Prison Strong w/ Rashida "Sheedz" Olayiwola: Motherf*ckin Mini Episode

Summary

Episode Summary: Prison Strong w/ Rashida "Sheedz" Olayiwola – Motherf*ckin Mini Episode

Podcast: My Momma Told Me
Hosts: Langston Kerman and David Gborie
Release Date: July 17, 2025
Episode: Prison Strong w/ Rashida "Sheedz" Olayiwola: Motherfckin Mini Episode*

In this captivating mini-episode of My Momma Told Me, co-hosts Langston Kerman and David Gborie delve into themes of resilience, personal struggles, and the grueling realities of prison life. While the episode's title references Rashida "Sheedz" Olayiwola, the discussion primarily revolves around the hosts' personal anecdotes, their perspectives on handling rejection, and insights inspired by the TV show 60 Days In.

Navigating the Harsh Realities of Auditions and Rejections

Struggles with Auditions

The episode opens with Langston Kerman expressing frustration with the audition process, highlighting the challenges of maintaining confidence in an often disheartening environment.

Langston Kerman: "It is hard because with the song it's like, you know Every song until that music starts." (03:02)

Langston and David discuss the vulnerability that comes with auditions, especially when involving significant others who may not fully grasp the nuances of performance.

Langston Kerman: "You gotta give me something." (04:04)

Coping with Rejections

The conversation shifts to the frequent rejections they face in their careers, emphasizing the mental toughness required to persist.

David: "We go out every single night to take an L... You have to be a beast." (05:33)

Langston shares personal experiences of bombing performances and the sting of returning to a hotel alone after a failed show.

Langston Kerman: "I bombed for an hour and I came back to the hotel by myself." (05:43)

The Emotional Toll of Constant 'L's

Both hosts reflect on the cumulative emotional impact of repeated failures, questioning how others might handle such relentless setbacks.

David: "People don't see. I have one of my close friends, she's a Lawyer and shit. And when she saw how many no's we just, like, roll off, she was like." (05:12)
Langston Kerman: "I get rejected regularly." (05:20)

Insights into Prison Life and Mental Resilience

Exploring 60 Days In

Transitioning from personal struggles, Langston and David analyze the TV show 60 Days In, which provides a glimpse into life behind bars. They discuss how individuals adapt and the mental fortitude required to survive in such environments.

Langston Kerman: "I think you give up on whatever you think you want your body to look like and you focus on getting prison strong." (14:08)

The Dual Nature of Charisma

A significant portion of the discussion revolves around the role of charisma in prison settings, suggesting that it can be both a blessing and a curse.

Langston Kerman: "Charisma is more of a curse than a gift because, like, bad people really monopolize it." (20:31)
David: "They’re charismatic, they're charming... pretty grounded people who will do a desperate thing in order to figure their shit out." (20:38)

Challenging Stereotypes

The hosts challenge common stereotypes about prisoners, arguing that many inmates are not inherently violent or unchangeable but possess diverse personalities and backgrounds.

David: "They’re sometimes pretty grounded people who will do a desperate thing in order to figure their shit out or who snapped in a moment." (20:38)

Personal Reflections on Incarceration

Langston reflects on whether he could withstand the pressures of prison life, acknowledging his limitations in handling constant stress and confrontations.

Langston Kerman: "I don't think I could get to... shitting in front of somebody else. He's gotta leave. You gotta leave." (17:46)

David shares observations from the show, highlighting how some guards displayed vulnerabilities that prisoners could exploit.

David: "It's a world where these people make them feel so good about themselves that they're willing to help them escape out of jail." (19:07)
Langston Kerman: "I think charisma is more of a curse than a gift because, like, bad people really monopolize it." (20:31)

Notable Quotes

• Langston Kerman: "Confidence gets me through rapping... I kill auditions when I'm by myself." (03:02)
• David: "We go out every single night to take an L... You have to be a beast." (05:33)
• Langston Kerman: "Charisma is more of a curse than a gift because, like, bad people really monopolize it." (20:31)
• David: "They're charismatic, they're charming... pretty grounded people who will do a desperate thing in order to figure their shit out." (20:38)

Key Takeaways

1. Resilience in the Face of Rejection: Both hosts emphasize the importance of maintaining confidence and persistence despite frequent setbacks in their careers.
2. Complexity of Prison Dynamics: The discussion sheds light on the intricate social interactions within prisons, debunking the notion that all inmates are inherently antagonistic.
3. The Role of Charisma: Charisma is portrayed as a double-edged sword within the prison environment, facilitating both positive relationships and manipulative behaviors.
4. Challenging Stereotypes: The episode encourages listeners to reconsider preconceived notions about prisoners, recognizing their multifaceted personalities and capabilities for change.

