came out. I should mention, I'm doing my new hour, 10 shows in Boston. We just added a ninth and 10th show in Boston. Get your tickets for that right away. 10 shows, completely absurd.

Dream come true in my hometown of Boston. Get your tickets for that right away. 10 shows, completely absurd. Dream come true in my hometown of Boston. I'm announcing several club dates in cities that I have not announced yet. The only way to find out, you'll be the first to know because you sell out fast, is to sign up for the mailing list on burbiggs.com. If you go to tour dates, at the bottom, it says sign up for the mailing list. You will be the first to know about some club dates where I'm working out new material for my tour.

So all of those, you can find on burbiggs.com. Enjoy my conversation with the great Gary Simons. Today, we're here with Gary Simons, my friend, my co-worker. You work on the podcast. Yep. And for the last roughly nine months, my opening act during the Working It Out club shows.

Yeah, nine months. That's crazy. What was the first one? The Columbus Theater in Rhode Island. And actually, I was always curious about this. When you asked me to open for you, and then it was the night, like the first night where I was just going to do five minutes, I remember I was so stressed because I was like, it wasn't that I was like, oh, am I going to do poorly or anything? I was more so concerned that if it didn't go great, that you would afterwards be like,

hey, so how about we hold a beat on you opening? How about we hold on you opening for a second? Just for a while. And I was like, were you worried? That first one, were you like, oh. I can't say hold a beat wasn't on deck in my brain. It's definitely, of course, yeah, always when you work with someone new.

I mean, I took a chance. I'm going to put this in context for people, how we met and all this stuff, which is like Gary and I, 22 years apart, won the funniest person on campus contest. I think for you it was the funniest human, for me it won the funniest person on campus contest. I think for you it was the funniest human. Yeah. It was the funniest person at Georgetown University.

Yeah. After you won that, you messaged me on Instagram. Yeah. I got to explain this to people. You messaged me on Instagram and said, hey, I want to meet you. Can we meet up? Could I possibly work for you? Could I, you know, anything.

I'm saying this to discourage people from messaging me on Instagram. Don't do it, even though it worked for Gary. And actually, one of our other producers on the show, Mabel Lewis, it actually worked for also. And then, so two of the people who work on the podcast are people who cold emailed or cold messaged the company. In most cases, it doesn't work.

Because as you know now, the amount of that that we see in the office every day is absurd. Yeah, I think about that. Not even that you would ignore it, but that there's so much going on. Honestly, I'm like, wow, that was just pure luck on a lot of ends. So we had this thought today for Working It Out podcast, which was, we usually have seasoned comics, people have been doing it a long time,

come on, and we talk about craft. And I thought, well, Gary's been doing stand-up out of college for about a year or two. Mm-hmm, yeah. So what if a new comic like Gary asks a seasoned comic like me just sort of anything that's on their mind? Mm-hmm. And that would be maybe instructive

because I would say a vast majority of people listening to the show, a lot of them are creatives, and a lot of them who are comedians aren't comics who've been doing it 10, 20 years. And I've been at it, at this point, 23 years, whatever it is. So we thought maybe it would be helpful for you and I who spend an extraordinary amount of time together, and we're spending a ton of time together this fall too

because we're going to do club shows together in the fall, like D.C. and Philadelphia and Buffalo. And you're killing. You're doing great. Not only are you doing great, but even like the other day on Instagram, you posted a clip from when you opened for me in Madison. You got 12 million views. Yeah, that was intense. Yeah. So that's what we're doing today.

We're cracking open, okay, what does a new comic ask to a comic who's been doing it for a long time? Yeah, I'm curious, one of my first questions for you, trying to get into the mind of any comedian at any level might be wondering, is that you're Mike Papiglia, you just graduated from Georgetown, you've been doing some stand-up at the DC Improv, you come to New York and you start out

as a now New York comedian. Yes. When you first got here, what were some of the mistakes in comedy that you had made? What were some of the things that you thought were the best moves you could have made at that point? I think in hindsight, the mistake I made

was this kind of, I put my foot in my mouth a lot with other comics. Yeah. Like how so? There's just a handful of times where we talk about this on the Tom Papa episode where you're just asking people

for so many favors. Right? And then you end up sometimes in these situations where you're not expressing enough appreciation for the favor that you're asking. And it just gets all really tangled up. The other side of that, we talk about that in the Tom Papa episode, is when you're starting out, you have to ask for favors. There's no way around it. Like the whole thing is a conundrum. And then what did I do right, I think, is I said yes to everything.

