Chris Pronger on Investing, Business, and Life Outside of Hockey – EP 66

Interview with Chris Pronger

Chris Pronger on Investing, Business, and Life Outside of Hockey

Today, I’m talking to Chris Pronger. And yes, I’m referring to the NHL Hall of Fame Hockey Player!

Chris had an absolute legendary career as a defenceman. He got to the Stanley cup finals with three different teams, won the cup with the Anaheim Ducks in 2007, won the Hart Memorial Trophy as the NHL’s most valuable player for the 1999-2000 season, won Olympic gold medals at the 2002 and 2010 Winter Olympics, and was named one of the “100 Greatest NHL Players” in history.

While Chris is considered a major success in the world of hockey, it’s not the only thing that defines him. He’s also a father, husband, investor, and entrepreneur. And today, we talk about all of it.

You’ll hear some fun stories from his playing days, his guiding principles for making smart investing decisions, and the story behind building a boutique luxury travel company with his wife. That and a whole lot more!

Featured on This Episode: Chris Pronger

✅ What he does: Chris Pronger is a retired hockey hall of fame NHL player, Investor, and Founder of Well Inspired Travels – a boutique travel company focused on creating tailor-made wellness experiences.

🔎 Where to find Chris Pronger: Website | Twitter | Instagram |

Key Takeaways with Chris Pronger

  • Chris Pronger career highlights.
  • The 3 most important qualities that lead to greatness
  • The chances of making it as a professional athlete
  • Being hated by fans and getting booed early in his career
  • Getting a slap shot to the heart and nearly dying.
  • Becoming much more than just a hockey player.
  • Starting a luxury travel company with his wife.
  • Why the pain of losing money is your biggest teacher
  • Why you don’t have to hit a homerun in investing to win

Clips from the Show with Chris Pronger


Episode Highlights

Keep Reaching for Your Goals

I think a lot of people go wrong as they reach, I want to get to the NHL, and that’s their goal. They don’t set another goal. They don’t say, okay, well, I’m here. Alright, I want to be a top 4 defenseman. I want to be a top 2 line forward. I want to be a 50-goal scorer. I want to be a Norris Trophy winner. They don’t keep setting new goals and they’re just happy to be there and happy to be along for the ride. And I think early on in my life, I figured you got to keep setting goals, and once you attain those goals, you gotta keep moving the ladder and moving the rung of the ladder to get higher and try to achieve those higher goals to push yourself.

 I think too often, we don’t push ourselves enough. And maybe I went even further and pushed myself too hard or too far. But you need to be able to push yourself and then create discipline and boundaries and what you’re willing to sacrifice and not willing to sacrifice to be successful. And I would say when you look at the greats of any game or any sport, sacrifice, discipline, and work ethic are the three most critical things that they go through that allow them to get to where they are. Talent is, obviously, inherent and a part of it, but without those first three things, the talent doesn’t really matter.” – Chris Pronger

Overcoming Adversity

Yes, I was beloved, but early on, was booed and hated because as you said, when you come into a new place, I was traded to St. Louis in 1995 as a young 20-year-old and was traded for a fan favorite and Brendan Shanahan, and I got booed every game. I was hated because I was the one who got traded for the guy, the other one. And so, it’s like anything else, sacrifice, discipline but also adversity. You’re going to hit those forks in the road and then you can cave and crumble or you can push through and find a way and become successful.

 And it certainly wasn’t easy that first year. There was a lot of sleepless nights, a lot of painful memories, and a lot of painful games, but that particular time in my life certainly made me stronger and gave me more character and more strength to push through the difficult moments in life that you’re ultimately going to face as you get married, have kids, and go through a family process and all the rest of that. And then, when you start making investments and making decisions of that caliber, you need to start relying on a lot of those decision-making skills and a lot of things that you went through early on in your life that ultimately help guide and steer you.” – Chris Pronger

A Puck to the Heart

We were playing a playoff game in Detroit, and the defenseman got the puck, and I went out to block the shot. And it happens in Little League a lot. I blocked a shot, and it hit me directly in the heart. And what happened was my heart was in between heartbeats. So, when the puck hit my heart, it triggered something in my brain to basically say, okay, the heartbeat, I skipped one heartbeat and I got hit, and it hurt, and I was like, alright, you’re in Detroit, and I’m like do not let these people see you laying on the ground. So, I’m like, alright, cover the puck up, get a whistle. And then I’m like, hey, get up and get to the bench because I knew I was in our corner, and the bench was like, I don’t know, 30 feet away.

 So, in my head, I’m saying get up and I think I’m getting up, but I black out, and you could see my eyes are kind of out of it. And I stand up. When I go to skate to the bench, down I go. And to our good friend’s point, I had an arrhythmia where it’s called commotio cordis. My heartbeat skipped one beat, and that’s how much oxygen gets pushed through your body in one heartbeat. I didn’t have enough oxygen and down I went.” – Chris Pronger

So Much More Than A Hockey Player

Yeah, I was never a big fan of being called ‘Chris the Hockey Player.’ There’s so much more to life and so much more to myself and to what I bring to the table than just being ‘Chris, the Hockey Player.’ Yeah, that was my job at some point and I was passionate about it, but it’s only three hours of your day.

