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Aware and Aggravated

37. You Have To Lose Before You Win. Let It Get Ugly

Sun, 27 Apr 2025

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The reality of outgrowing yourself & some of the hardest and most life altering decisions I just had to make.  Substack:  https://substack.com/@leoskepi?utm_so...  Social Media: https://www.instagram.com/leoskepi https://www.tiktok.com/@leoskepi https://www.snapchat.com/add/leoskepi Merch:  https://leoskepicollection.com My App Positive Focus: (Apple) https://apps.apple.com/us/app/positive-focus/id1559260311 (Google) https://play.google.com/store/apps/detailsid=com.positivefocusapp&hl=en_US&gl=US&pli=1 Business Inquiries: [email protected] 

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Chapter 1: Why did Leo Skepi quit his podcast deal?

56.811 - 85.686 Leo Skepi

But it all feels so in line and the way that it's happening is crazy. I'm in one of those in-between periods. So let me just hit you out the gate with it. I'm going to kind of talk with what feels good to come out, but this has more people involved. So... I quit my podcast deal. And what I mean by I quit it is... I'm done with it.

0

86.366 - 108.892 Leo Skepi

So the way that podcast deals work is you basically sign on with the company and you have an agreement for typically a year and you give them the rights to sell ads on your podcast. And they usually will give you a minimum guarantee. So a certain amount of money, they'll pay you monthly. Like a minimum guarantee could be $100,000 for the year or $250,000 for a year or a million dollars for a year.

0

114.133 - 141.935 Leo Skepi

but I'm not going to be able to tell you what I had or what was going on. But the amount of money that I personally had a minimum guarantee of was substantial. And it's not something that is like, oh, it's fine. You lost it. No, it's my only set income that has been consistent. And the only thing, whatever, it's gone. Yeah. My soul wanted to get out of it.

0

142.956 - 165.171 Leo Skepi

But with a podcast contract, it comes with certain guidelines you have to have. So I had to do ads in, this is for the audio version I'm talking about. So the podcast deals for the audio version and then certain ads come through when their hosts read on YouTube. So I'm letting you in behind the scenes of all this shit. I'm just giving it to you straight. I don't have time to protect the industry.

0

165.371 - 185.06 Leo Skepi

It's rotten and it's bullshit. So this is the truth of it. You get paid for the ads that go on your podcast, but I'm a very specific case because I'm very picky. I don't read ads for anybody and any products I don't like. I don't care how much you pay me, I'm not doing it. And I'm selective with the ads that I do.

185.46 - 206.674 Leo Skepi

So I always need like a specific contract and it's highly negotiated and it takes months to get the contract negotiated and done. With the audio version of my podcast, I was required to put allegedly I don't know if I could talk about this in the contract. Who gives a fuck at this point? Okay? I'm getting irritated because I'm trying to censor my soul and you're watching me get mad.

206.754 - 228.493 Leo Skepi

It's like it's coming out. So this is just what it is. I despise ads. I hate listening to ads, hearing ads when they're in stuff. So... This is the dumbest business decision I could make to care more about the person listening to the podcast than me making money from the podcast. I don't like that my podcast was getting interrupted with ads.

Chapter 2: What are the challenges Leo faced with podcast ad interruptions?

229.594 - 252.409 Leo Skepi

And I have like this weird thing with my intuition and my soul of like, it don't want to be interrupted. The way I'm talking, the way that I'm doing things now of recently, the past like five episodes, um, I don't like it being interrupted and I care about you guys listening to this and not being hit with ads every fucking like 10, 15 minutes. It's annoying. I like for things to flow, whatever.

0

252.429 - 275.769 Leo Skepi

It doesn't matter. That's the whole thing. I didn't want to be interrupted no more, but it's not just that there, this podcast deal that I signed, I signed it back in like January and I've not been able to get a clear answer around the money and And when I'm going to be paid, the contract has it written out a certain time. And then, oh, we need to push it back. I hit a breaking point.

0

275.95 - 298.379 Leo Skepi

Absolute breaking point. Chasing the money and having to check in. I hit a boiling point because it felt disrespectful. It felt like I was disrespecting myself to constantly be chasing money. I agreed to be paid. When I'm doing my end, you ain't holding up your end. I'm not chasing you. And I'm not spending the next year of my life chasing after some motherfucking podcast deal money.