Like if there was a show on the Upper West Side where it was at a bar on a Monday night and there was six people in the audience, I would do it. And I would give it my heart. And I wouldn't tell the audience that they stunk. Yeah. You know what I mean? I wouldn't get upset.

I'm not going to come for you. I'm not going to come for the audience because they're not giving me the response I want. Yeah. So that was good. And then also just like, honestly, just like relentless, just trying, failing, trying, failing, and attempting to. It's funny because I've been watching the U.S. Open lately. The reason I'm obsessed with tennis is it's such a head game.

I think stand-up comedy is such a head game. Yeah. I mean, I'm feeling it early on, that it's like once you really start going every day, just forcing yourself to go, whether you do well or don't, and just trying to make it objective, the stand-up thing, which can feel very subjective, is like, oh, people laugh, that joke works.

But actually doing it so much that you're now looking at it like, okay, that joke gets this amount of a laugh, it's at this level. You're doing it so much that you can now look at it from a whole different perspective, which I only got from you telling me, I think the thing you need to do, Gary, is just get more stage time. The doing it right, what you do right versus what you do wrong.

It's like the doing it right is, I think, tenacity. Yeah. And I've heard this. This is not my piece of advice, but I think it's a smart piece of advice. Don't be afraid to share with people what your dream is. Yeah. Because the odds of people rooting for your dream

and helping you are higher than them plotting against you. Yeah. It's like most people aren't actually rooting for your downfall. Though it feels like that at times where you're like, oh, that's why they didn't book me for that show. That's why they didn't reach out to me. It's like no one's actually thinking about you. No one is. No one's thinking about me.

It's just like, just tell people what you want, and it's more likely people will give it. Well, that's the thing. And the downside is actually negligible. The downside is you're embarrassed. And if you're not willing to be embarrassed when you're pursuing being a stand-up comedian, good luck to you in this profession. Because I've been doing this 25 years.

I feel embarrassed all the time. Like, all the time. Like all the time. Yeah. I do gigs where it's like some college where like nobody quite knows who I am or some corporate event where like literally no one knows who I am. And the audience doesn't really want to be there. And it's like, it's embarrassing. Yeah. I'm up there doing my jokes that do really well on Broadway and they're bombing. You know what I mean? It's embarrassing. It's like this works every other time. So the inflection point was I said,

hey, can you show me what your recent stand-up set is? And I watched it, and my note was, and this is what you were referencing earlier, my note was, oh, yeah, you just need stage time. Because your jokes are fundamentally funny. They're based on funny observations, which is at the core of what stand-up comedians are. We're just observers. Yeah.

And your stage presence is like charming and I like you. Thank you. And it's loose. Yeah. And it was just one of these things where it's like, I'm watching your set and I'm just going like, oh, you could cut like 30% of the words in this. And if you did that, your laugh quotient would go up. And you just need stage time to learn that for yourself. The term like laugh quotient,

it's like once you can start turning this into math in a way where you're like, okay, no, that's like a five level joke. That's a seven level joke. That's a 10 level joke. And then be like, all your jokes need to be, or approach 10s. You're at a seven right now. So cut down these words or rethink that joke and start breaking it down and then put it all together like it's some type of Lego that I've just made.

And now it's like, this sets now so much better than it ever could be. Yeah, the math of it in some ways is a trick you're tricking yourself into doing artistic work that is hard yeah it's actually harder than math homework yeah it's harder than math homework like math homework is easy yeah that works a breeze compared to sitting down and being like how do i feel about my dad yeah how do I feel about my dad? Yeah, how do I feel about my dad? And then you're writing down these things that hurt when you write them down.

You're like, oh, that doesn't feel good. Like, am I a mama's boy? And then breaking down being like, okay, in what ways am I a mama's boy? Okay, well, I guess I have to call her all the time. Like all these embarrassing things that I'm not about to tell an audience. And then sometimes it doesn't work.