 And so, for me, it was being smart and being a sponge and learning about investing, learning about being an entrepreneur, learning about business, learning about other things that interested me while I was playing while still being focused on my career and knowing that that’s the breadwinner and that’s what I’m good at, but also knowing that at some point my career is over and I’m going to be a young man. And what’s next? And how do I get there? And what’s going to get me there?” – Chris Pronger

Building a Luxury Travel Company

24 years ago, the hospitality space was pretty small as it relates to health and wellness. And so, my wife would source properties and things of that nature. And then when social media kicked on the final end of my career in Philly, she had a little social media account and private account with friends and family and followed some athletes and some entertainers and whatnot. And they’re always asking, ‘Where do you source these properties? How did you find them?’ And so, she started just helping people out as a friend, just setting up trips, and 20, 30 trips later, the light bulb moment goes off, like, okay, there’s something here. There’s that trust factor that bonds that ability to connect with people and understand what they’re going through, what they’re needing.

 So, it was really just helping support her. It was a passion of hers. And I was working as senior advisor to the GM in Florida at the time and helping her build out the business plan and make some connections and whatnot. And I was always the guy that set up the golf trips, the fishing trips, the Super Bowl pool, the Masters’ pool, and I’m kind of quasi event planner if you will, and really sort of enjoy just the happiness that is extended through hospitality and talking to people and just the joy. I mean, sports, when you’re invested and involved in it, is pretty miserable. It is pretty negative. Only one team wins a year. So, you’re brokenhearted. It’s just doing it for 30-plus years and being told where to go, what to do, how to do it.

 This was such a change of pace and a passion because knowing what we know, what we’ve experienced, our niche clients are athletes, entertainers, CEOs, business owners. And when you look at that niche clientele, our unique ability to understand the demands in their time, the pressures of the job, the fame, the fortune, the stress on home life, the pressure on kids, all of that stuff we’ve been through it, we understand it. So, for us, when we’re talking to our clients, we really get to know them on a much more personal level, asking questions to really kind of dig deep to figure out what they need, where to steer them. And as my wife says, it’s matchmaking for travel.” – Chris Pronger

Chris Pronger Tweetable

“I was never a big fan of being called ‘Chris the Hockey Player’. There’s so much more to life and so much more to myself and to what I bring to the table than just being ‘Chris, the Hockey Player.’” - Chris Pronger Click To Tweet “You’re going to hit those forks in the road and then you can cave and crumble or you can push through and find a way and become successful.” - Chris Pronger Click To Tweet

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Read the Full Transcript with Chris Pronger

Justin Donald: Well, Chris, I’m so excited to have you on the show. This is going to be so much fun. You and I, we’ve had a chance to really get to know each other here the past year and a half. And I’ve just thoroughly enjoyed your humor, your stories, the adventure that you live your life through this lens of just, hey, what’s next, and how can I conquer the next thing? And so, I’m really excited to really share your story with our audience back from kind of the big days of hockey to what it is today that you’re doing. And so, thanks for being on the show. So great to have you.

 

Chris Pronger: Thank you. Thanks for having me. I’m looking forward to it.

 

Justin Donald: Yeah.

 

Chris Pronger: I see, do you want me to treat you like I normally treat the media?

 

Justin Donald: No, but I do know some funny stories that you’ve shared with me about things that you’ve done with the media, particularly a cameraman who kind of got in your way or got in your face at an inopportune time.

 

Chris Pronger: That’s accidentally on purpose.

 

Justin Donald: Yes. I don’t know if we should have that, be a cliffhanger. I don’t know if you want to get into that.

 

Chris Pronger: We’ll let that marinate out there for a while.

 

Justin Donald: I like it. I like it. Hey, I love seeing The Lifestyle Investor on your bookshelf right behind you. Nice placement.

 

Chris Pronger: Great reading material right there.

 

Justin Donald: I love it. Well, that is very flattering.

 

Chris Pronger: Always trying to improve my knowledge.

 

Justin Donald: Love it. Thank you. That’s really cool, man. Well, it’s neat to know someone that has really played the game of life at such a high level. You meet people all throughout life, and some people are okay to certain things. Some people gain mastery in a certain thing, but you are one of the greatest NHL players. I mean, you think about how hard it is to get in the NHL, and I’ve heard your story from you via something called that we do in Tiger 21, called the Portfolio Defense where you get to kind of share your story and share how you got to where you are.

 

And so, I know how hard it is to get into the NHL. I know how hard it is to stay healthy and continue playing in the NHL. And then for you to go on and do all the things that you did where you won a Stanley Cup, which is the ultimate pinnacle. It’s the thing that everyone dreams of. And you did that and you were an MVP many times over and you were an Olympian. I mean, you lived this life as an NHL player that even NHL players would only or could only dream of. And so, I’d love to kind of hear some of your thoughts around that, what it’s like, if it was surreal, if you had a vision of that, and so, it wasn’t odd for you, you knew that that was going to happen.

 

Chris Pronger: Yeah, well, I think you touched on the good parts, and as we all know, the glamorous side of things is just that, the glamorous side. But there’s also the other side, the hard work, the sacrifice, the discipline, and things of that nature that help get you there, help keep you there, and help elevate you in your career. So, it was always a passion of mine to play hockey, play in the NHL. I think you go through stages of you’re pretty good and then you match up against players, you’re like, alright, I am pretty good. Now, alright, what’s the next step? And you keep hitting these hurdles.

 

And I think a lot of people go wrong as they reach, I want to get to the NHL, and that’s their goal. They don’t set another goal. They don’t say, okay, well, I’m here. Alright, I want to be a top 4 defenseman. I want to be a top 2 line forward. I want to be a 50-goal scorer. I want to be a Norris Trophy winner. They don’t keep setting new goals and they’re just happy to be there and happy to be along for the ride. And I think early on in my life, I figured you got to keep setting goals, and once you attained those goals, you got to keep moving the ladder and moving the rung of the ladder to get higher and try to achieve those higher goals to push yourself.

