Jeff Williams sits down with comedian, producer, and podcasting educator Kimbrough for a lively conversation about building a career through humor, community, and persistence. Kimbrough traces his path from Midwest roots and early stand-up gigs to college tours, cruise-ship stages, podcasting, filmmaking, and the launch of Team Comedy USA. Along the way, he shares stories about recovering from jokes that fell flat, earning an audience’s trust, helping new podcasters find their voice, and staying consistent through the inevitable slow seasons. The episode closes with Kimbrough’s advice for creators and business owners: use the quiet stretches to sharpen your skills, because the momentum always comes back.
Jeff Williams the host of "The Construction Cowboy Show" sits down with comedian, producer, and podcasting educator Kimbrough for a lively conversation about building a career through humor, community, and persistence. Kimbrough owner of PodBrothers Nation Network and Team Comedy USA that traces his path from Midwest roots and early stand-up gigs to college tours, cruise-ship stages, podcasting, filmmaking, and the launch of Team Comedy USA.Along the way, he shares stories about recovering from jokes that fell flat, earning an audience’s trust, helping new podcasters find their voice, and staying consistent through the inevitable slow seasons. The episode closes with Kimbrough’s advice for creators and business owners: use the quiet stretches to sharpen your skills, because the momentum always comes back.
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Jeff Williams (00:00)
Good afternoon, folks. Welcome back to another dusty trail ride with the Construction Cowboy Show. Your host, Jeff Williams, and today's theme is building a business through creative comedy and connection. We have a very special entertaining guest today, Mr. Kimbrough, owner of Pod Brother Nation Network. He’s launched a new campaign called Team Comedy USA.
Which he'll share with us a little bit later here and just in short. so, let's kinda learn more about the man behind the microphone. so, Kimbrough, you've worn a lot of hats, comedian, entrepreneur, podcast engineer, writer, director, and producer. So, but first tell us a little bit about yourself, background, and what ties all of those roles together for you?
Kimbrough (00:45)
Well, I was born in Chicago and raised in Indiana. I went to Indiana University, went to high school in Indiana, and I started my comedy career in Chicago in the mid-eighties. So, I've been doing this for a while. I got a couple of decades in, and I really love it. What I have been told, and I am a true testament of this, is there's two most important days of your life. The first day is the day you were born.
The second day, well, actually three days. The first day is the day you were conceived. The second day is the day you were born. And the third day is the day that you discovered why you were put here on this planet in the first place. And I discovered that very early as a class clown in school, disrupting class, cracking jokes, cracking on each other, cracking on the relatives at the graduation shows.
I DJ'd in high school and I used to get on the mic and crack on people on the dance floor. And I discovered that I had a quick wit, I had a funny bone, I had a keen observation for comedic opportunities that I could then parlay into some quick quippy laugh. And when I got married, my wife said, you know, you should do this stand up because I think you're funnier than the guys on Evening at the Improv.
which was a brand new show that was launched on a brand-new cable service. Back in the day there was only networks. And then out of nowhere you could buy cable, and you could get the language you want. You could get comedy. You could get all the adult content. And we just really gravitated to evening at the improv and the standup comedy cause we just loved it. And so she signed me up for a stand-up open mic without my knowing. And I went in
And really did well. The owner was very surprised. That was my first day, first time doing stand up. And he said, you know what, you should come back. Let's see if you're consistently funny. And if you are, I'll put you in a lineup and I'll even pay you. So you don't get paid right out of the gate from doing stand-up. It takes years, but I think I was at the right place at the right time with the right club, right club owner, the right situation. I think all the planets lined up where I
I did really well right from the beginning and I was able to actually earn twenty-five bucks a show. and it his club had like eight shows a week. It was at the Rosemont Horizon at the Holiday Inn. Back then it was a Holiday Inn. I don't know what it is now. But that's the where I was birthed as a comedian. And from there I just worked my butt off as hard as I could to be as funny as I can.
And I found myself working any possible stage I could to get stage time and to get better. And then I started doing one nighters. I started doing some of my own shows. I got on the comedy caravan, which was brand new back then, which was owned by Yoder and his son now runs it. And I just took off. I was very aggressive in booking a lot of my own stuff.
And I found that this is where I was supposed to be and I'm now making money at it. And this was a beautiful thing. So I just dug in, met a headliner that worked on the colleges, and said, You could make some really good money if you could put together an hour show. Like back then I had about a half hour. So now I got a milestone ahead to build another half hour so that I could do an hour.
But I started reaching out to the college just in case, you know, because I figured it would take some time. They said, you know, if you reach out to the college, they'll book you for next semester. So I'm thinking, okay, I got a few months to build that 30 minutes in order to do a college show. And then right when I started looking into the college, I got booked. And I got booked that semester. And I was like, my God, I don't.
I don't really have a full hour. Like, what am I gonna do? So I'm really working hard. And I only have about 45 minutes at this point. The gig is like a week later. And I'm like, how am I gonna put 15 minutes? How am I gonna get 15 minutes of material in like a week? And I just worked and worked and worked. I wasn't able to do it. So I got to the gig with about 40 minutes of really strong stand-up. So
Back then there was a commercial out that was called Taste Great, Less Filling. Remember the Miller Light commercial? so I went out and back then, a you beer companies were actually promoting on colleges and they were promoting in sports and they were promoting at the frat parties and it was no big deal for a beer brand to be on campus, you know, hosting and sponsoring
college parties and football games and all these things. So
Jeff Williams (05:23)
So what year was that? Do you know do you remember?
Kimbrough (05:25)
this was eighty this was eighty five,
Jeff Williams (05:28)
Okay.
Kimbrough (05:29)
eighty six, and so it was it was back when it was the the wild, wild west of beer and comedy advertising and promotion on the on the college circuit. MTV was just launched and they did this whole T V spring break thing and the beer beer company sponsored that. So, you know, it was kind of a understood open, you know.
