Talking Comedy with Shereen Kassam

In this episode, Shereen spoke with us about how she got her start in comedy after her new roommate drank all of her liquor and dragged her to a comedy show in Boston. Shereen hated the show so much she asked for her money back. The venue instead challenged her to go on stage herself to see how hard it was, and the rest was history!

In addition to her standup career, she also is a manager for a Fortune 100 company, an award-winning podcast host, and is getting ready to perform her first Ted Talk. We’ll talk more with Shereen about her podcast and Ted Talk in an upcoming episode!

About Shereen Kassam

Shereen Kassam is an internationally touring stand-up comedian and host of the top-rated Apple podcast, Creative Breakthrough. She has performed worldwide, from New York to Saigon, and has appeared on HBO and NBC. Shereen's comedy draws on her unique background as an East-African (Kenyan/Tanzanian), South-Asian Muslim woman who grew up in the United States. She has won awards such as Florida’s Funniest Female and has worked with renowned comedians like Arsenio Hall, Preacher Lawson, and Carlos Mencia. In addition to her comedy career, Shereen enjoys acting and has appeared in commercials and web series. Off-stage, she helps people live their best lives at My Pain Center and has a background in roles at JPMorgan, Deloitte, Disney, and Amazon. Shereen holds a BA from Brown University and an MBA from The Wharton School. She currently resides in Orlando, Florida, where she has a serious problem saying no to chicken wings. Connect with Shereen on Facebook and Instagram @funnybrowngirl.

Make sure to listen and subscribe to the Sound Connections podcast on your favorite podcasting apps including Apple Podcasts, Spotify, and Google Podcasts!

Welcome to the Sound Connections podcast. Recently Clinton sat down with comedian and podcaster Shereen Kassam, aka FunnyBrownGirl. Shereen has been named Florida's Funniest Female, has previously won the Orlando Improv Clash of the Comics, and is the host of the Creative Breakthrough podcast. In this episode, Clinton talked with Shereen about her career in stand-up and what inspired her to become a stand-up comic in the first place.

Clinton

So welcome to another episode of Sound Connections. Today we have Shereen Kassam, and she is by day a strategy manager for a Fortune 500 company, and outside of that also an internationally touring stand-up comic, actor, TED Talk speaker…. There was something else that I'm forgetting. Oh yeah, and of course podcast! The whole reason we're here, podcast. So welcome.

Shereen

Thank you. Thanks for having me.

Clinton

Thanks for coming. That's so funny. So yeah, so the one thing that brought us together is the one thing I forgot. I told you before we started I’d mess that up, but we're going to go with it anyway.

Shereen

Totally fine. Yeah.

Clinton

So yeah, so again, thanks for coming. I mean, you obviously got a busy schedule, lots of doctor appointments too.

Shereen

Lots of doctor, a lot of COVID testing happening. Yeah. Who doesn't like to sit on rush hour traffic on a Friday?

Clinton

Yeah. Right. Yeah. Right. But this is out of your way too. So you know, you might still get lucky on the way back.

Shereen

Maybe. We shall see.

Clinton

So I was curious, I thought, you know, even though what brought us together was podcasting, I thought maybe we would start with comedy. I've never actually—I mean, I've been to lots of comic shows. I've seen lots of it on TV, but I've never sat down with a comic. So, like, how'd you get into it? Like, how did that, like, how did that get started? I mean, who, I don't know. I don't know many people that grow up wanting to get into comedy.