Like I just told them like, yeah, I have to call my mom to know my allergies and they didn't laugh. Yeah, no, it's embarrassing because essentially Pete Holmes and I always talk about how the best comedy is telling secrets to an audience. Telling secrets that you have to strangers. And when you tell a secret

to the audience and they're like, we don't care. It's really embarrassing. Go on, what else? Yeah, what else? That's not really funny, that's kind of sad. When they go on what else that's not really funny when they go aww I do like when the audience makes some type of response because I'm learning but when an audience member says aww to a thing

that I did not feel bad about before I then immediately feel like this isn't a good thing people feel bad for me up here welcome to my world I'm still living that you're just kind of pointing to these things People feel bad for me up here? Okay. Welcome to my world. I'm still living that. Yeah.

You're just kind of like pointing to these things. That's Pete Holmes calling. Oh, I'll put him on speaker. Hey, Pete, I'm recording the podcast right now. I got you on speaker. Old man in the pool. More like weird naked guy in the locker room you gotta laugh from you gotta laugh from gary from you no you gotta let big laugh from gary simons here who's been opening for me on the tour

hi pete zero from you love gary zero from you i was focused on the sound and making sure that the sound went into the microphone i thought it it was very funny. I really enjoyed it. I mean, this is a classic ears-burning situation. I was talking about you two minutes ago on the podcast. I literally said on the podcast two minutes ago, I go, Pete Holmes and I always talk about, because Gary's been opening for me, and we're talking about questions from a new comedian

to someone who's been doing it for a long time like what are the questions you'd ask and I said Pete and I always talk about how you're telling secrets in the best case scenario you're telling secrets to the audience yeah and they're laughing you said it better than that you said if you're not telling secrets, who cares? I appreciate that. And then you also once said to me, you go, are we going to save our best stories for when we're dead? Is that?

Yeah, I think that's a fun one. We used to say that on Crashing all the time, if we're not telling secrets, who cares? And that, honestly, when I'm watching people and my eyes glaze over, I'm stand-ups i mean i'm like well they're not telling me a secret i just want secrets i just want i'm it's so funny you should say that pete i'm exclusively i'm secrets only now when i watch comics that i've become only two i i'm a snob i'm secrets only when someone secrets only when someone tells me a secret on stage,

and I'm going, oh, this is the real dope. I'm like... And by the way, it doesn't have to be I like farting in my car or something stupid. It doesn't have to be a personal secret. The secret can be a feeling. And one of the jobs of the comedian is to say, no, I'm a decent person.

Like, I'm kind. I'm trying to be compassionate. I'm trying to be good. But also sometimes I'm on a plane and I'm like, I don't know why, but I hate that the back of this guy's head. I fuck this guy's head. And that's a secret. You know what I'm saying? Yeah.

I love it. I love it. you know what I'm saying? I love it and then do you have, before I jump off I'll call you later but do you have any advice for Gary who's a comic who just moved to New York two years ago and is a really funny stand up

comic and is just trying to sort of find his way um you know yeah of course I do I think it's funny that you and I talk about this so much. So the part of me is like, does Gary want to hear this? So I'm hesitant, but I'll just say it so I can get off and leave you be. The most challenging question is, when would you laugh?

If you were in the audience, be honest, when would you laugh? That's so smart. It's like brutal. When would you laugh is so smart. When would you laugh? And also, you know, I just feel like when you're coming up, attach yourself. You're a product of your environment.

And, you know, you want to be a creature of a place, not just a thing, but a place. So like watch your place, like your geography and partner and sidle up to the people that are at your level that you admire. And also the people that are just half a click ahead of you doing the rooms you'd like to be doing,

have the career that you'd like to be having, but not, you know, not huge ahead of you, just a little bit ahead of you. I just sort of copy them. We call that Burger King because Burger King only opens where McDonald's is. Isn't that crazy? Isn't that crazy? Burger King saves billions of dollars, or millions of dollars, doing no research on where to open because they just open where McDonald's is. Dude, have you done a bit about this?

No, it's just advice I give. Oh, no, this is great. This is great. You should put that in your act. Yeah. Oh, really? I would put that in your act, yeah. I don't know where it would fit I love it

Someday Mikey I want to perform for 300 years You know what I'm saying? Because you love the most interesting Like you want it So many bits and things Interesting thoughts get cut Because I just want to mow it down I want to mow it down

But with a Birbiglia crowd I'm like I can chew gum, put my hand in my pocket And just kind of talk from my heart I just want to mow it down. You know, I want to mow it down. But with a Birbiglia crowd, I'm like, I can chew gum, put my hand in my pocket, and just kind of talk from my heart. All right, buddy. I love you. I love you, too. Bye-bye.

