What Devin McCourty Has Learned About Managing Money After 13 Years in the NFL – EP 297

Justin Donald: What’s up, Devin? Good to have you on the show.

Devin McCourty: Man, I appreciate you having me on. It’s a long time since we connected back in Arizona, man.

Justin Donald: That’s right. Well, we had such a good time. I love so many of the people I’ve met at the Pro Athlete Community events. They do a great job. I’m interviewing Chip Paucek right after we’re done. So, I can’t wait to share with him how excited I am. I’m an investor and I’m on the advisory council. I’m just a big believer in everything that you guys are doing. But you and your brother Jason crushed it as hosts. Like, you guys are hysterical, you’re fun. I mean, it was, like, we couldn’t have had a better host duo at the event.

Devin McCourty: Man, I appreciate it. And it’s funny, you grow up with a twin and you spend almost every minute of every day together, same sports, school, all of that stuff. And then, you become adults and he gets drafted to Tennessee. We both have three kids, so very rarely do we get to spend time together where it’s just us two, no wives, no kids. So, when we’re up there and we’re emceeing, hosting an event, it reminds us of being 10 years old and learning how to play football and doing, like whatever it was we were doing, it brings us back into that space and we love doing it. So, we had a lot of fun in Arizona.

Justin Donald: Well, Devin, you guys, you clearly have the magic. It was a blast, and really it was just great getting to know you both, really good getting to know you. I mean, of everyone there, I feel like we got some really good time and just really appreciate, like, how down to earth and humble and kind and just awesome you are because not everyone in Pro Athletes, that’s a Pro Athlete or this majored in or been a professional athlete across the board that’s done it at a high level like you shows up that way. So, I want to just honor you by saying that right out of the gates.

Devin McCourty: I appreciate that, man. And that’s what’s fun about that event. Like, yeah, there’s former athletes, there’s current athletes, but there’s other people who are pro, whatever you want to call it, in whatever field they’re at. So, when you put everybody together, I think you see people slowly start to go, “All right, like I can drop a little bit of my ego. I can just come as I am.” And that’s why we had such great conversation throughout the day, all up until we got on a– I’m sure we’ll talk about on a pickleball court, and I had to drop you as a friend, you know?

Justin Donald: Well, it’s the one thing that I’m– between volleyball and pickleball, those are my two sports. And it feels so good for me to at least be able to hang with athletes in something. I joke because I work out at this really cool facility in Austin called Nutrabolt, and they do the pre-combine workout. So, all the guys, before they hit the combine or doing stuff there with Tim Rhodes and it’s awesome seeing, like, everything there.

And then a lot of other athletes are there. So, you’ll have some NBA players that come and play outside of season. And for NFL guys, there’s a ton of them that show up off-season. And it’s just, I mean, it’s an incredible gym, so it just attracts the highest quality athletes. And I love joking with them. I’m like, “How come no one’s ever asked me what sport I play?” I’m like, normally, at 6’1”, I’m pretty tall. Like, I’m a tall guy in a room. I’m like a shrimp compared to a lot of these guys. It’s hysterical. And so, I love just joking around with them. But pickleball is like the one sport I can hang with, with the athletes.

Devin McCourty: There you are. You didn’t just hang. You dominated on the pickleball court for that day. So, you should be proud of that. That wasn’t a just hanging. That was a, “I’m the best out here, and I had to feel that pain early in the day,” so…

Justin Donald: Well, I just love that you’re into it. I mean, that was your first time playing, and I hope you keep coming back. An athlete in one sport. I’ve seen Tim Tebow play. I thought he was good on the football field, as you know. Didn’t have as long of a career as you. He’s a friend. And I played him on the pickleball court, and that man can move. I mean, there are some football players coming out there that can really play some ball.

Devin McCourty: Yeah, man, I saw him. I saw some clips of Cam Newton playing, and I’m like, some of these dudes, especially like a Cam and Tim Tebow, they move so well, but then they’re, they’re big human beings. Strong, powerful. Some people shouldn’t be probably allowed on the pickleball court when you can move and have that kind of size, but both of those guys kind of freak athletes.

Even once they got college NFL, they still became the top of the top from an athletic standpoint. That was the fun part of my career is when you get somewhere and you’re like, “All right, I belong,” but then you also, you got to realize and say, “Okay, but that guy right there, man, God filled his cup up when he made a size, speed.” So, it’s always fun comparing and seeing how that all works out.

Justin Donald: Well, I play paddle here in Austin with a bunch of former pro athletes. So, we got a guy who used to play in MLB, a guy that used to play in the NFL, like, I mean, these athletes in their own sport and they are so good at paddle, it’s amazing, how... I mean, it’s like sometimes people are just good in their one thing. You got some people that are just freak athletes, and they’re good at everything they do. And it’s really impressive and really humbling, being around them.

Devin McCourty: Yeah, no doubt about it. You start to say, “Damn, what am I doing wrong here?” And other people wake up, get a quick 10-minute stretch, and then they go do something. And you’re like, how is that possible? I’ve been working out, warming up for an hour, and I still can’t do some of the things they can do.

Justin Donald: Yeah. Well, you’ve had quite the storied career. We’re going to get into it today. And really, like one of the things I want to say is, I hope that our time today, like, in this podcast episode, for anything else, like I hope this can be a place that really has impact on athletes. I hope that people that are playing professional sports can listen to this and what we’re going to talk about today can change the trajectory of their life. I want people to learn that they don’t just have to rely on these big contracts because in NFL, specifically, you get a big contract, X number of years, X number of dollars, probably half of it goes away right away to taxes, so it’s not as big and lucrative as you think. A lot of it’s incentive-based.

