Season 2 · Episode 22 · Jan 21, 2026

Transcript: Terry Lipford on Roots, Responsibility, and REACH

Hosted by Charlie Martin & Jack NelsonMiddle School Faculty43 minutes6,589 words

In Episode 22 of Season Two of The Late Start Show, we sit down with Mr. Terry Lipford ’98, University School alum, middle school teacher, basketball coach, and Director of the REACH Program. Growing up on Cleveland’s east side in a family of educators, Mr. Lipford reflects on the early influences that shaped his value

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Good morning, and welcome back to the Late Start Show. We are here today with Mr. Terry Lipford, University School Class of 98, middle school teacher, basketball coach, and director of the REACH program. How are you doing today, Mr.

Lipford? I'm doing very well. Thank you guys for having me. Yeah, of course.

Thanks for being on the show. So, Mr. Lipford, before we jump into US and REACH and all the million other things that you do, can you just take us, you know, all the way back where you grew up and what a young Mr. Terry Lipford was like?

Sure, Jack. Yes, I'm a Clevelander. I'm born and raised in Cleveland. I grew up on the east side between Cleveland Heights and East Cleveland.

Mostly Cleveland Heights. Went to public schools through sixth grade, Rochville Elementary School, I believe, up until sixth grade. And then it was right around my sixth grade year, my family we moved to East Cleveland border Cleveland Heights in East Cleveland and it was it was at that point where we decided to look at private school and came over to behind me he came over and figured I was here seventh grade I had a chance to attend the middle school here at the Shaker Kemper school graduated in 1998 so I know I come from a family of educators So my parents have always tried to instill in me and my siblings for opportunities in school, taught us to work hard, to carry ourselves with a level of discipline. And so, you know, I was also always big into sports, you know, when we have athletes, you know, and try to follow in their footsteps and participate in sports.

You know, so, you know, those those those were kind of my interests as my interests, you know, throughout my entire life. you know and when you think about your family growing uh whether or not your siblings your parents kind of people around you what's some of that like home life that really shaped you going forward oh again family was was very very important um you know in my immediate family i am the oldest of three i've got a younger brother younger sister um we were always very very close, you know, very, very tight growing up. And again, going back to my parents, my mom and dad, they taught us that there's nothing more important than family. You know, and then I'll extending, you know, beyond just my immediate family, my father has a big family. He comes from a big family.

He has five brothers and three sisters. And so, you know, we were always, getting together with his family at holidays. Family was very, very important and continues to be to this day. Now, with my own family, I have two daughters, a wife, and I'm certainly trying to pass along to my kids those values that were instilled in me.

That's awesome. Let's go back to when university school first got on your radar, but what made you say like, yeah, let's do this, let's make this change? Well, again, coming over, you know, in middle school, and like I said, seventh grade, I had to be 11, 12, somewhere in there, so not sure I really had a whole lot of say in the decision. Again, my father was a longtime educator, teacher, administrator.

So he certainly knew, you know, what would be good, you know, for my brother and I, even my sister, you know, in terms of our education. And I don't know how they found out about university school. Any university school being here in Shaker Heights is not far from where we live so perhaps just you know being you know close to to in our neighborhood and when we grew up maybe put the school on a radar but it was a no-brainer you know knowing the reputation of the school academically the resources the opportunities that are here for students. You know, the only question was, you know, would we be accepted, you know, and would we have an opportunity to come?

And once the door was open, there was no question that we were going to walk through it. So again, mostly a decision that was driven by my parents. Having attended public school in Cleveland Heights for six or seven years, you know, I had a lot of friends, a lot of connections, a lot of ties. Like I mentioned, sports and athletics were a big part of my childhood, and I can remember playing on travel teams in Cleveland Heights.

And growing up in elementary and middle school, the only thing that we thought about was being able to play for your middle school team, for your high school team at Cleveland Heights High School. And so I can't say I necessarily wanted to leave, you know, when I did. But, you know, this was an opportunity that we just could not pass up. And it turned out to be a great one, a great fit.

You know, obviously, as you said, you got to look back all the way when you were 12. But do you remember your first day at U.S., the kind of vibe of the school, the people, the first impression, or even maybe that first year and what you were kind of really thinking? My first memory at U.S. was obviously football. You know, you start football before the school year begins, and those were my first memories, you know, of the school, of the community.