Deal. So I go on stage and I'm thinking, how am I going to kill 15 minutes? And where am I going to kill 15 minutes? Do I do my set and try to win them over? And then at the very end, try to improv with the audience, or do I improv in the beginning for 20 minutes and then go into my set and then end strong with some stand-up? And I remembered the headliner says, No matter what you do, open with the strong.
Open with the second strongest joke you have to get them to like you and close with the strongest joke that you have and nobody remembers anything in the middle. And if you want to do any like weak stuff or improv or or anything that is crowd work, do that at the very, very beginning after you get those first few laughs, and then you can get away with anything until you get to your material and then close
Jeff Williams (06:40)
B.
Kimbrough (06:40)
strong.
And that's what
Jeff Williams (06:41)
Wow.
Kimbrough (06:41)
I did. I remembered that commercial, Taste Great, Less Feeling. And I got on and I told my first two jokes. I got really good laughs. I'm like, okay, I think this is gonna work. And I divided the audience into Taste Great, Less Feeling, and I had them practice Taste Great, Less Feeling, Taste Great, Less Feeling. So when I point to you, you guys are gonna say, Taste Great, and you guys are gonna say, Less feeling. You guys got that? And so I did a couple of
samples and I had the whole audience go, Taste great. Let's feel it. Taste great. Let's feel and then
Jeff Williams (07:13)
Ha ha ha.
Kimbrough (07:14)
I'm looking at my watch and I'm going, Okay, I got another ten minutes to kill. And so I started saying, What's your major? Where are you from? you know, and I made some little jokes about their answers and I'm looking at my and and out of the blue I would just just raise my hand. They would be like, Taste great, less feeling. And then I ended that set with a really strong forty five minutes that I had worked on.
And that was the the beginning, the birth of my college tour and my college experience with my stand-up. I ended up doing colleges for eight years after that. And the colleges was really, really amazing, made a lot of money. Some of those shows were hell. The colleges, you don't know what you're gonna get sometimes. It could be the best show you've ever done, and it could be the worst show, and you wanna go slit your wrist in the bathroom.
And it's it the you don't you don't know what you're gonna
Jeff Williams (08:01)
Yeah.
Kimbrough (08:05)
get. But you sign up for it because the money is good. And if you were to hit a home run, it's a grand slam. Like these kids will love you forever and it's amazing. So I decided to go out to Vegas and Bud Freeman, who owned Evening at the Improv, launched the very first Las Vegas comedy convention. And I drove all the way out there from Chicago with a buddy of mine who
Was helping me promote my comedy. And I'm walking down the hall into the convention, and this woman stops me. She's like, Are you a comedian? I go, Yeah. She goes, Do you have clean material? I go, yeah. She goes, Are you funny? I go, yeah. She goes, Okay, I want to book you on a cruise. I go, You haven't even seen me yet. She's like, I I can tell that you you'll be fine. I go, Well, I got a tape here. You want to come and see it? She's like, No, you'll be fine.
So sight
Jeff Williams (08:49)
Yeah.
Kimbrough (08:50)
unseen, she booked me for cruise ships.
Jeff Williams (08:53)
Wow.
Kimbrough (08:54)
And I think she probably figured that she'd booked so many comedians for so many ships over so many years. Either they're gonna like you or they're not, but at least you get one week to find out to find that out. And so she was willing to take a chance.
And so I signed a contract with her to go out and do cruises. And I did cruises for five years. I was on five different cruise ships and or cruise lines and I did over thirty different ships, something like that. And I was able to travel the world, travel the Caribbean, down to Mexico and Canada, and it was really, really, really a lot of fun. I mean
When you work on a cruise ship, you're basically a celebrity because it's a floating country, a floating world. And like in the real world, everybody in the world knows celebrities. But on a cruise ship, it's a micro world, but everybody on the ship knows the comedians. So you can't escape anybody.
Jeff Williams (09:49)
Ha ha.
Kimbrough (09:49)
Everyone knows who you are. And that's kind
Jeff Williams (09:52)
Yeah.
Kimbrough (09:52)
of weird. That's kind of it's like it made me understood what celebrities felt like.
you know, when they don't want to be bothered or they're kinda mean to fans or, you know, they're kinda irritated with everybody just kinda, you know, trying to act like they're in a relationship with you just because they saw you on a movie or they saw you in T V. And it was it was a it was a humbling experience because I, you know, you have to understand that, you know, they see your show, they know who you are, they've seen your set, have
Most of your life and and your insecurities and your vulnerabilities are in your materials. So they feel they ha they feel like they're a friend or a relative on the inside of your world because you've exposed yourself via this comedy. And they walk up to you in a full-on relationship. So when you act like you don't know or you're mean to them or whatever, they're a a bit distraught, you know, they're upset with that. And that's why they can become rude.
So I recognize that being a fan and knowing that and then now I'm now a comedian and having people come up, I was a little bit more apathetic to like where they were coming from. So I was always nice to any fans that came up or anybody that came up and that appreciated me. And on the cruises, you have no escape either. On land, you can always there's a thousand escape exits, but on cruises, where are you going?
Jeff Williams (11:12)
Ha ha
Kimbrough (11:12)
They they
you can't go anywhere. You're gonna bump into them again at the buffet, you're gonna bump into again at dinner, you're gonna bump into it again on a tinder, you're gonna you know, you it's like you everybody's gonna see you and you're gonna bump into them again. So if you're not nice, if you're not kosher, then it can be pretty brutal. But also if
Jeff Williams (11:32)
Well what
Kimbrough (11:33)
if you don't do well, it's like you're a leper on board and you just basically go hide until the next group gets on.
following weekend.
Jeff Williams (11:40)
it's a great life lesson that you learned early on in your career that probably sets you up for a lot of good greats even greater success, in that experience. And so I wanna take you back just a little bit. I am from Indiana, I'm a Hoosier also, Midwest. I was born and raised in southern Indiana on the farm and ranch and all that kind of good stuff. But so we got a little bit of Midwest common ground from way back. But my question to you
Kimbrough (12:04)
Girl closures.
