Sept. 18, 2025

#223: David Conwill (Redwood Living) and Jimmy McCarthy Jr. — Mr. Football

Jim McCarthy Jr. is a filmmaker and the director of the new documentary Mr. Football, and David Conwill is the Executive Vice Chairman and former CEO of Redwood Living as well as an executive producer of the film.

Dave’s career spans two decades of building Redwood Living into a national leader in single-story rental neighborhoods—scaling from a handful of units in Northeast Ohio to more than 20,000 homes and multi-billion dollars’ worth of developments across nearly a dozen states. Alongside his work in real estate, Dave has recently ventured into storytelling, teaming up with Jimmy to bring Mr. Football to life.

Jimmy’s journey is deeply personal. As a member of Benedictine High School’s 2004 state championship football team, he lived through the triumphs and tragedies that Mr. Football explores. The film captures the roller-coaster highs of playing in three consecutive championship games, the enduring spirit of the school, and the lows of Lorenzo Hunter’s murder and a tragic night that changed many lives. The title itself comes from the “Mr. Football” award, Ohio’s high school version of the Heisman Trophy.

Two decades later, Jimmy has turned that experience into a screenplay and ultimately into a powerful documentary, working alongside co-director Sean Rech, CEO of Cleveland’s Transition Studios, as well as Ryan Kelly, partner at Substance and a producer on Mr. Football—both of whom have also shared their stories on Lay of The Land (episodes 85 and 221, respectively).

In our conversation, we talk about Jimmy’s inspiration and the process of making Mr. Football a reality, including the cathartic experience of revisiting Benedictine’s championship run and its aftermath. We also explore Dave’s entrepreneurial journey building Redwood Living and the lessons learned from scaling it into billions of dollars’ worth of development. We discuss the creative process of bringing a film to life, the parallels between entrepreneurship and filmmaking, and what Jimmy and Dave each think about success, impact, and the future of Mr. Football.

Dave and Jimmy’s collaboration bridges business and powerful storytelling in a way that is uniquely Cleveland, and I’m grateful to share this conversation with you today.

00:00:00 - The Heart of Benedictine Football
00:09:35 - The Journey of Telling a Story
00:17:08 - From Real Estate to Film
00:17:59 - The Process of Creating a Film
00:22:15 - Healing Through Storytelling
00:26:36 - Messages and Takeaways from the Film
00:29:54 - Challenges in Documentary Filmmaking
00:33:40 - Building from Scratch: The Documentary Process
00:35:02 - Pivots and Perspectives: The Evolution of the Script
00:39:50 - A Cleveland Story: Local Roots and Universal Themes
00:42:06 - The Release Journey: Reactions and Reflections
00:44:40 - Looking Ahead: Future Projects and Aspirations
00:50:46 - Lessons Learned: Overcoming Doubts and Challenges
00:52:44 - Honoring Legacy: Memorials and Scholarships
00:55:56 - Hidden Gem


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LINKS:
https://www.linkedin.com/in/david-conwill-b099434/
https://tv.apple.com/us/movie/mr-football/umc.cmc.4bj5i7tx1hef4shqkmk16asw0
https://www.primevideo.com/detail/Mr-Football/0U57SLRHOHWDVTTCP6XMQ56SRZ

 

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Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.

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Transcript

Jim McCarthy [00:00:00]:
It's easy to tell yourself why something can't happen or why you're not right for this. It's so easy to make those excuses. But it's a testament to keep pushing, keep learning you can do it. And it took us almost four years, but we figured it out and we're really proud of the end result. And I think we're both really glad that maybe when we there were certain times where we were questioning it or not sure if we could keep pushing, we just, we just believed in what we set out to do and we kept pushing and thank God we did it. So I think that's the lesson for everybody out there, is don't tell yourself you can't do it.

 

Jeffrey Stern [00:00:38]:
You can welcome to the Lay of the Land podcast where we are exploring what people are building in Cleveland and throughout Northeast Ohio. I am your host Jeffrey Stern and today I had the real pleasure of Speaking with Jim McCarthy Jr. Thank you, filmmaker and director of the new documentary Mr. Football, and David Conwell, executive vice chairman and former CEO of Redwood Living, as well as Executive producer on this film. Dave's career spans two decades, building Redwood Living into a national leader in single story rental neighborhoods, scaling from a handful of units in Northeast Ohio to more than 20,000 homes and multi billion dollars worth of development across nearly a dozen states. Alongside his entrepreneurial work in real estate, Davis recently ventured into storytelling, teaming up with Jimmy to bring Mr. Football to life. Jimmy's journey is personal.

