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A
So for everybody who's, I guess, seen my podcast, they're probably wondering, who's. Who's this really beautiful woman that I'm sitting with here today? For anyone who is someone who knows me personally, they obviously know who this person is. This is Tara Hannaford. She is my wife.
B
Hello.
A
Her and I were talking, and I actually came to her and I said, you know, you're so successful at what you do. You're so thoughtful in how you do it. Have you ever thought about maybe interviewing me on the podcast? Because I feel like for a lot of people who. Whether they have questions about the agent business as a whole, questions about any sort of stuff that happens behind the scenes, I thought there's. There's kind of no better person than you to come on and grill me, but also ask me questions that you think would be interesting for the listener. So thanks for coming on.
B
Yeah. Happy to be here. It's exciting.
A
I love that.
B
I do, too. It's exciting to be able to interview you and maybe bring some perspective that is new to your listeners. Since I'm not necessarily from the industry of. Of baseball, but I feel partially part of it. We talk about it all the time.
A
Yeah, we certainly do. She is my.
B
Linguistically, I've gotten better at it.
A
Yeah, exactly. You are certainly my better half. You were somebody who, I would say, whose education around baseball has grown exponentially in the last. I mean, five years, 10 years.
B
Yeah.
A
So I think this is going to be an interesting conversation, but I also want to give you the freedom to ask whatever you would like to ask, so.
B
Well, I wasn't doing this without that, so let's just.
A
Yeah, you kind of. Those are the prerequisites to get you to actually take some time away and to do this. Yeah. So where do you want to start?
B
Well, I think it'd be fun to start, you know, a little foundation setting. I know that there is some great content out about your story and about how you became an agent. So if someone has not yet listened to that, we should definitely drop a link into one of those interviews to revisit it, because you tell it so well, and it is. You go through it. It takes a little bit of time, but it's worth it. It's really, really interesting, and it's fun. So instead of going through that as it's, you know, because it exists out there in the world, you know, I'd love to ask you, though, still, about some of the foundational moments. Um, and maybe now fast forwarding to. Okay, you're an agent. Right. So you've been a. An agent for 25 years.
A
25 years.
B
Okay, 25 years. And now you spent time at a couple, you know, different firms representing the biggest players in the game. Now your own firm representing some of the biggest players in the game. If you had to part out the experience thus far, how would you describe that? You know, how would you kind of say the first part of being an agent really represented A.
A
Good question.
B
The second part, B. And now where I am today. And we won't go too much into the future, but just kind of holistically again, because so many people know about how you got to become an agent and what shaped that decision. So I'm curious, now that you are an agent, how do you part that out as kind of from where you started to where you are now?
A
Yeah, that's a great question. Thank you for. For the thoughtfulness behind it. Yeah. So for those who've never heard my story, if you have questions, you can certainly go back. There are plenty of episodes where I've talked about it, both on this podcast, but also on others. So if I had to, I guess, parse out over the last 25 years, what did the, you know, and I guess to make it simple, what did the first 10 years look like? What was the lesson that I learned?
B
Yeah. And well, also, too, maybe I should have been more specific. I think it'd be interesting for the audience of where you really feel like there are some significant mile markers as an agent. Like, you know, is it in your first five years that you're an associate, even if you're working on big things, where is it, like, after year, what, that you're like, okay, I've got a handle on this on my own. Or you can kind of step in. So I'm thinking of maybe people that consider being an agent.
A
Okay.
B
Or even families that are curious, like, yeah, what. What is the significance of 25 years as an agent?
A
So, like, I understand.
B
Yeah. From a time perspective.
A
Perspective.
B
When were you kind of like guy in training to your own guy?
A
So when I first started. And I will weave in all of those questions. So when I first started, I was obviously still in college. Right. So I was limited by the amount of hours that I had in a day. But with that, just a little tidbit of information. When I ended up interning at the first company that I worked for, you know, this company represented Barry Bonds, Jose Canseco, Ricky Henderson, Kurt Schilling, Trevor Hoffman, Mike Piazza. Piazza. And I ended up changing my class Schedule where I was in college. And I said, you know, if I really have an opportunity to do this, number one, I want to get the most out of it. So in order to do that, I want to actually make the classes night classes. So I could work every single day during the week, and then in the office. Yeah. And then on the weekend, I would work, you know, a normal restaurant job. And so the first couple years up until I graduated, I was a little hamstrung by that. But even then, what my responsibilities were was. Was kind of, you know, a little bit of everything. I was a jack of all trades. It was essentially the four main agents at our firm, and then there are various people underneath them. But I was somebody. Because I was the same age as a lot of the players, they would utilize me to interact with the players on a daily basis. So whatever was going on in a player's life, I was building relationships with them. And so they would start to call me about all these various things. And, you know, a story that comes to mind is, you know, Mike Piazza, who at the time was with the New York Mets. I had just gotten back from spring training while I was still in college and missed a handful of classes, and so ended up showing up in one of my finance classes that day. And the professor immediately upon all of us sitting down says, all right, guys, put all your stuff away. We got a test. And I remember looking at him, you know, thinking, oh, my gosh. Because I had been gone in spring training for weeks, I did not know we had a test. And so inside, I'm kind of panicking a little bit, like, how am I going to do this? And immediately upon everybody starting the test, my phone on the desk starts to vibrate. And I look at it, and it's Mike Piazza. And so I look at my teacher, who's now making eye contact with me because he can hear the phone vibrating. And I remember there was a moment in time where I'm thinking, okay, Mike Piazza, my teacher. Mike Piazza, my teacher. What am I just remember feeling, given the time of the day, it was that if I don't take this call now, he's going to be in the clubhouse, and I'm not going to be able to reach him for the rest of the day. And so at that time, when the phone rang and it was a player, whether it was Mike Piaza status or not, I had to, like, I thought, I need to answer this. Like, I'm not letting it go to voicemail. And so I immediately picked up the phone, walked outside and my teacher is looking at me thinking, this guy is nuts. What is he doing? Because he doesn't know who's calling me. Normal to him, would it matter? I would think, right?
B
Yeah.
A
So take the call. Hey, Mike, what's going on? And at that point, I feel a tap on my shoulder. And it's my teacher who looks at me and he's saying, like, what? What are you doing? And I remember thinking, and I just show him my phone and it's Mike Piazza, obviously. And he's, you know, kind of takes a step back, clearly is curious how, like, why is Mike Piazza calling this person? Is that the Mike Piazza?
B
Yeah.
A
And so he ends up going back into the classroom. I finished my call. It only lasted, you know, a handful of minutes.
B
And.