Jeff Williams (12:05)
kinda going yeah, going back to the Midwest is that your roots they had to shape your humor in a way that you do business as of today 'cause there's you know, there's foundational principles we have all grown up with with the Midwest versus East Coast or West Coast or whatever. And so you know, what happens that made you think, you know, I wanna do this forever, but having your Midwest roots
What do you take away from that growing up? And then you still carry that today. What is that?
Kimbrough (12:33)
That is a great
question. I feel very, very lucky to have been raised in the Midwest and get some of the foundation and some of the community experience with comes with the Midwest. Because in the Midwest, everything is about community, no matter what you're doing.
And everybody kind of kicks in to help everybody, no matter what your thing is. And I was able to leverage that when I was doing, you know, any events or comedy shows or parties or DJs. You know, there was such a community of people that would support everything that I do, which is another reason why I became very good very fast, because I could tell 10 people I'm doing a show tomorrow night, and a hundred people would show up. And
That kind of spoiled me because when I went to the East Coast, it that didn't exist. That did not exist. You literally had to earn your relationships and you had to earn your group. It wasn't like an automatic community support thing like I was experiencing in the Midwest. It was no, you know, I don't know who you are.
From Chicago, we're East Coast. You gotta show us you're funny. You gotta show us that you can get in where you fit in. You gotta show
Jeff Williams (13:52)
Yeah.
Kimbrough (13:53)
us and you yeah, and it's gotta be at our speed, not your speed. And
Jeff Williams (13:58)
Yeah, East Coast
is East Coast is always about, you know, they don't trust you, so you have to build trust. And that's hard to do. You're absolutely right. Spend some time
Kimbrough (14:04)
Yeah. Yeah.
Jeff Williams (14:06)
out there in the Massachusetts in that area and things. you're absolutely right, the Boston market. but one of the things that also to with that is that, you know, you and I grew up with that who's your hospitality, right? And so we're always hospitable as they say, hospitable and
friendly and we wave and we shake hands, we do all those things that are just humanly nature or natural for us as a Midwestern. Midwestern person and yet the rest of the country it's it's hard for them to grapple around that. Yeah. Go ahead.
Kimbrough (14:38)
Yeah. I
I call it the trust purse.
Jeff Williams (14:41)
Yeah, yeah.
Kimbrough (14:41)
The trust purse is okay, you have your coins and your bills and your trust purse. And in in the Midwest, in Indiana, all right, we'll give you like fifty percent of what's in that purse right off the bat and as trust. And then
Jeff Williams (14:56)
Yeah. Yeah.
Kimbrough (14:58)
and then you can either earn more.
what's in the bag, or you lose the fifty, you know, the fifty like if I got
Jeff Williams (15:04)
Yeah.
Kimbrough (15:05)
a hundred bucks in my trust purse and I give you fifty bucks right after I'm trust you. I don't know you. I'm Indiana. You're in the I don't know. I'm trust you with fifty bucks. So now you got fifty dollars worth of trust to build more trust on or to lose the trust you already have. But you start with something to entrust. On the East Coast, it's a penny.
But you can't start with zero. Because you have to give me something that I can be like, okay, I'm gonna take care of this. You can trust me with this. So it's a penny, and I know it's nothing that you know, you're okay with losing. So there's no weight on it. But the Midwest, we give you so much trust, there's a lot of personal and sometimes professional weight that comes with that. So the disadvantage of
Of that in Indiana is if you have too much personal investment or business investment in that initial insertion of trust and you lose it, they don't they're not worthy of it, then it's like, ooh, you know, it's just like I just gave that person. But because you're from the Midwest, if that's not going to prevent you from doing that again for somebody else.
Like, it's just baked in that no matter what happens, I'm just going to trust you with at least 50%
Jeff Williams (16:17)
Great analogy.
Kimbrough (16:19)
of my trust purse. But on the East Coast,
Jeff Williams (16:20)
Yep, great analogy.
Kimbrough (16:22)
on the East Coast, it's like, nah, nah, nah. Here's a penny. And if you know, if you lose that trust with me, then you'll never get another penny. And you can earn
Jeff Williams (16:30)
So go away.
Kimbrough (16:31)
your way over.
Time or over action. And sometimes since New York and the East Coast work so quick, you can build trust quickly because they work faster. And each thing that they do has so much weight. And you can instantly put money in their pocket. You can bring business to them. And you can bring and develop it quickly.
And you can work off of that. You could still lose it, but at least it an insertion from the trust purse can happen pretty quickly if you're the right person, if your head is straight, your heart is straight, you bring something to the table, you got talent, you got skill, they can see that if they were to collaborate with you, it's gonna be a win-win. You're gonna win something keep you from that that keeps you doing it, they're gonna win something.
you're both are building something that you're not gonna try to tear down and then it can happen very, very quickly on the East Coast. You can go from just getting off the plane, getting a penny, to in a very short time, you could be rolling large.
Jeff Williams (17:30)
Absolutely. I wanna transition a little bit back into Pod Brothers Nation Network and Team Comedy USA. And if you'll take a minute and drill into that and tell us a little bit more about your business and the foundational pieces to those, that and then, you know, then just wrap it into Team Comedy USA and a little bit more in detail what that might entail and how
somebody can get involved,
Kimbrough (17:54)
Yeah, yeah.
Jeff Williams (17:55)
you know. Yeah.