Bye, Gary. When John Mulaney and I spent a lot of years traveling together and touring, talking comedy. We always talked about how when you write a joke, if you imagine a laugh, there's no laugh. Yeah. That's my issue. When I'm writing,

all of it feels very funny, and then you try it on stage, and then you're like, oh, that one line was funny. That one thing is kind of humorous. I really think you have to make yourself laugh. You have to get every joke to be something that is funny. It honestly is so funny that you're dying to tell somebody.

Yeah, and I think that secrets point is the thing that actually makes me laugh most. It's like when I say something that feels kind of vulnerable, but I feel so, like it feels so true that it's almost like, it's like I actually don't mind sharing it because it's so true to me. It makes me laugh that I actually feel this way.

Or something is so, like I have a joke that I'm working on that's my brother's getting married and I'm excited for him that I'm working on that's my brother's getting married and I'm excited for him I'm happy for him but I'm also kind of worried because I've only ever been

to one other wedding and those people got divorced and then a few years ago I found out they got remarried to each other and I wasn't invited so I'm bad luck right

like so I'm bad luck and that's like that makes me like that part makes me laugh because it's like a very true feeling like why wasn't so I'm bad luck, right? Like, so I'm bad luck. And that's like, that makes me, like that part makes me laugh because it's like a very true feeling. Like why wasn't, like all I'm thinking about is why wasn't I invited? And it's still together now. Like what was it?

Well, it's funny because like that actually speaks to the clip that went viral from your Instagram, which is that you're an overthinker. Yeah. Which is like, can you say your overthinker joke so people know what it is? So basically I'm an overthinker. Yeah. Which is like, can you say your overthinker joke so people know what it is? So basically, I'm an overthinker, which if you know someone who's an overthinker,

don't tell us we're overthinking it. We know. And it's insulting to think that you would think that we haven't thought that we're overthinking it. We don't need your underthinking thoughts. Yeah, we don't need your underthinking thoughts. I love that joke. It's very economical.

It's one of my favorite jokes because it establishes who you are, what your point of view is. And then, interestingly, it helps jokes like the one you just told me, which is to say that you think you're bad luck for weddings or whatever. It's like, no, you're not. You know what I mean? I can't be, but it feels like that but because in the set list if you put the overthinker joke before that then the wedding story which is a good story on its own yeah is a heightening

of the premise that is that you're an overthinker so in other words like if you put overthinker in the front of your set you're actually setting up for a lot more success in other words, if you put overthinker in the front of your set, you're actually setting up for a lot more success in other jokes that you have that are true to you. And this, by the way, is what Neil Brennan said on this podcast before, too. Neil always has this great analogy, which is, as comedians, our brains are the internet before the internet existed. They can't stop associating. Yeah.

And clicking to this, and clicking to this, and clicking to this, and clicking to this. And our job as comedians is to slow that down, analyze it, write it down, take copious notes, look at the notes later and go, aha, there's the funny part. It's oddly like our whole job is overthinking, which probably drives people nuts.

Probably drives people nuts in your personal life. Gary. But as a comedian, I think it's not only a strength, but it's oddly essential. It's funny that you say that thing about it affecting people only a strength, but it's oddly essential. It's funny that you say that thing about it affecting people in my personal life. I have a girlfriend.

One, trying to have this hustle of becoming a stand-up comedian and also managing a relationship, managing a job can be a lot. One, when you're in a relationship, being the annoying person who's always... When Jim Gaffigan said being married to a comedian is like being married to a conspiracy theorist. I'm just curious, what advice do you have for a comedian who's in a relationship and how, on one end, to manage that

and one's own career and also just being a good partner to that person. It's funny, your shirt says be kind always. If you open that up to camera, be kind always. I think that's a good rule of thumb. It's trying to

and of course I'm not doing this probably as well as I should be and I always have to think about that in relation to Jenny and Una and my friends and my family is like trying to put yourself in their shoes. What I try to do with jokes, like I have jokes about having children and having a child and being married and all this stuff. I always try to see it from their perspective also to complicate and make more deep, really to deepen what the joke itself is.

So that we're actually not just seeing Gary's point of view about his relationship. We're seeing Gary's and actually a taste of his girlfriend's perspective of him. Yeah. And a little taste of what his parents feel about him when he talks about them and all that kind of stuff. And because I feel like it actually, it does more for making the jokes that you're telling a more real experience for the audience.

