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Podcast Host
In this lessons episode, explore why sudden wealth and identity tied to performance often lead many athletes toward financial struggles after their careers end. Discover how pressure and comparison push high earners toward unnecessary risk. Learn why focusing on consistent singles and doubles builds lasting wealth. And understand how evaluating character risk and deal structure leads to smarter investments. So a couple, a couple points. First thing, I was looking this up. 70% of lotto winners lose their money or go bankrupt in five years. So that's 70% of people that know they're not going to get another paycheck burn through that money. So think about that for a second. So imagine now you're making that kind of money and then you think you're going to get another paycheck you think you're going to get. And that's not just a one time event. Now that's ingrained in you over 15 years. So that's messing with you. So you're not, you're not thinking in the right mindset obviously now I think that you.
Former Athlete / Investor
And here's, and here's the second point to that. And here's the follow up to that. Your whole life you've been solely focused on your sport, solely focused on being the best at your sport that you can be. Most likely not focusing on your schooling as much as maybe you should. And now you're done. Now what? You're. You, you've solely immersed yourself in this sport. You spent every waking second grinding at your sport. And now what? And a lot of times your, your whole identity is built around your sport. Here's Scott, the hockey player. How you doing? It's not Scott. It's not Scott from Toronto. It's not Scott from whatever. It's got the hockey player. You're a hockey player? No, no, I, I play hockey, but that's not who I am. That's not my soul person. So it, it that. And that the more you hear that over and over and over and over again, it tends to get ingrained in you. And it's so, and so the football players. So now, now you think you're just a football player. Oh, you're just a dumb jock. You hear that over and over again. Now you're just a dumb jock. And, and you hear these things over and over and over again and people just end like, all right, maybe I am. Because you hear it all the time and they're unwilling to buck the trend and, and buck what people's perceptions are. And so, you know, you're, you're kind of just going with the flow as opposed to trying to break that cycle and, And. And being smart with your money and being smart with what you're doing and how you're kind of laying it all out there. You know, everybody wants to take care of their family, Everybody wants to take care of their friends, but at what cost? Like, you know, it. It just. It can. Some of the stories you hear, you're like, I can't believe that happened.
Podcast Host
So out of the guys you played, the guys you play puck with, what percentage of them do you think struggled to some extent? Guys that you're close with, huh?
Former Athlete / Investor
Yeah, I don't think a lot. A lot of the guys that I played with, you know, some are. Some are struggling. There's no question. Like, the problem is you don't hear about it, you know, because they're embarrassed because they don't want to ask for help, because they don't. They're unwilling to kind of open themselves up for criticism because they made mistakes, they got into a risky deal, they thought they were going to hit the lottery, and. Or they went to hit the lottery again. Like, you know, you think, oh, I just won the lottery. I made $10 million playing my sport. You should be creating a nest egg and, and building off of that. Instead, you're risking it all, thinking you want to be LeBron James or Kevin Durant and doing all the stuff that they do. Meanwhile, they're making 40, 50 million bucks a year playing their sport. They can take those risks, and they're making hundreds of millions of dollars in endorsements. People look at the cream, cream, cream of the crop and think, I want to be there. They have no chance of getting there. You have to be comfortable in who you are and where you are in order to be a sound investor, you know, and. And look, for singles. You know, I tell people I just want singles and doubles, and if a double turns into a home run, then great, but I just want singles and doubles. And the more you do that over and over again, as you know, you're. You're going to have a lot of success. And too often these people, they're. They're constantly trying to hit home runs. Why? I have no idea. They're not satisfied with whatever they've got, or they see this guy flying around on a private jet and this guy with a freaking McLaren or whatever, or he's on a yacht or whatever. I mean it. And they're. They're jealous. So they start risking it all for no reason. And. And it's really just the mindset and, and their mind playing games on them. So it's understanding and it's hard for athletes to, you know, you're. You're competitive, you're driven. You know that you're using that as a tool to push yourself, but it's. You're pushing yourself at. You're taking a lot of risk that you don't have to take. And it, and it's, it's hard for some guys to kind of get out of that competition and, and, you know, always trying to be better than the next guy and, and just being happy with where you're at. And, you know, there's. There's certainly lots of guys that struggle. There's lots of success stories, there's lots of guys that are struggling. I think you see that in all walks of life. You know, it's just as an athlete, it's front and center and it's in the paper, it's on tv, it's whatever, it's on social media. I mean, I see people all the time that, you know, had great jobs and made a lot of money, and now they're struggling for whatever reason, you know, whether they're trying to keep up with the Joneses or, you know, trying to be somebody who they're not. And, you know, I think that's, you know, the biggest takeaway for me is understanding who you are and then being who you are and not worrying about, you know, living this whatever dream they're living over there and just live your own dream, live out your own life. And, you know, I think that's where a lot of players really struggle because they're. They're trying to be something.
Podcast Host
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Former Athlete / Investor
Yeah, I. I made my fair share of mistakes too.
Podcast Host
Don't get me wrong, okay? Give a good. Give a good mistake. Give a good mistake. Because that's always interesting.