Conclusion

In this thought-provoking mini-episode, Langston Kerman and David Gborie offer a deep dive into personal and societal challenges, intertwining their experiences in the comedy scene with observations from prison life. Their honest and raw conversations provide valuable insights into building resilience, understanding complex human behaviors, and the importance of breaking down stereotypes. Whether you're navigating the highs and lows of an entertainment career or seeking a better understanding of the prison system, this episode delivers meaningful content that resonates on multiple levels.

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Note: This summary excludes advertisements, intros, outros, and non-content sections as per the provided transcript.

Transcript

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[Langston Kerman]

Mini episodes Mini episode Mini episode.

[Unknown]

Give me two seconds. I need to I'm ready now. I'm ready.

[Langston Kerman]

I'm ready. I'm ready.

[Unknown]

I got some I'm a bond it. I'm a bond it.

[Langston Kerman]

Do you write them down? No.

[Unknown]

But the song is where I always find myself getting caught up and then I have to remember like a thing that someone said that I liked.

[Langston Kerman]

It is hard because with the song it's like, you know Every song until that music starts.

[Unknown]

That's really the problem is that, like, I feel so confident, and then I remember that, like, oh, sometimes I be mumbling through these.

[Langston Kerman]

Yeah, it's a lot like. It's like, confidence. Gets me through rapping. Like, in my house.

[Unknown]

Yeah.

[Langston Kerman]

You know?

[Unknown]

Yeah, I think so. When you're alone, man. I kill auditions when I'm by myself.

[Langston Kerman]

That's the thing about auditions being taken out of the room. Part of that does feel good because you don't feel stupid, you know?

[Unknown]

Yeah.

[Langston Kerman]

Like, I do love that. But then sometimes it'll be like, I'll have to have, like, my girl, like, do it. And that's the worst auditions I've ever. Like, when she's recording me.

[Unknown]

Yeah.

[Langston Kerman]

So bad.

[Unknown]

I. I stopped doing it with Nikki because that's smart. I was like, whatever this is, it don't work.

I can't do nothing.

You can't help with.

No, I can't do nothing with a significant other. They play too much or they just don't know what to do.

[Langston Kerman]

That too. She. Yo, she. She's not great at reading lines. No, you gotta give me something. Yeah, you gotta give me something.

[Unknown]

Like, I hate. I had a guy stop in the middle of the page and was like, wait, so what's this? Oh, so you playing this? It's like, I come, man, just deliver the line.

[Langston Kerman]

Just say it. Change your voice a little bit in.

[Unknown]

Between characters, like, do what you feel is. Or do it straight, but there's never room.

Yeah, but do it right. And they ain't got it.

[Langston Kerman]

They got it.

[Unknown]

And then they see a vulnerability in you that you.

[Langston Kerman]

That's what it is.

[Unknown]

You'd prefer they don't see that's what it is.

[Langston Kerman]

Cause, like, there's like a. Do you get this with Nikki, where there's a level of, like, my girls see something I do for. For entertainment, and then there's just, like, you could feel it, like, so this is what you do all day. Yeah. You know what I'm saying? Like, oh, this is what you. I go to work.

[Unknown]

Yeah.

[Langston Kerman]

You're in the house pretending to be.

[Unknown]

A cartoon character, and you didn't even memorize it.

[Langston Kerman]

That good. Yeah. And you didn't walk the dog. Okay. No, no, no. Go cook dinner.

[Unknown]

Nah, it's cool.

Yeah.

Nah, it's cool. I see. Yeah. I believe in you.

[Langston Kerman]

Yeah, man.

[Unknown]

They couldn't take as many nos as we get in.

That's true.