Kimbrough (17:56)
Yeah, sure, sure. I started my podcast in Cannes, actually, with a buddy of mine, filmmaker. We worked on the Twenty Four Hour Film Challenge together. We made a film in twenty-four hours and we ended up winning the People's Choice and our film was up on the screens and we were invited to a bunch of yacht parties and can parties and it was an amazing experience as a young comedian.
young podcaster. And this was back when it was just like a an iPod you could listen on and it was like audio and then YouTube just opened up out of nowhere. And so we started doing the podcast on the YouTube. This was like the mid 2000s. So like 2004, 2005, something like that. And I fell in love with it back then. I thought, man, this podcast thing is kind of cool and the YouTube
And people would make fun of me. It's like, you're doing a pot, what's a pod anyway? You know, it's like a little apple thing that you can get, you can play music on. They're like, What's that?
so fast forward to tape, I was kinda in and out of podcasting for the next few years and I didn't take it serious, and I'd jump in, I'd do something, and then I did take it serious, I'd jump in and do something. And then I got offered a job to be the 3D coordinator at the John Lupis Podcast Theater in 2010. And
This was back when 3D really took off. This was the first Avatar movie, and we thought the film world was gonna completely and totally transform into 3D films, and 2D films were gonna be left behind as like old time black and whites, but that's not what happened. But in that process, John Lovitz launched the John Lovitz Podcast Theater at Universal City Walk, and I was like, I do podcasting.
Like I can feather right in this. So John Lovitz was coined the podfather of podcasting. And so I did my first podcast show as the Kimbrough podcast. And I had a bunch of friends on, and it went very well. Packed audience, got a lot of laughs. I had a lot of great guests on. This drunk guy in the audience came up to me after the show and he was like, Hey man.
Your Pod Brothers show was awesome. And I'm like, did he take my name and like merge it with the podcast and came up with Pod Brother? And people looked at him, they looked at me, and they're like, dude, that's a great name for your podcast. Like Kim Bro, Kim Brother, and Podcast, Pod Brother, Pod Kim Brother. Like that's a perfect name. It's like you, you the Pod Brother.
And so he's like, Yeah, you're the pod brother. Can I buy the pod brother a drink? And I'm like,
Jeff Williams (20:37)
Ha ha ha
Kimbrough (20:40)
Hell yeah, you can buy the pod brother a drink. So then I became the pod brother at John Lovett's Podcast Theater 2010. And so
Jeff Williams (20:48)
That's cool.
Kimbrough (20:48)
I just as I started doing shows with my comedy and my podcast thing, I kind of fused it together and then people started bringing me on for my stand-up and my podcast as the pod brother.
And so as I built my Pod Brother Fans and my Pod Brother Nation, which by the way, Live Nation had just turned from FSFSFX concert promotion to Live Nation. And I'm like, okay, everybody's building a nation in entertainment. So then I thought, all right, Pod Brother's gonna have his own nation too. So that's where Pod Brother Nation was born. And then when I start looking into
Cause other comedians and other people come to me like, okay, you're the pod brother and you're Pod Brother Nation. Can you help me with my podcast? Can you tape my show? Cause I want to submit it to an agent, you know? So I turned into like this film comedian, podcast dude. And from taping guys and helping them with their podcasts and having them on my show for my podcast and being a stand-up comedian and the pod brother and having Pod Brother Nation.
And having this little network, somebody came up to me to be like, Man, you like CNN, except for you PNN. And I'm like,
Jeff Williams (22:02)
I like that.
Kimbrough (22:04)
it's like you peeing in. They're like, you should go and act like you're peeing on CNN on the building. I'm like, well, that's going too far. But but
Jeff Williams (22:12)
Yeah. Absolutely.
Kimbrough (22:14)
I said I said, that's funny, bro. PNN. it's like, yeah, I'm not CNN, I'm PNN.
And so
Jeff Williams (22:21)
I love it.
Kimbrough (22:21)
I was like, Yeah, that's cool. So I w I went ahead and got a a domain name for the podbrother dot com, for podbrother nation dot com. And since I was teaching and helping people with their podcasting and their stand up and their videotaping, then I launched PNN Academy where I could teach people stand up, I could teach people podcasting, I could teach people
Jeff Williams (22:42)
wow.
Kimbrough (22:42)
how to do film challenges since
I was doing film, I was producing the film challenge in Cannes since we won it. They asked me to come back and produce it. So I did that for five years. So being a person who produces and teaches film challenges and stand-up and podcasting, it made sense to me that okay, wait a minute. I'm in a comedy lane with these different mediums. I should create a coalition.
Where no matter what you do in any of these lanes, then there's a resource and there's a community for you to collaborate with. And that's where Team Comedy USA came in. Where how do I pull together these industries that I'm in? I'm working with a lot of podcasters, I'm working in with a lot of stand-up, I'm working producing films and doing film challenges. And now with all these online platforms, everybody wants to know.
Well, how do I get my stand-up on a platform? How do I get my film on a platform? How do I get my stand up my stand-up with my film challenge onto it? So it's like, okay, it made sense for me to get into distribution. And that's where Pin Flex comes from. Pod Brother Nation Flex, where you can flex your content on my Netflix style online distribution channel. So I became a coalition.
of stand-up podcast, film production, film festivals, and distribution, all focusing on comedy. And that is where I sit today. So with the Olympics coming in 2028, I it makes sense to me, the timing is perfect. I now have this perfect coalition of comedy resource that when the world comes here,
And they're looking to get access to a Hollywood comedy USA experience. I want to be the brand that comes up that they go to get that. And they get to learn it too. So if they want to learn how to do this stuff and then do a show on Hollywood and feel that Hollywood buzz of being a content creator in Hollywood, I can provide that for them. So that's where I'm, that's where I am, that's where I landed. That's my story. And I'm sticking to it, Jeff.
Jeff Williams (24:51)
Cool, very cool. So, I'm gonna go left on you just a little bit. what's the joke that fell flat and that you recovered? What was the funniest thing that ever happened to you? That the joke went out there, it fell flat, and then you turn around and try to recover it or whatever, and then do you remember that the first time
or one of the biggest times ever? Because usually those are funny
Kimbrough (25:09)
Yeah. Yeah. Yeah. I
Jeff Williams (25:14)
things after you think about it.
