2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Tom's Dad STOLE Dynamite & BLEW UP A Bridge w/ Barstool Big Cat | 2 Bears, 1 Cave
Mon, 02 Jun 2025
Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee https://www.youtube.com/watch?v=ihy5odp5G9A SPONSORS: - Make life easier by getting harder and discover your options at https://BlueChew.com! And we’ve got a special deal for our listeners: Try your first month of BlueChew FREE when you use promo code BEARS -- just pay $5 shipping. - If your revenues are at least in the seven figures, download the free e-book “Navigating Global Trade: 3 Insights for Leaders” at https://NetSuite.com/BEARS. - Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears This week on 2 Bears 1 Cave, Tim Segura and Bert Kershire are LIVE from the Barstool Chicago studio and share some stories of their latest shenanigans in the Windy City. The Bears also talk about bombing in Hawaii, jokes about slurs, fathers, women fading, whatever's going on in Bert's mouth, plus the internet hate for WNBA player Angel Reece and alleged royal Meghan Markle. The Bears are then joined by Big Cat who talks about stuff his kids are into lately and his favorite hobby aka gambling. Speaking of which, he also teaches the Bears about Dana White's infamous Tunnel of Chaos, before they pivot to the series "MobLand", and Tom shares a story about almost buying Dr. Dre's house. Bert also trash talks Tom's home base for some reason and compares us...I mean...it, to an abortion clinic or a dentist office, which, let me say is totally an exaggeration....I love working here. Enjoy the episode! 2 Bears, 1 Cave Ep. 291 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:02:36 - Chicago Shenanigans 00:16:06 - Mouth Stuff 00:19:39 - Bombing Hawaii 00:29:01 - Friends 00:36:51 - Internet 00:43:28 - Women 00:49:04 - Big Words 00:59:18 - Mandela Effects 01:03:51 - Kids Stuff With Big Cat 01:12:09 - Gambling 01:20:42 - MobLand 01:24:17 - Work From Home 01:30:37 - Big Cat's Other Interests Learn more about your ad choices. Visit megaphone.fm/adchoices
Chapter 1: What funny stories do they share from Chicago?
Part of the idea of this podcast is how you can become successful as living as just a regular human. I went to culinary school and I only went for a few months and I dropped out.
Look at that, kids. You can drop out of culinary school and get two Michelin stars.
I do what I can do so I can come back and do it all over again. Not a damn chance. Not a damn chance. You see yourself somewhere. Take all the necessary steps to get there.
I just don't know how to quit.
That might be my superpower. You can all try and stop me.
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Chapter 2: What happened during their bar takeover?
I hope you do.
Consistency was exactly what life was all about. Don't be genius here and wild there.
There's a beautiful moment where obstacles become opportunities. Messes become messages.
I got shot in the face.
Jail was the best thing that ever happened to me. And I did put my head in a noose.
You heard 300 people dying. Nobody can tell me, like, you're breaking the rules, you're doing this wrong. There's no right or wrong. I don't care what it takes. I'm doing this.
We have a phrase for that. It's called, not a damn chance.
And white people, you're like a white, you know, fixture. Like, people look at you like Hitler, you know? They're like, we love this guy. Guten Tag, Bert. Welcome. Big shout-out to Barstool, to Big Cat.
Do they own High Noon?
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Chapter 3: How did Tom Segura's dad blow up a bridge?
Probably not.
I'm going to say no, and I'm going to say the same about Big Cat.
I'm going to say the same about me and you. I was going to say, I mean, I think if I met you in high school, I wouldn't be like, yeah, this is going to work out. Yeah. Well, hold on. We got to say thank you, Barstool, for giving us, accommodating us, and letting us do an episode here. We're both, we're fucking idiots, dude. We should have done this yesterday morning, not the day.
Yeah, why didn't we? Because, I don't know, it was dumb. God. God.
Yeah, we did a... I'm so hungover. We did a bar takeover, and we got Fun Tom. This is the beauty about owning a vodka company with Tom, is Fun Tom shows up every time we do a bar takeover. Every fucking time. Every fucking time Tom ends up on stage. I mean, I just want to tell you how beautiful the women of Chicago are. We walked into the Old Crow Smokehouse last night. In Wrigleyville, yes.
In Wrigleyville, and a woman... Behind the bar, in front of the bar, handed me a remote control and said, press the button. And I went, okay. And I pressed it, and she went, huh. I said, what? She goes, I have a vibrator in my vagina. That turns it on. And I went, let me get my friend real quick.
Yeah. And then you just handed it to me to go press it. And I did the same. I was like, what? You go press it. And I said, okay.
Ladies, ladies, that's the move. I'm telling you right now. You want to own a man's inner dialogue for the rest of the night? That is the move. If you are a party fun girl, you do that. And you go to a bar. You're in college. You find a guy. Give him the remote and say, I'll see you in like 10 minutes. And that guy will do nothing but think about you. I woke up thinking about her.
I woke up... I'm pretty sure her boyfriend...
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Chapter 4: What are the latest controversies in women's sports?
She'd be like, wow, that was so sexy. I'm so glad I got you that. Sitting here watching you just nut aggressively. So fucking arousing. Oh, fuck. That was one of the worst things I've ever seen. Because you acted that so well. Fuck.
I feel like I just pressed the button and you did it. Oh, my God. Are those linen pants? Yeah, I'm switching to linen.
It's good for summer. Except my asshole sweats. And so I have an ass sweat stain in my asshole. So, like, if I sit down for too long, you just see, like, a wet mark. Dude. It's real sexy. It is.