A
And as I walk back in, I'm thinking the teacher's going to be like, come here. He's not even looking at me. So I go in, I take the test. As I'm leaving the class, he pulls me aside and he says, what? What are you doing? Like, why is Mike Piazza calling you? And I shared with him, well, I have this internship at the sports agency. We represent Mike Piazza. He was calling me because he actually needed help with his housing arrangement or whatever. And it was a moment in time that I look back on and I. I'm so appreciative of because he acknowledged me and said, well, look, is this why you were gone the last couple weeks? Because I noticed that you weren't here. And I said, yeah, I was at spring training. He goes, well, next time just give me a heads up. Like, this is what we want to encourage our students to do, so this is great that you're doing it, but next time just like, give me a heads up. And so this is a long winded way of me saying, like, that's an example of something that I was responsible for. But it went well beyond that. And that lasted a year and a half, roughly.
B
Would it be fair to call that, like, you were a utility guy?
A
Yeah. See, there you go. That's good job, by the way. Well done. Yeah, so I was a utility guy. I was kind of serving in multiple different roles and ended up doing that for, yeah, a year and a half or so. And then at that point, when I graduated from college, then it was, okay, you need to go develop as an agent. Right. And so that from the standpoint of what did my day to day look like, it was a lot of the same stuff. I was still having the responsibility of all these various tasks, but then above and beyond that, it was, I need now to go out and go get my own clients. So I need to go to baseball games and recruit clients, whether that was in the major leagues, the minor leagues, or the draft. And so that stayed consistent over the next, you know, at that point, eight and a half years.
B
Well, what's that to go out and try to recruit your own clients early on?
A
Right.
B
When you're still understanding and developing in that early stage? Is there a lot of trepidation around that or is it like, I'm just so pumped to go do it?
A
No, I mean, there was a lot of excitement. I would say you gotta remember too, because I was 19, 20, 21 years old. I'm the same age as a lot of the guys that I'm recruiting. So it wasn't this feeling of. I mean, there were moments of intimidation. And I'll give you guys one example. When I was recruiting draft players, because I'm roughly the same age, it was very. It was like second nature. It was like talking to buddies. Right. So that didn't make me feel uneasy at all. But when I was tasked with going to recruit a player, let's just say I had to go meet him at the stadium or at a hotel. And this player is 35. Right. And I'm 21, that was a little different. Obviously, you know, this. This player that I'm going to go approach maybe doesn't know I'm there to talk to him.
B
Yeah.
A
And so you're in the back of your mind, you're wondering, like, what's he gonna say? What's this kid, this young kid, how's he gonna be looking at me first off when I'm walking up to him? And so, yeah, in that regard, there was. But that was, you know, a moment in time that I looked at more as a challenge to myself than. Than anything else.
B
Of course. Of course.
A
Well, so back to your original question. So if you break up the time and what I was doing during those different stages, so first one and a half years, like I said, kind of a utility role, then when I became a full fledged agent, you know, at that point, it was really a matter of really showing myself, but also the people that I worked with, that not only did I enjoy doing this, not only was I good at doing this, but like, I have a desire and a hunger to be great at it. And so over the next seven, eight years, it was me essentially building my book of business. And so then at that point in 2010, I left that company, then co founded the second company. And yeah, at that point I was handling guys on my own.
B
And so it's, I mean in summation then, I mean really it's every bit of 10 or 12 years of like development in a way or getting your, getting your foundation set.
A
Yeah, well, so something comes to mind as you say that because I think for anybody who's out there who wants to be an agent, I think this is an important thought to consider. A lot of people think that when you get in the agent business, there's a lot of, I mean, think about the people that get into the agent business, right? You have to be aggressive, you, you've got to be motivated, you've got to have a lot of different talents. You're clearly intelligent, doesn't guarantee that you're intelligent. But like the majority of people that do get in the business are on some level. And so you get this pool of people who are so hungry to prove themselves that I've had to mentor certain agents that, that, you know, me at the prior company, even the company before that we would hire who are really, really ambitious kids. And I remember on various occasions having to sit him down saying, look, I know that you're motivated and I know that you're hungry, but you've got to learn this as you go. Like there is no book you're going to read and get to the end of the book and now you're ready to negotiate a multi year contract. Like that's not how this goes. You have to figure out not only the, like the heartbeat of a negotiation, not only the heartbeat of representing a player and what all that entails, but you have to build relationships, right? Like you've got to figure out, because one of the. If and maybe it's a question that you have in here. But one of my biggest frustrations just in the agent business in general is people think I can say the right thing. I can read the book, I could sound like I'm a good agent and people should want to sign with me and people should in fact sign with me, right? And I get really frustrated when I hear these stories because, you know, any agent can tell a player what their value is, but going out and getting that from a team is a totally different thing. And that requires strategy. It requires various things. But I think anybody who is, is quick to take kind of that shortcut. Like, just give me the opportunity. Let me go show you I can do it. The frustration that I have is like, well, no, because you're learning off of this player. That's not fair. To the player.
B
Yeah.
A
And so naturally you've got to take your time and you got to crawl before you can walk and then you got to walk before you can run. And you just have to be comfortable that we don't know how long it's going to take, but it's going to take some time. And I think that's probably something that a lot of people don't want to hear, but they need to hear it. And it's certainly something that I would hope players would want to hear because any, any, any agent out there who's like, oh yeah, I just took my agent exam and I'm an agent and so therefore I'm ready to represent the best player in the game. I mean, that's not how this works.
B
Well, it sounds like, and you know from watching it that a certain term comes to mind which is nuance and nuances. And you know, if you're going to get into the business, it sounds like you, you need to come in with commitment because it's going to take time. Um, I think in any high skilled profession you have to understand the nuances that, and, and, and you know, managing those. And that is only done by experience. And experience only happens with time.
A
Yeah.
B
So what I just heard you say, confirmed, like it, you know, you can, you need to be good, you need to have that hunger. So there's gonna be part of it, it's like, it's like tempering, right. Tempering a young gun, like tempering, you know, how fast you can get out of the gate. You want that because it shows passion, it's excitement. You need that because this is going to require it.
A
Yeah.
B
But just know it's going to take time and the experience that you get is what's going to make you good if you have the goods.