Shereen

Yeah. I didn't grow up wanting to get into comedy. I didn't even know comedians existed. I was so sheltered. I didn't know a lot of these professions existed. Like I didn't know you could be on the radio. I thought those were just people inside the box. Like I didn't know they were real human beings on the other side. I was so sheltered. And in my mid-twenties, I was living in Boston, and I had this woman staying with me, and I didn't know her. It was one of those, my mom called and was like, this girl needs a place to stay for three days. And I know her mom. And so then it ended up being three weeks, and she was a drunk, and nobody told me that. And she was a lightweight drunk. So she was doing shots one Saturday night, and she was wasted. And then she was like, I'm going to Cambridge. We were in Boston. She was like, I'm going to Cambridge to a comedy show. And I was like, you're not going anywhere. You're wasted. And you drank my liquor, which means I'm responsible for you! And she was like, no, I'm going, and you can't stop me. And I was like, oh my God, it's cold outside. And now you're going to make me get dressed and take you to Cambridge. Went to get on the subway, gross. And so I took her to this comedy show and I've never been to a comedy show before. Right? Like this is my first time seeing comedy, and I'm dating myself, cause this is pre-Netflix. This is like pre you could sit on the couch and see comedy, right? So we go to this comedy show, she goes and sits with her friends. They're all wasted. I'm sitting there like the mother hen, babysitting, and I'm in my mid-twenties. So I'm not that old, but I'm like, can I get drunk? Cause now I have to watch this girl. Like who's, who's going to be the designated? Yeah. Subway driver. Right? So we're sitting here watching this show, and I am bored out of my mind. Like I'm just like, I'm watching these comedians, and I'm like, what is this? Like, what—aren't you supposed to be funny? And, and I hate saying that because comedy is so subjective, right? Right. So like now that I'm a comedian and people are like, you weren't funny. I'm like, well, that's because I'm just not your type of funny, but it's bad saying this, but I was bored.

Clinton

I'm going to use that when people, when people say—

Shereen

Yeah, I get offended, but then I'm like, I was that person, right? But I was so bored. So after the show I went up to the host, and I was like, I want my money back. And I'm not that kind of person. I don't really ask for my money back unless it's something very serious. And I was like, I want my money back. And she goes, ‘it's not that easy to make people laugh.’ And I said, can't be that hard. Like I was like, I'm just a little condescending, arrogant, little millennial child. And she, she was like, ‘I'll give you your money back if you can make people laugh.’ So she showed me how to go about figuring out how to be a standup comedian. I took a class, I read a book and then I came back and I did it. And I was like, I was hooked. Like second, I got that first laugh. I was like, this is what I was meant to do. And that's how I started on a dare because the woman wouldn't give me my money back.

Clinton

So did they ever give you your money back?

Shereen

She didn't like literally give it to me, but they bought me some beers after the show, and it added up. Like, I used to be able to put them away pretty quick.

Clinton

So, and that was, was that in Boston?

Shereen

That was in Boston.

Clinton

All right. So you got to, that's a big crowd, right? Like that's a, I mean, big city, lots of people. Like real comedy clubs.

Shereen

Very. Yeah. Real comedy clubs, people who appreciate comedy who've, who've grown up watching comedians, right? Like Gary Gorman, Louis CK—all came from Boston. So just like they know humor, they don't get offended, and they know smart humor, which is very different than Florida humor. Right? Like they can, they can take a step outside of fart jokes, you know, and be like, we can talk about politics without getting offended. Because these are smart jokes. So I really like that up there. But right now it's kind of split with this whole COVID thing. But the fact is you'll never—well, I shouldn't say never—but I wouldn't be afraid to go into a club in Boston and make a pro-Muslim joke or pro-Biden joke. Or a COVID exists joke versus here [in Florida]. Those are some of the topics I would stay away from [in Florida] because not only will people not laugh, somebody will get angry and upset and disrupt the whole show. Like they don't have manners. Right.

Clinton

Well, that's a whole nother story.

Shereen

That is. And I've offended half your audience.

Clinton

Well, that doesn't matter, but I mean, they can turn it off, but yeah, I just think the manners thing, right? I think a lot of things, maybe it's social media too. In fact, I read something about that, that, you know, this is a bit of a tangent—but that social media has caused this thing, you know, with manners, so where somebody in the past might've been polite, people can comment on things on social media without any repercussions. Right. And it's kind of transferred into real life now, like in person. So where people say and do things that 10 years ago, they would have never done. And a lot of it's really rude and offensive and just, you know, not cool. So anyway, but that's all another story. But yeah, so if you're in comedy, it could even be worse. Right. So, or if you're on stage or a celebrity or, you know, it's a…yeah

Shereen

Yeah, you get it all. You get it everywhere. You get it before the show starts while you're on stage after the show, when you get home and on social media, there's always somebody waiting to say something.