So, the numbers aren’t what you hear. And then you’ve got a lot of people going after them because it sounds like there’s a lot of money. And by the way, it still is a lot of money. But I love what we do in our community at Lifestyle Investor where we teach people how they can have passive income and cash flow for life, and I love seeing the athletes that embrace that so they’re never on the hook to have to sign another contract that they can work and get that passive income up so when the contract year comes up, it’s like, “Oh, well, now I got enough passive income, so I can choose yes or no,” not like, “I need the money. I have to take this contract.”

Devin McCourty: Yeah, man, I think exactly what you’re talking about is the conversations I try to tell guys to have as soon as they get into the NFL. I remember my rookie year coming in, and I was fortunate, I was a first-round draft pick, and when you have a twin in the year before, he’s a sixth-round draft pick, I lived that with him. I lived the, “Hey, sixth-round draft pick, I’m getting a $90,000 signing bonus. All right, I got it. It comes up to $61,000, so now I have $60,000 in my account. That’s all the money I have. I don’t know if I’m going to make the team. I got to go to training camp.” So, like, everybody back home has this mentality of, “Man, Jason made it. He got drafted in the NFL. Oh, this is awesome.”

But I knew the reality, just like him, was, “Hey, if you get cut, you got $60,000 from the NFL, and that’s it.” And I think, for me, I was lucky seeing that and living that with him. He obviously made the team, ended up getting paid and all of that. But that next year when I got drafted, I got drafted and I got my signing bonus, and my signing bonus was a million-dollar check. But I still remember the $60,000, and I remember my financial advisor was like, “Hey, let’s see. Like, let’s live off $60,000 a year for this first year.” And my wife still laughs because my townhouse that I had in Foxborough, Massachusetts, I furnished that whole thing, $5,000 at Bob’s Discount Furniture.

And that was, for me, I lived by myself. I was 23 years old. I just came from living with four other guys in a house in college. I didn’t need much, and I wasn’t, and I still am not, I’m not the guy that needs to have the appearance of, “I’m a first-round draft pick. I’m going to get an interior designer to make this look good,” And the only thing I do is watch TV and go to sleep in the house. So, I’ve always tried to keep that mentality of, get what you need, get a few things you like, but most importantly, have conversations with people who are smarter than you or more experienced in exactly what you said, how to make your money make more money, that you’re not out here, especially in our job, you can’t rely on playing football as long as you possibly can because it’s not realistic.

Justin Donald: Yeah, I love that. I got a chance to hang with Eli Manning, and he basically did the same thing, where it’s like live frugally, spend well beneath your means, Devon Kennard as well, who you know. I mean, it’s such great wisdom there. And then I’ve talked to a few players, and I didn’t even think about this, but it’s like, this player’s got rent here, but this team drafts them. And then, you get, like you said, let’s say it’s $60,000, and keep in mind, half of that’s going to go to taxes or in some states, right? Or maybe it’s 40%, 45%. So, let’s say that you sign a lease, and a lot of people sign a one-year lease. Then you get cut, but you’re still on the hook for that lease. Then you get traded, or maybe you don’t get cut and, and you just get straight-up traded. You got no say in it.

Now, you’re somewhere else. So, I was talking to some players where it’s like they had three rents, and they signed a year contract on all of them. Like, that is a really tough situation as well. So, you got to be smart, especially in the beginning years. But I would just say, like, through and through, nothing is a given, nothing is guaranteed. Maybe good to just stockpile some money on the side, have some cash to be able to put into assets that produce income so that you’re never reliant on a single stream of income.

Devin McCourty: Yeah, no doubt about it. And I think that’s the tricky thing because I try to tell young players all the time, talk to each other. When you get inside of a locker room, right away, there’s going to be great players in there. But that’s not always the guys you want to get to know, to follow. When you’re in there for a week to two weeks, even a month, it starts to be very clear, okay, that person has their head on the right way. Okay, coach keeps pointing to this guy even though he’s not a star and I never heard of him till I got there.

For instance, me in New England, I got there, I didn’t know who Matthew Slater was, but I kept seeing how the coaches reacted to him, how other players kept going up to him. And he’s only two years older than me, but I was like, “This is somebody that I want to be like.” And I think that’s the key because then through knowing other players, you start to build a team and people around you outside of football who can help you make the right decisions because I look at some guys, you just talked about that, you got rent in multiple places. And some guys get in and they do have the right mindset. They want to invest. But are you investing in the right things?

I remember having a meeting with a young player, had money tied up in insurance and money in this and that, and they had a good amount of money that they couldn’t touch until five to seven years down the line, which is not a bad thing at all. But this player was only in his second year and he was a third-round draft pick, which good, like, you should have a bright future. But the reality was, hey, what if you get hurt next year in year three, then year four, your contract year, you don’t produce and you never get that big payday, and now, we’re two, two and a half, three years in and you still can’t touch that money, and you have a wife and a kid. Are you going to save enough money to live until you get another opportunity?

So, it’s so many different things that guys have to think about, and a lot of it, it happens fast. You just said it. You’re in one situation, you get traded. All of a sudden, you get traded to the West Coast in California. You were living in Carolina where you were paying $2,000 for rent. You had a nice play space. You get to California and they’re like, “Hey, this is going to be $10,000 of rent.” And your mind’s blown.