A
Right. So I think, so what comes to mind when you say that is Naval Ravikant, obviously who I know you're a fan of, I'm a fan of. For anybody who doesn't know who Naval is, look him up. But I just saw a post that he made. It may have been old, but I just, I just saw it again. And everybody's familiar with Malcolm Gladwell's 10,000 Hours. Right. A lot of people have heard that various times. What's interesting is Naval's argument was it's actually, it shouldn't be 10,000 hours, it should be 10,000 iterations. And when I hear that from an agent's perspective, it almost makes me cringe because the thing I like about the idea of 10,000 hours is. It gives you this impression like, oh, this is going to take a long time. And I would rather up and coming agents know and accept. My ability to be good at this is going to take a long time and I need to be patient. That is better for that agent than, oh, I just need 10,000 iterations. So let me go out and get as many players as possible and learn as quick as possible, and then I'll be ready. And it's like, well, you just. All those guys that you just learned off of, you just ruin their careers. So that's where I push back on that.
B
Yeah. Or another way you could look at it is 10,000 at bats. Right. So, like, the iterations could actually.
A
You're really big on the baseball lingo today. I love it.
B
Hey, I know what I showed up for. But no, I now use baseball analogies in my profession. In my profession, in everyday life. But no, I think another way, though, to maybe think about that is iterations, meaning you've got to give it 10,000 tries. You got to get 10,000 at bats. So it's not that you're going to go and have 10,000 prospective clients to try on. You just need to go try to get 10,000 clients. And after that 10,000th try, you're probably going to be ready to represent a guy.
A
Yeah. It's also not or even good or.
B
Ready to actually recruit a real guy.
A
I mean, I think a lot of times people hear the 10,000 hours or 10,000 iterations or 10,000 at bats, and they think, oh, this is like linear thinking, like A plus B equals C. It's like, no, it's not a formula. You don't literally have to get 10,000. And when you get 10,000, you're like, okay, good job. You're ready to go now.
B
Yeah. Or not 10,000 of the same thing. I mean, we talked about this earlier this year. I mean, similarly, I've come to a place in my business, and for those that don't know, I am in branding. I build brands in the consumer product space, identifying white space, creating brand story, and then melding that into launching something from a sales and marketing perspective. Right. So storytelling and then connecting that to consumer wants and trials, et cetera. But what I was saying is that, you know, I will. I've also been in my career now for 20 years, and I'm so comfortable for the first time. And I've been good for a while, but I'm really comfortable now. And I think that has to do with it isn't linear, but I'm sure I've had 10,000 ways of trying something. A lot of those, some of those being good and some of those being mistakes. But it's the continual, day in and day out of going in the same direction.
A
Right.
B
Going towards the same goal. And even what we're talking about right now. Right. So whether you're thinking about being an agent or you're thinking about being a player, all of that makes sense. Like, you just have to take a step every day.
A
Right.
B
You need to step to the plate. You need to get some at fat. All the things.
A
So good.
B
Um, so in line with that, do you remember who your first big recruit was? Like, notable recruit?
A
My. Well, so I talk about this a lot because I still work with them. So. Alex Zumalt, who is the big league hitting coach with the Kansas City Royals, was the first recruit I had in the Arizona Fall League. And what's interesting and the reason I bring him up is so he, you know, he's had a career, obviously, as a player in baseball, then he goes into the front office in baseball. Now he's the hitting coach, but now his boys are going through travel, baseball in the draft. And it's kind of this. It's a. It's a wild thing to think about. Like, wow, we've both been doing this a very long time.
B
Yeah.
A
You go through that, that, you know, representing of a player and you never really think, like, oh, yeah, I'm going to represent your sons one day. It's kind of a crazy thought. And so, yeah, so he's. He's the first guy that comes to mind, obviously, Brian Wilson, who, you know, closure with the giants, who won two World Series with them in 2010 and 12.
B
Share the beard.
A
Yeah, he was the first, I would say, kind of like rock star, not major league star. I would say, like rock star. Right. There's a different level of, you know, very good players statistically and like, as players in the game. And then they're like, you know, I was with him at the ESPYs when he's wearing the spandex tuxedo. I'm with him at the ESPYs when he's walking around with the Sasquatch.
B
Yeah, he was. He had a. A notoriety outside of the game.
A
And so that was. He's one that comes to mind that, that I oftentimes think about. Which, by the way, he's going to be on the podcast. I'm talking to him next week.
B
That's great.
A
Yeah, but he's. He's somebody that comes to mind for various reasons.
B
Do you remember how that felt, though, regardless of which particular player? But when you did have your first recruit, like your guy, do you remember that at all?
A
Yeah.
B
Was that like a notable moment or was it so fast moving that, like, is that something that you celebrate or is it like, good, keep going.
A
No, no, no. So I will tell you what. What. And I believe this is a great, like, it's a great response that I had in the moment, but the word that comes to mind, and I don't remember if I like, took a moment and was like, oh, I'm gonna. I'm gonna sit with this. I don't remember that.
B
Or did you call your parents?
A
I'm sure I did. I don't remember that. But the feeling that I had, I do remember. And that was. I'm. It's. It's what I imagine parents, on some level, when they go home with their kid, like, I'm responsible for this thing. And so I felt really responsible that an individual is putting his career, so to speak, in my hands. And what he's doing is he's essentially saying, like, I'm trusting you and we're in this together. And I think every agent, or soon to be agent needs to understand and grasp that because it is. It's a responsibility. It's not to be taken lightly. And I think that's where I take things so personally, to a fault at times where. Yeah, I mean, when my clients are having bad seasons or bad year or bad days or bad weeks, or even in their personal life, like, I wear. Doesn't feel good. You know, these are people that are. I know this term gets thrown around a lot. Oh, they're family. But like, the investment emotionally is as a family member. So imagine if your mom or dad or brother is going through a hard time. Like, this isn't anything. You're just like, oh, yeah, it's not my life. I don't have to worry about it. That's not happening at all. I mean, it's truly something that you're wearing it, like clothes. So I. The responsibilities, like that's the word that comes to mind when you ask that question.
B
That was a very clear feeling early on. Can you think of a specific time in your life prior to going down your professional pursuit that prepared you for it? Like, is there anything in particular?
A
Absolutely. There's something that comes to mind immediately. My dad's gonna love this. So my dad, you obviously know, is somebody who is. And I think his dad was this Way to him, his dad's dad was this way to his dad. Very, very hard workers. And we were, you know, my dad, as an example, had to work his grandfather's farm for like an entire summers. So for me, what it was is we obviously had kind of like the normal chores. And then when I was, you know, I think 11, 12, 13, you know, I'm obviously playing sports, various sports, and seventh to eighth grade, I was in year round school up in Sacramento. And so what that means for anybody who doesn't know is like, you, you're not on the normal track where you have like a summer. It's you go to school for, I think it was like four months. And then you have a month off or three months and have a month off, and then another three months and then a month off. Yeah, so. So you're. So for me, I think my months off were like January, you know, April.
B
Oh, what a crappy month to have off.