Clinton

Yeah. Yeah. So, so you started, and then where did that take you? So you were, cause now you're in Florida, but you've been doing comedy all this time here and there. Not that you're that old, but….

Shereen

I'm not that old, but I had to take some breaks. Like my parents found out I'd lost my job, and I was supporting myself on comedy, and that became an issue. And then I had to go to grad school for two years, and that became an issue. And like, so it's, it hasn't been—

Clinton

Steady.

Shereen

Steady. And then I get bored sometimes with it. Cause I'm just like, there's only so many times you can make jokes that aren't to your…. Like I said, like there's jokes I like making. I like making smart jokes where you have to stop and think. But a lot of the rooms in Florida that I do, I can't make those jokes. And then you just get bored after a while. You're like, well, if I can't tell the jokes I want to tell, why am I doing this? You know? So then I take a break, and then I go and do a TEDx talk. Cause I'm like, at least I get to talk in front of people, and still be an attention whore. Cause I think that's what I really like doing from the most is being an attention whore.

Clinton

So that's really what's intrinsic.

Shereen

I think so. Sometimes when I look back, and I'm like, what do I want to do with my life? I'm like, anything that just gets you attention. Yeah.

Clinton

So, um, so, so you did the grad school thing and then, you know, which took you to your real job, I assume.

Shereen

Yes. In Seattle.

Clinton

Yeah. Oh, okay. Seattle.

Shereen

I worked for an e-commerce site. You can guess which one.

Clinton

Oh yeah. Okay. Yeah.

Shereen

And I did not get to do any comedy while I was there cause we worked ridiculous hours. Like anytime I scheduled a show, I couldn't go because there was something at work. Yeah. So for a whole year I was like, what am I doing? This is not what I want to do with my life.

Clinton

So what brought you to Florida? Is it, was it your job?

Shereen

Um, a little bit of both. I was in Seattle, and I had this prominent job that was paying too much money. Like, you know, when you make too much money, and you're like, what do I do with all this money?

Clinton

I haven't had that problem, but I look forward to it.

Shereen

Well, for the number of hours I was working, maybe it wasn't too much money, but for like a young kid, I was like, whoa. And then my sister was getting married, and they were like, you can't go to the wedding. Oh, and I was like, why not? And there was this whole thing about, you know, you’re not allowed to travel during the holiday season. Cause like that's big in e-commerce and you've got Black Friday and all this stuff. And they wouldn't let me go to my sister's wedding. And I was like, well, that's not going to work for me. So I ended up leaving my job. My parents live in Florida. I moved here to help my mom plan the wedding. Cause our weddings are not like a day or two. Our weddings go on. Her wedding was two weeks.

Clinton

Oh my gosh. I didn't know that long. I knew there were.

Shereen

It was because she was doing a destination wedding for a week. And then my parents were like, but what about all the people we want to invite that can't travel? So we should do another wedding here. And so it became this huge issue. So yeah, I became a wedding planner, and then I was just chilling here. And then another company called, and it was like, what are you doing? Come work for us. And I was like, okay. And here you are still here. Yep. Still here. Cause once you move here and you get a house, and you’re paying less for your house than you are paying for rent for a studio apartment…. Like now I have a house, I have a wall between my bedroom and my kitchen. I have an actual kitchen, like with a dishwasher. I have a washing machine in my house. I don't have to go somewhere and get quarters. I have a car. I don't have to go on the subway with people. There's just so many things you get spoiled with that you're just like, now, how do I leave this, and like go back to—not slumming it—but now you're like, oh, I have to go back to this studio apartment, and use the subway again. No, thank you.

Clinton

Yeah. It takes…. yeah. And in real estate,to have what you have here up there would be insane. Yeah. Right.

Shereen

So what I was paying up there and it was, it was subsidized by the company too. And it was still more than what I pay here.

Clinton

Yeah. So my sister's in television. She's an editor, and she lives in Los Angeles, and she lives in a place like you were describing, and pays a lot of money for it and still has to deal with people making noise and issues. And a couple of weeks ago, there were some girls that live next door that had a little party at their apartment and broke the sprinklers. Yeah. Flooded. Oh yeah. So she was next to and under them. And yeah, so she had to move out for two weeks while the remediation company came in and cleaned up all the water, took down the drywall, and put it all back up. And I'm like, oh my, I do not envy. I like my house now, you know, my four walls, and not being attached.