So, it’s just so many things. And then a lot of it that’s hard is a lot of guys that when you first get in, this is the first time you’re doing any of this stuff. And you got good money, you got money coming in, but you don’t always have the circle around you because sometimes in a lot of households and a lot of guys that make it, your family’s not used to dealing with this. So, they’re trying to help, but they don’t have the resources.

So, I’ve always thought that’s one of the most important things of building and knowing your resources around you. And the best way to do that is communicate with the guys, the veterans in the locker room, see what they’ve done, learn from their mistakes, learn from some of the things and advice that they want to give you. Because if you have to navigate everything on your own, you’re going to make mistakes. But the mistakes you make with your money in football, you never can make back because the time’s ticking from when your career’s going to be over as soon as you play your first game.

Justin Donald: Yeah, it’s like 3.2 years on average in the NFL. And it’s so tricky because you’re a pro athlete, and this can be any sport, but let’s take the NFL because it is the most widely watched sport with the teams that are worth the most. The most money goes into this sport of any sport. Okay? You got a big target on your back. Anyone who knows your name, looks you up, follows your team, like anyone’s coming after you to like try and get you to invest in this deal, that deal, do this tax strategy, do that. And as an athlete, you’re equipped to play your game really well and your craft.

And maybe there’s a few other skill sets, but for most, you don’t know how to vet a deal or vet a tax strategy or vet someone in financial services. Most people in financial services underperform, just someone investing in the index. I mean, 97.7% of people over the last 20 years, based on the newest study, underperformed the S&P 500 index. I mean, these are the professionals in the space.

And then you’ve got some bad actors that are kind of moving in. I mean, at my very first PAC event that I was at, so Pro Athlete Community event, one of the players said, and this is for education purposes, so I don’t want to make anyone feel bad, but this is a good learning opportunity where he’s telling me, “Oh, I’m about to sign the papers on this deal.” And we’re like, “Cool. Tell us about the deal.”

And I’m there with Ryan Casey, who you met, our COO, and he’s like, “Yeah, here’s the split,” and it was a horrible split. and the preferred return was super low, and the fees were super high. I mean, this was like as retail of retail as it gets, but it’s even worse. It’s like worse than a retail deal.

And then here’s the kicker, we’re like, “Okay, they want you to put in this much money. How much are they putting in?” It turns out they’re putting nothing in, $0. We would never in a million years invest with a sponsor that put in $0. Like, that disqualifies that deal. So, we’re like, “Hold on. Pump the brakes.” I mean, he literally pulled up the agreement. He was going to sign it that day. We’re like, “Pump the brakes. Let’s talk through this. We’ve got some chops here.” And what we do at Lifestyle Investor, we don’t make money in that way. We just want to be advised. We want to teach.

For anyone that does any of the deals that we do or the tax rates, like, we don’t make any carry. I get the same terms as everyone else. I just think it’s so important that there is unbiased information, but that does not exist in the world of financial services and money management, wealth management.

Devin McCourty: I mean, it’s probably double to triple the amount of bad people compared to good people when it comes to athletes. Like, I can vividly remember the amount of stories of people coming up to me. I remember my rookie year, I make it to the Pro Bowl. I’m in Hawaii. I get a call to my hotel phone, and I’m on the phone and I’m talking to this person, and we’re probably five minutes in and I’m like, “How am I on the phone?” This person was, like, supposedly a pastor of a church, and now, we’re 10 minutes in and we’re deep in this conversation, but I’m like, “I guess this person knows me from somebody because, like, how did they get my room number to call?” And then, 15 minutes in, I was like, “Hey, man, I got to go.” Like, what is the plan here? And he was like, “Man, you need to be a part of this saving churches. We need $100,000.”

I just hung up the phone because it was like, you randomly, but that’s what happens for athletes. And then you get the people who are really good at it, and they drop this deck that’s super impressive, and you get on a Zoom call with them, and they start throwing numbers around. And then they start throwing different vocabulary around that if you’re not in that world, it sounds good, and they’re trying to explain it and telling you different things. And I tell guys, I go, “The dumbest thing you can do is get on that call and pretend that you understand.” That’s dumb. And it’s okay.

Like, you’re not in that space. You’re not an expert in that space. So, don’t get in there and pretend that you are an expert. You get the call with somebody, I said, “Get a feel for the person. See if you like the person.” And as they keep going over numbers, tell them, “Hey. Hey, I’m not qualified in that decision. I know some other people who will help me look at those numbers and figure that out. I just wanted to get to know you and see if we could.”

And you say that to guys and they’re like, “What do you mean?” And I think the hardest thing is, like, I played in New England, right? And Robert Kraft is one of the best owners, I think, in all pro sports. He’s down in the locker room. He’s down in the meeting rooms. Like, he sat by me in our meeting room. So, I’ve had numerous conversations with him.

And I think, then guys start to sit next to him, and they’re like, “I want to be him.” And the reality is they don’t understand his journey. Like, we’re watching a guy who owns a team now, but we fast-forward past all the other tough decisions he had to make, what he had to learn when he went to Harvard, then went to Columbia. Like, we’re skipping past that and we’re saying, “We don’t need that. We’re just going to get all the way to the end because now, we have this capital.”

And I tell a lot of people, more guys go broke trying to do some of the right things to become a hundred millionaire, a billionaire than the guys that are spending money on jewelry and cars. Like, yeah, you have that, but this whole kind of myth that, like, every player just wastes his money on frivolous things is just not true. It’s guys thinking they know what they’re doing and they get deep in. And the difference between pro athletes and somebody else, somebody else can go get another good job, and they can keep working, and they can– pro athletes, like the job that you know how to do the best.