A
No, no, it's crazy. So you got to pick, like which one you wanted. That was the one I picked. And you line it up with your buddies, like, which one are you taking? Like, I'll do the same. Well, so my dad would say to me, hey, I know you have the month off, but you have to paint the house. So you're not gonna do anything until you finish painting the house for five hours in the morning. And then when you're done, then you can go do whatever else you want to do with your buddies. And so that.
B
Paint the house.
A
Paint the house. But what that taught me, people hear that and they're like, okay, no, I hear that.
B
And I'm like, how did it look?
A
Really good. So that's what's funny is what I got to experience was the feeling that you get when you accomplish a task well, right? So what starts to happen to anybody? And this is why, you know, God willing, we're able to have children, like, I will instill that in our kids. Where I'm gonna want them to not like, you know, slave away and paint the house, but go do this. Because I want them to learn. When you achieve the task and you see it through, the feeling that you're going to get, at least what I got was like, yes, victory. Like, that felt great. I felt accomplished. And I took that into baseball, I took that into hockey when I was playing hockey, I took that into this career. So when I got into the business, I remember the gentleman that that brought me on, he tells me, he's like, hey, I'm gonna bring you on for an internship. We're not hiring. So do this for three months. And then, by the way, you know, we'll see you later.
B
Yeah.
A
And I, like, never left. And my. My thought the whole time was like, I'm gonna prove you wrong. I am going to work so hard that you're literally going to be able to. You're not going to be able to say, like, this kid, like, there's. There's nothing he won't do. Right. I wanted to be the first one in the office, the last one to leave. I mean, I was giving them every reason to think I'm crazy.
B
They're not going to want to, like, cut you loose.
A
Yeah. But, like, to this day, it's not that I'm trying to do it. It's literally who I am. I learned that by painting the house.
B
So how many years did your dad make you do those things? Was it.
A
I did it twice. I don't remember how many years I had to do that twice.
B
But there were different.
A
But every year, various chores like that. Yeah. I was like, oh, yeah, you're gonna clean the gutters. You're gonna reorganize the entire garage. And so I took literally everything out of a garage and then re. Like, re. Essentially decorated, but put every. And then wrote on little, like, stickies, like, what's in this? This, like, cupboard and drawer.
B
So is that why you don't like to do that now at our house?
A
Absolutely.
B
He got all of it out of you. Oh, that's great. Oh, so it set you up to just, well, talking about something that requires repetition that we just finished discussing, like, if that would be a skill set that would make you say, hey, I can show up and do this every day.
A
Well, there. I think there's a value. There's a value that you get that you don't even see at that age. When you're doing it at 11, it's the last thing you want to do. It's the worst. Right. All you're thinking about is, I want to go hang out. Like, my buddies don't have to do this.
B
Right.
A
And so the act of doing it isn't fun. It's not. You don't. By the way, my dad wasn't telling me you're gonna thank me one day. He wasn't saying so. That wasn't even in the picture. But reflecting back on it now, there is a value that anybody gets when they're forced to do something they don't want to do. And then they figure out this is whether it's this is a part of life. I'm good at it. I actually now enjoy the hard work.
B
Yeah.
A
Right. I can apply this to other things.
B
You really hone the reward system, too. Like, you know, it feels good when it's done.
A
Yeah. But I. I do think there were life lessons in that, and that's the reason why he was having me do it that I knew probably would kind of come into play one day. I did not realize they would come into play at that, at that extent that early. Yeah. I kind of took it like, oh, yeah, one day I'm going to have my own house and I'm going to have to do this stuff, was how I thought about it, but it was much, much different. Wow.
B
I'm sure he would. He will love to hear that.
A
Yeah.
B
I think any parent enjoys hearing how they've impressed upon their children in ways I've told him, and I'm sure a lot of listeners. So what. What is a mistake? Right. So that's something that. A way in your life that one of your parents influenced, you know, a work ethic and an approach for the rest of your life that you still carry today. So what's a. You know, what's something that you see families, your young players will call it maybe a misstep or a mistake that you see families or young players make early that cost them down the line.
A
So what comes to mind.
B
And I'm sure there's a few. So.
A
Yeah, no, but what comes to mind is. So I think what happens is we were talking about linear thinking earlier, right? Like, A plus B equals C. And I think what comes to mind or what comes to mind, for me, not. I think what comes to mind is parents who approach their son's baseball career and experience as they're younger, and they basically want to outsource all of the heavy lifting. So. And I get, like, on this podcast, I get comments from parents all the time saying, what should we do? What team should we join? You know, I just answered one the other day from a parent who is basically asking me, or telling me, rather. You know, my son is not to brag, but he's. He. He takes this really seriously. And the other kids that he's playing with don't take it quite as serious, and they're not quite as good, should we change teams? And so they just want, like, tell us what to do. And so I think one of the mistakes is they outsource their agency. And what they need to realize is what I'm giving them is advice right now. What I give to my players when I represent them is at a much deeper level. I do know various things about their lives, so I can give them a different level of advice. But to a lot of families, I think they just want to be told whether it's from a coach, a scout, a college recruiting coordinator, an advisor, just tell us what to do, and then we're gonna do it, and it's gonna work out. And so what happens? And the mistake that I think is being made is it's not that it's lazy thinking, it's that it's never gonna work out quite like you're hoping, because the advice is only as good as it's being put through your filter to make the decision. So if I had to encourage anybody, I'm actually realizing I need to do a podcast on this right now. If I. If I could encourage anybody, the reason why I think they're doing it is they. They think the solution is out there. You're gonna give me the solution. And the reality is, they're the solution. Right? So that's the mistake that comes to mind as far as.
B
So play out this example we just talked about. You have a listener sends you a request. My son, you know, is performing at a better level than his teammates, takes it more seriously. Should we switch the team? What was your answer? So, and how then should they.
A
My first question was, well, how old's your son?
B
I was gonna ask that. How old is he?