Shereen

But I do miss on-call maintenance and concierge. I do miss both of those. I miss concierge because it stops random people from just showing up at your door. Yes. And then I miss the maintenance because like when something breaks in the house, I have no idea what to do. I'm like, now I've got to depend on somebody to find time to come fix it. And I don't know how much it's supposed to cost.

Clinton

Another doctor's appointment.

Shereen

I know, right? And the world is so crazy. You can't just let anybody in your house.

Clinton

No, no. Yeah. We, uh, my wife just recently dropped her wedding ring—maybe it was on purpose—into the sink, and she called me to come get it out. So I had to, I had to disconnect the P trap, and I put it back together and it leaked. I'm like, well, that sucks. I was in a rush, so I just left it. And then the next day I took another stab at it, and I made it better, but it still leaks. So in the end, we had to call a plumber, and it was a thing. You had to call the first one. The first one didn't call back. Then we call the second one. So three days later it's working, but even he had to go to Home Depot to get something. So, I know it's a tricky one. Yep.

Shereen

So your AC breaks and they're like, ‘Oh, well we can't come today. Maybe in like four or five days.’ Uh, it's 90 degrees outside. What do you mean in the four to five days? What do you want me to do between now and then?

Clinton

Yeah. So I've been a homeowner here in Florida for 20 years now. I get my AC serviced like twice a year, and it just got serviced. So right before summer comes, and right before winter comes, so that it hopefully avoids any issues.

Shereen

That's smart.

Clinton

Uh, so, you know, it costs money to do that. And, uh, but then by having this service contract, they give you a little bit of a discount on future things, but then they came, and then of course, uh, like one month later, something went wrong with it. Luckily it wasn't hot. Yeah. But, uh, so, you know, knock on wood this summer. I'll be okay. Yeah.

Shereen

Cause it always happens to break on a weekend. That or the smoke detector batteries at 2 am. I don't know why I was at 2 am. And I'm like, who's coming to reach the ceiling? Cause I don't know how to get there.

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Clinton

So I think things like that, like my little thing with the AC scheduling. You know, sometimes I think about these things, and it lets me become a responsible adult. Because the other thing I do that I just started like two years ago—maybe it's on my 50th birthday or 49th birthday—but on my birthday or around there, January, I have a reminder, an annual reminder on my Outlook calendar that to replace all of the batteries in all the smoke detectors for that reason, because it always happens. And here's the other thing that happens. You know, once you start living with somebody, you're married to somebody, it happens when I'm out of town, right? It doesn't happen when I'm there. It happens when I'm out of town, of course. And then, you know, 10-foot ceilings, it's, you know, it's a thing. So, so, um, yeah. Yeah.

Shereen

So text me next time. Just be like, I'm changing my smoke detector batteries. Maybe I'm going to procrastinate and not do it. Cause I'm like, well, the battery hasn't started beeping yet. There's still life in it.

Clinton

Yep. So, um, that's funny. So locally now—let's talk about Orlando. So, um, so you're working for this company here in Orlando, but you're still finding time to do some standup?

Shereen

I am. Yep. Well, not as much right now because of COVID. Oh yeah. And I just find it weird that people sit in the front row and then laugh without their masks on and all that spit is coming out. Like, I mean, my spit is coming on you, but you paid to see my spit. I don't want your spit coming on me. So I've taken a little break from live performances. I love Zoom performing. Like it's so nice. You don't have to get dressed up. It's so casual. Half the show takes place in the chat. Like everybody—like people won't laugh out loud. They'll go in the chat box and LOL. And like, they'll have a whole conversation in the chat. And so it's like, you feel like you're at a coffee house doing comedy with your friends, you know? I don't know. I like it. And you get the same amount of money. So it's like, why have I been getting dressed and coming out to your shows when I could do it at home?

Clinton

Yeah. Like that's, I didn't even know that was a thing. That's kind of cool. So you don't get the instant, like, you don't get that audible. Yeah. But, um, so it's gotta be an adjustment, right?