I retired when I was 35. I played 13 years. When I retired, they were like, “Hey, buddy, that’s it.” And when you walk away from there, there’s no plan. There’s no, “Hey, we’re going to onboard you into this next thing.” You got to figure out what’s next. And a lot of times, for every Magic Johnson, which is awesome, how he made even more money, a lot of us when we walk away, you’re walking into entry-level jobs.

So, you go from making millions of dollars to now, you’re looking, if you were living like you were making millions year after year, that $60,000, that was a check. That was a check after a game. So, it’s a difficult mindset to kind of understand how you have to move forward.

Justin Donald: Yep. You’re spitting gems here. I mean, this is so good. and I love the leadership role that you’ve taken with sharing this. And even a guy like Robert Kraft, who I think is a brilliant businessman, I mean, he did a deal with this e-sports team, and I think this is public, or at least by the time this comes out, this should be public, but things did not go well with that deal. And I’m invested with another e-sports group, and we look to kind of acquire or merge the two brands. And so, I think the ink is now signed on that, where we’re kind of combining forces to create super team. But it’s fascinating. Like, you got to be careful at every level.

And then, just because a guy like Robert’s putting in X amount of dollars, keep in mind, like, a million dollars to him is, like, one penny to everyone else, right? And people remember that, because what these sponsors are going to do is they’re going to name drop and they’re going to tell you how much money they put in, and you just have to be able to look past that. And it sounds like you’ve done a good job there.

Devin McCourty: Yeah, and I try to tell all guys that I know and females, it’s all a learning process. And you don’t ever want to be all in when you’re a former athlete because if it works, great, but if it doesn’t, it’s understanding, okay, now what do I, like, you just want to be comfortable. You don’t need to, and that’s what I think me and my wife and my brother and his wife, we talk about it all the time of, “Hey, man, life’s good, and do we want to keep growing and keep doing different?” Of course, we do.

And I think that’s the important part of building your network and knowing people and understanding how they’ve done different things and how you can pace yourself. But ultimately, when someone comes and I like an idea, I get on a phone call with a few different people and we’re like, “Oh, we really like this.” And it’s like, “All right, well.” Then we get to the, “All right, well, how much should we put in?” It’s like, “Eh, if it works out really well and we put in this small amount, will we be happy with this return?” Yeah, we would be pretty happy with that return, then let’s do that. Let’s not always think of every opportunity as if we’re super aggressive, then we get to exit at this high number and now we chain, because that’s the conversation every time we do something. If we make X amount, me and my wife talk about what changes in our life.

Justin Donald: That’s good.

Devin McCourty: And then if we don’t feel like, hey, this is going to change, then we say, “Well, if we lose it, what would change in our life?” And that’s the bigger question is if it doesn’t work out and we lose it because it’s hard to go backwards. And that’s what we try to talk about of, hey, if we make an extra million dollars somewhere, we’re going to be ecstatic. Like, don’t get me wrong.

But we’re not going to change how we’ve been living. Like, we’ve been blessed and we enjoy what we do. We’re not going to go buy each kid a new car and hope that they drive it in 10 years or something. So, it’s trying to understand that of what you really want out of what you’re investing in and want out of your life, and then try to take that mindset, and not everybody you meet try to kind of replicate the success they had or how they invest. I think it’s trying to find exactly where you’re slotted, and that’s what football was.

When you got in a locker room, and I tell young players that all the time, you better understand your worth to the team. Some guy’s going to be able to mess up a lot, they’re going to be able to maybe come late, they’re going to get away with it, but you better realize that guy’s immensely more talented than I am. He means more to this team. And if that’s the case, you can’t act like that. And I think investing, it’s very similar. You can be on a cap table with a bunch of different people, doesn’t mean you’re all the same, and that’s okay.

Justin Donald: That’s good. Hey, incredible advice. And again, we just love to teach. Don’t put too much money with any single sponsor. Don’t put too much money in any single sector or any single business. It’s nice to kind of test groups out and kind of go in on a minimum and have them prove it before you kind of level up. And so, I love that you’re even, like, one of the things I think that’s beautiful that you said is, how will our life change if we lose this money? If this deal goes bad, like, does this put us in dire straits, like, can we get by? Does life actually continue on pretty much the same? Because that is a powerful question to ask, and hopefully, can get you to say, the goal is to say no more than you say yes, right?

And if you can learn to do that, you’re going to do a lot better and learn from other people’s mistakes as much as possible. But I will tell you, for me, the more success that I have had investing at one point early in my career, I thought I was better than I really was, and I let my guard down, and I got involved in a couple deals that really went south and I should not have missed what I missed, but I did because the ego was too big, right? I’d had too many, like, singles, doubles, triples, maybe a couple home runs in there.

And I’ll tell you what, the real humbling happens when you lose money. Those are the best lessons I’ve ever learned in the moment. They’re literally, it’s the worst experience ever, especially the first time, especially if it’s, like, if you over-allocated, right? But I’ll tell you that, I’ve learned, those losses have transformed the way that I invest today, and I am such a better investor because of it. And it keeps me a lot more humble, keeps me a lot more even-keeled, keeps me less emotional, more logical, and a lot more kind of like matter-of-fact. Like, “Here’s my investment criteria. Does it check all the boxes or does it not?” Okay, then it works or it doesn’t work. Like, I’m just taking the emotion out of it.

Devin McCourty: How did you get over that for, like, that next deal that came? And I know you hit the checkpoints, but still, like, at that last checkpoint, it’s like, “All right, how much do I want to put?” How did you get over that and make that decision?