It's coming to practice, you know, and this was my first time playing tackle football with pads, And so I can remember to this day, coming up during the summer, like I said, before the school year started, and really establishing some friendships and some relationships with other students and players that were on the team and some coaches as well. And, you know, that allowed me to, I think, feel like I was a part of the community, you know, feel like it was a place where I belonged, you know, and kind of make that transition easier because I had those connections, you know, through my team, you know, through sports. and that certainly made the start of the academic year a lot easier. And moving into high school, did you continue football or did basketball kind of take over as the main sport? And then maybe what other extracurriculars did you kind of throw yourself into?

Yeah, athletically, it was all basketball in high school. I'm going to say I might have dabbled a little bit with track, but really didn't stick with that for too much. So it was it was pretty much four years of basketball and, you know, playing, playing year round, you know, playing in the fall, obviously in the winter, the spring, the summer, really kind of focused in on basketball from from an athletic standpoint. But then outside of sports, I mean, I certainly remember our black student group.

It certainly was not called the Pembroke Society at the time, but I think we certainly had a cultural awareness society or cultural awareness club. I think it might have been called, but it's a student group for African-American students and, you know, was very much involved with that group in high school. And then and then also did some work with the REACH program. That was my first introduction to the REACH program, actually was was working with the program as a counselor in high school.

And then, you know, obviously many, many years later, the opportunity to come back and serve as a director of the program. you know kind of think about what's one memory either from us or any of the extracurriculars that you did that really still sticks with you whether it's funny or just really just something that sticks out that's iconic wow iconic um that's a good question i don't know that i have an iconic uh memory that that jumps out uh i thought you guys might ask me to to think back to uh to my years in school um i can't believe it's almost 30 years that i've been out now so um yeah i mean i can't think of an iconic moment but um you know i mean i i remember uh you know during during the school day uh you know when we had study halls or free periods if if we weren't doing work um i remember playing cards you know with with my closest friends in between, you know, the locker area, you know, and trying to pass the time and, you know, whatever way we could again, you know, when we didn't have commitments in our classes and homework and, you know, a project of papers that we had to complete. But yeah, I mean, I would say the relationships, relationships that, you know, you developed during school and then that you carried with you, you know, after graduation and into adulthood. Looking at some of those mentors or coaches, teachers at U.S. that had an impact on you, do you remember any of those that really stick with you and still, you know, you kind of take something from them and use it today For sure Teachers you know Terry Kessler probably my most memorable teacher favorite teacher teacher that I thought you know had the biggest impact on me Remember having Mr. Kessler in an AP economics class in high school and appreciated him because expected a lot from me, you know, and really from all of the students having those high expectations.

Really, really appreciated that. And I think I was a good student. I wasn't one of the top students in our class, but I did what I had to do, took care of business. But Mr.

Kessler always made you feel like you know you were one of those top students you know regardless of what your perception of was of yourself um you know he made you feel like you could do anything uh as long as you you put in the effort you put in the work um you know and he expected you know that excellence in terms of the work that you produce for him so i definitely remember mr kessler pat aliazzi another legendary teacher at university school someone that when we were in school you know if you didn't have Mr. Aliazzi you know you were worried that you would have him at some point but then when you got in the class and you worked with him you realized that you know he was just trying to to get the best out of you and again teach you how to communicate to teach you how to to think critically, teach you how to make an argument and stand on something that you believe in. And again, just another great teacher. Gustavo Pla was a foreign language teacher that I remember very, very well.

Great teacher, great mentor. You know, Jim Garrett in terms of teachers, coaches, Jeff Morton. I was a teacher, coach, administrator at U.S. when I was here as a student. I remember Mr.

Morton very fondly. He was my first high school basketball coach. And then Tom Lombardo, who is still coaching now. I think he's a football coach over at St.