0

298.919 - 320.655 Leo Skepi

And then on top of it, getting interrupted on my pod, everything about it. I've been pushed to a point of fuck it. And my soul is fully behind me on it. Like my soul's mad as hell. It's like, I don't want to be interrupted. Let it flow. Let it be what it's going to be. And then logical me is like, I'm like ready to beat my head into the wall, trying to talk and like get an answer.

0

320.815 - 335.363 Leo Skepi

Everybody tries to give me their word and their word falls through everybody. Oh, you're going to get the money next month. Oh, next month, the beginning of this month, it will be the ending of that month. Everybody's word. Shit. I don't trust nothing. And for this to just happen,

336.923 - 357.755 Leo Skepi

keep unfolding oh it's gonna nobody could give me a set date a set timeline they just jerking me the fuck off i'm not tolerating it and the fact that it's my soul now that it's speaking and like i'm letting my everything just come from the heart and full authenticity mode it's not getting fucked with and i'm not begging nobody for nothing i'm pissed

359.178 - 380.364 Leo Skepi

But I'm so happy because that anger comes with so much clarity. I made the right decision, even though it seems stupid as fuck. But the whole thing of getting to this boiling point, I want to talk about my experience because maybe it'll make you understand yours or you'll feel better about your situation. So the past four months since January. I've been waiting for the money.

380.685 - 396.144 Leo Skepi

And this money is money that I've been dependent on because I had a podcast deal for a year before this that was supposed to start in January. So I was living this year, the past four months, like, okay, the money's coming in. In the back of my mind, I'm like, okay, the money's coming in.

397.31 - 418.849 Leo Skepi

I've been spending and still had a little bit of restriction with myself because I'm like, I don't have the money yet, but the money's coming in. I've been living in this in-between period for four fucking months. And I'm like, I need this podcast money. It's like, what's going to... Help me. And this is how I survive. It kept getting held up and delayed. And I'm tired of fucking excuses.

Chapter 3: How did delayed payments affect Leo's decisions?

534.85 - 555.19 Leo Skepi

There are a couple of companies who bought ad slots where I like to do host read ads where I read the ads and it's companies I like. But there's a couple that I will be doing to honor them because they paid for an ad. I'm not going to have them walk away from a situation being like, I bought an ad on Leo's podcast and he didn't do it.

0

555.651 - 576.717 Leo Skepi

So I'm going to do the ads that were bought and I'm not going to have any more after that. So I don't do bad business. I honor it. So when you hear me do the ads, Hey friend, fun. Like it's because I like the company and it's because I'm honoring it. And I'm, I don't do bad business. I don't let nobody walk away from an interaction being like Leo fucked me over. No.

0

576.897 - 599.655 Leo Skepi

If somebody ever says Leo fucked me over, you ask them how bad they fucked me before I fucked them. That's the question you always ask. So I'm just being fully transparent with it. There is going to be one in this episode, but the other thing, this got hard. This got real difficult because the agency that I was with, I was with UTA and I've been with UTA for almost three years now.

0

600.416 - 623.714 Leo Skepi

And through all of this, um, I decided to end that relationship also. A lot of people ask me how I'm so confident and how I don't give a fuck. I will walk away from anyone or anything. I don't care what name you have. I don't care what association or status you have. If I'm not being treated right, I'm out. That's it.

0

624.654 - 641.458 Leo Skepi

And like the weirdly, like the ego boost and the balls you get when you make a decision like this. Like I've lived my life like this so many times. When I've needed money the most is when I've turned it down to save my integrity and I got balls. Like I got confidence that comes from decisions other people can't make.

641.878 - 665.19 Leo Skepi

This is a big source of my confidence is I'm willing to walk away from anybody and anything no matter what happens. So... I didn't like how things were going. I love the agents that I was working with personally, but just like the way that things were going for me specifically, I'm a very hard person to represent because I'm not like these fucking influencers who can be told what to do.

665.97 - 684.601 Leo Skepi

Like this whole podcast deal thing. Other people would be able to be bitched out and would just be able to be calmed down and say, no, no, it's okay. You're just going to have to keep going. It's going to come. It's going to come. And they would sit there and take it. I'm the type to buck back. I'm going to say, fuck this whole contract, scrap it.