Yeah. Because life doesn't have a single perspective. Yeah. It doesn't even have two. But if you have five, six perspectives on the same thing, I think you can start to have a deeper experience with the audience. Okay. I do want to help out all of the other comedians who are listening.

Young comedians listening to this. So can I blitz through some like what I thought were general comedian questions? Okay, so one question is how do you get an hour? Where do you go from I've just moved to New York to I now have an hour of stand-up that I'm doing around the city and the country? Like how do you go from nothing to an hour? I think the goal is, when you're starting out, to come up with, at first, five minutes that works anywhere.

And when I say anywhere, I mean anywhere. It works at a bar mitzvah, it works at a birthday party, it works at a comedy club. It works in an alternative room, it works at a mainstream room. It works in Kentucky, it works in Boston comedy club. You know what I mean? It works in an alternative room. It works at a mainstream room. It works in Kentucky. It works in Boston. Yeah. Five minutes.

Well, you know, no matter what, that's going to work. Yeah. And once you do that, I think you start to go, can I do that for 15? Can I do that for 25? Then it's, can I do it for 45? And then I think it's for an hour. And part of those time increments

have to do with the conventions of stand-up comedy. So for example, at a comedy club like the DC Improv, which is where I started out working the door, the MC does 15 minutes. The feature act does 25 to 30 minutes. And the headliner does 45 minutes to an hour. In my case, I do like 70 or 80. And so I think thinking in relation to those being the stair steps are just, honestly, they're just convenient markers. Okay. Next question is,

next question is, how do you, how does someone get booked at a club? This is impossible. Yeah. Truly, truly impossible. I mean, and Pete Holmes and I talk about this all the time.

The challenge at this moment in time for someone like you, you graduated from school in 2021. Yeah. When I came up in comedy in the late 90s, if you look at the wider picture of stand-up comedy, the 90s was a bear market for stand-up comedy. And currently, we are in a bull market for stand-up comedy. So the question is, what do you do if you want to get booked? I think part of it goes back to what Pete was saying,

which is like aligning yourself with comedians who you think are funny. So if they have a show, they'll book you on their show. You book, you can book them on your show and you'll feel good about it because you're like, Oh, they're funny. I'm funny.

It's, it's, it's this mutually beneficial thing. And then honestly, it're like, oh, they're funny. I'm funny. It's this mutually beneficial thing. And then, honestly, it's like stage time. A majority of it is stage time. And that's why way back six months ago, when you were like, what do you think I should do with my stand-up as it is?

I'm just like, you need stage time. And it was a lucky thing. It just so happened I was doing some club dates and I was like, well, you could come out and do this. I feel like your act has improved in the last six months

50-60%. It feels like it's improved so much. That stage time thing, I can't say it more. Stage time, it's can't say it more. Stage time, really, it's like you learn through doing. It's like, do as many shows as you possibly can

because you'll learn something new through going through it, as much as thinking about it. I'll have friends who say, oh, I kind of want to start stand-up comedy. I'm like, do it because you will learn something as soon as you do your first open mic. You will learn what it feels like to be up there, and then you'll learn what it feels like to do it over and and then you'll learn what it feels like

to do it over and over and over again if you just keep going. I think it's a perfect time for me to say, at Gary from Connecticut, where you can be reached on Instagram. Message Gary if you are, honestly, anywhere. Because I think Gary would entertain stand-up comedy offers from almost anywhere.

I think if you said you were in Montana right now, I think Gary would say... I would go. I would be there. Maybe. I'll figure it out. I'll be there. I'll be there. But particularly New York and the tri-state area. Let's go to another one.

When should someone get a manager agent? How do you get a manager agent? I believe this is a fundamental mistake of young comics writers, et cetera, starting out. They're focused on agent, manager, et cetera, et cetera, representatives. Yeah. And the reason I say that is, essentially your representative is someone who, and I don't have a manager, I have an agent. My stand-up agent is someone I've worked with, Mike Berkowitz, for 23 years, 22 years, something like that.