A's, was one of my coaches when I was here, one of my basketball coaches. great coach that I enjoy working with. I could go on and on, you know, I mean, a lot of great teachers that I had a chance to work with at U.S. and coaches that had a great impact on me when I was in school. And now that I'm a teacher and a coach myself, I've tried to kind of follow in their footsteps, follow the example that they set. You know, looking back at high school obviously as us being students of you and us being also kind of being coached by you in basketball we know how good of a basketball player you are do you have some of your kind of favorite games or maybe some moments in basketball that like really stick out to you maybe like a buzzer reader or something um you know i i was very fortunate to to play on uh some successful teams at U.S. in high school.

A couple of games that I remember, I remember we played, you know, one game against St. Joe's over at their place. You know, I think both teams were very good, you know, and it was a typical high school game where the stands were packed and, and, you know, highly contested game back and forth. And if I remember correctly, I think we were down late in the game, needed to, you know, make a shot.

I think we may have been down three and needed a three to tie the game up. And so Coach drew some kind of play up, and I think I was able to make a pass to one of my good friends on the team, Ryan Schneider. I think he hit a three, sent the game into overtime and I believe that we may have pulled the game out into overtime but that's a game that certainly stands out as it was a good win for us back then. There's also a game that we played against Cleveland Heights High School which got a lot of press at the time. back in the late 90s, Cleveland Heights was, you know, had a really good team, had a really good run, you know, and they were one of those top teams in the city, top teams in the area, in the state, and we went to their place, you know, and I guess even though we had some good teams in the mid to late 90s that I had a chance to play on, we were still trying to kind of make a name for ourself, you know, and our school in terms of our basketball program.

So it was kind of a David and Goliath type game where, you know, we went to Heights and most people didn't give us much of a chance. I mean, they were really, really good. And honestly, we probably shouldn't have been in the game with them. But, you know, it was one of those nights where we played really, really well.

I think they might have been missing some guys. And, you know, they got into a game, and before they knew it, they were just in a bout, but maybe they didn't expect to be in. And we ended up winning that game. And, again, a game that I think most people thought, you know, we wouldn't have a chance, and we were able to win that game.

And so that's a game that, you know, I think people still talk about to this day, you know when when us went to heights and won that game in the 90s so that was great and also for me going back home to where i grew up you know playing against a lot of people that i knew uh certainly that's a game that you know i remember for a long time and in all of our playoff games you know the last game that i played in my career i think we lost to saint vincent saint mary um you know and like the district final you know and it was like you did but we had a really really good team, you know, and thought that we might have been able to make a run, but unfortunately ran up against a good team in St. V and weren't able to pull it off. So, you know, we'll always remember that last game. And then as, you know, as a coach, had a lot of great memories, you know, coaching in high school and now in middle school for the past, you know, eight or nine years.

And, you know, I've always loved sports and appreciate what, you know, what they've done for me throughout my life. That's awesome. And what do you think some of those lessons that you kind of learned as a player and now can pass on to your players as a coach, what are some of those lessons that basketball has given you that translate to life? I mean, just, you know, the importance of hard work and the benefit of hard work.

You know, when you go after something, and you give maximum effort, you make a commitment to it and you work toward it diligently every single day, you can reap the rewards of that effort. Certainly resilience and how to come back and bounce back and get back up after you fail. If something maybe doesn't go the way that you wanted it to or the way that you would have liked, you got to be able to keep moving. You're not going to win every single game that you play.

Even when you do work hard and do everything that you think you need to do in order to win, you just don't win all the time. You don't succeed all the time. And so being able to keep pushing, to keep moving forward, even when you run into some obstacles and like I said, maybe things don't go your way is, is, is a very, very important lesson. The value of teamwork, you know, I think I, I certainly realize and appreciate that nothing that I've done in my life, nothing I've accomplished in my life, you know, has, has happened solely because of the things that I've done, but there are a lot of other people that have, that have contributed to, to my success and allowing me to accomplish the things I've been able to accomplish.

And I think leaning into that teamwork, you know, and the importance of working with other people in order to, you know, maximize your potential and realize all of the things you want to realize is another incredibly valuable lesson, I think, that you learn through sports and through athletics. You know, after university school, you chose John Carroll. What pulled you there? What were you hoping the college would really give you?

And what was your major there? Sure. So I went to John Carroll because it was local, it was close to home. I did have, my uncle went to John Carroll and, you know, I had a good experience there as a student athlete.