A
Yeah, yeah. And you know what's interesting about it is I think he was 14. What are your goals? Right. Is he still learning? If he's still learning, okay, he's 14. He doesn't have to do anything right now. If he's not learning and he's not having fun, well, then, yeah, it's probably a good idea to go ahead and search for another team, because then you're just wasting time and money, right? And that doesn't really make any sense. And so I think what parents should at least start with is, well, what's the experience like for my son? Right? Not what do we need to do so that he can one day get his college scholarship or get drafted? Like, if he's 14, we're not even going to know if that's even possible for a couple years. But the most important thing, I think, for these parents is just to realize, first and foremost, you are the solution. It's you. So don't look out there for someone to give you some, like, magic potion that's going to work. There are things that people can tell you that's going to help, but it's only going to be based on you thinking about the advice and saying, well, what's going on in my circumstance that makes that a good idea or a bad idea? Let's play it out. Let's think through those, those things. And so I'm not blaming parents. I'm not saying that they, they've made mistakes because at the end of the day, and let's be real, the parents all have full time jobs. Right. They are full time parents. And then they throw this kids. Yeah. Then they throw this travel baseball thing on top of it. And it's like, I don't have time to do this. So, like, tell me what to do, I'm just gonna do it and it's gonna work, right? Yeah, it's gonna. Okay, that's all I needed. And, and again. And the reason for this podcast on some level is to help them understand this stuff. Because what I want, as much as it makes me feel good for a parent to call me on the phone and say, you're the reason why we had all this success, like, let's be real, I want informed parents. So if I can give this, these parents information to encourage them, information to help make better decisions, like they're informed, we've won. And so I think there are a lot of people out there that would rather have them be told, you're the greatest. That's not what I'm doing this for.
B
One of the things that I take away from listening to the show and listening to your engagements and interactions is it seems like parents have a lot more time than they think. Would that be a true assessment? Meaning that, you know, with this example of, let's say a 14 year old, you know, there's a lot of time left. It seems like if the focus is always college or pro, you know, is there some sort of truth in that? Hey, these families have a lot more time than they think. You know, there's a lot more time for development. There's a lot more time for play.
A
I misunderstood the time element that you're referring to. Yeah. You're not saying they have more time in their day than they think they have. It's really. I get it. They have more time to make decisions about things that are going to impact their son's career and they don't need to be in such a rush. You're absolutely right.
B
Yeah. If they think every, if they think the timeline is short, every decision is so heavy. But it's like, oh, he's 14, you've got a lot of time.
A
Well, and, and I've said this on the podcast before, but. And it's funny, I've actually had a major league player commented, who I didn't represent, who I don't even know commented on this. And I'd like to call this out because, like, I'm not. I'm not big enough where, like, people won't criticize some of the stuff that I say. This is my belief.
B
Yeah.
A
Right. But I said, you know, you can't possibly know how good your son's gonna be until like, 15, 16 years old. From my experience, that's the reality. Right. And part of the reason why for that. And again, I just responded to a parent the other day about this exact thing. Part of the reason I say that's 15, 16 is because the kid has to hit puberty and, like, fully mature. When a kid is 14 years old, he's going through it, but he's not done with it yet. And so we don't know how big he's going to be, how fast he's going to be. Exactly. So for a parent to see a kid, let's just say, who's 5, 8, at 14, and maybe he's not the strongest. He's still growing into his body. He's not the fastest. And they're like, we've got to hurry up and do something because this isn't going to get it done. Well, at 16, he could look vastly different. And it's not because he went to a better coach. It's not because he went to a speed guy.
B
Yeah.
A
It's because he hit puberty and played.
B
On a different team.
A
Yeah. And so that's where I'm saying to parents, like, give it time isn't because I'm saying, you know, you're overreacting. Don't worry about it. It's not that big of a deal. It's no, like, you've got to give the kid time to mature and fully grow. And I mean, look there. There are plenty of kids who, yeah, 13, 14 years old.
B
That's young.
A
They were tiny.
B
Yeah.
A
And then they get to 16 and they're like six, four. And you're just like, oh, well, this is a different thing. And so forcing that kid at 13, 14 to go do all this crazy stuff because you. You think he's behind, all that could potentially do is risk him getting burnt out. And then by 16, he's like, I don't even want to play.
B
Yeah.
A
So that's where I just Think we need to be mindful. And to the, the player who reached out to me in a comment and was like, yeah, I don't. I disagree. All good. Like, in his experience, maybe to him, maybe he has a son, and to him, like, his son at 15 or 13 or 14, he's like, my son's going to be a big leaguer. He knows, okay, that's fine. But that's not the majority of kids.
B
Well, there's exceptions to every rule. And, you know, there are some people that are just born with outstanding abilities. I mean, I can. Tiger woods being one of them. Right. I'm sure Kobe Bryant from a very, very young age was showing incredible skills as a basketball player. And I'm sure we can name some baseball players, too, but those are the exception, right?
A
That's not the rule.
B
It's not the rule. So, yes, I would agree that there's probably some people that do display those talents early on, but I can also see, especially for, especially for young men, like, women develop a lot earlier.
A
Right.
B
So, like men, it happens a little later. So that makes sense to me. I know, you know, you get a lot of questions and you discuss a lot about the draft, and I find the draft to be fascinating because there's not a lot of predictability around it, even when you are an expert. And a lot of nuances because you're dealing with people, I think is what also makes the draft, in my opinion, exciting. Exciting to watch. But you're always handling your clients in the manner that you know best. I'm sure people would love to know, like, if it was your son. Right. If it was our son going through the draft tomorrow, how would you handle it? And that may be too abstract of a question because.
A
Yeah.
B
Do you mean it would depend on how he's playing?
A
Yeah. Do you mean, handle, like, the whole experience leading up to the draft?
B
Do you mean, how would you guide him, you know, differently than a client? Or would you. Or would it be.
A
I mean, yeah, I, I wouldn't. I would guide them.
B
The.
A
I mean, literally, I, and I say this to parents. What, what I am doing and, like, who I'm embodying as I'm representing players is I am doing everything that I would be doing if my son were sitting next to me and he was the one that I was representing. And I think everybody should do that, and maybe they do, but that is the level of care that I believe you have to have doing this. And it's one of my critiques for any agency that has a ton of players in the draft because I think you couldn't parent 40 kids. Right. Well, maybe you can. I think it'd be really hard. And so how can you represent 40 guys out of the draft? I think that's. That's. That's not in the best interest of the families. And that's not to say anything wrong for any of the agencies that do. Like, they have a different belief system. Totally fine.
B
I just think multiple agents.
A
I mean, it goes into a bigger point about, like, well, what constitutes, you know, valuable agents.
B
I'm not there yet. You're not in. This is not your show today.
A
I didn't know that was a question. Sorry.
B
It might be.
A
Does that make sense? Did I answer your question?
B
Yeah, I did. I think ultimately you're just saying that the way that you guide clients, and I. I know that to be true because I see the level of care that you exert when dealing with families and dealing directly with players. You care deeply. You think holistically, and it's very. It's very meaningful.