 

I think too often, we don’t push ourselves enough. And maybe I went even further and pushed myself too hard or too far. But you need to be able to push yourself and then create discipline and boundaries and what you’re willing to sacrifice and not willing to sacrifice to be successful. And I would say when you look at the greats of any game or any sport, sacrifice, discipline, and work ethic are the three most critical things that they go through that allow them to get to where they are. Talent is, obviously, inherent and a part of it, but without those first three things, the talent doesn’t really matter.

 

Justin Donald: Yeah, there’s no doubt about that. And obviously, you’ve got to be ultra committed. You have to eat, breathe, sleep hockey, or whatever the thing is to become a true professional, true expert, in your case, a Hall of Famer, an Olympian, a multiple-time MVP. So, quick question for you. So, I remember you sharing a stat when you were talking about getting into the NHL. What was that stat? How hard is it to get, to actually make it into the NHL?

 

Chris Pronger: Yeah, so when I had just gotten into the NHL, they did have just the stat of Ontario. I’m from a small town in Northwestern Ontario, but they took Ontario as a whole because of Toronto being the mecca that it is. And I think there was something along the lines of there are 100,000 minor hockey kids playing. Of that 100,000, 5,000 play AAA hockey. Of that 5,000, 500 get drafted into the OHL, let’s say, which is the Ontario Hockey League junior hockey. And of those 500, 50 of them might get drafted. And of those 50, five might play a game in the NHL. And of those five, one might have a long career in the NHL.

 

So, you start breaking it down and looking at percentages and looking at how it all plays out. And then you look at the league and go, okay, well, that guy’s been in the league 10 years and he doesn’t look like he’s going anywhere. And you start mapping out the openings and things. There’s not a lot of openings every year. And so, you got all these first-round picks and all these players signing new contracts and free agents and all this stuff. How do you get– you’re in? And then how do you take advantage of it? And then how do you stay there, and then, all these things that transpire afterward? And from a statistical standpoint, I think to play professional sports, in general, it’s like winning the lottery.

 

Justin Donald: Yeah, there’s no doubt. In fact, this reminds me of one of my all-time favorite movies and one of my favorite lines from that movie, so Top Gun. So, you’re the one, and truly, you’re the one. I mean, that’s incredible because not only does it take it like, not only is this hard to get there, Chris, but on top of that, you have to stay healthy. So, a lot of people, they’re good enough to keep playing, but they can’t stay healthy. A lot of people, they actually aren’t good enough to compete with the next generation of athlete that comes in the following year, two or three years down. And you can see a big gap in their game versus the new young, hungry, in shape athlete that hasn’t yet been injured and beat up the way that the professionals have. And so, it’s amazing that you were able to play such a gruesome sport. I mean, there are tons of injuries. This is a rough sport, but you can play it for so many years. How many years were you a pro hockey player?

 

Chris Pronger: Nineteen years. While I was playing, I had 13 surgeries and then two knee surgeries post. And then I recently just had knee replacement surgery to hopefully remedy the last part, so that I don’t have to do that ever again.

 

Justin Donald: Wow, that is intense. And I’ve seen some of the scars, some of the wounds that you’ve shown me and…

 

Chris Pronger: Hold on, let me show you now.

 

Justin Donald: It’s not for the faint of heart, that’s for sure.

 

Chris Pronger: No.

 

Justin Donald: I mean, man, but what’s cool is you’re going to go down in history you already have as one of the greatest defensemen of all time, just the history of the NHL. And I got a chance to really experience how beloved you were because I lived in St. Louis for a good part of my early career. And so, I mean, people just adored you, the fans there loved you. And so, I’m sure that there’s this interesting relationship with the fans where people love you, then you get kicked out, then they’re mad at you. You go to a new place. They haven’t warmed up to you yet. Talk us through what that’s like because I know there’s energy that you feed off of, but as a general rule, you were loved, not just loved, beloved.

 

Chris Pronger: Beloved, and early on, was booed and hated because as you said, when you come into a new place, I was traded to St. Louis in 1995 as a young 20-year-old and was traded for a fan favorite and Brendan Shanahan, and I got booed every game. I was hated because I was the one who got traded for the guy, the other one. And so, it’s like anything else, sacrifice, discipline but also adversity. You’re going to hit those forks in the road and then you can cave and crumble or you can push through and find a way and become successful.

 

And it certainly wasn’t easy that first year. There was a lot of sleepless nights, a lot of painful memories, and a lot of painful games, but that particular time in my life certainly made me stronger and gave me more character and more strength to push through the difficult moments in life that you’re ultimately going to face as you get married, have kids, and go through a family process and all the rest of that. And then, when you started making investments and doing decisions of that caliber, you need to start relying on a lot of those decision-making skills and a lot of things that you went through early on in your life that ultimately help guide and steer you.

 

Justin Donald: Yeah, Chris, you have such an incredible life and story, and I love that. Unlike most people, you don’t know it, you can’t find it. With you, there’s just so much like out there because you’re such a big name. So, if you really want to get to know the Chris Pronger that I know, you can see the highlight reels and all the different things. And what’s so crazy is just how intimidating of a guy you were on the ice, like people, I think, were afraid of you. And I mean, the number of people that you just took out was incredible. And I know you had this reputation of like, don’t mess with me. And I’ve got to imagine there weren’t that many people that existed where maybe you felt that way. I feel like you were the guy taking people out, which is cool. And then, of course, I get a chance to know you off the ice, which is nice and you’re a big teddy bear and nice, although I can tell you’re a guy I would never want to offend because you tower over me. I would never want to get checked by you. I mean, that just seems like you would crush people.