Former Athlete / Investor
Poor investments, you know, Like, I, I, I, you know, bought a second. Why? I don't know why. I bought. I bought a second home, thinking, okay, well, I'm gonna. I'm in St. Louis. You know, it'll be a good, great place for my wife to take her kids in the wintertime. They're young. They can go hang out in the beach while we're off for a week playing. And then I get traded. So now I'm like, well, that one wasn't finished yet. So then I'm like, all right, we'll wait over here. I mean, you just. You don't logically think things through, and then next thing you know, you're saddled with two properties that you don't use. You're like, okay, and you have your main one, and you're like, hey, why do I need all this crap? And then the market tanks. You're like, okay, great. And it just. You're, you know, you're. You're not paying it. You don't. First off, you're not paying attention to all that stuff because that's not your job. You're focused on your job, and you're just doing things without really looking at the. With. With unintended consequences. And then you're not. You're not realizing how deep you're into it, you know, And. And, you know, you're thinking, all right, this looks like a great idea. You know, you're look, you know, you see some of these deals, and they're just totally bloated with fees and all kinds of stuff. Basically trying to take advantage of you.
Podcast Host
Yeah.
Former Athlete / Investor
You know, it's Just some, sometimes it just. You make mistakes, you know, and I, I tell my financial guy all the time, listen, out of those mistakes and out of that money that was lost came a really good guidelines for what we want to invest in and then guidelines for who we don't want to invest with. And, and, and as you make those mistakes, you're able to really understand what good deals look like and what bad deals look like. And, and ones that are in your wheelhouse and other ones that they may, you know, what, they may be home runs, but they could just as easily go to zero. And you, you have to kind of be willing to, you know, let those potential grand slams go for the, you know, singles and doubles that, you know, you're just going to kind of chip away, chip away, chip away, because you don't have to, you don't have to hit the home run. If it happens, great. But the, the premise around the investment is that it's not going to be a home run. It's going to be a really good deal and you're going to make money. Wealth preservation versus crazy risk for no apparent reason whatsoever. And so, you know, once, once you make those mistakes, you learn real quick. Okay, I don't like that feeling. I don't like that. And I, and I'm not a big gambler. I learned, I learned early on when I was a kid. I started playing in between and I hit the post and I lost a crapload of money. And I'm like, As a kid, and I'm like, all right, I'm not, I'm not a gambler either. I don't like this. So I just, you know what? I learned my lesson. All right, that was my, that was my investing gambling story. And I'm like, all right, I'm done. I'm not doing that no more.
Podcast Host
So, so what's the lesson that you learned? So when, when you look at, when you look at investments now, who do you invest in? What's safe for you? What do you, what do you try and focus on? Give it. Obviously, this is not parameters, parameters and guidelines.
Former Athlete / Investor
Parameters and guidelines would be a character of the people, structure of the deal, leverage, you know, upside versus downside. You know, what's the, what's the risk reward look like? You know, there's, there's a number of factors, but, but a lot of it boils down to the, the character of the deal maker and, and then, you know, what, what the risk profile looks like vis a vis, whether it's leverage, you know, what the sector is what type of investment it is and. And kind of really anything that doesn't fit in inside those guardrails, I just. I just get rid of them. Like, I'm not interested.
Podcast Host
Are you. Are you more personally invested in, like, things that are more early stage, or do you like doing more profitable cash flowing later stage? Get a piece of. Yeah, Shaq does all these franchises and whatnot, right?
Former Athlete / Investor
Yeah, yeah. He's got a little bit more money than I do.
Podcast Host
Listen, everyone plays at their own level. It's all good.
Former Athlete / Investor
That's right. I was just saying that. But you gotta know. Yeah, yeah, yeah. More cash flowing. More. Less risky. Yeah. You know, you know, there's a. There's a time and a place for venture capital and for risky. You got. You got to understand, you got your buckets, and you got to use those buckets appropriately. I mean, it's not like you don't do any risky stuff, but you try to look at the tranches and how big the buckets are, and then you allocate them accordingly. And, you know, obviously, if you're talking venture, that's crazy risky, but the rewards there. Yeah. So kind of picking and choosing.
Podcast Host
Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one.
In this insightful "Lessons" episode, Scott D. Clary speaks with NHL legend Chris Pronger—now an investor and entrepreneur—about the pitfalls of sudden wealth, pressure-driven risk-taking, and the identity challenges athletes face transitioning from professional sports. Chris reveals personal mistakes, discusses why consistent "singles and doubles" build lasting wealth, and breaks down his own investing philosophy. The conversation provides real, tactical advice for athletes, entrepreneurs, and anyone navigating the pressures of high earnings and public expectation.
On athlete identity issues:
“You’re a hockey player? No, no, I play hockey, but that’s not who I am. That’s not my soul person.”
— Chris Pronger [00:58]
On financial pressure and risk:
“They’re jealous, so they start risking it all for no reason... You’re competitive, you’re driven... You’re taking a lot of risk that you don’t have to take. It’s hard for some guys to get out of that competition, always trying to be better than the next guy, and just being happy with where you’re at.”
— Chris Pronger [03:11]
Learning from loss:
“Out of those mistakes and out of that money that was lost, came a really good guidelines for what we want to invest in and... As you make those mistakes, you’re able to really understand what good deals look like and what bad deals look like.”
— Chris Pronger [11:48]
Investment philosophy:
“You don’t have to hit the home run. If it happens, great. But the premise around the investment is that it’s not going to be a home run—it’s going to be a really good deal and you’re going to make money.”
— Chris Pronger [12:38]
This episode is a must-listen for anyone—athlete or otherwise—grappling with pressure, sudden wealth, and the search for sustainable success beyond the “game.”