That people don't see. I have one of my close friends, she's a Lawyer and shit. And when she saw how many no's we just, like, roll off, she was like. And she got one. It was devastating.

Yeah.

[Langston Kerman]

Yeah, that's a good point. People don't.

[Unknown]

They couldn't do what we do.

Damn.

[Langston Kerman]

I get rejected regularly.

[Unknown]

I've never thought about it like that. But I think that's a really true statement.

[Langston Kerman]

That makes me feel good.

[Unknown]

So the people who think our shit is just like, you know. And I'm saying this in such a loving way, but they could not take as many. We're so like, you have to be a beast.

[Langston Kerman]

Yeah. I'm saying it direct, Alana.

[Unknown]

We go out every single night to.

[Langston Kerman]

Take an L. Yeah.

[Unknown]

Like, fully prepared to take an L, bro.

[Langston Kerman]

I take some huge Ls, and I never even get to talk about it. Like, on the road. I'm just in Milwaukee and I bombed for an hour and I came back to the hotel by myself.

[Unknown]

Yep.

[Langston Kerman]

That's some people's worst experience of their life.

[Unknown]

And you're in Milwaukee, so you broke your diet.

You're already right.

[Langston Kerman]

Whatever you.

[Unknown]

Whatever nuggets, whatever version of you, you wanted to be already got destroyed. And then your ego got destroyed. And then you had to sleep somewhere bad.

[Langston Kerman]

Yeah. Because I broke the diet on Thursday. It's Saturday. I broke the diet at the airport. I said, fuck it.

[Unknown]

Yeah, here we go. It's one of them weekends.

[Langston Kerman]

I'm gonna catch up on Monday.

[Unknown]

The new standups. And even, like, the, like, standups who don't know they're getting paid in drink tickets till they get there, it's like, yeah, that's an L, yo.

[Langston Kerman]

I used to. You know how many times I've gotten on a plane not knowing where the money to come back is? Yeah. Like, straight up, just like, I think I got 150 here. And then if I can tie it to you, like, I don't know when I'm coming home. That's ass. Yeah, bro. Fuck, bro. I was telling somebody that one I.

[Unknown]

Can'T even relate to. That's crazy.

[Langston Kerman]

You want it? This is crazy. I was telling somebody about this the other day. I flew Spirit one time to go do a festival when Spirit first came out.

[Unknown]

Yeah.

[Langston Kerman]

And it was me and my friend.

[Unknown]

An early investor in Spirit.

[Langston Kerman]

I was early on. I was early on Spirit out of the Oakland Airport as me. And it was like. It was like a midnight flight. And my friend calls me at, like, 10, and he's like, you know they charge for every single bag on Spirit.

[Unknown]

Yeah.

[Langston Kerman]

Even the carry on. And I have. I have $15, right? Just like, just like in life.

[Unknown]

This is where you're at.

[Langston Kerman]

I gotta put all my clothes on.

[Unknown]

Nigga, are you for real?

[Langston Kerman]

I swear to God, I put all my clothes on. And then the worst part is it was to Denver from Oakland, but there was a layover in Las Vegas. Oh, no.

[Unknown]

So we. Yo, Vegas is hot.

[Langston Kerman]

Yo. It was. But it was overnight.

[Unknown]

So you're just Frosty the Snowman walking through this airport because you couldn't afford a bag.

[Langston Kerman]

Yo, the craziest thing, the craziest thing too was like, it was me. I think I did it with some tact, right in that there's no classy way. No, no. This is what I'm telling you. This is what I'm telling you. I did it with some tact in that it was smaller shirts and then the hoodie over it all.

[Unknown]

Okay.

[Langston Kerman]

And then underwear, shorts, pants over everything so I just look fatter. My homie, who is Indian, yeah, did not do it.

[Unknown]

He was doing fun combinations.

[Langston Kerman]

He had like a hockey jersey and we were live. It is at the Oakland airport. And I was like, you look like a terrorist.

[Unknown]

For real though.

[Langston Kerman]

Like, we're gonna get caught. But we didn't. But anyways, I say that to say, yeah, my girlfriend's not doing that. Damn.

[Unknown]

Was you comfortable when you slept overnight? Because it's like kind of like a.