Justin Donald: Yeah, it was hard because the first time I lost money, it was a million dollars. And at that time in my life, that was a lot of money. And by the way, like, just in general, a million dollars is a lot of money.

Devin McCourty: Exactly.

Justin Donald: But that was early in my career. So, I mean, that was a million dollars before I had a whole lot of reserves, okay? And man, did I ever take a long time to get back in the game? It was tough. Now, luckily, I had done well on some other investments. I still had cash flow coming in. That was a cash flow deal, but it was a high percentage cash flow deal. Too high. Like, it made me think, I should’ve thought, “This is too good to be true,” but what I thought is, “Wow, this is an easy way to have the lifestyle I want.” And so, I totally got wooed by the sexy numbers, and what a poor mistake that was.

And so, I built this, I mean, really after that, I came out with Murphy’s Laws for the Lifestyle Investor. So, it’s like my checklist of everything that I learned from that experience. So, part of it was like I had to heal, I had to not blame anyone else. Yes, it was their fault. Yes, they made some poor choices. And it turned out to be a fraudulent deal where I literally went to court.

Devin McCourty: Oh, wow.

Justin Donald: Okay? I was a day-one witness in court watching a man get sentenced to, well, I think it was like 17 years in prison. So crazy, crazy story, and I had a lot of the info. But before I could make another deal, I had to say, “No, this is on me.” Like, I had blind spots. I missed some things I should have seen. My attorney even raised some red flags and was like, “This doesn’t look right.” My attorney literally said to me, “The way this contract is written is really unprofessional. It seems like their legal team isn’t a top-quality legal team.” And I was kind of like, “Oh, give me a break.”

Devin McCourty: I see small detail.

Justin Donald: Making a big deal about– these weren’t grammar issues. These were, like, indentations and whatever. So, he even goes, “I feel like these guys are shady.” He goes, “This could even be a Ponzi scheme.” This literally came out of his mouth before that. Now, keep in mind, this attorney, who’s a dear friend of mine, he had also said that on some other things, too. And, for whatever reason, I felt like, I know better than he knows. I’m an investor. He’s not.

Devin McCourty: And you’re like, “Just trust me.”

Justin Donald: And it was just such a poor way of showing up at that time in my life. And so, you think that I would’ve learned the lesson. So, I came up with all these laws or rules for the lifestyle investor and I actually included them in my book. And so, I should have been following that, but it took another investment where I lost $3 million that really kind of solidified. Justin, you got to learn the lesson.

So, one of the things that I tell people, I make a lot of mistakes, but right now in my career, I’m really good at not repeating the same mistake. So, unfortunately, on that one instance, I repeated the mistake because I didn’t use my own checklist, my own criteria, because I got emotional again. But the good that has come from that, Devin, is since that happened and that was– we’re going back a handful of years now, the track record for me personally, and luckily, these deals that I’m talking about, the money I’ve lost, it’s like kind of before we had things that we’re doing in our community. So, our community has benefited from the fact that we…

Devin McCourty: Some mistakes.

Justin Donald: Yes. But for me, I’ve now had a long track record of having made more conservative bets, having more deals go full cycle, having more deals performing at or above pro forma because I’m just saying no more. I’ve hired institutional vetting. Like one of the things that we did for the Pro Athlete Community is we gave every athlete access to our vetting deals course, just as a gift, just to say, “Hey, if you want to learn how to vet deals.” And so, I’m really proud that we show up spending $300,000 to $350,000 a year on our team that vets the deals that we do that help us become smarter, more logical, less emotional, and they have a different criteria, different checklist. It’s a different level of diligence than what I am able to do myself.

Devin McCourty: And that’s huge because I remember at that event, Candace Parker was on stage and she was like, “I have a person that helps me figure this stuff out.” She said, “Because me personally,” she said, “every deal I look at I’m like, ‘Ooh, I like this. This is good.’” And she said, “And as I’m sitting there thinking of” exactly what you just said, thinking about what’s going to change, she said, “Then my person comes and goes, ‘This deal’s awful. No, we’re not doing it.’”

And I think that’s one of the hardest things, I think, for athletes who don’t have experience in investing in, and I do think with all of the things that come up about the modern athlete and how they’re different, I will say I think one of the things that they’re better than athletes of my generation and before is they’re all into multitasking. They don’t want to just be the best basketball player or football player. They are coming out and saying, “Hey, I’m getting NIL.” And I’m not saying every guy or woman is doing this, but there’s a handful of them are like, “Hey, I want to learn how to be an angel investor. I want to go and I want to learn myself. I want to sit and meet people. I want to take courses.”

So, it’s a lot of credit to them, but you need that because athletes, they’re so driven by the answer no or you can’t do this, or I’ll show you. And that’s not always the best mindset when you’re investing in something because you kind of sometimes want to double down or you want to believe in something so much because you resonate with the story of the founder or whatever. And that’s not always, like you said, that’s the emotional thing that you bring.

And I just think about, like, my career, emotion was a big part of how I was successful and what I needed to do of being down in games or being doubted or whatever you needed to do. You were driven off that emotion and how to accomplish some amazing tasks. And I think that’s the hard thing to try to realize. And then you take your zero experience and you try to throw it in there and try to vet a deal or understand a deal. It’s hard to do. Sometimes I sit there and I’m like, “This is nearly impossible.”