Shereen

In the beginning it was a real adjustment, but now I'm like. I got it. I just know, keep, watch the chat box, find a few people to pay attention to and go on your way.

Clinton

That's cool. That’s cool. The thing, um, so I do love comedy a lot. I love to laugh. I would imagine most people do.

Shereen

You'd be surprised. There's some angry people in the world.

Clinton

Yeah. Yeah. So, um, but one thing I, I, I'm always afraid of and I don't do it very often, but it's when you go to an improv place, and you're sitting in the front or not, some of them, like come out into the audience, and then they pick on you, you know. So, unlike you, I don't like the attention.

Shereen

I don't like that kind of attention. That's just, they're just doing that because they don't have anything else to say or do.

Clinton

Oh, okay.

Shereen

So I'll only pick on you if you're interrupting my show or if you sit at the whole show like this, yeah. Like, I'll be like, what's your problem? Like, hello.

Clinton

Yeah. So, uh, another little comedy story…back to my sister. Um, we should add her here. She's in Los Angeles. We could have brought her in on the zoom.

Shereen

Oh, that'd be awesome.

Clinton

Um, but she, uh, she got to work as an editor on the Last Comic Standing. Do you remember that show?

Shereen

I do. That was a dream. Great show. Always my dream.

Clinton

I mean, what a great show. I'm surprised it's not still going right. I mean—

Shereen

I don't know. There must've been some financial….

Clinton

Maybe, maybe, maybe it just doesn't get the ratings, right?

Shereen

Maybe. Well, then they started, um, America's Got Talent. So I think they kind of, yeah—combined it.

Clinton

So maybe they uh, combined it because comedy as a single genre is not enough for people with short attention spans in the US. I don't know.

Shereen

There must be something cause it's huge in India. India does a lot of America or this Last Comic Standing stuff.

Clinton

Oh really? Yeah. I loved it. I thought it was great. And of course, you know, not all of them I felt were funny. Right. And then there were others that I thought were hilarious, and then of course you're rooting for the ones you like. And I thought it was a great show, and we got to go to the finale in Vegas.

Shereen

Oh nice!

Clinton

Yeah. So I was on TV for like two seconds, like as a camera panned through the audience.

Shereen

I wish I had been there with you. Then I could at least put Last Comic Standing on my face! Nobody knows whether it was on the show or not.

Clinton

Yeah. Yeah. So, um I think it was a woman that year that won, she was a little blonde woman, like, like petite. And I just can't remember her name. My sister would remember cause she edited all those episodes, but there were some funny people in there, and some of those comics have gone on to…oh, you know.

Shereen

That opens doors for you. If you get a late night show or like something like that…oh, like you're, you're ready to go. Then you don't even have to call people to get booked. They'll call you. Yeah. Like that's like the comedian's dream. I just want to do a late night show and then retire. Like that's my dream.

Clinton

That'd be fun to do a late night show. And, um, you know, who I think is really funny?

Shereen

Who?

Clinton

Is—even though I'd never stay up that late, I go to bed at like nine—but is Jimmy Fallon. So I don't get to watch a lot of YouTube. I don't get to watch a lot of anything because my life is so busy. But when I do somehow—I don't know if it's my, if it's a Tik Tok or if it's in my reels on Facebook or whatever it is—but once in a while, the Jimmy Fallon thing will come on. And if it's, if it's in my reel, it's usually really funny. Or if it's being put in front of me, it's because millions of people already thought it was funny. Right. So, uh, so I enjoy that. I think he's, he's hilarious. He's hilarious. So you should be on his show.

Shereen

If you can make it happen, make it happen. I'd be on his show or Trevor Noah's show.

Clinton

Oh yeah. He is hilarious. So I remember him from when he was like with John Stewart. Yeah. Yeah. He was great. I like John Stewart as well. So, um, or at least I used to back in the day when I used to watch him, but, um,

Shereen

Yeah, it's a little late for me to watch him too, but yeah, I love Trevor Noah. I would love to be like a correspondent on his show. Yeah.

Clinton

That'd be fun. That'd be fun. So, um, I forget who it was. I don't remember her name. I think Trevor did some of this too, maybe. And, and so did, um, the other guy who has a late night show now, um, the glasses, uh, yeah….