685.461 - 708.466 Leo Skepi

I'm not the type that can be told what to do after I've been disrespected. No, no, no. I'm hard to manage. I'm hard to represent because I require a certain level and like a certain standard of myself. And I require that from everybody and even opportunities that come in. I understand when opportunities come in and they're disrespectful. It's like, oh, you should be appreciative of this thing.

709.267 - 721.913 Leo Skepi

But I see it as so disrespectful because it's like, bitch, I see what other motherfuckers are getting paid. Why are you over here trying to pay me a fourth of that and telling me I should be grateful? Fuck you. You know what you're doing and I know what you're doing, but you just don't like that I say it.

Chapter 4: Why did Leo end his relationship with UTA agency?

904.818 - 921.087 Leo Skepi

So I can see how both of them, like I see how it both plays in, but I ended the partnership, uh, There's no bad blood, which is crazy because the agents that I worked with, I like them. Like they're still cool and I don't wish nothing bad. I'm not mad at them. Like it was a very civil thing.

0

921.907 - 940.853 Leo Skepi

Um, cause it's just like an understanding of like, there's certain departments, certain departments I don't fuck with, but the agents that I worked with one-on-one the most, those are the ones where it's like, cool. Like we just get it. But these are decisions I never thought I would make. And these are decisions most people would never make.

0

940.933 - 964.364 Leo Skepi

Most people are so desperate and would do anything to be with UTA. Most people would be so desperate and would do anything for the money that I was making off my podcast. I can't do it. I'm not the type. I don't care how many people want something. If I don't like it, if it ain't for me, if I'm being mistreated, if I ain't being respected, I will throw it away.

0

966.383 - 984.666 Leo Skepi

Do I have a little bit of reluctancy every single time? Yes. But this time I didn't get a chance to like hesitate. Like just trusting myself, trusting my soul and like my heart and like my intuition. It was all just so like boom, boom, boom. Like clear, it just happened. I didn't hesitate. I didn't hold back. I did nothing. It was just like, okay, bink, bink, bink, bink.

0

985.206 - 1007.975 Leo Skepi

And it fell into place and everything has gone so civil and smooth. But looking back, it all makes sense how everything has happened. I was meant to get to that point of frustration. To get to the point where I am now. Because some people aren't meant to go with you where you're meant to go. Everything that was built on old me is... very obviously crippling and having to be shed.

1008.755 - 1025.301 Leo Skepi

And this is not fun. This is not a fun thing to do. These are not fun conversations to have. These are not fun decisions to make, but they feel right. And a lot of people ask me, does it feel good? Not always. It doesn't feel good to follow your intuition, follow your soul.

1025.781 - 1046.475 Leo Skepi

Sometimes it feels like you're actually being burned alive emotionally, but it feels right because it's a whole shedding process that has to happen. I feel like I'm, I don't know, being skinned like a fucking cucumber or like a potato. You like skinning a potato before you cook it. Like that's what I feel like is happening to me. I'm getting all my layers scraped off.

1047.775 - 1070.453 Leo Skepi

But I feel confident in my decision. And that's just what it is. I didn't really want to talk about this, but that's what the podcast is now. It's not what I want to talk about. It's what the truth is. That's what gets talked about. One more thing that wants to come out about this is like being able to hold yourself. You're never too heavy to hold for you.

1071.353 - 1090.898 Leo Skepi

And I kind of want to talk about holding yourself for a second before I get into all the synchronicities and good shit that lined up. It costed me money, but things lined up. The whole thing with like holding yourself. What the hell do I want to talk about with that? I don't know. You hold you. Like I was putting myself in other people's hands and they couldn't handle it.

Chapter 5: How does Leo view integrity and self-representation in his career?

1161.497 - 1185.148 Leo Skepi

I have no one besides my business managers who are fucking great. They're the ones who manage all my money and review contracts with me. And when I wanna buy houses and do things, they handle all that stuff. But as far as management, my sister is gonna step in because it's weird. She's been with me like every step of the way of all of this. Like she's seen everything happen.