When I was applying to school, I wasn't one of those that applied to like 10 different schools. I tried to kind of to keep my focus narrow. There were probably four or five schools that I was looking at a couple schools in state couple school out of state probably my number one school going into the process was Columbia and I got accepted I remember going to visit the school for like an accepted students weekend you know something like that and I can remember like sending sending in my my deposit a main, I was going on to Columbia. So I thought up until that summer after I graduated and kind of got cold feet, thought, man, I don't know if I can live in New York, you know, while it was great to be up there for a couple of days and to visit just didn know if I wanted to to live in New York City for York City for four years And I also had some friends back home that I didn know that I necessarily wanted to leave.

And so I decided to stay close to home and go to Carroll. I also wanted to continue playing basketball. And I had some relationships, knew some people at John Carroll and thought that I would be able to continue to play over there. And so decided to stay at home.

Studied business. I always knew when I went to school, I wanted to study business. Math, numbers has always kind of been my thing. And so I think I started out as an accounting major.

Didn't necessarily know what I wanted to do with it, but I thought that it was a practical major. It was something that I certainly could use to get a job when I got out of college. And so we started in accounting and I wanna say after about a year, year and a half, I switched to finance. That I've given my degree in finance and worked in the corporate world for about five years before coming back to US.

So I enjoyed my time at Carroll. You know, I also, you know, went over there, maybe thinking that if I started there, maybe I could leave, you know, and transfer and go somewhere else if it wasn't a great fit. But once I got there, I realized that it was, you know, a good school, good place for me. And like I said, I was able to be close to home, but, you know, not be at home.

And so it turned out to be a pretty good experience. and how did us come back into your life i know you mentioned you switched from corporate world into teaching but what was that journey that brought you back to here as faculty it was actually basketball you know believe it or not i think it was uh 2006 i went to it was it was during the summer i went to we were having a reunion of that team. I mentioned that Cleveland Heights game. I think that was in 96 that we played Cleveland Heights. And so we were doing kind of a 10-year celebration of that game.

And I came back to either to school or it might have been off campus, but there was a get-together for that team. And then the coach who was coaching at U.S. in 2006, he was at that gathering. And I just, I mentioned to him, working in business, I got a great job. You know, my schedule's a little bit flexible.

If there were a way that I could help out with the team, you know, I'd be glad to come back and help and assist, you know, and work with the guys. And so I came back to coach, and I think it was that 2006-2007 season. I was just assisting the varsity head coach, Chris Oslin, at the time. And after practice one day, as I was leaving, I ran into Bill O'Neill, another great teacher and mentor from my time at U.S.

And Dot O'Neill mentioned that they were looking for a new director of the REACH program because the previous director was moving on. this was a middle of the school year, but REACH kind of picks up in the middle of the school year as you prepare for the summer. So they were looking for somebody to fill this role. And I mentioned to him at the time, I said, I don't have any experience in education. I never thought that I would be a teacher.

Yeah, I might have some teachers in my family, but I don't teach. I don't anything about teaching and he said well this is this is more uh admin this is this is more of an administrative position there'll be other teachers that you'll be responsible for but this is more just directing the program he remembered me as a student thought i was a good kid and you know i thought i could be a good mentor role model for for these boys in the reach program and he encouraged me to take a look at it and so i interviewed for the position um certainly appreciated you know us and like i said i had had an experience working at regions of council so i knew the program a little bit um and just the idea of of being a mentor and also you know a position that might give me a chance to develop some leadership i'd be responsible for for adults i thought it could be a good stepping stone regardless of whether i would you know be there for a long time or not uh and i was offered a position you know and things kind of went from there and so now here we are almost 20 years later still doing it you know and and certainly love what i do you know for the people not who for the people listening who don't know what is reach and also how do you kind of measure impact in a program like reach you have kind of a special job being the program director so what kind of tells you that it's working whether it's the grades or numbers and how do you believe in it and how do you get other people involved with it yeah thank you for asking about it so uh yeah reaches is is a partnership you know kind of this public private partnership between us and and the greater cleveland community uh that has been in existence now for you know over 30 years program started back in 1992 and it's something that us has been committed to for a very very long time and i think you know a lot of people at the school and and that are connected to the school know about the program but um you know probably quite a few people don't but it's it's a great thing that we do uh it is a summer academic enrichment program that that targets uh designed for african-american all uh african-american middle school boys students participate in the program for three consecutive summers when they're in middle school. They start the summer after fifth grade and they finish the summer when they're going into the eighth grade. And it's enrichment, you know, so it feels a lot like summer school, if you were to ask students that have participated in the program.

