From Broke Comedian to Viral Disruptor: The Florida Man Story

You're either gonna make it or be the funniest homeless person. He learned comedy not from performing, but by filling three notebooks with jokes no one ever heard. It was just like a real bad, like, year, where I was just, like, alone. I didn't know anyone. I pretty much, like, put myself in a spot where I had no other option but to, like, figure it out. The only thing that keeps you going is like some notes. Yeah. You know, in your pocket. Exactly. Like that's it. Welcome back to the Bill Pod where authenticity trumps authority. Today's guest is unapologetically just himself. In fact, he's unapologetic about going viral. So today's guest is Mr. Sean Madden. Welcome. Woo! Thank you for having me. Thank you for having me. Well, thank you for coming. I really just have to talk about our relationship. Well, I guess we have a new relationship and how we met. I feel like it's kind of like a love story. Yeah, I feel like you met the alter ego first. Yeah, I feel like I did. So I got to tell you guys how I met Sean. So I do, I don't know if you guys know this, I do a Zoom call three days a week. And this is where I get to hire people that are interested in selling health insurance. Well, little did I know that my husband went and contacted Sean behind my back and Sean showed up on my call as the Florida man. Never thought twice about it, which was even stranger because he's on the call. He has a hat with long hair. And at the end of the call, I do a Q&A where I just kind of let an open forum where people can ask me questions if I didn't answer anything along the way. So Sean is on there, but not as Sean, but as Don, right? Don? Don Drexler. Don Drexler. And the first question he asked me, this is how, because I always say, you know, hey, does anybody have any questions? First thing he asked me is, does he need to get drug tested? And that's kind of how our relationship started. Now, little did I know at the end, he was on there to prank me. I didn't know this. And my husband was looking for some good content, but he definitely did a great job. He is hilarious. So it is a pleasure to have you. Thanks for having me. It was so funny to see the message, especially when he was like, oh, it's my wife. And I'm like, you're really going to do this? But yeah, it was so fun. And I love when it's a group interview. Yeah. Because then you can just see. I haven't even watched it back completely. But it's so funny to see everybody's reactions. We've watched it. It's very funny. It's hilarious. I think you got me eight applicants from that. Really? Yeah. Really. It does actually. I've had people message me saying like, thank you for bombing the interview because it made me look that much better. Oh, that's great. Especially when it's like the interviewer and then just one other candidate versus Florida man. Yeah. They're going to get that job. That's hilarious. Most of the time. Well, let's talk about, okay, so we'll, we'll come back to this whole story. So what I'm really interested in, because that's, I mean, it's a very unique job venture that you're on or career venture. So you do comedy. Yes. to do comedy that's like your big thing is stand up now let's how did you start bombing online interviews that's that's like a very um it's very niche during 2020 i moved back to florida i was in la at the time and that whole city you know was shut down moved back to florida i didn't know what was going on i was like is stand up even going to be a thing anymore um you know all the money was kind of tight I was like maybe I'll just get you know a remote job so I could keep like maneuvering around the country and figure out where I can go get shows or you know set up the podcast again and I started doing all these these zoom interviews for remote work and there's like 20 30 40 people in some of these and a lot of them were like we're only hiring one person at the time and so usually I'm pretty good at getting jobs but I was doing not even kidding like 10 zoom interviews a day and just not hearing anything back not even like a second round and i'm like are these even like real things or are they just you know how some companies they have to like hot say we're hiring yeah just to like hit a quota or some kind of like government thing like oh we're hiring we're interviewing this amount of people on the books and i'm like well if you're not gonna hire me let's see if you hire florida man and once i started doing the character on zoom interviews then i started getting calls back and i was like you guys like this guy more than more than me he's out he's out of control wearing sunglasses and everything so the first video i did you know i felt weird doing it but i was i was like angry at the time so i was like doing it out of spite yeah um and just for the love of it because it wasn't like no one was paying me to do them or anything right and uh the first one got like a million views on Facebook and I was like oh there's something here because people love the raw reactions you know like the live the live interaction that's why crowd work now so popular people just want to see like a spectacle they do they wouldn't even get off my zoom call they were just sitting on there waiting for you to say something crazy which was insane they just started like they were sitting on there I probably was on there 15 minutes and I'm like all right guys any other questions and nobody was raising their hand they were just sitting there waiting for you to do something insane oh i can't wait to finish that video it was it was so fun and it's it is true like i can't imagine how many people you see like we're talking about