 

Chris Pronger: Yeah, you know what? It’s funny because when I would meet people off the ice or meet fans in other cities or whatever, they want to hate you, they want to be like, “Man, I didn’t think you’d be so nice.” I’m like, “Well, I’m playing a game,” like, that’s how I play the game, and this is who I am off the ice. And people think that it’s like WWE, like, oh, this is who you are your whole life, in and amongst your whole life. So, I think once people kind of get to know you off the ice outside of the arena, I learned early on that I had to play a certain way and I had to compete at a high level to bring out the best in myself, and therefore, bring out the best in my teammates.

 

But off the ice, almost to a person, whether it’s myself or any other teammate or player I play against or what have you, we all play our own games in certain ways, but off the ice, I can’t tell you how many people are like, oh my god, I can’t believe so-and-so, he was the nicest guy ever and he fought 50 times last year. And so-and-so, oh my god, you’re so mean out there, but man, you’re so nice. And I’m like, that’s the game. And people would always be like, these two guys fought each other today and they’re going for a beer now. Like, people don’t understand how that works, and it’s like, listen, it’s a game. We’re getting paid to win a game. At the end of the day, you’re being paid to win, you’re being paid to play the game, but really, you’re being paid to win. And competitive juices get going, and what happens on the ice is going to happen on the ice. And so, really, the hard part, I think, for some people and where they struggle is they take the persona or they take the game back home with them and they can’t differentiate the two and they can’t step out of that lifestyle or step out of that persona and they struggle.

 

Justin Donald: Yeah, it’s like the mixed martial arts fighters that trash talk each other to the end of the Earth, and then after the fight, they’re like hugging, like, “Hey, man, nice job. That was so great.” And then some of them do go out for beers together, which is great. So, it is funny because, for you, there is an incredible contrast. Like, I know you as this nice, happy, jolly guy that just loves to hang out and loves to tell stories and just likes to have a good time. But you are definitely the opposite of that, you are a beast on the ice. And I will tell you what, if I were on the ice, and obviously, you tower over me, I’d be skating away from you as fast as humanly possible and I would not do anything to ever offend you. I would be one of those people. So, yeah, it’s fun watching the highlight reels, though, let me tell you. Now, you had an incredible, let’s call it an incredibly scary moment on the ice, and man, I mean, I got chills when I watched this, and you talked about this in your Portfolio Defense.

 

Chris Pronger: It wasn’t a heart attack, it was an arrhythmia.

 

Justin Donald: It was an arrhythmia. That’s right. Yes, we learned that from our friend, our medical doctor, who actually is so smart. he is so smart. He became a doctor, a medical doctor, just so that he had the ability to do it, not because he actually wanted to practice it, he just wanted to know it that well, which is incredible. I just love how smart and sophisticated and incredibly gifted our Tiger 21 community is. I feel very blessed and I’m so glad you’re part of it. But let’s talk about this scary moment because life almost ended on the ice. You got hit with a puck in the heart like a slap shot that just someone hitting the puck as hard as they possibly could, it literally hit you in the heart. And I saw you go down. Walk us through that.

 

Chris Pronger: Yeah. So, we were playing a playoff game in Detroit, and the defenseman got the puck, and I went out to block the shot. And it happens in Little League a lot. I blocked a shot, and it hit me directly in the heart. And what happened was my heart was in between heartbeats. So, when the puck hit my heart, it triggered something in my brain to basically say, okay, the heartbeat, I skipped one heartbeat and I got hit, and it hurt, and I was like, alright, you’re in Detroit, and I’m like do not let these people see you laying on the ground. So, I’m like, alright, cover the puck up, get a whistle. And then I’m like, hey, get up and get to the bench because I knew I was in our corner, and the bench was like, I don’t know, 30 feet away.

 

So, in my head, I’m saying get up and I think I’m getting up, but I blacked out, and you could see my eyes are kind of out of it. And I stand up. When I go to skate to the bench, down I go. And to our good friend’s point, I had an arrhythmia where it’s called commotio cordis. My heartbeat skipped one beat, and that’s how much oxygen gets pushed through your body in one heartbeat. I didn’t have enough oxygen and down I went.

 

Justin Donald: Wow.

 

Chris Pronger: And so I woke up in the middle of Joe Louis Arena, staring up at the rafters and looking at all the banners and remembering, okay, I was in the corner, and now, I’m at center ice in between the two benches with my shirt cut open, and they’re doing all kinds of stuff to me, and I think they had the poof.

 

Justin Donald: Yeah. I mean, that has to be scary.

 

Chris Pronger: So, it was a pretty scary moment. At the time, I was 23, I think, and I didn’t really know what was going on and wasn’t really paying too much attention to it. So, I got to the hospital, they started monitoring me. I wore a heart monitor for 24 hours and then played the next game.

 

Justin Donald: Yeah, that’s unbelievable. Probably…

 

Chris Pronger: Had it happened in my 30s, let’s say, I probably wouldn’t have played. I probably would be like, I need to figure this out, but I was in my early 20s, and you’re invincible and I want to play.

 

Justin Donald: Short-term decisions.

 

Chris Pronger: Yeah, exactly.

 

Justin Donald: How does this serve me right now? I’m a hockey player. Let me get out there and make it happen.

 

Chris Pronger: That’s right.

 

Justin Donald: Yeah. Well, you are like me and so many other hard-charging entrepreneurs that whatever it is that you’re going to do, you’re going to do it to your best ability and you’re going to just take off. You’re going to go, go, go. And that’s really how I see you. While you are a hockey professional, you just took off and you charged and you did everything that you could to serve your team, to lead to the championships, and everything that you were able to do. And what I love is that you’ve been able to transition very seamlessly, at least it appears very seamlessly, where most athletes based on the athletes I know, and I know a good number of athletes, they have a very hard time with that transition because there’s a lot of egos tied in being a professional athlete. Like the identity is, hey, I’m an athlete versus I am a person, I’m a family man, whatever it is that truly could be or should be kind of the focal point. And that being an athlete is just like one ancillary component of it.