But it's not that we're trying to to get students that have not performed well and help them get caught up, bring them up to grade level in terms of their performance. This is for students that are academically motivated, that are talented, that have performed well in school, and they're looking for an opportunity during the summer that will allow them to continue to take those positive strides in their development as scholars and as gentlemen. So they come to U.S., they take classes, math, science, English classes, some art, music classes. But like I said, it feels a lot like summer school.

The boys are in the classroom working with teachers for most of the day, and they are learning concepts that they're going to be introduced to, exposed to when they go back to school in the fall. So when we're working with students that are going into the sixth grade, we're trying to introduce them to some of the topics that they're going to study and they're going to learn about when they get in the sixth grade. And they're doing this during the summer so that when they get to school in the fall, they feel very well prepared. Maybe they end up seeing something during the school year.

They did a little bit of work with at reach during the summer. So we're taking talented students and trying to help them continue to, like I said, make those positive strides in their development as students. We also certainly lean into the cultural aspect of the program, you know, by us working with all black boys. We're trying to encourage them to embrace all of the positive aspects of their identity, you know, and help them build a level of confidence and pride in who they are as African-American young men.

You know, we talk a lot and teach them a lot about Black history, you know, and want them to embrace their roots and their legacy and where they have come from and help us as a community continue to create this positive narrative around Black boys and what Black boys can do in school, you know, how Black boys can lead in their communities. And, you know, a lot of people maybe kind of misconstrue what we do as it being kind of this admissions tool and this admissions vehicle for U.S. where we're trying to, you know, find students that might be good for our school and then have them come to U.S. And there's a little bit of that, certainly, that happens where families are introduced to U.S. through the REACH program, and then they want to come or they want to look at us as a full-time option and if that's the case i mean we certainly will work with them you know to to see if this might be a good opportunity for their kids full-time but that really isn't the intent it's mostly about outreach we want to provide this space like i said for students to be meaningfully engaged during the summer and then wherever they go to school in the fall wherever they return to school if it's here or somewhere else we want to try to prepare them to be successful. So, I mean, that's what we're trying to do in terms of how we measure success.

So, when the boys are in the program, they have to share the report cards with us, you know, each summer. And we're regularly checking in with them and their parents and their teachers to make sure they're continuing to be successful in the classroom. After the students graduate from the program going into eighth grade. While we don't have any formal programming for them beyond that, we certainly have some programming that we do with the students when they're in high school to introduce them to college options and prepare them to take their SAT test and their ACT test And then we always you know checking in with them you know conducting surveys to see how they performed on those tests, where they matriculated to college, you know, and how they're doing in college.

Another big, big measure of us in terms of the of the impact of the program is when the students come back. So a lot of our teachers are former students. We also always have kids similar to U.S. where students graduate, whether it's spring break, winter break, summer break, they come back and they see their teachers. We always have students coming back to our program and talking about the brotherhood that they were a part of when they were in REACH and that extends well beyond their time when they leave.

So just knowing that the program is impactful for students while they're in it, as well as for years when they finish, is an indicator for us that the program is powerful and impactful. not only do you guys have talented students, but a lot of the kids that I've talked to that have been through the REACH program talk a lot about their teachers as being mentors for them. So it's kind of like being the leader of those leaders. What are some of the things you look for in the teachers and the mentors that you think makes them so special for the kids? Well, I think you said it.

I mean, we want them to be mentors. We want them to be role models for the boys. I mean, we work with students for five weeks during the summer. So there's only so much ground that we can cover in terms of the academic curriculum, you know, of a sixth grader, you know, or that four-year curriculum for seventh grade, you know.