it now this will probably be out when that interview drops so everybody go check that out but just to see people's reaction the one guy with the fur coat that was hilarious the mink and the the giant watch it's so funny people that interview in their cars i've done an interview in bed I saw you on your page. And they still acted like it was fine. I did an interview in a pool. Like I was swimming with the laptop like at the edge. And they're like, wow, nice pool. Like they just doesn't even like phase them. That's so funny. Now, did you always kind of know that you wanted to go and be a comic or do something like to make people laugh? Not really. I started out in music. Like it was like sports and then music. And then, you know, I went into sales. Yeah. and I was doing a sales job and uh I was living in California at the time and I remember like Thanksgiving Christmas and my birthday I just I didn't come back to Florida to see family I just couldn't afford it at the time and um it was just like a real bad like year where I was just like alone I didn't know anyone out there in like Silicon Valley and it was just like a I had like a dark time and I just watched like every single comedy special I could YouTube I was listening to like how to do stand how to get into it Basically studied like the entire game for like that year I was writing like horrible jokes. I got filled up like three notebooks, which is garbage. So I feel like I got a lot of the bombing out of the way. Most people bomb like their first few years. I feel like I got all the bombing out on paper. And then I saw a couple comics that were like doing really big. and I was like, man, my friends are funnier than these people. Like I could do this. And I don't know if it was like stupidity or just like going for it. But I moved back to Florida for like six months. That's what I was saying. I actually have been in this building before because when I moved back, I got a job in this building and it was a nightmare. It was like selling makeup business to business. Like you walk into Target and like try and sell the employees makeup and they're like, we have it here. Oh, no. Like a disaster company. That does not sound good. Yeah. I lasted like two weeks before I'm like, what is this? And then, uh, then I just moved to New York. I had $400 and, uh, and an old Saturn. And I just drove through Manhattan and like had no idea what I was doing. Got a hotel for two weeks, um, through this company that was like, oh, we'll pay you to like relocate. And I just figured it out. But I was like, you're either going to be like, you're either going to make it or be the funniest homeless person in New York. That is so funny. So did you do stand-up in New York? Yeah, that's where I started. You know, I lived there for like two months before I got on stage. I was just like scared. And then my roommate was like, well, why'd you move here then if you're not going to go, go and actually do it? So I started hitting one mic a day. And then I was like, oh, you can do two mics a day. And then I was like, oh, you can do eight a day. So I started doing like eight to ten open mics a day. Some started at noon and then some ended at like 2, 3 a.m. But I just became like the day-to-day. started bartending three days a week and that kind of floated the whole operation um and then you just get your get your chops as they say um get the reps in get comfortable on stage and then i got an opportunity in la so i moved out there and um was doing kind of the same thing you know started getting more started like winning competitions getting passed at certain clubs meeting the right people and then that all just came to a screeching halt in 2020 yeah and then that's when i moved back started the florida man character just because everything was digital and then um met a few good people met met jari um cam like guys like david jolly and now florida's winning everybody's everybody's doing their thing so yeah there's some funny people here it's awesome miguel yeah miguel yeah shout out miguel colone don't be mad at me miguel don't be mad um well that so does it come from a place i always want to know like when you go into comedy are you like there for the people because you genuinely want to make people laugh or does it come from like a dark i know you were talking a little bit about a dark place inside so which is it a combination of the two or originally it was how i was feeling i was like how stand-up got me out of like my situation and how like i just couldn't get enough of it i was like i need to watch another special another clip another monologue and it just kind of made me feel like it just gets you through the day like that laugh and i go i want to be the person that provides that for somebody else and um that was kind of like the like the foundation of it and then you know like after three years four years it does get to a point where it's like you're like oh i gotta get rid of my day job i gotta like so it becomes like a selfish thing of like the louder the audience is the more opportunities i'll get so it becomes like this like formula of like how could i draw the laughter out as much laughter as i can but within the last few years i've went back to like let's give the people a show like a lot of people there i keep in mind they're leaving their house that's huge in itself they're finding parking they're buying tickets they're buying drinks some are getting babysitters so if i don't give them a good show why would they come back to see you yeah why would you know what i mean so i keep in like before i go on i always kind of like replay that in my head like these people are here to have a good time give them