 

And so, you’ve been able to kind of move, pivot as an investor, as an entrepreneur, building out a business with your wife, Lauren. So, it’s really cool to see. I’m curious what that transition was like for you, though. Was it hard? Was there an ego that you had to let go of? Was it as seamless as it looks like it was?

 

Chris Pronger: Yeah, I was never a big fan of being called Chris the Hockey Player. There’s so much more to life and so much more to myself and to what I bring to the table than just being Chris, the Hockey Player. Yeah, that was my job at some point and was a passion and was something that I– but that’s three hours of your day. And to your point, talking about investing and talking about I was always fairly involved in a lot of investing decisions, I wasn’t tracking. I still don’t track things day to day and really follow my portfolio, so to speak, but I know where things are and I know what I’m invested in and things of that nature. And just trying to pay attention and read books and use your time wisely when you’re not on the ice or when you’re not preparing and you’re not doing all the things is just really trying to keep current and stay up to date on what’s going on in the world.

 

I do think that’s really where a lot of athletes struggle and where they really can’t get past the I’m an athlete. I’m Joe Blow the Hockey Player. I’m Joe Blow the Football Player, baseball player, whatever. They begin to believe that’s their identity and they really struggle with (A) when you retire, you’re no longer famous because you’re not on TV, you’re not doing interviews. People can’t see your face every day. You kind of slide off into the sunset. And some people really struggle with that, and others take off and they enjoy that. They don’t like the notoriety, or they didn’t like it, and they want to kind of just do their own thing and look at 2.0 or 3.0 or whatever it’s going to be.

 

And so, for me, it was being smart and being a sponge and learning about investing, learning about being an entrepreneur, learning about business, learning about other things that interested me while I was playing while still being focused on my career and knowing that that’s the breadwinner and that’s what I’m good at, but also knowing that at some point my career is over and I’m going to be a young man. And what’s next? And how do I get there? And what’s going to get me there?

 

Justin Donald: Yeah, you have such a cool story, such a cool transition. It was really inspiring to see what you’ve done financially because as I said, I know a lot of professional athletes. And one of the things that I notice at first, for athletes, they often think that because they made it, now, their income is going to be that way for the rest of their life or for a long stretch, whereas most athletes, they actually don’t last past the first or second year. So, you get into the professionals of whatever that league is, they’re not even still a professional athlete the year after, and then it even decreases more than that two years after. And so, the income that it was really isn’t what it was.

 

And then you have the athletes that did make a lot of money, but they didn’t take it seriously on managing it, they left it to someone else or they just spent it like crazy, thinking that more was going to come. And I know we both know a lot of athletes that have blown all their money or most of their money or a lot of their money. And so, it was inspiring for me to see how a guy like you who, I mean, you had a 19-year career and you were one of the highest-paid hockey players. And it’s neat to see that you were able to keep that and invested and compounded, and you’ve done something that most athletes have never done, you’ve done something that most people have never done.

 

And it’s cool seeing you say, hey, instead of just sitting around and doing nothing, I mean, you could be sipping margaritas and pina coladas at the beach. I mean, you own a travel company, for goodness’ sakes. You could do that. But that’s not who you are. But you could, you don’t need to work. That’s where I think it’s exciting because you’re spending your time on something that you value that’s important to you. And so, you and Lauren started this boutique luxury travel company, and a lot of athletes and professionals use your company to book incredible travel. Our Tiger 21 chapter is using your company to book this incredible trip, a trip later this month to Cabo San Lucas, just kind of top of the line all the way, A to Z. And I’d love for you to share kind of the purpose, the passion behind starting this travel company and kind of what that looks like today because you guys do some cool trips.

 

Chris Pronger: Yeah, really the best has been the baby for my wife and something that’s been in the back of her head since she was a young kid, and her dad was diagnosed with stage IV colon cancer, was given a 10% chance to live and with that, looked at his wife and the kids and said, “I want to travel the world for as long as I’m on Earth.” And that first summer, when the kids got out of school, they went off to Europe for two months, so all of Europe. And he was off his chemo and radiation, and she got to see him full of passion and life and joy and really just a sponge learning all about new culture and culinary and adventure, and that really left a mark at a young age of six to her.

 

And they came back home and he started planning the next trip, all the while getting pounded with chemo and radiation and was a shell of himself and really was beaten down but fighting for his life and chose Asia for their next trip and wanted to learn more about holistic healing methods and transcendental meditation and acupuncture and a lot of the Eastern medicine, a lot of the hallmarks that we look at now, and it’s kind of emerged in, 40-plus years ago, he was really at the forefront of kind of looking at that as a means to using that as a way to fight for his life, waiting for Western medicine to catch up. And he would immerse himself in the jungle for two or three weeks with the medicine man. And they would go off looking at the Great Wall of China and the different sights and sounds of Asian.

 

He was just using travel as a tool to fight for his life and learn more about the world and what it could do for him, and really the healing powers of travel and got back home. Two months later, a radical new surgery had been formed, and he got it and two years later was given a clean bill of health and never had cancer again. So, that really left a mark on my wife at the age of six and seven, what travel can do for your spirits, the mind, body, spirit, the healing powers of travel, all that. And so, she really traveled the rest of her time growing up as a kid. And when we got together, I always wondered why I didn’t travel more and I was at the peak of my career and training hard every summer and not really getting a chance to enjoy my spoils, if you will, and get out and see the world. And she always was wondering why we didn’t travel more. I said, “Well, I’m spending two or three months training, preparing, eating a certain way, lifting weights, doing all the cardio, all that stuff.”