I've shit so aggressively today. Oh, I haven't shit yet. Oh, my God. I have nothing but just violent puree coming out of me. It is so gnarly. And I've had like four already. It's absolutely the most. And by the way, this place is massive. Yeah. And really impressive here at Chicago Barstool. I think there's three bathrooms and there's 80 guys. It's the craziest thing.
I walked into three bathrooms and three guys were there.
There are 80 guys.
I'm shitting. I'm like, I have to shit. And they're like, go to the other one.
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Chapter 5: Why do they discuss the Mandela Effect?
I'm like, okay. This, I mean, let's talk for a second about Barstool Chicago. This is... This is competitive with Rogan's setup, in my opinion. I'd argue... The facility? This is better than Rogan's setup. Well, it's a totally... Very different. Rogan's one guy, so it's his thumbprint. It's just him. Yeah, it's just him.
But, like, this is, like... I mean, High School Bird is, like, going, well, can I quit my job and just work for you guys for free? Oh, my God, I know. I would be... I'm blown away. They have a basketball court. They have a golf simulator. They have a gym. They have fucking... By the way, it's like something about the chicks that work here. They're all pretty and cute.
And they got little sister energy. And they're like, what's up? Hey, you want a high noon? Yeah, yeah, yeah, yeah, yeah. I mean, I fucking love this place. I feel like I fucked my life up. My studio is like... It looks like we sell knitting supplies out of it. There's so many fucking women. There's so many women. Why do I have so many fucking women working for me?
Why can't you get some more dudes in there? I fucking can't hold on to dudes. Really? Yeah. I lose dudes quick. I think it's a den of snakes, those women. Yeah. They're just all fucking little fucking just... Like women, they're mean girls. And so when they decide they're going to do something, they do something. I got to fucking have a coup d'etat. Do it.
I'm going to start sexually harassing them.
I would pivot from that. Whatever you plan on, you should stream it live. I would love to watch. By the way, I ate shit.
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Chapter 6: What insights do they share about gambling and kids?
And someone's gotta have the video. It's gotta have video. You took like a epic spill on the stage last night.
So, and by the way, it's what woke me. I set my alarm. I didn't need my alarm today. Really? Because my knee fucking woke me up. So we're on stage. We're pretty lit.
I mean, I'd had an edible, I don't know how many shots, I don't know how many drinks, and we're saying goodnight, basically, and thank you for everyone coming out, and we're on a stage, and there's a DJ set up there, but the floor is black, his table's black,
uh it's not he was black he may have been black that might have affected it too but the thing is dude he had like a two foot subwoofer on the ground that like you just don't see yeah so i walked over this way and just completely hard i thought you i thought you blew out your knee well i was joking about it and then this morning i was like oh what if i really didn't because like it
it hurts to put it up like that yeah oh yeah yeah it kind of sucks um i got some cool bruises too you got bruises on you yeah ate it hard man it was hard oh and i was i joked with you i was like i tore my acl and you're like wait i'm just kidding but i go with me you probably believe it and you're like yeah and then this morning i was like i think i did tear my acl i'd be so mad if i did
And then I got back to my room, and I fucking smoked DMT. I hit the DMT. What is it with you and DMT these days? It's the best fucking vape pen I've ever had in my life.
But you disappear.
Dude, I was fully hallucinating last night. Like, out of my mind. Wait, how did you get a DMT vape pen? Just cool guy.
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Chapter 7: How do they navigate the world of online hate?
I want to know the breakdown of this. I've been given a few. You've been smoking DMT more than I think you're supposed to smoke DMT. Doing DMT is like anal sex. You're supposed to do it once a year. Yeah, until you find out it's the only way you come.
And then you go, I'm going to do it all the time. Yeah. I kind of want to do DMT. You know what? Here's the thing. You go on a, first of all, like you can't lift your head up, you know, like you're kind of paralyzed. And then, and I like it because I feel like just give up, just life end right now. And then you go on these crazy, like crazy visual shit happening, right?
You're seeing shapes and colors and all this shit. And then like a door opens and and you go into some life path realization, and you're completely lost in it. You're in an alternate reality, and maybe you're resolving something, or maybe one of your fears is coming up, or maybe you're just processing something, and then all of a sudden, it's over, and you're like, oh, how much time went by?
15 minutes? That's it? Yeah, sometimes, but then you hit it again. You're like, let's do it again.
Chapter 8: What are their thoughts on Meghan Markle?
Yeah, it's pretty great. It's crazy. Me and you do drugs and alcohol for different reasons. Yeah. It's so fun to watch you get fucked up because you make a decision. Yeah. Yeah. Like, I never make the decision. The decision just shows up. Right. It's like lunch for you. I'm like with civil rights in Europe. Like, yeah, they're black people. Just let them do whatever they want. In Europe?
Yeah, in Europe, right? Isn't that how that works? And then you're more like the United States where you're like, all right, now they can use our water fountains.
right right like you're but like you made a decision to get fucked up last night you're like i you said something you said you said something like uh all right that's it it's over something i went oh well yeah because i whenever i go to any of these things i feel like the you know you have like this balance like are we just at this thing and you have a drink yes and then you go i don't i don't know that balance but i've heard of it
So for me, I'll be like, is it just a drink? And then we're leaving here. You know, it's like one is fine. But then like the atmosphere there was so fun. Everybody was so nice. It felt like we were actually at a celebration, like somebody's birthday party or something. And the music and, you know, our crews together just like hanging out.
So after I had like a couple, I was like, oh, this is like right now I'm standing on the line. Like you either are going for it or you stop now. So I was like, all right, we're in. Let's go.
You know what's so funny?
Tim Dillon once said... And then I drank, by the way, about a gallon and a half of water.
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