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A
This is the Jocko Underground podcast number 203, sitting here with Echo Charles. And we have received quite a number of questions from you, the troopers in the field. And we will provide, to the best of our abilities, answers, possibly recommendations, guidance, or at a minimum, some courses of action that you can follow in order to move forward. And that's what we're doing. Let's get into it.
B
All right, first question. Hi, Jock. Welcome. I won the lottery a few years ago in my state. Literally won the lottery. Not, not the, you know, any other kind of the real lottery. Okay. Long story short, there are family members and friends coming out of the woodwork asking me for money. They asked for loans and also. And also just asking me for money directly. I'm fully aware that they believe I don't deserve this money and that I. That it was all one big freebie. Two relationships that I've had are already completely gone because of this, just from me saying no. And a few, a few are strained at the moment. Part of me doesn't mind, but how do you suggest I handle my situation when people that are close to me and others not so close ask me for money, loans and or quote, unquote, help in my situation?
A
Yeah. Well, congratulations, I guess, right? Win the lottery. Good job. And that being said, have you not heard of like all these kind of. I don't know if they're urban legends, but I don't think they're just urban legends that like people win the lottery and everything goes to in their lives. Have you heard that kind of urban legend before?
B
Yeah, from my understanding, all the people that talk about it, this is. It's a factual thing. So they do like the study on like lottery winners and stuff and. Yeah, I think it's like, it's like 80 something percent of them. Yeah, they're worse off after a certain amount of time.
A
All right, so it sounds like you might be feeling just at least a little bit of that, right?
B
Starting to, yeah.
A
So I think just out of the gate, like setting boundaries and just telling everyone no sort sort of is kind of what you're going to have to be and get that reputation out there where people just, bro, you give money to one person, they're all coming for it. Maybe too late for that. You know, you might have already given it. You know, you loaned your mom some, you loaned your brother, and then your brother's friend came over and then his brother's friend's sister was also in a kind of a bad situation and it was just a few thousand but you see what I'm saying, You know where this goes. And so I. I think that's one of the best things to do. It's a little late right now, probably, but you can still start being like, yeah, no, I don't. I can't give away any more money. Like, nope. And you don't even. Even that reason. You don't even need to give a reason. You know, when. When someone asks you for something and you say no, and then you give them a reason? It's almost like that reason that you give is something that they can negotiate with.
B
Right. Feels like. So.
A
Hey, can I. Hey, do you mind if. Do you mind if we come by tonight? Well, no, not tonight, because I've got the, you know, my daughter's practice. I'm picking her up. Well, we can come over after that. You see what I'm saying? As opposed like, no, you can't. And so, look, you're gonna go through a little bit of. What's the, you know, little bit of people go, I can't believe you. You know, it doesn't. Won't give me any money, but fine. So that's. That's something that you can do is, you know, definitely no beating around the bush. No. No money. Another thing that you could do. And again, I've never been in this scenario, but invest the money. Kind of like a public, relatively public kind of way where, you know, you say, actually, no, I can't give any money right now because I bought this and I bought that, and I have this business going and I have this property over here, so I don't have any money to giveaway again, you're kind of programming yourself a reason, and they'll go, if you knew you. You can buy that business. You can give me a few thousand type stuff. So again, I don't know. That's the best. You know, you're basically tying up your money or you're giving yourself a reason. But again, the warning around that is when you have a reason, people will be like, well, I can still wait until next month. Or, what about when, you know what I mean? They'll be there for you. You can also maybe. And again, this is something I've not been through. Maybe put the money into some kind of a trust or like an executor who controls it and that. That way when someone's like, hey, can I borrow some money? Like, no, I don't. I don't. I don't even manage that money. What do you mean you don't manage them? Yeah, I gave it to this company. They manage all the money. I don't touch it. Why'd you do that? Because it's too crazy. I don't know what to do with it. I'm too young, I'm too dumb, I'm too immature. Too many people are asking me for it and I just didn't want to deal with it anymore. So I don't touch it anymore. Well, where'd you get money for that new Ford F350? Well, they allotted me a certain amount of money for a vehicle and I got the vehicle. Well, where'd you get the money for that boat that you bought? Well, they gave, you know, I set aside money for the boat, but, you know, that's where I'm at. But where'd you get the money for the ATV that you brought? You know, I asked them and they give me what they allot me. But one thing they're not allotting me is to give money away. So, no. So kind of cutting yourself out of it, you know what I mean? Kind of cutting yourself going, look, somebody else manages that money now. And by the way, that's probably a smart thing to do, you know, as long as you find a trustworthy person. But you find a trustworthy person that can manage your money, they'll put it into good stuff and you won't have to worry about it. And you say, no, I don't deal with. I don't even touch that money. That money that I want, it's not my money anymore. It's in the trust. What's a trust? It's a place where I can't touch it and give it away and spend it all in dumb shit. But what do you mean dumb? You need to live it up a little bit. I'm living fine. I got a house, I got my truck, I got my ATVs. That's all I'm getting. So if you want money from me, if you want to hang around with me to get my money, you're hanging around with the wrong person. You're better off going down to the local pub and see if you can get someone to buy you beer, because I ain't buying beer. It's a bummer, man. When you get this kind of money and people find out, then it's like they're coming after you. It's, it's, It's a bummer to hear that. You know, I'd love to tell you if someone wants to borrow money from you, cool, get terms and, you know, get interest. But like, they don't give a. You ain't gonna see that money again. So, you know, you could say, I'm gonna put your house for collateral. What, are you gonna take their house from them? Yeah. You know what I mean?
B
Yeah. Like, make it worse.