And I’ve had, I’ve sat down with friends and mentors that we go through stuff, they teach me vocab, and I’m like, “Oh, I feel better.” Then I do a meeting and I’m like, that helped very little, but like I still don’t know. You know, it’s so much and I just try to tell people, find people who are smarter than you, build real relationships with them, and then go forward, ask questions. They’ll ask you. It’ll be just hanging out with a buddy, and it’ll also be a way to help you in business and all the other things. And I was like, “That’s the best thing that I’ve learned of being able to reach out to different people and have conversations.”

And I’ve been amazed. I reached out to some people and they’re like, “Man, I’m so happy you text me on this.” Because they’re like, “This is what I do every single day. You’re not asking me a big lift. I do this anyway. I love to do something with a friend of mine and, hey, if I can help you.” So, it’s a hard thing. I know I’ve had to learn that of not feeling like, man, I’m asking somebody to do something. It’s a relationship, and you build that relationship. And you can’t ask everyone, but when you start to build good relationships with people, it goes a long way.

Justin Donald: Yeah. Yeah, more minds, more smart minds working on things together. I love it. There’s learning around it, but you’re going to come out with a better result, which I think is great. And I will say that for most people, like, doing a bad deal and losing money is going to be, in the moment, one of the most painful things that’s happened, depending on sizing. But in the long term, it’s one of the best things. And it’s not about people that get caught up in that one deal. It’s like, I kind of look at it as like, I lost that battle or those two battles, and those two battles added up to a lot, right? 4 million bucks. But I’ve won the war, right? I’ve made a lot more than I’ve lost. I’ve had a lot more deals go well than go poorly. I can count on two hands every deal in my entire career. It’s not even two. It might be six. Every deal in my career that has gone bad, right? And it’s less than 10, somewhere between 5 and 10, 6 and 10.

And so, by the way, I’m destined to have more, right? Like, I know this. As an investor, I’m going to lose, I’m going to make a bad bet. I’m going to read someone wrong. Or it may be everything would be great, but the economy, I can’t predict that, and this happened and that happened. So, I have to be comfortable, like you said, with, if I put this much in, I have to be comfortable losing it. But how many times can I just get it right versus wrong? Can I get it right 80% of the time, 90% of the time? And luckily, for me, the track record for me has been in that higher range, which is great.

Devin McCourty: Man, that’s so important, what you just said. I have three young kids and they all do sports and I’m a believer in sports. Like, I’m a former NFL player. I don’t force my kids. My middle son is going to start tackling. I’ve told him probably 100 times, “All right, now we’re going to find out if you like football, and I’m telling you, if you don’t like it,” because I’m like harder the other way and I’m like, “It’s not a sport that you’re going to naturally like. You’re going to get hit, you’re going to hit people, and then you’re going to have to do it again. And it’s going to hurt when you hit someone, and you got to be a little crazy to say you want to do it again.”

Justin Donald: Right.

Devin McCourty: But I just love what the sport brings and, yesterday, my son, he’s in second grade, but he got moved up and he’s playing in the third and fourth grade championship rec game. And the best player on the team, he has to pitch the next day, so he’s not pitching in the game. And in the fourth inning, they asked my son, “Hey, we’re going to put you on the mound.” So, he’s warming up and they call him to go in. The score is 1-1, bases loaded. There’s only one out. And as a parent, you’re sitting there and I’m like, “Why?”

Justin Donald: You’re like, you’re setting him up for failure.

Devin McCourty: I’m like, “Why’s he got to go in? Put somebody else’s kid in.” So, now the sweat starts dripping and I’m yelling to him, “Hey, same motion. We practiced this.” And I’ve been big on my kids of you’re putting in some practice time, let the nerves go away. When you practice, you owe it to yourself to just go do whatever it is. It might not always go well. So, he walks the first kid, and then the next two kids he strikes out.

Justin Donald: Wow.

Devin McCourty: And I’m excited. I’m like, “Man, I can breathe again.” But then he has to go back out there. And I know him. I work with him all the time, and I’m like, my brother came to the game. I go, “This inning’s not going to be great.” I was like, mentally and physically, it’s hard for him to now go again. I was like, after getting out of that, and I didn’t say anything to him. He went in there. He ended up walking three guys, so he got pulled. And after the game, I said to him, I said, “That’s what sports is about.” I said, “You had an unbelievable moment and a bad time.” I said, “And then you had to go again.” I said, “And now you’re going to have another game today where you’re going to have to play again, and all of that already happened. Some good, bad. You end up losing the game. The guy who came in for you, he didn’t perform well. You guys lost.” I said, “Now, we got to move on, and we got to go try to win another championship game for your other team, and you got to try to play your best.” I was like, “That’s life.”

And I try to tell people, that’s around me in my town, because, obviously, I’m the former athlete, so everyone thinks, like, I’m, like, the crazy guy that my kids got to be pro athletes, and I’m like, “No.” But, like, I love that sports makes my kids competitive. They see somebody else who’s trying to do what they’re trying to do, and it’s either them or you. And sometimes it’s them, sometimes it’s you. You got to turn it back on time and time again. You got to work with other people, build real friendships. And then, most importantly, you learn how to fail. You learn how to lose.

And this spring was my son’s first time he lost a playoff basketball game, first time I watched him break down and cry. In the winter, I watched my daughter. She’s nine, she broke down. And I’m looking at them and I’m like, I’m smiling a little bit because I’m like, “It matters to you,” I said, and then I use it against them. I’m like, “But if you’re going to cry, let’s go get some work in.” So, don’t cry when you lose the game and then you don’t want to come put in some extra work. And I love that point of it because I think, like you just said, you’re an investor and we’re talking about youth sports, but like, that mentality shows up. But you’re also an athlete. You love to compete. You love to go out there and play volleyball, play pickleball, play paddle. Like, all of that to me is a part of who you become, how you love to be in different arenas and try to be your best and whatever that is.