A
So. So what just came to mind? And this, hopefully is funny for everybody. You know how you see presidents, like, before they go into office and then after they go into office, people oftentimes like, why do you have so much gray hair? And I'm like, when you go through this business and, like, you actually do care, and this is a joke kind of. But, like, no, you, like, you emotionally wear. Like, it bums me out when a player, you know, wants to sign out of high school and the circumstances don't go, you know, his way, and he ends up going to college and he's, like, bummed out. Now, there are things that I do to prepare him for that in advance. So it's not like, what. What just happened. But I see that, like, oh, yeah, he would have chosen to sign had he got his number. I wish he would have gotten his number. Right. And so you carry that as you represent them, you know, like a parent would or like an uncle would.
B
Yeah.
A
And so that's why I have gray hair.
B
At least it's not my fault. So I'll take that. So I have a couple we're gonna go into. Kind of the.
A
Look at this. Like, what. What do we have here? Can I look at it?
B
No, I just have some questions. I just have some questions. Okay. I will be curious, though, as. As being an agent for 25 years, what does success look like to you today? Success as an agent versus maybe what it looked like 10 years ago or, I don't know, maybe five years ago.
A
What does success look like for me today?
B
Has what success looked like remained constant, or has that changed as you've evolved as an agent?
A
As. Yeah, I. I understand. So the thing that comes to mind is. And I'll give a shout out to our friend Jason Jaggerd for this. I love Jason because I learned this as I was coaching with him. So he. And maybe you've seen this too. So like a pyramid, right? And I don't remember what he called it, but basically at the very bottom of the pyramid, I think we call that like the high performance pyramid or something like that. So the very bottom of the pyramid is somebody. And let's just say in this question, it's an agent who says, I want to do the least amount of work and not get fired. Right. And above that is what Jason calls, like the Applebee's of high performance, which is, I want to do a good job. Right. And then above that is a high performer who says, I want to be the best. Right. And like, that is a pyramid that I think a lot of people would agree with. Like, yeah. And the majority of people would say, well, I'm a high performer. And I think people in the agent business, if you're even in it on some level, like, you are a high performer, you view yourself as a high performer. But what I learned, and this is like, maybe who I was and it probably longer than 10 years ago, I'd say it's more like 15 years ago was I was a high performer. And when you understand high performers, high performers, there are limitations to being a high performer. Right. High performers oftentimes are closed minded. They're people that think they're great. And ultimately what ends up happening is they're. They're closed off to ideas of how they can improve. Right.
B
Unteachable.
A
That's right. So coachable. Yep, exactly. So someone comes in and says, hey, man, love what you're doing. Have you ever thought about this? And the high performer's like, I got it. I don't. I don't need this. I got this. You don't need to tell me what to do. And they get really territorial and sensitive around all that stuff. I would put the first 10 years of my career in that box because I didn't understand there was another level. And the other level that I'm talking about is someone who asks a totally different question. Not how can I be the best? But I'm wondering how good I could possibly be. Right. What more is there? Yeah, Right. And again, like this podcast is a direct response to that. The most valuable agent isn't me calling myself the most valuable agent.
B
Right.
A
The Most Valuable agent podcast is literally my vision for the company that I have, which is I want to be the most valuable agency that's ever existed. And when you start to live by this ethos, you're now asking yourself different questions about what's possible for your clients. So for me, it was, well, if I wanted to be the most valuable age that's ever existed, well, I wonder how I would handle this situation. I wonder what more there is for me to do for these guys. Above and beyond just being a high performer. Right. And so it truly makes you realize, oh, wait a second. I was limited by my inability to have vision. And so that is I. So what does success look like for me, it's continually pushing that higher and higher and higher. And what you. What's crazy is what you realize is there actually is no limit.
B
Yeah.
A
You'll do something great, and then it's, where's the next level? And so people may hear that and think, oh, that's unfortunate. Right. Like, you're never satisfied. It's not a matter of being satisfied. It's a matter of. Because, again, I am not the goal of the success. My clients are the goal of the success. So how do I continue to be even more valuable to them at the next level and then at the next level and then at the next level, and it literally is never ending.
B
Is it fair to say that? Or. What I'm hearing is if the goal is service, then you can never be done. Right. So if, like, to someone who might think, oh, well, that's sad, because you never. You're always chasing. I would actually say, as someone that spends life with you every day, I would say that you're very, like, right now, currently in this season, and recently, like, you're very satisfied, but you're never. You're never idle. So you're very satisfied, but you're not idle because you feel purpose.
A
Yeah.
B
So if you're. And I think of service as a purpose.
A
Yeah.
B
And I think this, the Most valuable agent podcast is an extension of service. Right. Because, I mean, in a lot of ways, like, the podcast isn't serving, you know, there's you as the agent. Right. And the clients in the major league that you're serving.
A
Right.
B
Or in that step. And then, you know, now you've got another audience here with the most valuable agent that are. Are working their way up, right. To making baseball a career. And so they are separate. But yet it feels like being in service is just like adding fuel to purpose, if that's what I'm hearing.
A
Yeah. So, yeah, interesting. What I'm experiencing, as you say, this is, I think, about my parents. Right. My dad was in service. My mom was a teacher. Yeah, right. And so I'm like, oh, right. The agent side being good at it came from my father. The podcast side and the care factor.
B
Yeah, right.
A
Came from my mother.
B
I never thought about that. That's funny.
A
I didn't either until you just said that. And I thought, oh, this is interesting.
B
Yeah, look at that.
A
Bob and Ange.
B
Bob and Ang. They're saints. For anyone that doesn't know them, they are saints. Very lucky to have them, as in laws. So let's talk about the podcast then for a little bit, because it is something that takes. Like, your day is very full as an agent and running a line sports agency. You, quite frankly, don't have extra time, and yet you said, I'm gonna jump in with both feet. You had an idea, and I think, honestly, you had a heart for this. You talked about this for quite some time and not necessarily starting a podcast, what you talked about for a long time was reaching par and reaching amateur players and recognizing that they just weren't getting any guidance because they don't get the attention, you know, at that level and wanting to share some of the knowledge, wanting to share the experience. So that was obviously something that you were mindful of for a long time. It then manifested into, okay, what's a way to reach people to do that? The podcast was born, and you're finding time to make it happen. You're finding time to make it happen every week. What has surprised you about that? Like, what have you been surprised by? Has it been more or less what you expected? Has it been. Has it given you more than you thought from, like, a fulfillment standpoint? Has it been more work than you thought? Like, what are just some things now that you're. I think we're like a year and a half in on the podcast. Is that a year and a half? So, yeah, we'll call it 16, 18 months into this ride, which is now the most valuable agent. What are ways that it fills you and what are ways that it surprises you, and what are you continuing to look forward to do through it?