A
Make it worse. Make their life worse. Make your life worse because now you're an asshole even bigger. You know what I mean? So listen, I think all this being said, I think the situation here is you just say no. Nope, Nope. Don't loan money. Nope. I don't give money away. What do you mean? You gave Jennifer, you know, 12 grand last year for her deck. New deck. Yep, I know. And that's why I can't do it anymore, because it was a new deck there, and it was a boat over there, and it was a college fund for this kid over there, and I don't. I'm not doing it anymore. Nope, nope. There's a. That. That thing again. I think that's the best thing is it's from you. Not. I think that's better than the accountant, better than the executor, better than the. The money's already invested is just the solid. No, I think that's the best way to go. Again, I've not been in this situation before, but let's. Let's make you. Not the statistics of things getting worse. Let's make you the statistic of, yep, you look up in 10 years, maybe you got a new set of friends, because maybe some of these people don't. You know, the only reason they want to hang around with you is because you got money. So maybe you got a new set of friends in 10 years. And, you know, I had a guy tell me one time, like, every. Everyone's going to want something from you.
B
Yeah.
A
And I was kind of like, I didn't really understand. He said, no, everyone's gonna want something for you. I was kind of like, that's really. And then I wouldn't say everybody wants something from me, but a lot of people do want something from me.
B
You understood what he was talking.
A
I understand it now. I can see, like, oh, yeah, people want something from you. And again, this is not just. This is like being in the military. Like, when I. When I'm the. When I became an officer, it's like, oh, people are gonna want stuff from you. Well, I don't know, man. I'm just one of the boys. No, guess what? You're not just one of the boys. They want this, they want that. So you got to pay attention to it. And I think in a scenario like this, man, as Nancy Reagan once said, just say no. I think that's what we got to do.
B
Yeah. And even then, that's not easy, you know?
A
No, it's definitely easy because, yeah, you're kind of. Damn.
B
It's crazy, right, what money does and is and whatever. So the especially free money, or perceived free money is. That's really the. The deal, you know, because, like, yeah, you. You just say unilaterally from the beginning, not, you know, sorry, across the board, right from the beginning. No, everyone's like, oh, my gosh, you didn't even earn that money. Maybe they don't say that, but, like, that's their feeling, right? You didn't earn that money. You got it as one huge, huge, abundant freebie. And it's like, what, you're that greedy, you know, like that you're just like, you got all this stuff not earned, and then now you just want to hoard it all for yourself.
A
That's the thought, right?
B
And, yeah, and you just watch people who. You're literally like the day before, like, it's your. One of your best people, friend, family, whatever, and then now they're just not. You didn't do anything to them. It's crazy, man.
A
By the way, you know what's interesting is, you know how many people, if you ask, if you take a rich person, just a rich person, and, you know, whatever they did, however they may end up with, they end up with a good amount of money. They're driving a very expensive car. They have. They have three expensive cars, let's say three expensive cars, and they have three sick houses, and they live in kind of a mansion. If you ask 10 people if that individual deserves that money, I say 7 out of 10 say you didn't deserve all that. So that is a little excerpt of what we are doing on the Jocko Underground podcast. So if you want to continue to listen, go to Jocko underground.com and subscribe. And we're doing this. We're doing this to mitigate our reliance on external platforms so we are not subject to their control. And we are doing this so that we can support the Jocko podcast, which will remain as is free for all as long as we can keep it that way. But we. But we are doing this so we don't have to be under the control of sponsors. And we're doing it so we can give you more control, more interaction, more direct connections, better communications with us. And to do that, we are. We're building a website right now where we'll be able to utilize to strengthen this legion of troopers that are in the game with us. So thank you. It's Jocko. Underground.com it costs $8.18 a month. And if you can't afford to support us, we can still support you. Just email assistanceacounderground.com and we'll get you taken care of. Until then, we will see you mobilized Underground.
Date: March 2, 2026
Hosts: Jocko Willink & Echo Charles
In this episode, Jocko Willink and Echo Charles tackle a listener's question about dealing with the social and emotional fallout after winning the lottery. They explore the challenges of sudden wealth, setting boundaries with friends and family, and maintaining discipline—tying these situations to broader themes of leadership, accountability, and human nature. The conversation is practical, candid, and rooted in both personal experience and common sense.
[00:25]
[01:18]
"I don't know if they're urban legends, but I don't think they're just urban legends that like people win the lottery and everything goes to sh*t in their lives."
— Jocko ([01:18])
[02:01]
"You give money to one person, they're all coming for it... You can still start being like, yeah, no, I can't give away any more money. Nope. And you don't even need to give a reason."
"That reason that you give is something that they can negotiate with."
— Jocko ([02:56])
[03:10]
"Somebody else manages that money now. And by the way, that's probably a smart thing to do... I don't even touch that money."
— Jocko ([04:05])
[06:35]
"I’d love to tell you if someone wants to borrow money from you, cool, get terms and, you know, get interest. But like, they don't give a sh*t. You ain't gonna see that money again."
— Jocko ([06:35])
[06:44 – 08:21]
"I think that's the best thing... It's the solid No, I think that's the best way to go."
— Jocko ([07:51])
[08:58]
"You didn't earn that money. You got it as one huge, huge, abundant freebie... And it's like, what, you're that greedy?"
— Echo ([08:58])
"If you ask 10 people if that individual deserves that money, I'd say 7 out of 10 say you didn't deserve all that."
— Jocko ([09:56])
This reflects larger social attitudes towards wealth, especially windfalls.
The conversation is direct, blunt, sometimes humorous, and always rooted in Jocko's disciplined, "no-nonsense" perspective. Echo balances the conversation, sharing relatable observations and reinforcing the emotional complexities. The overall takeaway is one of tough love, self-protection, and awareness of human nature.