Kimbrough (25:15)
Yeah, I got a couple of those experiences. my first one is the first joke I ever wrote, the first joke I ever did, and that was at Rosemont Horizon at the comedy cottage where I described where I was. that joke still works today, believe it or not. There's some jokes that are topical.
and they only laugh the timeline of whatever the topic or the element is happening in the news cycle and then as soon as it's over, then that joke is over as well. So this joke was
Ladies and gentlemen, welcome. I'm really happy to be here. I want to share something very exciting to you. I'm in the Guinness Book of World Records. And then that usually generates an applause. And then I go, Yeah, I'm the first black man from Chicago with car insurance.
And that would get a real nice laugh. And so I did that joke for years as my opening joke, very first joke. And no matter what town I was in, it always worked. So ladies and gentlemen, I'm in the Guinness Book of World Records. I'm the first black man from Appleton, Wisconsin with car insurance. So they would laugh. You know, and then I'd be like, and I'm the only black person in Appleton, Wisconsin.
I would have these different tags that would I get another laugh on.
Okay. So yeah, that joke that I first wrote, I'm the first black man from Chicago with car insurance, would you know, would get a laugh, it would work in every city, in every country. I tried it in every country.
Jeff Williams (26:41)
Yeah.
Kimbrough (26:41)
I did it in Montreal, I did it in Winnipeg, Canada, and it got a roar. So it was one of those timeless jokes that worked.
everywhere and it was solid. And so I'm in East St. Louis. I mean
Jeff Williams (26:55)
Of all places. Dude. Okay.
Kimbrough (27:00)
I'm like I don't I'm literally out of a Chevy Chase vacation movie where his car gets jacked. He stops to ask for directions and before he can get direction his car is up on blocks and all the tires and
I'm working a comedy club across the street from that intersection. So I go in. I mean, it is deep in the hood. I mean, there's all kinds of shenanigans going on. And I'm just going wow, I feel like I'm in a movie. And I go in, and it's just pure, not even controlled chaos. It's just
Chaos. There's like a pool table going that they're not shutting down for the show. There's like a TV going with the game on. There's guys at the bar talking. You know, there's women cackling at the tables and stuff. And I'm just thinking, man, this is gonna be a nightmare. But you know, I'm getting paid. I'm a professional. I want and need the stage time. So I'm just gonna go ahead and go for it. And it's all black audience.
And I've done all black audiences everywhere, but in East St. Louis, this was a completely different, different group of black folks, different breed I do
Jeff Williams (28:06)
It's a different breed. I've been there a couple of times. Yeah. And
Kimbrough (28:08)
my general opening. like, yeah, ladies and gentlemen, really happy to be here. got some exciting news for you. I'm in the Guinness Book of World Records. I'm the first black man in East St. Louis with car insurance and crickets.
Jeff Williams (28:23)
Ha ha
Kimbrough (28:24)
You could
Jeff Williams (28:24)
ha.
Kimbrough (28:26)
you couldn't you could hear a pin drop. And I go, I go,
Jeff Williams (28:33)
that's funny. That is funny.
Kimbrough (28:36)
so I'm now I'm thinking like, man, how do I come back from this? And then and then, you know, of course, as a comedian, you always have to have a dead joke comeback. And I go, apparently I'm not the only one in the Guinness Book of World Records at East St Louis
Jeff Williams (28:51)
That's a great
Kimbrough (28:51)
I think we're all in the Guinness Book of World Records. I didn't get a I didn't get a peep on that one. And
Jeff Williams (28:52)
comeback. That's a classic.
Kimbrough (28:57)
nothing. Nothing again. Not a peep. Not a chuckle. Not a word. And then this one
brother in the front, he's like, hey, man, man, I don't think that's funny. And I go, really? I go, okay, time out on a comedy show for a second. Let me just rap with this brother. I'll get back to you guys in a minute. Continue your pool. You guys watch the enjoy the game.
I get to you guys at the bar. Like I'm acknowledging like all the white elephants in the room in this all black bar. So
Jeff Williams (29:26)
that's a great
that's a great recovery though, no matter what. Yeah. Professional.
Kimbrough (29:29)
Yeah. So I go, Hi, bro. I go, let me let
me ask you this. Can I ask you a couple questions? He's like, Yeah, man, what up what up? I go, Well, do you own a car? He's like, Yeah. I go, Do you have it registered? He's like, Yeah. And do you have a driver's license? He's like, Yeah. And do you have car insurance? He's like, Yeah. Then I go, Bro, that don't apply to you. And then the whole place starts.
Started cracking them.
Jeff Williams (29:56)
that's great.
Kimbrough (29:57)
And so I lost them twice in a in a very non-comedy conducive environment. But I got them back when I got really personal with the guy in the front row and then just basically kind of broke down why the joke is funny, but in a kind of a heckle comeback kind of way. And then I was able to get them back.
But I threw my whole set away and I just did the rest of the set just going into audience and just cracking jokes with people who came up with whatever scenario they came up and they came up with some crazy scenarios. And so that's one experience. The other experience was working on cruise ships. I scuba dive. So when I am on a cruiser, I would go out to all these scuba excursions and I
came up with like a 20-minute routine of, you know, a brother from New York. I lived in New York at the time, that could go out and scuba dive. So I did this routine where I'm scuba diving with the stingray and I go down to get a closer look, the stingray settles in the sand and all you could see is the eyes just looking up. And I'm like, I see you. I went closer. He got up, swim a little further, settle in the sand again, looking up just the eyes.
I'm like, I can still see it. Water crystal clear, sun's shining, it's beautiful. Coral reef. I went to get closer and I saw this big shadow that went over me. I look up, it was like a 10-foot shark. I was in the sand selling in with the stingray.
Nothing but the eyes from the snorkel. Stingray was like, here he is, right here, man. He's been following and messing with me all day. Why don't you come and take a bite out of his ass? He's been messing with me all day long. Just follow me. So
Jeff Williams (31:34)
So
Kimbrough (31:35)
I did that bit, and I had been out on the cruises for about three months. And in the three months I was gone, Steve Irwin had died from a stingray sting.