[Langston Kerman]

Walking hair Mattress is horrible because I was also had. I had some stuff in my pockets. But like even wearing multiple underwear, I'm like a large man. This is terrible. It was really terrible.

[Unknown]

This is a nightmare.

[Langston Kerman]

It's really awful.

[Unknown]

This shit is hilarious.

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Even If Diddy got 10 years. You're. What are you going to do, come out?

[Langston Kerman]

I don't know.

[Unknown]

Cosby came out and his eye looked better.

[Langston Kerman]

Well, you know, I think it's like going to jail to get your teeth fixed.

[Unknown]

Yeah, that's true. Jail be had.

[Langston Kerman]

They listen like that's a. It's like a big come up for certain things. It is.

[Unknown]

My cousin came out with a clean, clean bill of health. He like, clean bill of health.

[Langston Kerman]

That's crazy. And that's like. That's the system working. That's the one.

[Unknown]

The one.

Dude, you gotta go to jail. You wanna lose weight. Y' all do ozempic and shit?

[Langston Kerman]

No, they got hemaglutide in there.

[Unknown]

They test this shit on us, right?

They tested ozempic on all them inmates and now they was like, give it to the streets.

Yeah, yeah. About 12 of themselves all the time.

[Langston Kerman]

But everybody else is.

[Unknown]

One of them lost muscle mass. But he look good.

[Langston Kerman]

Yeah, you could lose muscle mass in there. They're doing their push up routine anyways. Yeah.

[Unknown]

No, you already. You frankly had a surplus of muscle mass.

[Langston Kerman]

Do you think you would get very strong if you went to prison?

[Unknown]

I think I would have to.

[Langston Kerman]

Yeah. It's really my only hope.

[Unknown]

I think you give up on whatever you think you want your body to look like and you focus on getting prison strong.

[Langston Kerman]

Yeah.

[Unknown]

Cause you have to.

[Langston Kerman]

Gotta be able to do all those. You ever seen it when they hit it and it's just like, it's like down, forward, back. Bruce Lee. Yeah.

[Unknown]

You tie a fucking T shirt around a bar and you start doing weird pull ups and it's like, it's crazy.

[Langston Kerman]

You gotta lift the little weaker ones.

[Unknown]

Even the jail door. Like. I watched 60 Days in a lot. That's one of my shows. I like them. Look, I don't know. I love them type of shows.

[Langston Kerman]

You know what I like about 60 days in? Some of them love prison and they don't want to admit it.

[Unknown]

They don't. Like the Marine guy.

[Langston Kerman]

Yeah, the Marine guy.

[Unknown]

He was. I'll do three more.

[Langston Kerman]

Yeah. It's honestly not that different to me or fucking old boy. The chaplain who was in prison before and you could tell he missed it a bit. It was like, here's what I think about that. I think you don't. People forget that different people have different skill sets. So he's like, that's probably the best he's ever been at anything in his life. Yeah.

[Unknown]

Yeah.

[Langston Kerman]

You know what I'm saying?

[Unknown]

I think so. And he was dipping and dapping in that shit a little bit again. You could tell. I saw like his nose running twice.

This is a place where you thrived the first time and now you're. You feel even more centered this time. So, yeah, you're gonna put a little shit up your nose and you can control it better than last.

And he had it.

[Langston Kerman]

He had the whole shit clicking. He was running it in like a month.

[Unknown]

He was him and the marine dude. The marine dude thrives because literally he's in the military. Like he said. He was like, I've spent days in the hole. So no and holes and everything. He was like. So all that extra shit didn't bother him. Yeah, I couldn't do jail. I don't want to do jail because I am a person who. Crazy shit. I know I'm a say something or try to. And I don't have that type of capacity to. I mean, I either would end up being like the. The group person where people would be knocking on my door. Can you pray for me as shit? And I don't have time for that in jail.

[Langston Kerman]

Okay. Yeah. If honestly, for me, I'm just moody. I just gotta be alone sometimes.

[Unknown]

Yeah, and you can.

[Langston Kerman]

I'll be sad sometimes.

[Unknown]

You ever see how he would be the person. You know, when they add a person to a cell that's been empty for a while, it's just one person. So they got their own room. He would be the one who get mad because they be getting mad when they get added a person they like. I mean, it's right there, man. It's like this had his own room for six months and here you come. They'd be so angry.