A
Yeah, I think the thing that I've gotten out of it is. And there's so many different things that come to mind, it's the people that I've been able to meet that have been listeners who have messaged me and hearing their experience and seeing that it's making an impact is the most amazing thing in the world. Right. It just reinforces. Because you're right. I mean, I am an agent, and that does take a lot of time and energy.
B
Ton of time.
A
Right. And so you get to a place where. And that's why, like, And I hope everybody knows this, like, it couldn't be fake because you. You literally couldn't muscle your way through doing both.
B
Yeah.
A
And so what I'm doing is I'm basically like, things are happening every day in the agent space, and they're giving me ideas of like, oh, yeah, like, everybody needs to know this. Yeah, everyone needs to experience this and understand that these things exist. And so they blend really well together. So it's not. It's not a heavy lift in the extent that, like, I'm doing something that, oh, my gosh, I can't believe I have to do this. It's fulfilling in, In. In the regard that, like, oh, I get to. I am blessed, so I get to help bless others is how I look at it. So that's. That's what comes to mind.
B
That's great. What do you think the future of actually, you know, big news in. In the agency world this week, but agencies doing different things growing. Right. New ones starting, I feel like right now, too. It's funny talking about the arc of your career so far. Like, when you started 25 years ago, there weren't that many agents or there weren't that many agencies.
A
There weren't that many. Well, there weren't compared to today. Correct.
B
That's the point I'm getting to is, like, when you started, there were like, you know, a couple big players right. In. In the agent or agency space. So we'll say, and I'm talking specific to baseball, and now there's a lot more. So one of the changes that we can say over the last two decades is just like sheer, you know, volume or amount of agents on the scene. But, like, what do you see? And I know that you've seen the agency business changing for a while. Like, how do you continue to see that morph in the future? Or how do you think about maybe not even so much the agency as a business, but how do you see player representation kind of changing, Changing, if at all, in the future?
A
I guess the thing that I think will continue to happen, and this isn't necessarily only the agency business. I think it's just kind of a lot of businesses as we get into what I've found to be people's ability to communicate with the source a lot more. Where I think a lot of times, you know, the, the audience or in the agency case, like the players. Getting to connect with the source of information has never been easier than it is today. But I think if I, if I had to, you know, give you kind of like a timeline or a quick glimpse into the future, what I would say is I think the agencies, like, it's no different than in baseball. And I know I'm kind of all over the place. Let me kind of summarize my thoughts and then I'll. I'll narrow it down. So in baseball, right, pre technology, pre data, it was the front offices were filled with baseball guys, right. Ex players became GMs. Ex players obviously are managers and everybody was just an X player. Right. And there was no data. And then with the advent of data, now we've, we've swung the pendulum kind of almost in the opposite direction where the things that are making decisions for lineups are not people. Right. Oftentimes they are data driven. Right. And I think in baseball we're starting to kind of get back to a place where it is going back a little bit to the center. I think we have a long way to go till it kind of like blends both pretty well. And so I think the agency business is no different. I think what agencies are now doing is they're, they're trying to grow and be these massive companies that do a whole host of things, right. You see agencies that don't just represent players, but they represent brands. And they're negotiating these deals with Pepsi and Coke and you know, they're negotiating for FIFA and like they're, they're brokering deals that are massive. Right. But I think at the heart of it, it's always going to come back to like, what is the role of the agent? The role of the agent is to literally guide that player and to be their mouthpiece and to truly like, you know, add value to their career. Right. If you just fundamentally look at it. And so I think the future of the business is just that is going to continue staying important, but that is going to become even more important because all these other firms that continue to grow and get massive are going to lose that. Not because they want to, but because that's the byproduct of getting massive and doing all that is the personal relationship goes away.
B
Yeah.
A
And that, that to me is, it's doing a disservice to the players. I think there's a lot of good that could come from brokering those big deals and doing that stuff. But I think at the end of the day, you've got to be so committed to the player that oftentimes in experience, what I've seen is, oh yeah, they'll tell you they're committed to you, but in reality, just it's pure logic. Like, like money drives decisions. Oftentimes in the agent world, like I've talked about that. So if they're getting a commission for a billion dollar deal versus your $5 million deal, where do you think they're going to devote most time? Probably to the billion dollar deal. Right. Doesn't make them bad guys, but like that's the incentive for them. And like Charlie Munger says, like incentives drive behavior. The incentives are driving their behavior. They could be great guys, but the incentives are driving that behavior. So how do you set up a company to where like those incentives don't exist quite like that? I don't know how they're doing that in, in that space.
B
Yeah, that's a great point. It's hard to manage that because you do make a commitment. You, you make a commitment to your clients and you need to honor that and you need to show up for that and be wholly present and represent that to the best of your ability.
A
Yeah, I don't want to make it sound like I can't give credit where credit is due. There are a lot of agencies out there that do a lot of good work. Right.
B
Yeah, of course.
A
You know, you asked me a question about where in the future do I think the agency business is going? And I do. I see it very, very clearly that agencies are going to continue to be driven by this business obsessive money machine, which, okay, I understand, like the agent business is filled with those people. Yeah. But there is a natural downside to having that belief system that I don't care how disciplined you are is going to show at some point. Yeah, it will. So, and I, and I trust the audience, I trust parents and I trust players. They're going to be smart enough. And so I'm educating them. Right. At the end of the day, I want these guys to make good decisions, smart decisions, whatever decision they think is the right decision for them. Just with information that's actually valuable.
B
Yeah. They can do it with the right information.
A
Yeah.
B
And in that you answered my last question, which is what in fact makes, you know, an agent valuable, makes an agent a true advocate. And you just answered that it's truly being vested and maintaining that high Care for every client across the board, no matter what kind of deal that they're doing, but knowing what they want, making sure they're informed, that everybody across the board's informed.
A
Well, here I actually want to add to that, because here is something that I do think is interesting, is when you sit down with a player and a family, Right. And let's just say they're either interviewing agencies or they have an agent. The reality is, I think a lot of times parents and players don't really know how to define what a good agent is. Right. They think a good agent is someone who negotiates the biggest contracts. Right. That's an element of it. A good agent is someone who has the most clients. Right. I would totally disagree, but, like, I understand how they could come to that conclusion. Right. But I think what makes a good agent, it's. You have to be good at at three components, like, equally. Well. Right. There's like, the moral component, which is like, yeah, are you a man of integrity? Are you trustworthy?
B
Yep. Of course. That's the base.
A
Well, what's interesting is, like, trustworthy is different than you saying, I trust my agent. And I don't know if you follow that, but, like, being someone who's trustworthy is someone who is honest, not just here, but out there. Right. And so let's just say outside of our interaction. Yeah. Like, you trust your agent. Well, that doesn't mean that he's being honest with you. You just trust them. That's like your feeling.