Jeff Williams (31:46)
Yeah,
remember that.
Kimbrough (31:47)
The barb like got him right in the heart and he died. I don't know this. I haven't been on land, on mainland for a couple months. I don't know who's the president. I don't know the s the scores of my teams. I don't know what's going on in the news. I have no clue who's dead, who's alive. The cruise ships make it a point to, you know, make sure you have no connection with the mainland so you can focus 100% on your vacation, and they do a
Great job at it. So this next group that comes on, so I did the joke and I got a a huge roar on that. That was always a killer scuba cruise clean joke that everybody loves. And it kills. That joke always kills. sometimes I even close with that joke, it does so well on the cruises. Then
Those passengers get off on those seven days. The next seven days starts a new set of passengers. They come on. I do that bit and it's crickets.
Jeff Williams (32:44)
Ha ha.
Kimbrough (32:45)
And I'm
like, I'm looking at a room of 2,000 people collectively on a joke that always it has never bombed from the day that I wrote it to the day that I did it. It has never crashed, ever. Even on dry land when I do it, I even get stronger laughs because it's just they can relate to me being on the cruises. Nothing. It was dead air, calm sea.
Not a blow, not a breeze, not I was and I'm in shock and I just looked at the audience and I go,
apparently you guys don't scuba dive, you know, trying to come up with like a crew and some lady
Jeff Williams (33:20)
Yeah, yeah. A quick one, yeah.
Kimbrough (33:22)
in in the audience goes, You're an asshole. Steve Irwin just died two days ago. And I'm like, How am I supposed to know? Like, this
Jeff Williams (33:31)
wow.
Kimbrough (33:31)
joke killed last week. I've been on the cruises for three months. How am I supposed to know Steve Irwin is dead when they completely
Jeff Williams (33:38)
Well
Kimbrough (33:38)
shut us off from the world about any news?
I don't even know what my family's doing right now. So how am I supposed to know what Steve Irwin's doing? You know, is he still alive? So I went on this rant of being isolated on the cruises and not knowing. And I slowly was able to get them back laughing by just making examples of things that I don't have access to, that you have access to. So I started coming up with a list of all the things on the ship.
that you won't get access to until you get back on land. And that turned into a comedy bit that got me to win the crowd back.
Jeff Williams (34:16)
Saved ya. Yeah.
Kimbrough (34:18)
And but bro, when you get it's one thing to get a little smattering of laughs. It's one thing to get, you know, kind of like some hums or some ahs. But when you get zero, I mean when you get nothing
And then out of nowhere, a single person gives you a heck of comeback that everybody is on their side. That's the worst feeling in the world. At the same time, it is an opportunity for you to understand what it feels like to be alive. Because your heart's pounding out of your chest, adrenaline is firing through your body.
Dopamine is being shot in your brain, and dorphins are being released, and you could not be more alive than you are in that very second of thinking that this is the worst thing than death is to have collectively 2,000 people staring at you in unison and silent unity. Like they didn't communicate to each other before the show and says, okay, when he does this joke, we're all collectively.
not gonna laugh. It's like it was automated no laughter, no pre-coordinated conspiracy. It was like it was organically a no, this is not funny. Which
makes you really excited when it's the reverse. When they all collectively, without conspiring or organizing or communicating, they laugh
Exactly at the same time collectively, that could not be a bigger hire. And you got just as many chemicals firing off in your body as you do when you eat it. Because you're just alive. You're in a moment interacting with total strange humans. And the best and the worst possible scenarios can all happen within seconds. One second they collectively love you and are laughing.
The next second they are they wouldn't piss on you if you were on fire. And it
Jeff Williams (36:19)
What?
Kimbrough (36:20)
the just position of that in real time is I think the biggest high that most comedians get out of this whole journey.
Jeff Williams (36:29)
Well that kind leads me into I mean that's actually it's a per perfect segue into this question. And it I'm because you're such an entertainer, an experienced entertainer, and you deal with the emotional content from the audience live for it be a video conference or video show or film or production or whatever it may be. But my question is and I mean this is to podcasting, is that most common mistakes you see new podcasters make, is it with their sound, is it with their interviews? Take me for example, right? I'm a I'm a new podcaster. But also is the approach to building the audience and so the question really becomes it's kind of a three part question, is it just technical challenges that new people have, or is it figuring out what content to do, or just, you know, what
What do you see the challenges in the new style of podcasting in today's world? Cause everybody's doing it now. Everybody's trying to get out there to get something. And with AI it's almost like is it real? Is it not real? And that's the other part of it.
Kimbrough (37:28)
That's a very good question. and obviously everybody has different takes on it. you know, an engineer podcaster is gonna have a different take than a podcast host, a podcast host is gonna have a different take than a podcast producer, a podcast producer is gonna have a different take than a stand-up comedian or a filmmaker. Like whatever discipline that you have, you bring to the table is what you're gonna relate to as going to be
your demons and your angels in attempting to do a podcast. But in my experience, wearing several of those hats and kind of being in and out of that game, the podcast game over a few decades, the biggest challenge that most people don't realize is the consistency of it. It's like just sticking with it and posting regularly and creating that consistency because it doesn't matter how cute you are or how funny or how clever or how good looking or strong or athletic, like whatever it is that you do in the podcast world, there's a market out there for you. If your podcast is a a about a blind cat watching grass grow.
And you post it every week consistently for five years straight. Like you are going to build a fan base, and that fan base is going to be loyal to you for life. As long as you feed the beast every week another episode, you're gonna have them. So they will they will work through your technical glitches and your technical deficiencies. They will work through
You're trying to find your voice. And they'll work with through you trying to find your look, your persona, your perspective. They'll work with you trying to find your set. You start off in the attic or in the basement and work your way into a studio or not. Like a lot of audiences, if they like you or they like what you're saying, or they're entertained by you, if you're consistent.
you can lock them in for life. And all the other stuff, that just comes with just doing it so much to where you eventually by default sort it all out. You know, you you'll sort out your lighting. If you keep doing it and you keep looking at it, it's like, man, the lighting could be better. And each week you tweak it and like the sound could be better.