[Langston Kerman]

Yeah.

[Unknown]

Yeah. If. If a man moved while I was sleeping, I. I'd try to murder them.

[Langston Kerman]

Just like just hearing him move around the.

[Unknown]

The fight or flight would have to activate every single time that happened. To the point that I think I would eventually snap.

[Langston Kerman]

And I just don't think I've ever been personally. Like mom raised me. Lot of women. I don't think I've spent that much time with men.

[Unknown]

You gotta be around one all the time.

[Langston Kerman]

And honestly, I'm not a man in that. I'm not that man. That doesn't sound like good to me.

[Unknown]

But that's how I was raised in a. You know, the women, men. But I know myself. I can't be around that much energy at the same time. And then it be different smells and shit. I don't have time. We didn't even get into that shit. Into the body stuff.

Yeah, that's wild hooping in front of another human being.

[Langston Kerman]

I don't think I could get there.

[Unknown]

Yeah, you do.

Yeah, you gotta.

[Langston Kerman]

I don't think I could get to.

[Unknown]

Like, shitting in front of somebody else.

[Langston Kerman]

He's gotta leave. You gotta leave. Yeah, you gotta get.

[Unknown]

It's crazy.

[Langston Kerman]

That's gotta. You gotta get out of here.

[Unknown]

But you ever seen another pre show Escape at the Dear Mora? I forgot the name of Escape at Dear Mora. I'm probably pronouncing it wrong. It's on Netflix. Y' all gotta watch it. It's good as hell. This prison guard, her name was. What's her name? Ego Wodom. Put me on this show, okay? And I watched it. I was literally in the middle of writing the SAG Awards, but I couldn't get shit done. Cause I was watching the show on assignment. Like, yeah, but this is good. These two guys escaped because they were sleeping with the prison lady, the guard.

[Langston Kerman]

That seems like your best bet.

[Unknown]

And they used her to filter in tools and stuff. They made her fall in love with them, and she was. Basically helped them.

It's so crazy that guards still let that happen.

[Langston Kerman]

I think it probably happens more than you would think.

[Unknown]

That's what I mean. It's just like, it feels so clear that the prisoners don't like you. They just want your help.

[Langston Kerman]

You couldn't. You can't think that he is. He's gonna run away from jail and then wipe you up.

[Unknown]

You're the only lady he knows that he see.

Of course he loves you. Yeah.

Introduce him to three of your friends and then decide if this is a meaningful relationship.

[Langston Kerman]

That's a good point. Yeah. You need to vet him.

[Unknown]

You can't just be like, nah, I believe you.

When y' all watch it, y' all gonna see why those people. It's always a prison in a small hick town. And the two guards that helped them. One dude, he was so insecure. He was like, this big. But the prisoners gassed him up and would make him feel good. So he would come to the prisoners like, hey, man, are you mad at me? And he'd be like, well, yeah, you took away my meat. I was thinking about making some meatloaf today. And the lady guard, she'd be like, I miss him. Cause one dude was actually mad at her. So he wouldn't come out of his cell to go see her. He wouldn't go to his. They have jobs in there. Like, so she ran the metal shop, and he refused to come to metal shop. And she was like, can you give him a message for me? Can you? This is how she signed it on the movie. And it was just this world where I'm like. It's insecurities playing on each other. So they end. Like, when we talk about the 60 days in. It's that same world of these people make them feel so good about themselves that they're willing to help them escape out of jail.

And we gotta remember that some criminals are charismatic as fuck.

[Langston Kerman]

The most. The most.

[Unknown]

Like, the most charismatic people, I think. So often people.

[Langston Kerman]

I think. I think charisma is more of a curse than a gift because, like, bad people really monopolize it.

[Unknown]

And I think we often treat every prisoner. And this is our own vile stereotyping. I mean, you know, fogging royal art. But, like, the idea that you sit around being like, oh, they're all mean and angry and violent and whatever. All that is is nasty. That's not actually what they are. They're charismatic, they're charming. They're sometimes pretty grounded people who will do a desperate thing in order to.

Figure their shit out or who snapped in a moment.

[Langston Kerman]

Yeah.