0

1185.188 - 1204.574 Leo Skepi

She's seen me hire managers, fire managers. She's seen me hire agencies and now walk away from agencies. She's seen me negotiate podcast deals. She's seen me in meetings. She's seen me on tour, but she's been through the headache and seen all of it. But this whole time she's been consuming everything. She knows everything about social media management by watching me.

0

1205.095 - 1223.367 Leo Skepi

All the conversations me and her have had about how this manager was stupid as fuck or this one, how did this... If they could do it, I could do it. It clicked. She's who's going to step in this with me because she's the only other person who could hold some of me and handle all of this. But she's fully prepped and ready to do it. It's weird how it just fell in line.

0

1223.407 - 1248.42 Leo Skepi

So I'm taking control of everything back in my own hands. Love it so bad. But she's also... going to help me and kind of like oversee. And it's like, it's crazy how it all kind of lined up. And I've talked about her being my manager before, but now it's like the slot opened and it's already filled. Like it, it just needed me to open the slot and it all made sense. So yay.

0

1248.78 - 1271.657 Leo Skepi

The other thing I am going to mention about the podcast deal is is I'm no longer obligated to do podcasts anymore. But I don't want you guys thinking I won't still do them. I do this because I want to. The first year and a half of my podcast, I did for free. I didn't have a deal. I didn't have a podcast, nothing. I do this because I want to. The past year and a half, hey.

1274.443 - 1295.815 Leo Skepi

That was kind of like forcing through, but like I needed to, I wasn't going to give up on myself with this, like with the podcast, you know, like I had to have something. And it was like my lifeline a little bit, which cocaine, we don't do that no more, but I am still going to be putting out episodes. This one it's because I want to do it. And I'm doing these ads to honor it, like good faith.

1296.255 - 1316.721 Leo Skepi

So speaking of the ad, we might as well do it now. So our sponsor for this episode is Manscaped and they got a little announcement. It's no longer just an online thing. They're now available in CVS. So anything you need for shaving, all you shave needs and stuff like that. They have razors, trimmers, shavers, really everything out of the sun to do with shaving hygiene and stuff like that.

1317.021 - 1336.927 Leo Skepi

They also have like nail kits with little like tools and stuff, little travel things. I like this because now you don't have to wait for shipping no more. You can just go to store and pick it up. But there is one product that is exclusive to the CVS stores, and it's the Lawn Mower 3.0 Plus Refined Kit. And the Lawn Mower 3.0 Plus is waterproof for wet or dry use.

1337.367 - 1355.271 Leo Skepi

And cleaning it's easy, you just rinse it under the water. Also, there's a little LED spotlight on it so you can see what you're doing. We got more information. The ceramic blade is rounded for enhanced comfort and includes a built-in guard to minimize nicks and cuts. That's one thing I be doing all the time is cutting my neck. I never cut my face, but I cut my neck a lot.

Chapter 6: Who will manage Leo Skepi going forward and why?

1540.857 - 1563.542 Leo Skepi

Next day, I wake up and I get this random urge. Don't know why. Don't know who, what, when, where, how. It's nine o'clock in the morning and all of a sudden I get this urge. It's like a Tuesday, I think. I get an urge to go... to Highland Park. That's like the outside shopping center in Dallas.

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1563.783 - 1586.836 Leo Skepi

So it's like all the designer stores, the nice shit to Cartier, to Tom Ford, to Chanel, all like the Hermes, like the nice place. There's like the inside mall. And then there's Highland Park. It's like the bougie shit where one of my houses is close to. But I get this urge to go over there. I'm like, I don't know why. I don't want to buy nothing. I don't want to go shopping over here

0

1588.228 - 1615.607 Leo Skepi

I just ended the podcast deal. So why are you over here getting an itch to go shop? So you ain't brought no money in yet. What's this? I want to go shopping at the nicest stores. Huh? So I'm like, all right, I'm just going to trust it. But I was like, I ain't buying nothing. And then I come upstairs and I get dressed. Put my chain on, put my outfit on. I'm real cute.

0

1616.307 - 1644.102 Leo Skepi

And then I go drive into the store. It's like 930. I leave the house. For whatever reason, my soul want to go to Tom Ford. So I'm like, okay, let's go to Tom Ford. You expensive taste having little bitch. So here I go. Me and my soul walking up in the store. Just like, all right. And... I walk in and there's a bunch of shit set up. There was a full photo shoot going on in Tom Ford.