Let me get a better microphone. Let me experiment with a mixer or my laptop isn't streaming fast enough. You know, I need a better laptop. Like my motto is start ugly, grow pretty, but just be consistent with it, and you'll be fine.
Jeff Williams (40:13)
Great information for our listeners. I so appreciate that. That's great as they say, great concrete foundational information and great value. So I'm gonna switch gears just a little bit more. I do that a little bit. And I know that we're almost into fifty minutes here and I know that you've got a busy schedule and everything else, but and I'm enjoying it. but so you've got any jokes for the cowboys of the world or any construction cowboy
or any kind of construction jokes that you may have, you know, you can share maybe one or two and if not, that's okay. But part of my show is all about construction and cowboys and I always try to put a plug in for that and a lot of times this is so much about education or information that helps business owners and construction folks that are you know trying to grow their business and in so many ways and I know that there's a lot of
construction companies trying to get into podcasting, but they just don't know quite how to get started with that. So kind of throw all those mixes at you. I know you're the professional in the industry and film and all that stuff. And you know, if you can't, that's okay. If you can, that'd be great too.
Kimbrough (41:17)
I do teach stand-up comedy workshop, and my motto is everything and everybody has three minutes of stand-up. It's whether you're a a person, no matter where you come from, what you look like, what your race, gender, sex, size, physical, you have three minutes. If you're a place, a state, a city, a country, you have three minutes. If you're an inanimate object,
a coffee cup, a light, a rug, you got three minutes. If a rug were to do three minutes of material, I would project on it a Rodney Dangerfield type of persona will, hey, I tell you, nobody gives me respect. They everybody walks on me. And I would do material about what a rug experience with people walking. And the life and time of a rug and what comedy routine
Would a rug come up with? So with construction workers and with cowboys, I would just take a look at like some of the things that you do that we could exaggerate to the ridiculous. So you being a cowboy and you know, like what are some of the things, what are some of the stereo types or stereo typical things that like a cowboy does? So if you give me like a couple things that you think is stereotypical that a cowboy would do, and I can formulate some examples of how I would develop material around that.
Jeff Williams (42:37)
Well, you know, one of the things cowboys do is that they're really kinda I put it in correlation to construction guys, right? they're working the dirt, they're always in the dust and filth and the cold weather, they're always out in the elements and they face the elements no matter what it has and that's just grueling in itself. you don't ever get those seventy six beautiful days like they are right now in this fall of the year. You get you get the extreme heat, you get the extreme cold.
and rain, storm, wind, rain, and you're always out in the middle of it. That's sort of the correlating factors. The other component to that is that no matter if you're riding a horse or a piece of equipment, you can always get thrown off. You gotta be careful. You don't get kicked in the teeth by whatever it may be. And so there's just so many different correlations to it. And so I that's why I'm so passionate about construction and building and
horses and training and riding and everything else and remote range is that there's so much correlation between the two. It's so scary it's not even funny. And so it doesn't matter if
Kimbrough (43:36)
Okay.
Jeff Williams (43:36)
it's work boots or cowboy boots, it's still boots on the ground. It's always, you know, forging in in things that nobody else wants to do and it challenges your strength and your wit to the nth degree. So there.
Kimbrough (43:48)
Okay.
Okay, those are some good notes. So what I would do is I would take those credible notes and I would find a a binary space where I could create some ridiculous scenarios based on the credibility of a cowboy or a construction worker. So for example, I would start off with something like, you know, when I do stand up I work with a lot of people, like black people, Latino people.
intellectuals, slapstick, but I went on tour with this comedian who was a cowboy, and you know, I don't know if you know anything about cowboys, but like they like roughing it. You know, it doesn't
Jeff Williams (44:24)
Yeah.
Kimbrough (44:25)
matter what hotel we got, whether it was a Motel Six or a Super Eight, like he would be like out pitching a tent in on a rough, you know, using a saddle as a pillow.
It's like, you know, we got pillows in the hotel room where we could we could, you know, you could come inside and be no, cowboy sleeps outside all the time. Every night. Rain and shine. And it's true. Rain and shine. We work in Canada, bro. It's forty degrees out there. Windshield factor sixty degrees below. Cowboy out there like head on head on the saddle. Yeah.
Freezing his ass up, but he's a cowboy. And the he cowboys
Jeff Williams (45:02)
Yeah.
Kimbrough (45:03)
sleep outside.
Jeff Williams (45:04)
I love it.
Kimbrough (45:04)
And they wear their boots too, man. It's like you don't you don't see a cowboy without his boots. I don't care what where it is. You know, it if a cowboy is doing stand up, he got his boots on. If he working construction, he's got his boots on. If he's scuba diving, he got his boots on. Cowboys be wearing their boots no matter what.
Jeff Williams (45:23)
Yeah. Yeah.
Kimbrough (45:23)
Even in a shower. Cowboy, you don't take his hat off or his boots off for nothing. You just take the hat off, do the shampoo, put the hat back on, but the boots are on in the shower. Like they don't take off their boots. So those are the type of the examples. You take a fact and then you use your imagination and you take it to the ridiculous. And the more ridiculous you can make it, the funnier it can be. And the cowboys will laugh because of
How familiar they are with the stereotype. The people who aren't are laughing because they're imagining how funny it would be to see a cowboy in a ridiculous situation because they don't know the world. They just assume that your introduction to the stereotypical credibility part of it is true. They take your word for it. And then when you take that to the ridiculous, then that's when
Their third eye mind takes over and they laugh at what they see based on what you're talking about.