In some ways, your agent is an extension of what it is you're doing and what level you're at. So in other words, if you were to get signed by an agent tomorrow, based on where you're at, think about what 10% of that is. You're not making that much money. Making 50 bucks a show, 100 bucks a show at the level you're at, whatever it is. Even 200, 300. Let's say high end, 300, 30 bucks. making 50 bucks a show 100 bucks a show at the level you're at whatever it is even 200 300 let's say high end 300 30 bucks yeah yeah so like that's what the agent is making 30 bucks yeah and that's a big win yeah for you you're like 300 bucks is great yeah that's that's chopping out part of my rent for the month. Yeah. Great.

Helping me out with some stuff. Yeah. So I think you have to think in relation to, a lot of times in this industry, people are like, I can't get an agent. I can't get a manager. Well, you're worthless to an agent or a manager right now. Yeah.

Right now. I think that what happens is you need to be your own agent and manager early on in your career. You need to be, when I moved to New York, I had a phone book out. This is back when phone books existed. Yeah. And I was looking up comedy clubs across the country, and I would cold call them. I had a spreadsheet that had all the comedy clubs that were in America.

And I would cold call them every day like I was a telemarketer. And I was my own agent. The other thing is like you start to get things. If things are going really well, you maybe get booked at Moon Tower Festival or Just for Laughs in Montreal. In my case, I got booked at the New Faces at Just for Laughs in Montreal. In my case, I got booked at the New Faces at Just for Laughs. And that really changed everything because a lot of agents and managers became familiar with me. And so then it becomes a conversation.

I think one of the traps is that you get excited that an agent or manager wants to sign you. Cut to they sign you. They do nothing. The reason they're doing nothing could be any number of things. But one of them is, there's no money in you for them. True.

And there's nothing worse than being just in a relationship where the moment you're in it, you're like, I want to break up with this person. But I'm now legally obligated to stay with them for at least a year. Right. And then weirdly, I don't mean to be

disparaging to agents and managers. Some people are great at it. Some people are terrible at it. That's just the nature of every job. But the ones that are terrible at it are really terrible at it. And oddly, they don't want you to break up with them.

Then you're in this weird situation where you're like, and oddly like they don't want you to break up with them. Yeah. And so then you're in this weird situation where you're like, you're kind of invested with this person who you don't really even trust. And you're just going, how do I get out of this? Yeah. So I would say don't be afraid to be your own agent for as long as it takes. Yeah. As long as you possibly can.

Okay. Two questions. What are good day jobs to have if you want to be a stand-up comedian? This is a great question. This is a great question because I've seen it done many ways. So like Jesse Klein has been a guest on the show, one of my favorite comedy writers, favorite comedians.

She had a day job at Comedy Central for years. She was a big executive. She was like a major major executive and so that's a path a path is staying in comedy and being super focused and then also writing comedy etc

that's a path another path is staying so far away from comedy, it's ridiculous. You know, working at a cafe. Yeah. You know, skipping work sometimes. Yeah.

Getting fired. Sometimes all it takes is to get fired. Well, that's what I did. I mean, truthfully, like I worked at the door of a comedy club, which was an example of like being adjacent to the business, witnessing a lot, which I always recommend, by the way. I always recommend young comics who want to learn,

get a job. The same thing with theater or movies. Get a job in a movie theater. Watch all the movies. You want to learn how to make movies? Watch 200 movies. Same with theater. Be an usher. Get in the room. Get all the movies. You want to learn how to make movies? Watch 200 movies. Same with theater. Be an usher.

Get in the room. Get in the room. Stand-up comedy. Work the door. Watch a lot of comedians. When I started out, I was watching George Lopez and Dave Chappelle and Brian Regan and Mitch Hedberg and Kathleen Madigan and Margaret Cho and all these people. And I'm going, oh, I'm learning everything. This is comedy college.

So I think you can go either way. I think you can have a job where you go, I don't care about this job. I can get fired, get another job. Or you can do what I was describing as like the Jesse Klein route, which is like be in the business. Yeah, which I think I did a mix of both

where I started in insurance. And then I now work for the Working Out Podcast company. It's now that pivot there. The next question is, when is it a good time to leave a day job for stand-up? When do you know? They'll tell you. Gary, I brought you here today on camera

for a very special announcement. No, just kidding. Yeah, yeah, yeah. That would be the ultimate insane move. That would be insane. To low-key fire someone on camera. To low-key be like, you don't have a job anymore. You don't have a job.

You employ yourself. What? Well, this question answers itself. Yeah. No, but I don't know. I mean, honestly, it's like it comes down to when your artistic job is paying enough bills or close to enough bills that you can make a leap towards the next lily pad, so to speak. It's not cut and dry, though. Yeah.