0

1645.122 - 1664.187 Leo Skepi

And they're in the middle of like breaking down and like putting all the backdrops and all the tripods and all the shit. Like they're trying to put all the lighting and like get it all wrapped up. And like they were doing a photo shoot before the store opened. And I walk in, I'm like, oh, is it a bad time to shop? And they were like, oh, no, no, come in. You're fine. I'm like, okay.

1665.231 - 1682.459 Leo Skepi

So I started stepping around like all this shit. I'm like trying not to be in the way. I'm like, oh shit, sorry. Like, I don't know. I feel bad. Like, I don't know why I want to stay in here. I felt uncomfortable and I wanted to leave. I was like, I don't want to be in the way. I don't want to be that asshole. I don't know how to take a hint. My soul didn't want to leave.

1682.68 - 1702.907 Leo Skepi

So I'm like, okay, I got to be the asshole. All right. I do not typically wear Tom Ford's clothes. It's not built for somebody like me. I'm 6'7". I got shoulders. I'm broad. I'm not a twink. I don't fit in, like, their stuff. Some stuff is fit for...

1702.927 - 1723.202 Leo Skepi

still like stretchy and some of it can go to my size but like most of it don't fit me like the colors of the shirts they don't go around my neck it's a little big so i don't know why i want to go look in the clothes so i'm like weird they do have some cool leopard shit so i go start looking in the clothes okay i don't know then somebody comes up to me

1724.281 - 1741.853 Leo Skepi

this guy, it was one of the guys who was cleaning up some of the stuff from the photo shoot. He's like, Hey, I'm a new supporter of yours. Like I see your videos. You're funny as shit. Like, I think you're great. I was like, thank you so bad. I was like, my bad. I'm in the way. Like, I feel bad. You guys are trying to like close everything down. He was like, Oh no, no, you're fine.

Chapter 7: Will Leo continue podcasting after ending his deal?

1881.915 - 1916.153 Leo Skepi

I'm sitting there. And then I started getting random ideas for products I want to drop for my clothing line. And I was like, Okay. And then the thought passed and I was like, all right, what the hell was that? Okay. Then the next day I spent the day in alignment with like everything that was going on. I had a full fledged moment where I was like as happy as I've been.

0

1916.173 - 1943.892 Leo Skepi

I was just like, Whoa, having a great day. I start seeing full fledged visuals of me, Three products that I want to drop. Like, I see exactly how they look. And what they are. One of them is the journal that I've talked about in previous episodes. I went through the whole thing of trying to make my own version of a gratitude journal because I don't like that whole fucking, today I'm grateful for.

0

1944.072 - 1960.799 Leo Skepi

Nah, I don't like that. I have my own way of doing a gratitude thing. And a lot of things have shifted. And I had an old manufacturer make it. They fucked it up royally. Couldn't make it to the standard that I wanted. It was pathetic. So I just threw away the whole idea and was irritated. And I'm not forcing nothing right now. And the idea for the journal came back.

0

1961.584 - 1984.836 Leo Skepi

And I was trying to pull it out of myself a couple weeks ago, but I was like, no, I'm not forcing it. It came back. Boots. So I also had two other products that I got an urge for, and I was like, these are more for me. They're products that I want. They're things that I want. I don't know if everybody's going to like them. And I just kind of had a weird, my soul was like, it don't fucking matter.

0

1985.056 - 2009.31 Leo Skepi

It ain't for sales. Stop forcing it. You're not forcing nothing. How people do the whole marketing thing, it's like you're so desperate and they're trying to sell you shit and they're trying to change what they're making to try to appeal to everybody. It's like Versace doing fucking silver to appeal to everybody. Tom Ford used black and gold and leopard and... Now you're doing silver everything.

2009.33 - 2033.227 Leo Skepi

They don't make no more gold... Why? Like these companies that are so desperate trying to appeal to everybody, it's like you've lost your identity. I despise that. So I don't want to be that. So I'm over here like test moment of like, I got to honor myself. It's like, I know these are products that I think only I would want. Maybe I'll be surprised. I don't know. But I see the visuals.