 

And 23, 24 years ago, the hospitality space was pretty small as it relates to health and wellness. And so, she would source properties and things of that nature. And then when social media kicked on the final end of my career in Philly, she had a little social media account and private account with friends and family have followed and some athletes and some entertainers and whatnot. And they’re always asking, “Where do you source these properties? How did you find them?” And so, she started just helping people out as a friend, just setting up trips, and 20, 30 trips later, the light bulb moment goes off, like, okay, there’s something here. There’s that trust factor that bonds that ability to connect with people and understand what they’re going through, what they’re needing.

 

But at the same time, I get hurt, her mom gets breast cancer, her dad has a debilitating stroke and gets paralyzed in his right side. And we have three young kids at home, so from a timing perspective, it wasn’t right. But fast forward, four and a half years ago, I’m healthy, her mom’s healthy. The kids are much older. Our oldest is driving. So, you know, you got some time coming back that can be allotted to you and building a business and…

 

Justin Donald: Get that insurance policy.

 

Chris Pronger: That’s right. That’s right. Unfortunately, her dad passed away. So, it was really just helping support her. It was a passion of hers. And I was working as senior advisor to the GM in Florida at the time and helping her build out the business plan and make some connections and whatnot. And I was always the guy that set up the golf trips, the fishing trips, the Super Bowl pool, the Masters’ pool, and I’m kind of quasi event planner if you will, and really sort of enjoy just the happiness that is extended through hospitality and talking to people and just the joy. I mean, sports, when you’re invested and involved in it, is pretty miserable. It is pretty negative. Only one team wins a year. So, you’re brokenhearted.

 

It’s just doing it for 30-plus years and being told where to go, what to do, how to do it. This was such a change of pace and a passion because knowing what we know, what we’ve experienced, our niche clients are athletes, entertainers, CEOs, business owners. And when you look at that niche clientele, our unique ability to understand the demands in their time, the pressures of the job, the fame, the fortune, the stress on home life, the pressure on kids, all of that stuff is we’ve been through it, we understand it. So, for us, when we’re talking to our clients, we really get to know them on a much more personal level, asking questions to really kind of dig deep to figure out what they need, how best to where to steer them. And as my wife says, it’s matchmaking for travel.

 

Justin Donald: I love that.

 

Chris Pronger: And really getting a better feel for how best we can advise them on where to go, what to do, and getting out in front of potential situations if a CEO is feeling stressed out at work, if they’re having home life issues, kid issues, whatever it is. We all go through things in life, and obviously, we’re very open and upfront about our struggles and our successes, and what we’ve been through both personally and professionally. And I think people appreciate that in this new social media age where everybody’s got a filter and everybody lives a perfect life.

 

Justin Donald: Right.

 

Chris Pronger: We’re pretty real about life’s not perfect, but we’d like it to be.

 

Justin Donald: Yeah, that’s awesome. I mean, I love that you really got to live the life of your dreams. And now, you’re empowering Lauren to live the life of her dreams, but you’re doing it with her, you’re partnering with her. By the way, Chris the Event Planner has a nice ring to it. I’m just throwing that out there. Alright. And I know it’s much bigger and better than that. But it’s kind of like a fun transition. Oh, what? So, what did you use to do? Oh, I used to be a professional hockey player. What do you do now? I plan travel. I plan events. It’s just such a big like night and day shift.

 

But what’s cool is, you mentioned this earlier, and I think this is a really important point because most people aspire to be, well, I should say most athletic people and even some that are not, they aspire to be a professional athlete, and the aspirations, there’s so much like fanfare and notoriety in that. But what people don’t understand is it’s the grass is definitely kind of greener because inside of that, it’s the hardest, most grueling work. You have this season that is a long season where you’re not able to travel or live life on your terms the way that you would want to, and a lot of different facets of it being an athlete not only is an incredibly tough job, but it’s a very restrictive job.

 

Now, for you, you’ve been able to reap the fruits of that now, and I’m sure today, you’d say, “Hey, this is great.” A lot of people don’t have the fruit that you have, and so, they do that and they don’t even have anything to show for it. And they learn later that their identity and everything is kind of tied into this one thing. I love that you can say, “Hey, I’m bigger than that,” or “that is just a facet or a compartment of who I am in my life.” And I think that that’s amazing, and that today, you have this freedom and this flexibility. But we have to be careful because anyone who has ever started a company knows that there are perks to starting a company, there’s a lifestyle that can be associated. But if you’re not careful, the business that you started for freedom and autonomy often can own you and strip your freedom and autonomy.

 

Chris Pronger: Correct. And that’s the juggling act that we go through. And early on, in startup phase, you give up a little bit of that, but in the long run, I think once we get past this COVID-induced malaise we are in, we’ll get out of that and we’ll be able to get back to quasi-normal life and be able to grow. And I think we’ve started to put in steps as to how to manage time and set up your calendar in a certain way to be able to read good books and learn and do the things that I’ve been able to do to kind of keep your sanity and not just be one particular person, so to speak. Oh, that’s the travel guy. Or, oh, that’s the athlete, or oh, that’s– no, that’s Chris Pronger, or that’s Justin Donald. And here are pieces of what they do. And you continually add pieces to the deck and build out your persona, build out your life, build out how you want to live.

 

So, it’s really just about understanding who you are, what you’re all about, being comfortable. I would say early on in my career, I was not very comfortable. I didn’t like people staring. I didn’t like, just because they’re like, oh, there’s so-and-so, the hockey player. And I just did not like people staring at me. And as you get a little bit older and you get a little bit more comfortable in your skin and you just kind of, oh, well, it is what it is, and you’re able to kind of let go of it and not let it bother you anymore.