I mean, if we're working with students, you know, trying to help those seventh graders get ready for seventh grade math or, you know, whatever, whether it's algebra, whatever, you know, class are going to be going into when they go back to school in the fall. I mean, we can't cover the four-year curriculum. So, while it is important, what we're doing with them in the classroom, in terms of, like I said, giving them exposure to those topics and different things that they're going to study, I think the work that we do to help them develop character and help them develop, you know, those abilities to be leaders of themselves first and then leaders of others after that is just as important, if not more important for us during the summer, you know. So identifying teachers that will embrace that is very, very important.

I mean, obviously we want teachers that know the discipline, whatever it is that they're teaching, but we also want teachers that care about you know these boys developing as people and as young men and are willing to help them intentionally develop those those skills and character traits you know outside the classroom so it's also important that you know we identify teachers that look like our students so a lot of uh the teachers that work with us in the program are black males you know uh young and old But they certainly don't have to be, but that also is a plus when you can find a teacher that when these students look at that teacher, they can see themselves and say, man, I want to follow in that teacher's footsteps. So we've been fortunate to have a lot of great teachers in our program and that's something that we work really, really hard to try to create. looking forward a little bit, let's go to this legacy piece a little bit. What legacy do you hope to leave, you know, through each, through teaching, through coaching, through all that you do, what would make it successful for you to look back on and say like that you did and you left that legacy? Um, I guess, you know, I'll go back to, to, uh, I think something I mentioned when I talking about lessons that you kind of learned through sports um again i just know that uh there are a lot of people that have helped me get to where i am today a lot of people have contributed to to me being able to uh to have the success i've had you know and to do all the things that i've I've done and continue to do.

And so I would hope that I could just pass that message along to the young people that I work with, is just to have an appreciation for those that have come before you, that have helped to contribute to where you are today and and help to open doors for you and to kind of own a responsibility to continue to allow doors to be opened up for those that are going to come behind you. And I also, from a young age, have been encouraged to be proud of who I am, my identity, the legacy that I come from, both in terms of my family and my last name, but then also as a Black man to have a certain pride in Black culture, you know, in my African-American heritage. And so hopefully people that have had a chance to work with me pick up on that pride that I have in being a successful Black man, you know. And, you know, any part that I can play in continuing to kind of drive that narrative that as Black people, you know, we're a great people, you know, and we should be a proud people in every space that I occupy.

I always want to be able to do my part, like I said, to continue to kind of shape and drive that narrative. So that's why I love the work that we do in the REACH program because, you know, we can and we do, like I said, talk about that, teach about that a lot with the students that we work with. But then I also think that I have a unique opportunity to do that as one of the few African-American teachers here at U.S. and hopefully all of the students that I've worked with here at university school that maybe don't necessarily look like me when they see me. They say, man, he's an impressive, he's a strong, he's a professional, he's a sharp African-American man. you know, they will see that our people are pretty special as well.

You know, Mr. LePert, something we ask every single one of our guests, what is your why? What is the core driving force that gets you up in the morning, keeps you come back every day, whether or not that's the coaching through the REACH program or just through school, what is it that really keeps you going every single day? Well, I will say two things, Charlie.

Family first. Again, from a very young age, as long as I can remember, my father has always told me, taught me that there's nothing more important than your family. You know, certainly my father, my uncles, my grandfather, you know, um worked very very hard to uh to kind of create a name for our family um and certainly i you know i feel a responsibility to kind of con continue you know that that legacy so so my last name certainly i that that's my why i mean everything that i do uh is you know certainly about making sure that I continue to show respect to my name, my family, and those members of my family that have helped to pave the way for me. And then certainly my two girls, you know, my daughters, they are my why, you know, and me trying to be successful and provide for them.

And my wife gets me up every day, you know, and keeps me pushing forward. And then I guess the last thing is just the community piece. Going back to, I think I've said it a couple of times now, a lot of people have contributed to me being able to be who I am and get to where I am. And um i feel a responsibility to to to play my part now and continuing to help those that are going to come behind me also have you know opportunities like the ones that i have had you know and being a part of communities like us um and playing a part to help keep this community great you know make this community a great place uh certainly continues to be a why for me and will always be a why for me as long as i'm here well mr leffert it's been great having you on the show thank you so much for taking the time to share insights and experiences with us to our listeners thank you so much for tuning in as always and we'll hope you'll join us next wednesday for another episode of late church show thank you mr leffert thank you jack thank you charlie you

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