Jeff Williams (46:22)
Very good, very good. Well I think we're gonna have to
Kimbrough (46:24)
But I could w I could write a whole HBO special for you though. So anytime you wanna take the workshop, let me know. I'll sign I'll sign you up. Yeah, everybody has three
Jeff Williams (46:27)
Yeah. All right. There you go. Well hey we'll come back to doing that sometime, that's for sure. But so
Kimbrough (46:34)
minutes, so
Jeff Williams (46:35)
yep. I think we need to go ahead and try to wrap up here a little bit. I know that being respectful of the time and everything, but so what are you working on right now that you wanna give a plug in and here's what I'd like for you to do right now is just give a website or some contact information somebody can get a hold of you.
I know that you're probably doing some contract for training and things and teaching and education and so whatever else you want to put out there we'll put it out there. We'll make sure it's in the transcript and and post it out on the you know, the networks and things and but go ahead and give a plug and give us a phone number or email or a website or something.
Kimbrough (47:10)
Yes, you can catch me all things Team Comedy USA . com. So if you want to know about any shows that we're doing or if you want to know about podcast or workshops, you go to teamcomedyusa.com and all the information that has anything to do what we're doing with leading up to the Olympics. We're working on a torch tour when they announce the cities, when the Olympics announce the cities where the torch is gonna go through.
we're gonna follow that tour and do some comedy and some podcasting, and you'll be able to find all of that there. the one thing that I'm excited about working on right now, if I can find the poster really quickly, let me just open this up. Am I is it possible to share my screen and I can just kind of show you what I'm working on?
Super excited. Diaspora groceries is I don't know if you can see that. Can you see my screen?
Jeff Williams (48:07)
Yeah, sure.
Kimbrough (48:09)
Okay. So Tiffany Haddish is the co-founder of Diaspora Groceries and we've been asked by that organization to do a comedy fundraiser. And I have some great headliners that are gonna be on the show. Tiffany's gonna host it and I'm gonna co-host it with her. She's gonna welcome VIPs and media and celebrities, and she's gonna do a little bit of some comedy and then she's gonna turn it over to me and I'm gonna bring on
Some very, very, very funny friends of mine. Brian Kylie, who wrote for the Conan O'Brien show. He's also a writer for the Oscars. When Conan hosts the Oscars, Brian Kylie writes a lot of those jokes. I got Kareem Matthews from Comets Unleashed. he just shot an episode a week ago and he's hysterical. And the closer of the show is Sherwin Ari. And he this guy is hysterical.
He's a super strong closer, very animated. And that show is November 4th. If you're in the LA area and you want to come in and have some laughs and participate in a stand-up comedy show for a good cause diaspora groceries and see some killer comedy. go to Team Comedy USA. You can get tickets. We have VIP tickets for $60, which comes with the
some food and some drinks and you get a chance to be introduced to Tiffany and the general admission tickets are thirty five dollars. So if you want to use my promo code, which is Pod Brother or Ref Kimbrough or Team Comedy USA, then that that would be awesome.
Jeff Williams (49:44)
Fantastic. So real quick, you're located out in the West Coast, I'm assuming, right? LA or not? Okay.
Kimbrough (49:50)
Yes, we're in Los Angeles.
Jeff Williams (49:52)
Okay, you're in Los Angeles. And I've gotta ask when when's your next time to be back in Chicago? Cause I wanna come and see you live.
Kimbrough (50:00)
well, I'm working on that because I want to do a welcome home show for my comedy documentary film. So I as soon as I do have a date, I will let you know. I'm hoping it will be maybe in sometime in the spring. So because I've got pretty slam packed with all everything that I'm doing in the fall and the winter. So I think the soonest I'll be able to
To get on a Midwest tour will probably be spring.
Jeff Williams (50:26)
Okay, perfect. do you know you're doing fundraisers right now cause you just described one. I'll talk offline with you about doing a fundraiser here in this area, for a couple of folks.
Kimbrough (50:34)
Sure.
Jeff Williams (50:35)
but and see what that might entail and at what level you gotta have to be able to come and do that and set that up. But that'll we'll yeah, we'll
Kimbrough (50:41)
Yeah, that's one of fundraiser, so I'd be happy to help you with that.
Jeff Williams (50:43)
chat about that offline. But so I got one last question and then we'll kinda roll into the close here but
Before we ride off, what's one thing you want folks to remember when the crowd is quiet, the business gets tough, and they're wondering whether to keep going.
Kimbrough (50:59)
That's easy. If this is what you're put here to do, from the time you are here to the time you expire, doesn't matter if there's a lull or a downtime or if it's slow, the pendulum is always going to swing back to why you were put here, and that's to do what you do. And if you stay in the pocket when the blitz is on and wait for the pendulum to swing back your way, it will. It doesn't feel
Good or comfortable when you're in that lull, when you're in that that calm sea, that that dead sea. But the breeze and the wind will come back. The pendulum will swing back. And the if this is what you are put here to do, then just hang out, be patient, and work on stuff that you can do until it comes back. Good example for me is.
When the pandemic closed the world down and there was nothing, I can't do shows, I can't make money, I can't do audiences, we're all quarantined. I spent that time to archive all my films, archive all my podcasts, to learn how to edit better, to learn all my film skills better to learn apps and so all the digital things that I didn't get a chance to do because I'm on the road making money and driving around. Here I am.
locked into my studio, quarantined, self-quarantined. So I took advantage of that downtime, that lull to get better in other areas. And that's my advice.
That's my take. That's
Jeff Williams (52:26)
Appreciate that.
Kimbrough (52:27)
that's my take.
Jeff Williams (52:27)
Yeah. Appreciate that. Kimbrough thank you for joining us today and providing great fun stuff. and again, Kimbrough with
Kimbrough (52:37)
Sorry about that.
Jeff Williams (52:37)
that's okay.
Pod Brother Nation Network and Team USA or Team Comedy USA, I apologize. So again, remember that and again thank you. and everyone riding with us today, thank you for listening to the construction cowboy show, take care of your people, stand behind the word and keep building something worth protecting.
Until next time, Keep Your Boots on the Ground and your business moving forward,
Happy Trails to you until we meet again.
Bye for now!