I mean, it's on you to figure out, and it's also risk-based, right? So it's like, you think about that your own time is valuable. Yeah. And in a certain way, when you're starting out in comedy, you're putting a value on your own time,

and you're taking a risk that your time is worth as much as you think it's going to be for someone else. Yeah. So in other words, like when I was starting out, it's like at a certain point, I took a risk. Okay, I'm not going to do my day job. This is probably when I was 23, 24 years old.

I'm not going to do a day job for these three months. And I think I can cobble together enough stand-up comedy to make that work. And it worked, but also for a lot of people it didn't work. So you decide you're going to do three months, this three months you're not going to have a job, and see if you can make it work.

Are there points where you want to give up? Like where you want to stop? Where you get close? Because you didn't. But did you get close at any point? Right now, today, I want to give up. I feel like you never don't want to give up.

Weirdly. There's never not some part of you that thinks, wait, what am I doing? Yeah. This is nuts. What are jokes that you have in your act right now that we could talk out what a process could be for that joke? Or that you feel like there could be growth there? I have a thing about being a mama's boy and like part of the issue of being a mama's boy is the fear that like one day I'll have to choose between like my mom and my girlfriend.

Yes. And it's kind of like this fear of like, what if like my mom and my girlfriend were hanging off a cliff? Like, yes. And the hard truth, knowing that I'm a mama's's boy Gary's about to say this on air the hard truth is that I would probably at this point in my life I'd probably save my mom Sophie's choice between your mom and your girlfriend

saving one or the other probably save your mom probably save my mom because my mom knows my allergies it's like I know my allergies but my mom knows my allergies and It's like I know my allergies, but my mom knows my allergies. And the part that I don't really laugh at is the part where I then continue and give an example of which I call my mom.

So I'll be like, oh mom, can I eat shrimp? And she's like, no Gary, you're allergic to shellfish. You're allergic to shellfish. So I've seen this joke a lot. That's part of the reason why I'm not maybe laughing as much because the surprise is not there. But my inclination, my pause, and I like the joke, but my pause when I hear the joke is the phrase mama's boy to me feels oddly like outdated. Like when I was a kid, the phrase mama's boy was outdated. And so maybe it came into common vernacular recently,

or maybe you're pulling it from something that I just don't know that well. And in which case, I think it's worth extrapolating out to the audience. A, did someone call you a mama's boy? Is there a specific anecdote where you go like, one time, my brother, this person, my friend said to me, you know what, you're a mama's boy. B, to use Ira Glass's note, he always says, how did that make you feel? And then C, go into the

stuff that you're saying about, you know, I'm a mama's boy, and then your jokes about it. Because I feel like we're missing currently, in the current version of the joke, I actually think we're missing the bridge to the mama's boy concept. I always think of jokes in terms of like, you're flying people on a rocket ship to a planet. And the planet essentially is the joke. Yeah. And it's a universe of stuff and ideas. And once you get there, then you spend time pointing out what the vegetation looks like,

pointing out the craters and making observations about what's there. But I think, oddly, you're a little bit missing the rocket ship. Yeah. Like, in other words, I think your planet is there, but I don't think you have a transportation mode to get there. I haven't gotten there yet. I'm just personally reacting to it in the way that I feel when I hear it. I'm laughing, but I'm a little bit going,

yeah, I'll take your word for it that you're a mama's boy. I kind of know what that means, but I also kind of don't. Yeah, and then as context for the audience, the joke continues into saying, I'm a mama's boy. Like, I love my mom in a normal way. Yes, yes. I love that. Like, there are not normal ways you can love your mom, and you can find those online. Yeah, yeah, yeah.

But I love my mom in a normal way. Yeah. And then it's like, my dad will get upset that I'm a mama's boy. He'll say like, Gary, you're always up under your mom. How come you're not a daddy's boy? And I'm like, because that sounds like you're my pimp daddy. Yeah, yeah, yeah. I love that joke.

I, again, I have a caveat in my mind, which is, did that happen? So yeah. Did your dad say it? And if he did say it, did he say those words? This is the thing I say all the time. Pete Holmes, my closest friends. People have been doing this 20 years. I go, did that happen?

