Interview #23: To Play College Ball or Not
Tyler Herb, from Benicia, CA
So this was the interview I was least ready for. Not from a prep standpoint or anything, I’d just had a long workday and we agreed on 1:30 Pacific time, which was 2:30 in Arizona (not anymore though! The rest of y’all need to learn the joys of never having to change your clocks). So I had to run out to my car and the hot leather seats where I could get a cell signal. I was convinced I was gonna be awful for this interview. But as soon as we got started, catching up and then on down to business, the hour flew by. Most of these interviews have energized me, and this one was the one where it was most obvious that not only do you guys enjoy the interviews, but it’s a huge boost for me, too.
A couple quick details before getting into it. Tyler was born in 1986 and from Benicia, California, a city 35 miles northeast of San Francisco. He went to Cal Poly, that’s where I knew him from as he and I lived on the same floor freshman year in the dorms. He lived in San Francisco for most of the years after college before recently relocating back to San Luis Obispo (SLO) with his wife and kids, who are now getting ready to start their own baseball path.
Playing days and coming to terms with them ending
What's your favorite baseball memory?
“It would probably be, for me, playing baseball. One that pops in my mind first is the very first home run I ever hit. I had a home run in farm at the little field. At that time, people had started to do that, you'd see a home run here and there. And I remember talking to my dad about it, my dad was my coach, and I remember asking him, ‘Man, how do you hit a home run?’ He said you just gotta be patient and it’ll happen, and almost like the next game I hit one and I just remember that being one of the best feelings ever at the time. So I'll go with that.”
Do you still play?
“I played in one (adult league) in San Francisco for a while. But, man, it was so brutal to go from, I was a good baseball player back in the day, and I sucked in that league. It was just like the older I got, the more suckier I got. I couldn't do it anymore. I can't even imagine trying to play now.”
How long did you play then? All the way through high school?
“Yeah, through high school competitively.”
Is it your favorite sport?
“It definitely was my primary sport growing up, and was absolutely my favorite sport for a long, long time. It has ebbed a little bit for me as I've gotten older. I don't really know why that is. I would still classify it as my favorite sport, just because it's been the thing that I grew up with my entire life. It was the singular focus for a long, long time, and I would say in the last decade or so, maybe half decade, I've shifted more… like I got into golf a lot more now. So golf has become my number one favorite thing to play. That's without a doubt. I wouldn't say I necessarily watch more golf than I watch baseball, though. But yeah, I’d still say it's my favorite, but it's changed a bit.”
Who got you into the sport?
“My mom signed me up for T-ball out of nowhere. And my dad had no idea, because my dad was kind of into baseball, but not really at that time. By the time I got past coach pitch, it was clear I was pretty good, and I think the better I got at it, the more interesting it got to me. And my dad started coaching me when I was in farms, and so he coached me from 8 years old through 12. He also coached summer league, so that became a thing for us as we got older. But to start off with, my mom randomly just signed me up. So it's funny, because my son is 4 in March, and I just signed him up. So just kind of thinking through like, hey, you never know how it'll go. But it’s one of those things that is, I started doing and was good at it.
As I got into baseball, I became a huge Giants fan. My parents are from back east, my mom’s from New York and my dad’s from Ohio, so they liked baseball growing up but weren’t huge fans by any means. But as I became a fan, they then became fans, too. Now they're heavy Giants fans as well, but I would say that started from my interest in in the game.”
You played year-round, were you doing travel ball and things like that, too?
“Yeah, summertime was always like the tournament team. And so there'd be a tournament team that would play all summer from Memorial Day through Labor Day, and then in the fall, there was always a fall ball league. The only time we were really traveling was during summertime, like I wasn't on one of the club teams. Club teams were a thing, but it wasn't like it is today. Today is insane. Back then, I did whatever was available to us in our hometown. We played in our travel summer league team and then the local fall team, too. So it's basically playing all year except for the winter months, and we’d start again in the spring.”
Did you have any goals of playing in college?
“Oh for sure dude. Until I was a sophomore in high school, I thought I was gonna go pro, so that's the delusion that I think every high school kid has. I definitely wanted to play in college. Probably my junior year, though, you kinda realize, like I was good, but not nearly good enough and it's just you don't quite realize that when you're younger. I held onto it as long as I possibly could until it was clear it wasn't gonna happen, and it probably wasn't clear to me until I was a senior that like, oh, I'm probably not playing afterwards.
When you’re going through the college applications thing, I'm like, oh, I wanna go to Cal Poly. You know, Larry Lee (Cal Poly’s baseball coach) is not knocking on my door to come play for Poly. You kind of put two and two together after a while, and I'm sure I could have gone and played Juco somewhere and done that route. But to be honest, by the end of the high school run I was ready for a mental break as well.”
What had you burned out at the end of high school?