And that’s what I’ve learned from football. That’s what I do now working in TV and doing NBC Sports. It’s all about how can I be my best even though the last time I did this, I wasn’t, and that’s in my head. How do I get past it and try to do it? And it’s challenging, but it’s so much fun.

Justin Donald: Well, I got to tell you, I think coaching is in your future, youth coaching, because you’re saying all the right things that most people don’t say, and I love it. Like, the way you look at the game, and it could be any sport. You look at it from a very experienced lens. You’re a guy that played in the NFL with the Patriots for 13 years, as a captain for 12 years. And so, to put that in perspective for the people that don’t follow football, you’re opposite side of the field of Tom Brady. Same team, but you’re the captain. You’re running the defense.

And to be kind of, like, promoted by coaches and players, 12 years is really incredible. You went on then to win three Super Bowls with the team, which, I mean, most players, like, their goal in playing is a Super Bowl, right? So, I mean, you’re just spoiled in such a good way. But the way that you’re able to articulate the reps and the emotions and we got to forget about this and move on or knowing the tendency of hanging onto it or letting the nerves go, it’s like these are the things that these youngsters need to hear. Not winning and losing, not being hard on them in unreasonable way, but kind of meeting them where they are.

Devin McCourty: Exactly.

Justin Donald: And teaching them. Teaching them life skills through sports.

Devin McCourty: And that’s what it’s about. I look at my kids and I’m like, “All right, I was a pro athlete, so that gives you a shot.” But the chances, I was like, well, I tell my kids all the time, I go, “When I was your age, whether it was good or bad, I thought basketball and football was the only possible way I could be successful.” I didn’t know anything else. I didn’t know about venture capital. I didn’t know private equity. I didn’t think about people owning real estate. I didn’t know those people. They weren’t in front of me.

The people in front of me had 9 to 5s, some good jobs. The other people who were assistants or something somewhere, or a secretary, like, that was seen as a good job. They had a salary. So, I had very limited knowledge of what was outside from right in front of me. My kids now, like, their friends’ dads work in finance or one owns a construction company. They’re going to see so many different things that they’re pulled. Like, as much as they like doing their sports, they’re going to like doing other things. Like, what saved me as an athlete was when I was in ninth grade and entering high school and everyone started doing marijuana or drinking, I was scared to death that if I did those things, that I couldn’t do my dream. My dream wouldn’t be realized because I heard of Len Bias, who did drugs, and at that time as a kid, I thought he did drugs one time, and then he died. So, I was like, he was going to be better than Michael Jordan, my older brother told me.

So, that pushed me along the way, and that’s my biggest thing. And I tell a lot of parents, I was like, you want to just, whatever your kids enjoy, jump all in. I am not a baseball fan, like, at all. I never played baseball. I don’t really watch it. I’ve had three shoulder surgeries. I’m in pain at night because the kids, they want to get better in baseball and softball, and I want them to know, “Hey, whatever you’re in, I’m in.” “Hey, you want to go pitch? I’ll go squat down there and you throw me pitches.” “Hey, you want to work on fly balls? I’ll throw the ball as high as I can until my arm falls off.” And it just teaches them that, hey, whatever I’m passionate about, it’s okay to chase, no matter if my best friend does it or doesn’t do it, if my older brother doesn’t like it or– that’s what I try to encourage out of my kids.

And it is, like, being a parent and trying to coach them and all of that, I’ve learned way more than I’ve been able to give them. And I’m giving kids I coach in football, Pop Warner to high school to college to 13 years in a pro, I’m giving all that experience, and I still learn more from them every time we go out there of how to approach them, what kind of day they had. Did they have a big breakfast or not?

We had a kid that, he came in one day, in flag, he had a great day, and I was like, “What’d you eat today?” He goes, “I had waffles.” So, every day at practice and the game, I would be like, “Hey, Brooks, waffles this morning?” If he said no, I’d be like, “Oh, that’s not the Brooks we need. We need waffles.” And that was a big learning lesson for me because, like, as this kindergartner, he didn’t care about me telling him how to get big and grab a flag. He was so invested and loved me as a coach because I remembered he had waffles and he had a big game when he ate waffles for breakfast. And I just try to do those little things, build a little relationship with each kid just so they can enjoy the sport that I’m passionate about and they can see how much fun it is so they come back next year, then the year after.

And then ultimately, most of them won’t be pros, but they build these bonds with these kids that are all on the team with them that they now walk away with, “Man, I got 15 new friends that maybe five go to my school, five are from that town.” Like, I just think that’s awesome. That’s what I experienced as a kid, and I just want other kids to experience that.

Justin Donald: Oh, it’s so cool. I love it. And by the way, that’d be a beautiful place to end, but I’ve got one last thing I want to get into real quick with you. I feel like if I were a pro athlete, which I clearly was not, that the best next job is being an analyst. Like, if you love the sport, that’s a way that you can stay in it, you can preserve your body, you can use your intellect. You’ve got so much experience on the field, off the field, different teams, different coaches, different schematics. Like, just the whole nine yards, it just seems like if you were to want to continue working or need to continue working, that seems like an awesome path.

And I almost shot you a text with a video I saw of you on ESPN that I thought was so good, but I was like, “Ah, I don’t want him to have too big of a head when he’s on the podcast.” But I think you’re a brilliant analyst, and I’m just curious, like, has it been as smooth as it appears, your transition from NFL to analyst, and do you love it? Does it allow you to kind of stay engaged in the sport? Do you feel like it’s something that you are or can be really passionate about at maybe not the same level as playing, but maybe as high of a level as you can outside of playing?

