BILFPOD - From Broke Comedian to Viral Disruptor: The Florida Man Story

Episode Date: February 26, 2026

Everyone talks about confidence.Very few talk about fear.In this episode of BILF Pod, Sean Madden opens up about the parts of comedy people don’t see:• Moving to NYC broke and unsure• Being hesitant to even start open mics• Hating when the camera is on him• Turning rejection into material• Why confidence isn’t ego — it’s repetition• Why everything changed when he stopped caring what people thoughtThis isn’t a highlight reel.It’s the in-between.The bartending shifts.The doubt before the mic.The internal battle between “What if I fail?” and “What if I don’t try?”Sean breaks down how cringe is temporary — but regret isn’t.How rejection sharpens you.And how freedom begins the moment you stop performing for approval.If you’ve ever hesitated to start…If you’ve ever been scared to look stupid…If you’ve ever felt stuck between comfort and growth…This conversation is for you.

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, you know, in your pocket. Like that's it.

Welcome back to the Bill Pod. We're 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.

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 like a very, it's like 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 cue. 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 Drexley. 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 me. 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. Well, let's talk about, okay, so we'll come back to this whole story. Okay. 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, you do comedy. Yeah, that's like your big thing. It's stand up. Now, how did you start bombing online interviews? That's like a very niche. During 2020, I moved back to Florida. I was in L.A. at the time.

And that whole city, you know, was shut down. Move back to Florida. I didn't know what was going on. I was like, is stand-up even going to be a thing anymore? 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 they just, you know how some companies they have to like say we're hiring 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 going to 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 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. And just for the love of it because it wasn't like no one was paying me to do them or anything. And 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 crowdwork now is 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 stood. 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 who just did something insane. Oh, I can't wait to finish. that video. 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 giant watch. It's so funny. People that interview in their cars. I've done an interview in bed. And they were- 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 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 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 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 dark time. And I just watched like every single comedy special I could YouTube. I was listening to like how to do stand up, how to get into it. but basically studied like the entire game for like that year.

I was writing like horrible jokes. Like I 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 of 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 I just moved to New York. I had $400 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 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's hilarious. So 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 did 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. And then you just get your. Get your chops, as they say. Get the reps in. Get comfortable on stage. And then I got an opportunity in L.A.

So I moved out there and 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 met a few good people, met Jari, Cam, like guys like David Jolly,

and Florida is winning. Everybody's, everybody's doing their thing. Yeah, there's some funny people here. So it's Miguel. Yeah, Miguel. Shout out Miguel, Colone. Don't be mad at me, Miguel, don't be mad. 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's 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 standup 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 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 got to get rid of my day job. I got to like. So it becomes like a selfish thing of like the louder the audiences, 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, they're, 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 the, 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. No, yeah. I mean, you got to, 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. I like a horrible stepmom and it's this point of like oh 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. But right now it's just like fun, like funny stories or like things that have happened. 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 like piranhas just going to the next thing. But if you keep it original and, you know, stay true to your stuff. 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 overcome that? And like why did you want to go back? I don't know if I could handle that. So my first open mic went well. So that kind of was like encouraging.

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. Ooh. 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 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't 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 them 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. It's true. To war. But I'm like 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. For sure. You have to fail a little bit. It's the only way to get good. Yeah. So yeah, some of the worst. I mean, I've 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 a, 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.

And nothing. No reaction. Just nothing. There was one black family in the back that were just really enjoying my demise. And 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 turned like, or maybe it did?

All the time. All the time. You're going to have that. There's always one. I mean, even if like you get offstage and you think. oh my gosh every like everybody loved 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 I try and just do my act um my goal to me ultimately is like theaters so if I can 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, 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,

Is there 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 years that's like evolved. But it's constantly changing, you know, especially because 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 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 it is. But it becomes like sales because you know it word for word. 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 tell. Like you, the funniest I think is when you're off the cuff. Yep. And you're like finding things in the crowd or, you know, 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, off the cuff, because 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. Yeah. 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, he does, I don't know how many years he has on me as far as like stand up. Miguel is hilarious. Yeah. He, 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. Yeah. A half hour or whatever. But 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.

Yeah. You know, 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.

we walk in here, we tell all the agents, you know, 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 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. 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 kind of an alter ego or how did like how did this whole character come come about i have a friend he called me and he was like he's like i think sean madden is the character and you're actually florida man but um no i don't know if i was like a timid shy kid i definitely could be quiet at times around like certain people um but yeah stand-up will definitely make make you into a into a completely different person right um i think sales definitely helped but as far as the Fordman 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 cringe 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. 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, 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. 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 a, you know. Yeah. I try to convey this message to my daughter, too, like, even though I struggle with it. The reality 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 out. Nobody cares. Or I'm like, nobody knows. That's my biggest thing. I'm like, nobody knows. 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 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 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. Even your Python boots. They go with your belt. No, I love it. I think it looks, 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. Yeah.

So it's like, while 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 true that's 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 um it's at i'm sean madden i am s ea n m-a-d-d-d-en on all platforms youtube Instagram. All the full videos are on YouTube and then I 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.

there at Miguel actually did. He hosted the last years. 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 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 as 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 you that are

listening to 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.