“I think it's a combination of a couple of things. I’d been playing for a long time and been playing year-round for a long time. There’s an aspect of growing up where it's a combination of realizing, okay, I'm actually not good enough. And coming to terms with that for the first time, like, I think there's some people who never really come to terms with it. So they do go to a D-III school in Missouri or whatever. I started realizing like, okay, I'm not good enough. I wanted to go to Cal Poly. I was just at a point where, there were ups and downs in my baseball career, too. It wasn't all Hunky-dory, like I had a position shift my senior year. I caught my whole life, and then I got moved to first base. I was ready for I think a mental break at the time.
What was really tough for me was going down to school and like, I got the break right that I wanted, 6 months, but when baseball started up at Cal Poly, I legitimately felt like I should have been on the team. Like delusionally, but in my mind I was like I should be playing. And so going to games as a freshman and sophomore, and even probably junior year and beyond, I felt like, oh, I belong there. I got to scratch that itch in that men's league a little bit, but it's just funny when you're 18,19, you're a cocky asshole. You just kind of think, I should be a part of that, even though there's no way, I should have been, right?”
Tell me what it was like the first couple of games at Cal Poly you went to, sat there, watched a guy make an error, and you're just like, I can do better than that guy…
“It was almost like an unfathomable itch, I don't think I was the only one, but I definitely soothed it by drinking too many beers at the game, and just being a 19-year-old dumbass right? (note: obviously he means drinking before the game. The fine attendants at Krukow’s Clubhouse never let anyone underage drink beers 😉)
I really, truly in my mind believed that I could and should be on the team at that point in time, it was more an opportunity thing. Which again, I don't actually think that now. In reality, it's like, no, you're not good, you were never going to be good enough to play in that sort of environment. But I felt that way. And I think the reconciliation of those two things is a challenge that every ex-athlete has to experience at one point in time.
And actually, it's funny that we're even talking about this because one of my good buddies, who was a pitcher at Cal Poly, he just moved back to SLO a while ago, and I had dinner at his house maybe a couple of weeks ago. I was telling him the same thing, where I felt like I should have played, etc. And he's like, ‘Yeah, that same thing happens to everybody, though, at some point.’ Like he played for Cal Poly, but afterwards had the realization like, yeah, I'm actually not good for whatever the next level is. At some point, there's a level you're not good enough for.
I had that realization, probably sometime middle of high school and then it really hit home senior year. But I feel grateful that I was able to not have that influence my life path beyond that, even if it did, you know, end up with me, being at some of the Cal Poly games like, ‘fuck, it should be me out there.’”
I bet part of what pissed you off when you watched college baseball, you had to miss the clubhouse and the friendships.
“What I would say is, it’s the entirety of the camaraderie and bullshitting that happens amongst young boys, and becoming men together, as you kind of grow up together in a sporting environment. There's so much humor and watching each other evolve and grow, and fuck up and make errors, mistakes, dumbass stupid errors, or striking out when the game’s on the line, but then also getting game-winning hits and making diving plays. The whole totality of the relationships, you forge crazy deep bonds. Guys that still, to this day, like I never talk to them, but when I see them, it's like nothing changed. The bus rides to different spots, postgame grabbing burgers, bullshitting with each other, and like ribbing each other, but then, having each other's backs no matter what…”
So compare that to now and say, you just got your son into T-ball. Imagine he gets hooked like you did, are you going to let him go year-round like you did?
“Oh yeah, I got an opinion on that. I know where you're going and I got an opinion on this for sure. I can't stand it. I think it's a huge disservice to kids, and in a lot of ways, it's probably the thing that I regret the most about my personal experience. Here’s how I start to think about it for my kids is going back to what I told you earlier, where I felt like I didn't quite realize until later on… me and everybody I played with in high school, we all thought we were gonna go play college, right? And the reality was, we had one guy who was elite, and he did get a scholarship, and he went to ASU or something, and even he played like, a semester, and then was done. My point is, you’re not gonna make it. I wish I had a little bit of a better mentality about like, if you make it to high school ball, you actually made it. That is a really huge accomplishment and you should really focus on enjoying that. But I think every kid’s still thinking about that next thing, where it's like, oh, I'm gonna go to the next spot.
I think it's gotten way overboard. And what I wish I had done differently was I wish I had focused way more on multi-sport stuff. I spent all this time doing baseball, and again it was good for me, but I wish I'd spent more time trying to be an athlete. And this is what I would kids, it's the same, for, like the mentality when I switched from catcher to first base and like, I fucking hated first base because I was like, I’m a catcher. So I just never really tried to get good at it. It was like I floated through senior year, but it kind of sucked.