 

Justin Donald: Yeah, it’s a great point, and you bring up another good point, which is that so many people live this one-dimensional life, but we’re not one-dimensional, we are multidimensional. And I think that you intertwine that very well. And I love seeing the stage of life that you’re at today. So, now, you’re the entrepreneur, your partner, you and Lauren are building a business. You’re doing great things there. But then on the side of that, you’re an investor and you’ve had some great realizations here investing as this is a component part of the multidimensional you. And I’d love to learn just some of the wisdom that you’ve experienced and gleaned from you, just whatever you want to share in this world of investing because you’ve been doing it for a while, but you kind of had your hands on it even when you were a hockey player, like it wasn’t like someone was managing everything for you. You had a grip on it. I remember talking to you about that where it’s like, I’m not blindly going into stuff, I’m going to be involved in anything that we invest in. And now, today, you have more time to be able to look at it. And I’d love to know some of these lessons, these words of wisdom that you’ve experienced.

 

Chris Pronger: Yeah, I would say first, as you talked about athletes, the ones that run into the biggest problems are the ones that sign over power of attorney. Therefore, they have no say. Somebody can just randomly and blindly do whatever they want with their money. That’s where I think a lot of athletes go awry.

 

Justin Donald: And that’s common. That’s the scary thing.

 

Chris Pronger: Yeah, that’s quite common, which is crazy in today’s day and age that people still do that but whatever. I think for me, just like sports and life, my biggest and most valuable lessons are the losses. You make investments, you lose money. You realize, okay, what did not go right? What did I miss? And then as you kind of extract and look back on how the deal came together, what you did, and you kind of learn, I began to create with my financial advisor kind of parameters for each deal and what each deal has to have in it in order for it to pass the stress test or the smell test that it’s legit and real and something that we’re interested in. And yeah, you’re going to pass up great deals, but you’re going to pass up a lot of stinkers.

 

And really, as we talked about in my Portfolio Defense and in life, I already hit my home run. I already had my home run. And really, it’s about hitting singles and doubles. And in the process, you might hit a triple, you might hit a home run. But if you’re hitting singles and doubles and you’ve already hit a home run, what does it matter? So, whether it’s somebody with a company that sells, it has a huge exit, I had a huge exit. I’m all set and really, it’s about living within your means and living a lifestyle that you’re comfortable with, but under the guise that you know how much money you have, you know what your investable assets are, and you know how to live your lifestyle within that.

 

And as it relates to athletes that you talked about earlier, it’s just a matter of as I was getting towards the second half of my career, it was really managing and understanding how much you can spend, how much needs to keep going back into the pot to keep growing it so that it’s not going the other way, and really just managing the spend and managing what you’re putting out there. And then from there, reinvesting and doing all the things that most smart investors do, but understanding and keeping the investments that you’re looking at. If you’re not a real estate guy, but you’re interested in real estate, find a real estate guy or a real estate company that you trust, that you can invest in their deals. We’ve done that. Find hedge funds or private equity that you’re interested in, invest in those, and really, it’s about doing your due diligence and looking into companies and getting introductions to people and things like that. So, really, just talk to people and learn more about what they do and be interested. I think one of the biggest things for me is, I was, believe it or not, very introverted.

 

Justin Donald: That is shocking. I will tell you that is very shocking.

 

Chris Pronger: I’ve used probably the last eight or nine years since I retired to learn more about how to talk to people, how to ask questions, how to learn from talking to people and just again, being a sponge, being a fly on the wall, and listening, taking it in, don’t ask a question and then immediately start thinking, what’s my next question? Listen to what somebody is saying to you, take it all in, and then form a question or opinion based on what you just heard. And I think too often, people are too geeked up to get the list of questions here, and they just want to start asking questions as opposed to, yeah, you might have a list, but let the conversation go to wherever the next question might take it.

 

Justin Donald: Yeah, you had so many great points there, so many words of wisdom. And one of the things that I learned from Tony Robbins, and this is very profound for me when I kind of got into this is that you’re generally moving towards and away from something. So, there’s kind of like you’re towards goals or values and then you’re away from. And pleasure and pain kind of fall in that, you’re moving towards pleasure, but you’re moving away from pain. And so, you made the point that everyone loses at some point in time, and there are lessons to be learned inside of that. There’s no doubt about it. There is the pleasure of making money and getting a good return that feels good.

 

But I can assure you, the lessons learned from that pale in comparison to the lessons learned from the pain of losing money. That is one of the most painful experiences, especially at the beginning, especially when you don’t have a lot of it, especially when it goes completely different than what you would have thought, your expectations. The gap between expectations and reality is a huge chasm. And so, we both experienced this. I’ve been very open about many of my losses. In fact, I wrote about one in my book because I want people to know that’s normal, that that happens, but those are great opportunities to learn and grow. And so, I like that you…

 

Chris Pronger: They’re almost the only ways to learn.

 

Justin Donald: Yes. Yes.

 

Chris Pronger: Personal loss. I can tell you when I turned pro, my roommate, my defense partner, and I guess my mentor was brought in to do all those things. I was 18. He was 36. We’d sit around at dinner, we used to do dinners and all that stuff on the road. Everything that he told me when I was 18, as I went on in my career, and all this is going to happen, this is going to happen. Everything to a tee came true. And of course, I’m 18, going, yeah, yeah, yeah, yeah, yeah, you got to make the mistakes yourself. Some of them, I talked and like, okay, I get it. And some of them like, yeah, yeah, whatever. And then I got to his age and I was playing, teaching 18-year, 19-year-olds the same thing. And I’m sitting there going, I mean, it is amazing that you have to experience it on your own, you have to have the hard losses, if you will, to learn that valued mistake and then put in the right guardrails and parameters to make sure that you don’t make those same mistakes.