a show like love on the people yeah you got to love on the people because that's what you're doing it for anyway yeah you know so you must have a real love for people too individually yeah as a whole um no yeah i mean you gotta i want people to have a good time you know i feel like that's why you get into stand-up too because i don't know like i had issues with like family growing up and i always felt like a burden like getting kicked out of the house um i like a horrible stepmom and um it's this point of like oh my am i a burden like am I overstaying my welcome but with stand-up it's like I know if the whole room's laughing I'm in the right place now when you do your stand-up do you talk about your childhood at all and like make light of it or that's something that you just kind of keep off limits it's getting to the point where I feel comfortable starting to like talk about like real you know like the origin story of everything right um but right now it's just like fun like funny stories like things that have happened um i try and stay away from like topical stuff yeah try to keep it original because nowadays it's like how fast the internet is if something happens everybody's on it yeah like maduro gets arrested everyone's like oh did you see the nike tech suit like every every comic is already they're like piranhas just going to the next thing but if you keep it original and and you know stay true to yourself no one can take that so let me ask you a question i'm sure you definitely had some like negative feedback or like where you walked on stage and it was like you bombed it how did you oh yeah how did you overcome that and like why did you want to go back i don't know if i could handle that so my first let my first open mic went well so that kind of was like encouraging right um my first show three months after my first mic went well so i feel like if I bombed that I would have kind of had a what am I doing moment yeah but my first like bomb bomb wasn't until like two years in so I was already kind of too deep in the game plus I already moved to New York so I had nowhere else to go yeah so I and I and I started stand up in New York like the first time I ever went on stage was in New York City so I pretty much like put myself in a spot where I had no other option but to like figure it out. Right. So that definitely helps. I read a book I think it was The Art of War The War of Art And it was like Death Valley Like a lot of generals will put they put their men in a canyon to where they couldn retreat Yeah, I mean, I already kind of trapped myself in New York City. So there was no giving up or quitting. And then I read a book like The Art of War and how generals will put their men like in a situation where they can't retreat. like they'll have their back against like a canyon or a mountain and so they like actually fight twice as hard to like win the battle as corny as it sounds not comparing that to true to war but i'm like i i like did that to myself without knowing just by like moving to a city with no connections i feel like you have to fail though you can't oh for sure you cannot just succeed you have to fail a little bit it's the only way to get good yeah so yeah some of the worst bombs i mean i probably had three real memorable ones where like sometimes you're in the shower and you just think about it you know those shower thoughts yes where you're just like ah you try to burn yourself to forget about it but it was uh yeah i did this competition it was like new york's funniest and i made it all the way to the top 10 and then just had the worst set of my life and that was it you bombed it just the worst set i'm talking like 300 people just blinking at you just nothing no reaction just nothing there was one black family in the back that were just really enjoying my demise and like at the time i was like yeah i'm killing for them but then i realized like no they were just having such a good time watching it just be like that's horrible have you ever said anything on stage that was like controversial that could have ultimately turns like or maybe all the time all the time you're gonna have that there's always one i mean even if like you get off stage and you think oh my gosh every like everybody loves the show there's always one person that gets a fun now do you pick on people i think that's kind of funny i try and just funny i try and just do my act um my goal to me ultimately is like theaters so if I could just do theaters you can't really see the crowd oh yeah um but I've done theaters before and I just love that I just love that feel that's like true stand-up like it's just your act and it's based off that and nothing more but last night um down in Vero I did a lot of crowd work just because the room was hot and it was this drunk lady and she was like leaning against the wall not even in her seat and we were just all messing with her and the crowd loves it but yeah Sometimes you got to go into the crowd and have a good time, but I don't, I don't force it. I'm not like, what do you guys do for a living? Yeah. You know, it's not, that's not my style. If it happens, it happens. If not, we got the material. Now you have like the same act all the time where you just, or is there like, like your go-to or how does that work? Yeah. So I have like staple material, I guess I would say like stuff I've had for a couple of years that's like evolved. But it's constantly changing, you know, especially cause you get bored of it. Yeah. like you're up there doing i don't know how musicians do a world tour and do the same 10 songs right over and over but you got to do what works and you just got to switch it up like sometimes i'll try to