Yes. If so, what was the exact phrasing? Because I think the exact phrasing might help. Okay. Yes. Well, going through your exercise of like, did someone call me that? It's yes, my dad called me that.

And then what did he say exactly? Like there'd be moments where he would just get frustrated at something I was doing. Like he'd be like, oh, Gary, you want to go fishing with me today? And I was like, no, like I was actually going to like play with my action. I was going to play with my action figures and my toys.

I like, I had a whole day planned. And then he'd be like, like how come you don't want to be outside? Like I was always outside when I was your age. I was like, you couldn't keep me from being outside. I used to cry when they told me to come inside. And then all you want to be is inside. You're just a mama's boy.

You always want to be up under your mom. You want to go with your mom to places. I'm going to stop you right there and say, if I were you, I would lead with that story. Then when you get to the dad saying, you're a mama's boy, as though it just occurred to you yeah i want to talk about mama's boys for a second because i think maybe i am one but joke joke joke joke

that you've already written it's like yeah and that's already working yeah yeah it's like can i can i talk about mom's before like i love my mom yeah i think it like exactly i love her in a normal way i think you're good yeah yeah i think you're good. Yeah, yeah. I think you're good there. Yeah. Because I think like, for me, I completely find a way into your joke through the perspective of you and the perspective of your dad. Because in my mind, I'm like, oh, that's an old school thing to say. Well, your dad's an older guy.

Yeah. So then start, so maybe unpack more stuff with my dad, like the relationship with my dad. Oh, yeah. I love that. Yeah, I think that those ideas pivot one to the next, I think, really clean, very cleanly. Yeah.

Craig Mazin said this thing, who's a guest on the show, and created The Last of Us, and did Chernobyl, and many, many, many comedies. He said this thing to me when I was asking advice on a script recently, where he goes, it's not about the characters, it's about the relationship between the characters. What we're obsessed with is

how do these characters relate to one another? So the thing with your dad is not as much about your dad as a character or even you as a character. It's about what is your relationship? What is the dynamic? When people see that and they go, oh my God, that's me. The thing we should end on is working it out for a cause.

Is there an organization that you think is doing a good job that you want us to contribute to? And then we'll link to them in the show notes. Yeah, Connecticut Food Share. I'm from Connecticut, and so I think that they're a great cause. Well, we're always supportive of food banks here. I give to a lot of food banks in cities that I tour in because I always feel like the way that they stretch a dollar is really impressive and it's a very important issue right now.

And so we're going to contribute to Connecticut Food Share. We're going to link to ctfoodshare.org. And thanks, Gary. I think you're doing great thank you one for the opportunity to be able to open for you and thank you for the opportunity on the podcast

I appreciate it that's going to do it for another episode of Working It Out Gary Simons is a great comedian and I think is headed up, up and away. He's on a phenomenal trajectory. You should follow him on Instagram. He's at Gary from Connecticut. And if you want to message him on Instagram, you should.

And see if he wants to do your show. Wherever it is. I don't know if he's going to do it. I'm not committing him to it. I'm just saying, you can ask him. If you run a club or you run a comedy room or you run a bar where you have a comedy show, just ask him. You can watch the full video of this on our YouTube page. It's my Mike Birbiglia

YouTube channel. We've had a bunch of great episodes on there. Hasan Minhaj, Jim Gaffigan, Ira Glass. We love that we've added that YouTube channel because so many more people have just found the show. Our producers of Working Out Are Myself, along with Peter Salamone and Joseph Birbigli, associate producer Mabel Lewis, assistant producer Gary Simons. What? That was just the other guy.

Sound mix by Shubh Saran. Supervising engineer Kate Balinski. Special thanks to Marissa Hurwitz, Josh Upfall, David Raphael, and Nina Quick. My consigliere is Mike Berkowitz. Special thanks to Jack Antonoff and Bleachers for their music. Always a special thanks to my wife, the great poet J-Hope Stein. And as. Always a special thanks to my wife, the great poet J-Hope Stein.

And as always, a special thanks to our daughter, Una, who built the original radio fort made of pillows. Thanks most of all to you who are listening. If you're enjoying the show, write a little thing on Apple Podcasts. It helps people find the show. Tell your friends. Tell your enemies. Here's what you can tell them. I found a new comedian I enjoy.

His name's Gary Simons. He's just starting out, but this guy's going big! Alright, thanks for listening. We're working it out, everybody. See you next time.