[Unknown]

Like, for real. Like, who? Literally. And literally. When y' all watch this. Cause I know y' all gonna watch. It's good.

[Langston Kerman]

Yeah.

[Unknown]

When you see they do a episode where it shows what these two did to actually get in jail, it, like, blew my mind, because you couldn't tell. And when you talk about charisma, dude was a painter. One of the prisoners, he was, like, an actual artist. Like, people were buying his art.

[Langston Kerman]

Yeah. Yeah.

[Unknown]

And now that he's dead, his daughter owns, like, all his pieces. They still want to buy it because of, like, his expression through art. The other one was just, like, it. Just when they showed what they did, you would have never thought they do something like that. But, like, y' all said charisma and personality, it's a bad.

[Langston Kerman]

It's why you shouldn't trust comedians. Yeah.

[Unknown]

Not work or movies, because they got everybody in prison thinking they bullies. Like, it's just either. Hey, man, no, give me your shit. When really it's like, everybody's not a bully in there.

[Langston Kerman]

Nah.

[Unknown]

It's a bunch of people trying to finesse each other at all times.

Or the weird white preacher who's, like, running the joint.

I like the vibe in here. This is nice.

[Langston Kerman]

Yeah. Cause, yeah, man. Different people. You can adapt to anything, and you can thrive anywhere. Truly.

[Unknown]

Yep.

Damn.

[Langston Kerman]

Yeah.

[Unknown]

I think we did it.

[Langston Kerman]

Yeah. This was good.

[Unknown]

You follow me? At Langston Kerman, you can send us your own drops your own conspiracies. You can argue with [e-mail] we would love to hear from you. You can call us at 844-LIL-MOMS and most importantly like subscribe Rate Review follow us on YouTube, Instagram, TikTok wherever you enjoy consumable media. Bye.

[Langston Kerman]

Mini Episode Mini episode Mini episode Motherfucking mini episode. Many episodes Many episodes.

[Ryan Seacrest]

Hey it's Ryan Seacrest for Albertsons and safeway now through August 12th. Get big savings on your favorite products for the little ones in the family and earn four times points to use for discounts on groceries or on gas. Shop in store or online for items like Earth's Best Yogurt Smoothie, Gerber Pouches, Happy Baby Pouches, Huggies, Natural Baby wipes, Pediasure bottles, Earth's Best Crunchy Sticks and Gerber Yogurt Melts, snacks and earn four times points. Offer ends Aug. 12. Restrictions apply. Offers may vary. Visit albertsons or safeway.com for more details.

[Unknown]

Homes.com is the only place where you can find specialized neighborhood guides with the in depth insider info home shoppers want Very in depth info. Want to know if there's homes for sale in the area?

We've got it.

How long has a home been on the market? We'll know it. Average lot size?

Uh huh.

Proximity to local parks, of course. Insight into your neighbor's divorce? We're working on it. Homes.com We've done your homework.

[Danielle Fishel]

This is Danielle Fishel from Pod Meets World. Parents, Quick question. When is the last time you won snack time? The other day I handed my son a perfectly portioned Pinterest level snack and he traded it for a Mott's Applesauce pouch. I'm not mad, just impressed. And that's why Mott's no Sugar Added Applesauce pouches are perfect to keep on hand. They're made with real apples packed in a super easy pouch. Perfect for tossing in a lunchbox, keeping in the car, or grabbing as you're running out the door. Plus, they're a good source of vitamin C and kids love them. Win win. Make sure your kid wins snack time with Mott's Real Apples Make Real Good Applesauce. Learn [e-mail] this episode is brought to.

[Lauren Vogelbaum]

You by Hendrix Chin. I'm Lauren Vogelbaum, host of the podcast Brainstuff, where we are serious about curiosity and so is Hendrix. Their signature gin is infused with rose and cucumber and their master distiller is always crafting limited releases that riff on those flavors so that you can create something new. Hendricks is the refreshingly curious choice for marvelous summer cocktails. To learn more about Hendrix and to find more cocktail recipes, visit hendrixchin.com US Drink Responsibly Hendrix Gin 44% alcohol by volume 2025 imported by William Gratton Sons Incorporated, New York, NY.

[Unknown]

This is an I Heart podcast.