mess the order like switch the order and then if it doesn't go well you're like just stick to what what it is but it becomes like sales because you know it word for word yeah you could do it you could say it as fast but the art is people seeing it as if you're saying it Off the top of your head. So you can't sound robotic. It's just got to be natural. Sometimes the joke will come out different because it's just, you're not word for word with it. As soon as you're scripted, you die a slow death. And I feel like the audience can tell when it is. You can die. The funniest, I think, is when you're off the cuff. And you're finding things in the crowd. Or you're just kind of, you're feeling out the vibe. And when you can feel the vibe, that makes it seem like a little bit more authentic and it's funny. Yep. That I think is the funniest. Yeah. The off the cuff. Cause they can tell right away. And I started incorporating the crowd into the material. So like, I already know it's like a sales pitch. Like I already know where this is going, but I'm going to ask you a question just to like, invite you into the material. And I feel like that, that takes years to even realize that you're doing that. That's a skill. You can do sales. That is definitely like you, you're kind of narrating the whole thing. You can see it before it happens. Yeah. That definitely correlates well with sales. Yeah. If you can just bring the audience in. And that's why I like working with Miguel because he does, I don't know how many years he has on me as far as like stand up. Miguel is hilarious. Yeah. He murders rooms, but he's got like, I don't know, seven to 10 years on me like in comedic age. And so like I'll watch him and I try to just, you try and pick up on the details. how does that like coincide you know we all have good days and bad days so if you're going through something how are you able to get on that stage i think that's the only thing that helps is like you have to get on stage like i've had friends where you know someone in their immediate family dies and that night they have a show but you're not thinking about that when you're on stage yeah so it's like therapeutic in a way like time doesn't exist when you're when you're on stage until you get the light and you're like, oh, I've been up here a half hour or whatever. Would you say it's more of like a compartmentalized, like that's how you do it? You kind of just put it to the side. You perform and then deal with it later. Yeah, you have really no choice. It's like calling out of work. You can't. Well, you have to perform. I mean, it's the same thing here. The show must go on. Yeah, I mean, it's the same thing when we walk in here. We tell all the agents, here's the deal. When you're here at work, you have to compartmentalize. It's a hard thing, but you're here to work and everything else kind of has to stay over there because it's all about your mental state. I feel like if you're, I feel like kind of correlates, you know, 80% of sales is mind frame. And if you're not, you know, if you're not in the game, you're not going to perform. So I feel like now that what you're saying, I feel like comedy is kind of the same thing. Yeah. And it's easy too when it's all you have. There's some points where you're like, everything in your life is just hell. Yeah. But you're like, at least I have 10 minutes of good material. And that's the only thing that keeps you going is like some notes yeah you know in your pocket keeps you going like that's it now where does this like whole florida man i know you said like you were getting frustrated but was this like your alter ego who you always kind of were you like a timid i feel like i don't know i could be wrong were you kind of like a timid shy kid and then you always had kind of an alter ego or how did like how did this whole character come come about i have a friend who called me and he was like he like I think Sean Madden is the character and you actually Florida man But no I don know if I was like a timid shy kid I definitely could be quiet at times around like certain people But yeah, stand up will definitely make you into a completely different person. Right. I think sales definitely helped. But as far as the Florida man character, that was just some stupid I ordered online. Like the wig and the hat. just out of boredom and I was in LA so it wasn't it wasn't weird like that's the other thing too is everyone's trying to always avoid this cringe but it's like you're going to be cringed to someone you know especially yourself so I want to I want to touch on that for one second I think a lot of people are always scared of what other people think about them it's huge right I think that's a big thing I mean even me I always say I'm like unapologetically me but there are even with doing social media there's like things that i just won't do because i feel like it's like kind of cringy so how do you overcome just being like all right you know fuck it this is who i am you can take it or leave it having nothing to lose definitely gets rid of that um but secondly just understanding like people are going to hate you regardless yeah like regardless so you might as well do what you want to do anyway and then the fact that you have such limited time in this reality yeah that also helps like like i don't want to be the old guy that's like oh i could have done this yeah so that always helps like and then just trying different stuff like you can really just be anything you want right like anything and no one cares yeah in 14 days like look at the news cycle every four it's probably less now it used to be 14 days people forget about they don't care i would say after i honestly