2033.648 - 2053.962 Leo Skepi

I feel the urge to talk about everything and tell my manufacturers. So I messaged them. They all of a sudden had a meeting open. Hey, we have a meeting, like a spot open in like an hour. I was like, okay, let's get on the phone. I want to talk. An hour and a half, we're on the phone. We's having a time. We was having a key, girl. We was all on the FaceTime.

2055.175 - 2072.871 Leo Skepi

So many ideas came out and I have like six more products I want to start working on. And I'm so used to hearing like, oh, we can't do that. Like you have this idea, you're explaining it. We don't have the, you can't make it like this. You can't do that. The company I'm with now is like, okay, what else? What about adding this, adding that?

2072.931 - 2087.84 Leo Skepi

I'm like, ah, like the fact that they can do it how I want it. Such a refreshing thing. So the call went great and I'm very excited about all the products. But like I said, I don't know if it's going to sell. Like everything is just about taking risk right now and like taking chances on myself.

Chapter 8: What are the latest updates on Leo's house hunting and personal growth?

2109.881 - 2134.144 Leo Skepi

But the bet you make on yourself is one you will never lose. So go all in, hell. I put out my whole stack of chips, everything on myself. Let's see what happens. I don't have an option right now. Like my soul is blowing up every sense of safety and like every fallback plan, every everything. My nursing license came up and I renew it every time. Every two years, you renew it.

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2134.184 - 2162.677 Leo Skepi

I do the CEUs and then I renew it. The CEUs are done. Something is telling me not to renew it. And I always had my nursing license as a fallback plan in case I need it again. Like I haven't needed it in like two, three years, I think. But I just like that safety net. My soul don't want it. So that's another thing. It's like my soul is just blowing up everything and I can't keep track of it.

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2162.737 - 2182.654 Leo Skepi

I can't make logic out of it. I'm just following it and seeing what happens. Okay. But after all this today, ah, another secret history, this story, I have been wanting to remodel some things in my house and like have my wallpaper hung up in my bedroom that I want to get beside you while we put it on a ceiling. Um,

0

2183.894 - 2204.731 Leo Skepi

I went through a whole thing of like these certain people that came to my house and gave me a quote. They quoted me $12,000 just to install the wallpaper. They look at it and bust them across their fucking neck with a golf club. Disrespect me like that in my house. You think I'm that stupid? I know you looking at me being like, oh, this bastard, we could take advantage of him.

0

2206.325 - 2227.503 Leo Skepi

You're lucky I didn't hang you from my fucking balcony. Okay. I'm not stupid. I'm funny. I'm goofy, but I'm never to be underestimated. I'm never stupid. I know what's going on. $12,000 to hang some wallpaper. After the little scammers went, I stopped having an urge to like put the wallpaper up and remodel my house. So I'm just like, all right. whatever. It wasn't like discouragement.

2227.563 - 2257.497 Leo Skepi

It was just like, wait for a second. And all of a sudden my urge has like come back of like, I want to remodel things and get wallpaper and stuff. So I want to do my whole kitchen. Why am I having the urges after I just cut off my biggest source of income? I don't fucking know. We just going to go with it. So last night I tell myself that, Okay, so you want to have some urges to remodel the house?

2257.977 - 2277.377 Leo Skepi

Find me somebody then. Kind of like I did with the photographer. And I was like, I don't want this to be a hassle. I don't want to deal with trying to find people and post on social media and ask and have to vet through all these people. Just fucking make it happen. I don't want to deal with the hassle of it. I was being prude about it. I was being a little ethos.

2278.097 - 2301.005 Leo Skepi

I was setting a boundary down with my soul. If you want to desire all this shit, okay, line it up. And that is one thing that my soul will do is line it up. But it's going to test me first. So today I'm having a great day. Everything's been going great. And I was driving back home from running errands and shit. And I look over and I like saw this girl.

2302.335 - 2320.278 Leo Skepi

who was outside doing advertising for a sushi restaurant. And she had one of the big signs and she was holding it. You know how back in the day they used to have the people out front and they would spin the signs and flip them around? It's not like that. Like that shit is so obnoxious because I can't fucking read the sign. You over here slinging it, throwing it around. I can't fucking read it.

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