B
It's different than a marriage.
A
Right. So being more. We're going to call it morally good. Right. Is one component. But you have to be really, really good at that to be a good agent. Right. I guess the next one is. Is, like, functionally good. Right. So that's like, do you have expertise in the industry? Are you season? Do you have experience? Are you somebody who is educated in it? Right.
B
Do you have the relationships?
A
That's right. That's right. Like, can you do the job?
B
Yep.
A
Right. Can you do the job as an agent? And you've got to be great at that. Okay. So morally good, functionally good. And then the third component is, like, relationally good.
B
Yep.
A
Right. You have to be able to know your client and build a relationship with your client on such a level that when you're negotiating his contract, you're not doing it for what's best for you in that negotiation. You're doing it so that he meets his needs. He has said, I want to stay with this organization. So your job, despite the Fact that you may think it's to get him the most amount of money wherever is actually to get. Get him the most amount of money here.
B
Yep.
A
If that's what he is hiring you to do. Right. So you can't do that unless you are invested in the relationship. And so what I think the mistake that's being made is you can be morally good and that's it. And be a terrible agent.
B
Yeah. You're not a bad guy.
A
Right.
B
Yeah. But you're not.
A
You're a great guy, but you're not functionally good.
B
Right.
A
You could be morally bad and functionally the most amazing person ever. You're a terrible agent because your job is to literally be honest. If anything, it's to be honest with your client. Right. It's to be honest in your dealings. Mm. If you're manipulating your client and lying to your client, you may have done a phenomenal contract. You're a terrible agent. You could be amazing, morally amazing functionally. And have absolutely no relationship with your client. And I am telling you right now, you're not a good agent. You have to be great at all three.
B
Yeah.
A
So.
B
Well, and we weren't just saying a good agent. That's what we're saying, like, how do. You are the best. You know, how do.
A
Well, I. I did say good agent.
B
But, like, the best agent.
A
Yeah.
B
Um, no, I thought that was just gonna be something good to really define. Cause I think some people would say, well, if you're functionally a really good agent and you're doing great contracts, maybe I don't care if you're a great guy. It doesn't matter, because you're getting us our money.
A
Happens all the time.
B
So in your. In your premise, though, you're. You'll know perhaps what people don't. But perhaps what people don't see, though, is, like, maybe there was something on the table they don't know. Because if you're not trustworthy in the world, then maybe the team's not trusting you. And doing the dealings like, it's only as good of a contract that. That, you know, it could be. So I think that's an important call out is like, when you look at who's representing you or who's representing your child is. You can use those three guidelines and know that they're important and know that even if there's an outcome from it, it may not be the best outcome if your agent has a deficit.
A
Sure.
B
In three of those.
A
Well, remember you asked me the question earlier, like, what's a mistake that. That is being made that you see players or parents making. And by outsourcing the agency and thinking the solution is out there, they do that with the agent decision, too. And so it's like, okay, well, I know that he represents a bunch of good players, and I know that people know who he is, so I'm just going to choose him. And not because they think he's perfect for them, but, like, I don't want to think about it. I just don't want to worry about it. And it's not that. That. And I want to make myself clear. I'm not saying that that agent may not be good. What I'm saying is for you to understand, this is where you're the solution again, for you to understand who's the right agent for you, you've got to lift the weight. You've got. You're not going to get massive in the gym by watching a YouTube video. You actually have to be the one that lifts the weight. Right. And the same applies for all of this. And what's interesting is I think people hear that and probably think, that sounds like more work.
B
Yes.
A
No. Just like the gym. It's like, you may be miserable today, amazing tomorrow, best life tomorrow, but would you rather feel comfortable today and a miserable life tomorrow? Because that's. That's the other way this goes. I'm going to choose this agent. They're like, I don't want to think about it. He's my guy. Okay. And then you find out that you turn down a deal in the news and you're like, wait a second, I didn't even get the chance to say yes or no to that. Right. Or you find out years later that, oh, wait, yeah, that team offered you, and you never even got the phone call from your agent because it was his decision on what you should do. Like, those things happen.
B
Yeah.
A
And if you're choosing to be represented by that agent and you know that that's a risk, good for you. That is totally fine. That is your right.
B
Yeah.
A
It's not my decision. I'm not. I'm not saying I'm the only one. That's good. Right? No, it's. You have to understand how you're. You're valuing and how you're evaluating what you want and then see it clearly and say, that's who I'm choosing to meet my needs and feel really good about it. And that's all you can do.
B
Yeah.
A
So don't ever blame me for it.
Date: October 29, 2025
Host: Matt Hannaford
Guest/Co-Host: Tara Hannaford
In this special episode, Matt Hannaford—veteran MLB agent and host—welcomes his wife, Tara Hannaford, as his interviewer and conversational partner. Rather than focusing on Matt’s origin story, which is covered elsewhere, Tara takes listeners beyond standard agent talk and into the real-life evolution, challenges, fulfillment, and perspectives that come with a 25-year career as a baseball agent. The episode unpacks milestone moments, personal roots, values in agency work, and real, direct advice for athletes and their families—delivered with a balance of candor, warmth, and plenty of baseball analogies.
Early Milestones and Utility Roles
Transition to Full Agent
Mentoring and the Myth of Shortcuts
[20:00 – 24:00]
[24:03 – 29:45]
[30:06 – 38:38]
Biggest mistake: outsourcing all decision-making (“They just want to be told what to do...But to a lot of families, I think they just want to be told, and it’s never going to work out quite like you’re hoping.” – Matt, [31:58])
On switching teams: consider the child’s age, goals, and experience, not just performance
"The reality is, they're the solution. Right? So that's the mistake that comes to mind." – Matt ([32:12])
Tara highlights anxiety around “time pressure” for families; Matt clarifies that, developmentally, there’s more time than they realize before college or pro matters
“You can’t possibly know how good your son’s going to be until, like, 15, 16 years old.” – Matt ([36:08])
Overemphasis on early results risks burnout and poor long-term decisions
[39:49 – 42:19]
[43:27 – 49:38]
[49:44 – 53:14]
[53:39 – 59:29]
[59:32 – 66:38]
This episode is a masterclass in what makes an ethical, fulfilled, and successful sports agent—plus vital guidance for any family navigating baseball and representation. Matt and Tara’s insights are invaluable for players at every stage, as well as for aspiring agents. The episode encapsulates not just the “business” but the “heart” behind sports agency.
Listen for: nuanced advice, behind-the-scenes anecdotes, foundational values, and a memorable, often humorous exchange between a husband-wife team who know baseball—and each other—inside out.