Devin McCourty: Yeah, man, it’s been fun, but it’s been so much better than I imagined. It’s scary walking away from the game. Like you do something. I started playing when I was 10. I retired when I was 35. It was all I knew. I didn’t vacation at certain times. It was just everything. And then you walk away. And I remember Maria Taylor, who’s the host of our show on Football Night in America. We’re on our first game, preseason game. It’s the Jets versus the Browns, the Hall of Fame Game, and we’re down there in pregame, and I’m walking and I’m looking, and she’s like, “How much you want to be out there right now?”

It was the first time it dawned on me. I was like, “I don’t.” Like, the position I’m standing in right now of still being down here and getting to talk about, getting ready for your first preseason game as a rookie or as a veteran, and living that again and doing that, it brought so much joy back to me of just being a football fan.

Justin Donald: Oh, that’s great.

Devin McCourty: I don’t particularly, like when you’re playing, I wanted every team in our division to lose. I wanted Buffalo, Miami, the Jets, I want them to lose every week. Then you turn into, like, I just enjoy good football. I enjoy learning who new players are. It’s been so much fun, man. I think the only thing that would be close to staying around the game would be coaching. But my wife told me, like probably year five, she was like, “You will not coach. No shot you coach.” So, this is the next best thing.

And one of the coolest things about it is interviewing players and doing things with players. My kids know I played. My four-year-old right now still loves that I played, and he gets excited. He watches old Super Bowls. The other two really don’t care, but they all love when I show them a picture with Justin Jefferson, or I show them a picture with Josh Allen. Like, when I show them that I’m sitting down with these guys, I spent some time because of Kaleb, our co-founder at Pro Athlete Community, he’s with the Spurs. We spent time with the Spurs in the summer. I showed my kids a picture standing next to Wemby. They were like, “Oh. Is that Wembanyama? How did you...?”

So, that extra dad part on top of doing all of the analyst work has been amazing, man. I wouldn’t trade it for anything. And I think the best thing I can say is I’m having the time of my life. I thought all my good times were going to be in the past, but calling, being a part of the pregame for the Super Bowl this past year in San Francisco, being back at a Super Bowl, being in it, talking about it, being in a locker room, like, I had this rush when we finished. The Pats, that’s my hometown team. We had tickets to go to the after party. My wife was like, “Are we going to go?” I was like, “They lost, and I’m too happy right now to even be around. I don’t want to be around them.” Like, I’ve been in that situation when I lost two Super Bowls. I don’t want happy people excited about what they went through and how they were at the game. I wanted to win the game.

And we didn’t go, but, like, it was amazing, man. I can’t even put into words of, like, the amount of energy and effort that it takes, but how fulfilling it is. And then just the end, it was smooth that I love it, but it’s been challenging of how to get better. And at NBC, we have a lot of producers who are not shy. They’ve worked with the best, John Madden, great people when doing the Olympics, because NBC does the Olympics for year.

So, whenever you’re doing something, we’ll jump on a Zoom, or I’ll get a call, I’ll get a text, “Hey, you could have done this better. Hey, let’s try.” So, when you get that, but then you start feeling back up the athlete in you of, “Okay, I’m getting coached. I got to prove to the coach that I’m better.” And that’s the fun part that is challenging, but I’ve really enjoyed getting coached up and then trying to actually go out there and take that advice and those coaching points and put it to use.

Justin Donald: Well, I love it. Hey, what a great way to wrap. I mean, that was so fun. And for me, it’s just a gift. Like, I love the sport and like, I love watching. I mean, I watch so much football. It’s, like, such a fun thing for me, not even as a player. So, like, when I got to go to the ESPYs last year, and hang out with a bunch of the players, I mean, that was just so cool for me to just connect as peers and hear stories, hear how people got to where they are. So cool.

And you mentioned Wemby. I’m very proud to say, I think I introduced Wemby to pickleball. He came to my pickleball club at Urban here in Austin. And he was kind of like, “Hey, is there any way to play? Like, how do you get in?” I was like, well, I was the only one there. I’m like, “Well, my family’s here to play, so we’ll just let you in.” And I just wanted to treat him like he was nobody different. And so, it was fun watching him playing.

Devin McCourty: Oh, that’s cool.

Justin Donald: I believe it was his first pickleball he’d ever played. So, by the way, he is a big guy and really big on that court, like, wingspan-wise.

Devin McCourty: Yep. I was about to say he’s getting…

Justin Donald: Yeah. Yeah, incredible. So, hey, Devin, thank you so much for joining us. For people that want to learn more about you or anything that’s important to you, is there anywhere that they can go to connect or learn some of the things that you’re inspired by or want to draw attention to?

Devin McCourty: Yeah, just devinmccourty at Instagram and Twitter, and then, mccourtytwins.com is where we have all our youth football camps, when we do blood drives, do 5Ks. We’re very passionate about sickle cell. We’re sickle cell advocates. It ran in our family, so we do a lot in that space. So, it’s been a lot of fun, and that’s where, if anybody’s interested, you could catch up with all the different things that we do.

Justin Donald: Love it. Well, thank you for joining. I love ending every episode with a question for our audience. So, if you’re watching this, if you’re listening to this, my question for you is the same each week, but what is one step that you can take today to move towards financial freedom and really just move toward living a life that you desire on your terms? Not a life by default like most, but a life by design. Thanks so much for joining us, and we’ll catch you next week.