I think in retrospect, the mentality I'd wanna push for my kids is for one, focus less on being a baseball player and focus more on being an athlete. So therefore, don't play baseball year-round, like go play golf, go play soccer, go play football, or basketball, or whatever. Being a multi-sport athlete, I think will make you better in the long run.
And then, if you have a true love and affinity for it then, yeah, maybe you do do that a couple of times a year. But, like at some point, take a break from it and do something different.
If your kid, or you, are that good, you will be seen. I didn't understand or appreciate that until later. I remember, there's a game we played in high school, and there was this huge pitching prospect for the other team, and there was probably like 75 scouts in the stands. I was a sophomore and I was catching my buddy, he was also a sophomore. It was a really cool thing, we ended up beating them like two to one. The point is, I played that whole game all the way through. If I was that sick, if I was that good, it could’ve happened right then. They would have seen something. And so it's just like, you never know how that all works. If your kid is that good, or you were that good, you will get seen and you will make it.”
My favorite part of this interview was getting a realistic, down-to-earth recap of Tyler’s playing career. I’ve heard several times so far from others about how they thought they were better than they actually were and they would’ve gone pro or made teams in school if the coach didn’t hate them or they didn’t get hurt, etc. But it’s refreshing to hear Tyler’s perspective that, yes, he couldn’t stand the fact that he wasn’t playing in college. He would watch games at Baggett Stadium and secretly hold a bit of resentment that he wasn’t in the dugout, even over the last guy on the bench.
But then he mentions how he realizes now that being a successful high school player is something to be proud of. Baseball is so effing hard that kids just wash out in droves by the time they reach their teens. And as a father with kids entering their athletic phase, he (correctly) pushes back on this era of specialization of kids in sports, where suddenly by the time a kid is 8, he’s already playing baseball year-round (and heading for Tommy John surgery at 21), or playing soccer or hockey or basketball or whatever, all while draining their parents’ bank accounts to keep up on travel teams, private coaching, camps, equipment and everything. Youth sports generates over $15 billion in revenue annually in the US. Think about that and then think about how many kids in the past 20 years spent tens of thousands of dollars on their “specialty” when they would’ve been better off playing a variety of sports, going to school, learning different skills because kids need to develop to succeed in the real world, not to be the top catching prospect in Central California.
Living in SF for the 2010-2014 dynasty
So then, after college, you moved straight to San Francisco. So what was it like being in the city for that run. (Giants from 2009-2014)
“That was singularly the coolest, like outside of family and friends and whatnot, the coolest thing that I've ever experienced. To go through that whole stretch, they've never won, got close in 2002, I had season tickets in the bleachers starting in 2010, and basically to be a part of every aspect of that. If you think about the blip of them winning 3 world championships, and it happened in the time that I lived in San Francisco, and I was 23 years old through like 28, it was freaking unbelievable. The atmosphere that it created living in the city was, like, peak San Francisco, in terms of the vibes there, when things were accelerating with tech being there, and just there was a lot of hype around the city in general. So you couple that with the fact that the Giants were winning and they were a team that was super ingrained in the city. It was awesome dude, and honestly, I'll never forget that.
What I would say about 2010, it felt magical the whole way through, but that opening game when Timmy pitched that 14-strikeout, 1-0 one-hitter win over the Braves, that's when it was like, holy shit, this is nuts right? You could kind of feel something special could happen just based on the pitching staff that we had. It all felt improbable in a way, but at the same time part of you was like, I don't know, man, I can kind of feel this could be a thing. And I think when they beat the Braves, and then they went into Philly, just weird shit was happening. Cody Ross with those home runs off Halladay and like us, you know, you could feel that happening the whole way through like, it wasn't probable, but at the same time it was. It was legitimately a top three life experience for me was going through that 2010 season.”
“The thing that stands out to me is after, and they all kind of blend together now, but the game 5 win in Texas when the Giants won, we were downtown. We were watching the game at the Civic Center, and then just floating through the city after that, just seeing the euphoria. I get goosebumps even thinking about it now.”
Did you get season tickets right after moving to San Francisco?
“It didn't even cross my mind. But I had another buddy who we went to Cal Poly with, the big goofy guy on a scooter. I actually hated him in the beginning, which is funny. But he was also in San Francisco, and he got season tickets and was like, look, we got these tickets. I got this one by myself, we can get a packet of four over here right? And it was pretty cheap, I think it was like $500 for the season and we went to a ton of games.
So no, it wasn't a guarantee for me, but it was one of those things where he kind of, he pushed me with the point that I was like, oh, it's hard for me to say no, and, like, I spent legitimately all my disposable income at the time on the game. So it was a big decision to make. But I did it.”
You said you kind of lost a little bit of interest. Is that just because you have a family and all that now?