 

Justin Donald: Totally, and you made another profound point, which is I had my big exit. And I don’t need any home runs, all I need are singles and doubles, and what I want to do is I want to capitalize on that because I know a lot of people that have exited their business or have made a ton as a professional athlete. And they walked away just with a ton of cash, but I know a lot of people that have lost that money. I know many people that have made nine figures. They’ve made over $100 million. Okay, and many of them well into hundreds of millions of dollars. I know many people that have lost almost all of it, and it’s because there’s a big gap between being an entrepreneur, being an investor or being a professional and being an investor, but there’s also this feeling sometimes that people get where they have to hit a home run with everything that they do, and that’s just not the case.

 

And by the way, I’m the exact opposite of you, Chris. I didn’t have a big accident. I didn’t have the big payday or selling a company or anything like that. So, for me, I didn’t have like a big pot of capital to start with. I had to hit the singles and hit the doubles to get to where I’m at. And so, there’s value on both sides. But I hope that people listening here and people watching the show recognize it, it doesn’t matter where you are. You could have had a big exit. You might not have had a big exit. You might be working a corporate job, barely getting by, or you might be crushing it and exceeding all the competition. But you can hit singles and doubles today, and those singles and doubles can grow. So, what a single and double is 10 years ago might be different than today, might be different then 10 years later. But you hit the nail on the head with the fact that you don’t have to take on the risk. You just need to not lose money, lose it enough to learn the lessons and then stop losing it.

 

Chris Pronger: That’s it. That’s it. And understanding where you went awry and fixing that, and then to your point, it’s like gambling. If you’re going to gamble in Vegas or wherever you’re going, you bring the amount of money you’re willing to lose. That’s it. It’s no different than an investment. If you’re making your investment, you better be willing to lose that amount of money, which is why people don’t invest. If you’re worth $10 million, you don’t invest $10 million in one specific investment, hence diversification, and that’s why people write books and all this stuff because it works.

 

Justin Donald: Yeah. And the other thing is you’ll see people that grip and hold on to their money so tight they can’t let it go. And that scarcity mindset holds them back from investing. I know you know people just like that, right? That’s exactly what it is like. I’m just going to hold this thing. And it’s such a disservice because how are you going to make money? How are you going to capitalize? How are you going to create a return when you’re so fearful of losing it? And so, I think this mindset of abundance is saying, “Hey, I’m going to risk what I can afford to lose. But at the same time, I’m probably not going to make anything if it just sits there.” So, why don’t I do my best due diligence? Why don’t I talk to people that I know they’re successful, see what they think about this? Why don’t I just do the investments that other successful people I know are doing and then have the mindset of I can make more money? I’m going to invest this, I hope that this goes well. If it doesn’t, it’s not such an egregious investment that it’s going to put me out on the streets. But I can always make more money. I can always work hard, I can always figure it out. And I think when you come from that standpoint, it’s just easier to make investments. It’s easier to let go the money because you’re not putting the money on a pedestal.

 

Chris Pronger: And I think you have to have a long-term thought analysis to the investments that you have. I’m going to tell you a quick story, 2008, that beautiful time in life, ‘07, ‘08, when the market went down a ridiculous amount, the market was at the bottom that year at $6,300. And I don’t know whatever it’s at now, $40,000 or whatever it’s at. It was at $6,300. A friend of mine I was talking to was losing his marbles, losing his marbles. It got to like $6,700. And he’s like, “What are you doing? What are you doing? Are you selling?” I’m like, “I’m not selling. Why would I sell?” I go, “I don’t need that money. Do you need your money? Do you need that money right now?” “No.” I go, “Why would you sell? It’s going to go back up. Do you need it in a year and two years?” He’s like, “No,” I go, “Well, then, this is going to be gone. It’s going to go back up, and you’ll be fine.” He couldn’t take the stress of dealing with it, sold at $6,700. The bottom was $6,300, and then it spiked back again.

 

Justin Donald: That’s rough. Yeah, emotions generally steer you in the wrong direction in the world of investing. And I also find that when you make decisions out of fear, not from a place of strength, they generally don’t serve you as well. And so, anytime you can feel you’re emotional, try to not make decisions, try to get into a place where you’re calm, where you have peace, where you’re standing from strength because those generally are going to turn out better.

 

Chris Pronger: Getting facts.

 

Justin Donald: Yes. Chris, this has been incredible. I just have loved our time. And by the way, I just appreciate our friendship. It has been so much fun getting to know you and hearing your world travels and hearing these fun stories with you and different athletes. And it has just been a pleasure. So, I’ve got to thank you for joining me today, and…

 

Chris Pronger: My pleasure.

 

Justin Donald: I’d love to have you share where our audience can learn more about you.

 

Chris Pronger: Yeah, they can go to WellInspiredTravels.com. I’m now on Twitter.

 

Justin Donald: Alright.

 

Chris Pronger: Chris Pronger, @chrispronger. I’m on Instagram @thechrispronger, @wellinspiredtravels on Instagram. And that’s about all I got for platforms.

 

Justin Donald: What a great name, Well Inspired Travels. I absolutely love it. I’d love to end this episode the way I end them all, which is this. What is one step that you can take today towards financial freedom and towards the life that you desire, a life that you dream of, a life by design, not by default? What’s one thing you can do today to achieve that goal? Thanks so much for joining us, and we’ll catch you next week.

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