always say 24 hours nobody really cares yeah If they could, they could blast you all over the news right now and be like, this is the worst, most terrible person ever in four days. Nobody cares. You're back at Publix buying, you know. Yeah. I try to convey this message to my daughter too. Like, even though I struggle with it, the reality is, is that you're not that important that people are going to be fixated on you forever. So like you can bomb or do something stupid. And I guaranteed, I always say 24 hours, nobody cares. Or I'm like, nobody knows. That's my biggest thing. I'm like, nobody knows and nobody cares. Nobody knows. They really don't. They've moved on to the next. And the thing that you're insecure about, like let's just say like someone's like, oh, I have a big nose. It's like no one even noticed that until they realized you said it. Or I mean, there's so many examples. Like, look, I'm walking around in Python boots right now. This isn't even, I would never have bought these until this year. I'm just like, just try different stuff. I love that. I really love your message, especially the unapologetically you and you're okay. But I think that comes from, like that's a that takes a lot it took me a long time to finally say this is who i am i may not be your cup of tea but take it or leave it like you know whatever this is who i am that's okay it takes years i feel like and you can still battle with it like to be honest i don't even like when there's one camera on me and there's three right now so like i'm trying to forget yeah that they're there but that's just you know that's just like an example and hopefully like the stuff that I say or go through can ultimately help somebody else. Because once you break through that barrier of not caring what people think about you, you almost beat yourself up because you're like, Oh my God, I probably could have done so much more if I got out of my own way. Yeah. Like years ago. It's so true. And we get so hung up. I think just because of society in general, they put these like social norms, but the reality is we're living in 2026. And I think anything kind of goes in your Python boots. They go with your belt. No, I love it. I think first of all, it's like really well put together. You look good with the belt and the shoes. But, you know, so many people are afraid to just be who they are because they're so worried about what everybody else is thinking. And the reality is nobody really gives a shit. No one cares. No one is even focused on you. They're so focused on themselves. So it's like, well, you're worried about what other people think. They're sitting right next to you going like, well, I hope he doesn't notice my giant forehead. Like, you know what I mean? Yeah, nobody really cares. Everyone's on their own. I know. My girlfriend was asking me the other day. She's like, do you think I need Botox? She's like, my nose is big and they have like this liquid Botox or liquid filler that makes it smaller. I'm like, I never even noticed until you said that. Yeah. Like, what are we talking about here? I know. What's going on? So what would you say to somebody that is kind of struggling right now with, you know, wanting to pursue their creative career and just, you know, just kind of stuck in that rut? What would you say? What advice would you give? Like, what do you have to lose ultimately? Yeah. What, like, ultimately, what do you have to lose? It's true. That's really what it comes down to. And then how bad do you want to do it? Like if you're letting that hold you back, you don't really want to do it. Yeah. It's so true. It's absolutely true. And then if anybody wants to find you, where would they find you? It's at I'm Sean Madden. I am S E A N M A D D E N on all platforms, YouTube, Instagram, all the full videos are on YouTube. And then I'm just clip up for, for Instagram. But yeah, it was go check it out. We're constantly evolving, trying new stuff. What's your next big move? What's the next big thing for you? So in February, February 21st, we have the Florida Man Games. It's like the Redneck Olympics. I love that. I got invited to the one last year in March. This year, I'm actually competing. So come say what's up. We'll have the booth out there. Miguel actually did. He hosted the last year's. At the Sausage Castle? No, at the... I love that place. it's a wild time out there i just call it the castle now because as soon as you say sausage people get i might or might not have been there yeah yeah it's a good time i might or might not have shown up there once and then uh and then germany in march which is exciting because i've never been overseas for for shows that's incredible and that's where you really want to go is overseas take your show overseas i would love to just go i mean if this can take me all over the world why not let's do it i love your attitude i mean for those of you that are listening today's episode i think it's very clear to see that sean has an unapologetic attitude and he's just living life to his fullest and today's challenge is to really think about that one thing that you want to do and just do it nobody cares just take the plunge and do it i mean if you want to wear gator shoes or snake skin shoes wear them it doesn't matter anything that you want to do you can do and stop worrying about what other people think about you. That's my challenge to you. And of course, you guys know the deal. If you like today's material, go ahead and hit the like, subscribe, or even unsubscribe if you don't like it. It's okay. But until next time, thank you so much for coming on. It was a pleasure having you. Yeah, thank you for having me. I really appreciate it. Thank you.