Shereen

Stephen Colbert?

Clinton

Yes, Colbert. But when they do that thing where they're interviewing somebody really important and make them really look dumb, cause it was like the shoulder…. And I've always wondered if it's real or if it's editing, right? So where they're asking the guy questions, I remember there was this one about, uh, gun law and, uh, it was like the head of the NRA or something. [He] was being interviewed by one of those comedians. And, um, see, here we are talking politics. This is bad. But what was funny about it—at least I thought it was funny—is, um, they were backing him into a corner with their questioning about, you know, eliminating guns from the US he's like, ‘well, that would never work.’ And they're like, ‘well, you know, in Australia, they did that.’ And then he was basically saying, ‘no, that's impossible. They didn't do that. It didn't work.’ And then they're like, ‘no, but really it did.’ So, this is the thing where they made him look dumb, but I'm like, is he really? See if anybody…I'm going to get some enemies from this, but did he really say those things or was it edited?

Shereen

No, he probably did really say those things because those shows are taped live. Yeah. They're live taping. So you can't really edit stuff like that. Otherwise everybody in the audience would say something.

Clinton

Yeah.

Shereen

Oh yeah. He definitely said something.

Clinton

Well, I think they were like in a room. I think it was done like…it was more like a…anyway, I don't know. You have to look that one up. It would have been whatever that show was called the Stephen Colbert or it was John Stewart. Okay. Cause it was a long time ago. And it was quite funny how they had a habit of doing that, like just making people not sound….

Shereen

I can imagine that happens because people do that to me at work all the time.

Clinton

People do that to me here.

Shereen

And I'm like, Oh, okay.

Clinton

So, um, so you're still doing comedy, uh, but so you're doing mostly Zoom stuff right now.

Shereen

I do have a show. Well, I don't know when this airs, but I do have a show tomorrow or tonight. No tomorrow. I was like, wait, is it tonight?

Clinton

Is it after your doctor's appointment?

Shereen

Huh?

Clinton

After your doctor's appointment. So, uh, where, um,

Shereen

At the Bloodhound brewery, it's on Kirkman road out by Universal Studios.

Clinton

Okay. And are you usually doing comedy out that way? So, I don't even know—I'm out of touch with comedy in Orlando because I don't get out much. Uh, but there used to be the SAK comedy club.

Shereen

There's the SAK comedy club. It's still here.

Clinton

So where do you go for comedy in Orlando now?

Shereen

Oh, there's a lot of places. A lot of them are like bars and stuff or hotels, but like the main places that improv are over in Pointe Orlando on IDrive. And then there's just, there's places everywhere. Literally like restaurants are always having comedy bars…are always having comedy. Just, I would just Google your area. I can't tell you, cause I don't want to say this place and then tomorrow is closed.

Clinton

Oh yeah. Of course. Yeah.

Shereen

Plus they’re not paying me to promote them.

Clinton

But my wife and I actually said that we want to do stuff where you laugh more cause it's just good for you. Right. And like I said, I love it. So we'll have to, we'll have to search it out. I think you sort of say these things and then you forget, you know, but there's so many things to do. Yeah. Yeah.

Shereen

And it's, it's risky right now where to go. And well, yeah.

Clinton

And then for two years we haven't done anything. So, uh, we've really hunkered down a lot, partly because we had a nine-year-old that couldn't get vaccinated until a few months back. So we've just been, uh, super careful, but I'm hopeful now with numbers going down—that we can go and do stuff. I think my wife just ate indoors for the first time last night with her girlfriends because the place they were going didn't have any outdoor seating, and there was a group of them. So she made the call and then did it. So, um, in my line of work, I have to entertain quite a bit, so I've had to do it. Um, but you know, when I have the option, I choose a place, you know, except in the summer.

Thank you for listening to the Sound Connections podcast. We'll hear more from Shereen in our next episode. When Clinton talks with her about her podcast, her upcoming Ted Talk and her unwavering love of chicken wings. If you've liked what you've heard, please rate and review us on ApplePodcast. You can also leave a rating now on Spotify as well. You can also follow Mainline Marketing on Facebook, Twitter, Instagram, and LinkedIn. And you can watch the video version of this podcast on our YouTube channel.