“Yeah, that's a good question. I don't know. I actually ask myself if I lost a little bit of interest because I think the game changing around the 2015 mark, and really getting longer, slower, and more boring, more strikeouts. That whole shift where it's like the game isn't is as exciting as it was 10 years ago. So that's part of it, I think, in general. I was a huge fan of all the changes they put in place this last season, pitch clock, every bit of that was to me the right changes.”
I may have been less enthused when it was actually happening, especially since the 2009 Giants team ran down my Padres in the end, but I do love hearing stories from people who were at the epicenter of championship years, or even just exciting years in a franchise’s history. In San Francisco’s case, the last World Series was 10 years ago and the city is in a much different place in 2024. The team is still popular, but the days of that core group are officially over now that Brandon Crawford is gone. The city is struggling with empty office space, soaring real estate prices and a slight homeless problem. I wonder how you bottle up that community pride that you hear about when people of all backgrounds in a city are all in on their sports team, and turn that into social and economic progress as well, when all of a sudden everyone raises their guard again and ignores their fellow citizens in public.
Baseball lessons in the business world
What do you do for work now?
“I run an accounting org, so I'm a controller for a software design company.”
So you're in management?
“Yeah.”
And then, would you, loaded question, would you say you're good at that?
“Yeah, I think I am. I was not as good earlier on in my career when you're more just responsible for powering through work. I started in public accounting, and I was never looked at or considered to be one of the top guys on our team, even though I thought I was beyond adequate. But I just like didn't have that same appeal to the folks that were running teams for the first few years. As I got older or progressed in my career and I got to be a manager and whatnot, and I got a little bit more influence. I'm comfortable talking to people and comfortable communicating ideas in a simple way, right? And I think that's a really hard skill to have. So the higher up I got in my career, faster I started to progress. I feel like, that's something I'm actually really good at. You need to have a baseline knowledge of anything you're trying to manage or lead right?
But I always felt like I was better at the execution of vision and sort of the management piece, if you will. I could never be like an engineer. Right? I’d probably lose my mind trying to do that work. But I'm good at this part of it. So yeah, I would say so.”
So yeah, when I met you in the dorms, you were always the outgoing, friendly type. I was on one end and you were way down the hall and we’d still hear your voice all day.
“I was. I've always been pretty naturally comfortable on my extrovert side. I definitely have both, like I’m whatever they call the mixes. But I've always been pretty comfortable on the social scale of interaction and talking to people, and I feel the part that I appreciate the most about that is I feel equally comfortable talking to the janitor, or assistants, or whoever it is, as I do, to the CEO. There's no difference for me in terms of trying to engage with different people. I think that is what has helped me as I've gotten, in my career at least, as I've gotten older like. That's the part that I always had, but I didn't really appreciate that in terms of what that was.”
Being part of a team in baseball as a kid growing up all the way through high school. How much did that help you now? Do you feel like dealing with different people, having to communicate, are there any lessons from baseball you put to use as an effective manager today?
“I think you already just kind of said it. It teaches you, for one, how to communicate with different people. You're all sort of working towards a collective goal. So the concept of goal management is created right away, you all are working your way towards something.
The understanding that you can't treat every single person the same way. People respond in different ways, you get that exposure. And then I think probably the most important aspect is learning how to deal with adversity. You learn how to lose right away and what that means. And some people are bad losers, right? And I think that losing, in a lot of ways, also teaches you how to just naturally deal with failure in any way. In any career, you're gonna be dealing with the failure, of course. It's a cliche for sure, right? But it really does teach you how to process human interaction in a way that a lot of other things can’t.”
I mean, through sports and business I’ve managed a lot of different types. 18, 19-year-olds, 40-year-olds, everybody. And when I manage them, I have to talk to all of them in different ways. Some need to be babysat, some need to be left alone…
“That’s exactly right! Same thing happens to me. You nailed it, you have to learn how to deal with a lot of people in a lot of different ways, even when you're not coaching, even when you're just on a team with somebody. It's like, ‘Dude, freaking asshole over here won't hold his weight over here.’ And I think it's because you are working towards the same collective goal, and that's what everyone, in theory, at work is doing. And so you learn how to manage towards the same thing at an early age. So, I completely agree with that.”
The two things I take from this part are one, I always feel like the people who learned how to be part of a team earlier on in life are much better in the working world than those who had to develop those skills later on. Second is the adversity part. No one enjoys adversity, but it’s something that, the sooner you learn how to deal with it, the better off you’ll be. And when you see people who never learned how to fail or get kicked in the nuts and crawl their way back up, those are the people dragging teams down, in sports, work or life.
That was very insightful. I am not involved in baseball myself. I just got into the local baseball history when I found these 100 year old pictures of the early nines in St Mary’s. Then I read a log them and the early history in St Mary’s Pennsylvania. In 1916 there was a minor league team in St Mary’s. They were called the St Mary’s Saints. Three of the players went on to the major leagues.