 

Jeffrey Stern [00:01:30]:
As a member of Benedictines High School's 2004 state championship football team, he lived through the triumph and tragedy that Mr. Football explores, which covers the rollercoaster highs of playing in three consecutive championship games, the spirit of the school itself and the lows of Lorenzo Hunter's murder and one tragic night that changed many of their lives. The film itself is named after the award for the Best Player in Ohio, the state's high school version of the Heisman Trophy. Two decades later, Jimmy has turned that experience into a screenplay and ultimately into a powerful documentary, working alongside co director Sean Reck, CEO of Cleveland's Transition Studios, as well as Ryan Kelly, partner at Substance, and a producer on Mr. Football, both of whom have shared their own stories on Lay of the Land, episode 85 and 221, respectively. In our conversation today, we cover Jimmy's inspiration in the process of making Mr. Football a reality, cathartically revisiting Benedictine's championship run and its aftermath, Dave's entrepreneurial journey through the origins and growth of Redwood Living and lessons learned, scaling it to billions in development, the creative process of what it takes to bring a film to life, the entrepreneurial and creative parallels between building a company and producing a documentary, and ultimately what Jimmy and Dave each think about success, impact and takeaways of Mr. Football and what might come next.

 

Jeffrey Stern [00:02:56]:
Dave and Jimmy's collaboration here bridges business and powerful storytelling in a way that is uniquely Cleveland and I'm grateful to share this conversation with you today. Please enjoy Lay of the Land is brought to you and is proudly sponsored by Roundstone Insurance, headquartered in Rocky River, Ohio. Roundstone shares Lay of the Land's same passion for bold ideas and lasting impact from our community's entrepreneurs, innovators and leaders. Since 2005, Roundstone has pioneered a self funded captive health insurance model that delivers robust savings for small and medium sized businesses. They are part of the solution to rising healthcare costs, helping employers offer affordable, high quality care while driving job creation and economic growth throughout Northeast Ohio. Like many of the voices featured on Lay of the Land, including Roundstone's founder and CEO Mike Schroeder, Roundstone believes entrepreneurship, innovation and community to be the cornerstones of progress. To learn more about how Roundstone is transforming employee health benefits by empowering employers to save thousands in per employee per year healthcare costs, please visit roundstoneinsurance.com Built for entrepreneurs, backed by innovation, committed to.

 

Jeffrey Stern [00:04:08]:
Cleveland so I had the chance to watch Mr. Football a few days ago and it is a powerful film and I was struck by how the film captures really the clear magic of Benedictine's football program in the early 2000s, the promise of all these remarkably talented student athletes and the energy around those seasons, and then really the heartbreak and tragedy of kind of what transpires, but ultimately how it comes through as a real human story about choices, adversity, persistence, reflection, redemption, community. And Jim, maybe we can just start with you. Since you've kind of lived through this era as part of the team, you know what it was like for you to revisit it and relive it through what I imagine was hundreds of conversations with people from that time in your life and ultimately see it come together on a, on a big screen. Just help us set the stage for what this film was all about and why it matters to you.

 

Jim McCarthy [00:05:22]:
Absolutely, yeah. Thanks, Jeff. So, you know, you, you mentioned, you know, Benedictine High School and you know, you kind of said quite a few buzzwords there that, you know, I think you were kind of describing the film, but really most of those words encapsulate the spirit of what Benedictine is and you know, they're going to celebrate, they're going to celebrate their 100th year anniversary next year. They are such a pillar of this community. I mean, obviously if you're around 100 years, you're doing something right. And so they had the chance, you know, 20, 30 years ago, like a lot of the private high schools in the area had done, where they were able to have the opportunity to move into the suburbs or just a newer area of town, build, build new, a new school and new facilities. And they had some benefactors that were willing to write the check for all of this. And the monks and the faculty kind of got together and had a discussion and they just felt like they would be turning their back on the community if they, you know, left for brighter, newer, brighter pastures.

 

Jim McCarthy [00:06:31]:
Right. So instead they invested in a fleet of buses. And that was kind of their way of, hey, if we're going to stay here and we're going to be, you know, loyal to this community, why don't we invest in something that can bring other kids throughout the city here to us? And so we're such a close knit community, the Benedictine alumni and faculty. And so it felt like making a movie about your family. And it wasn't exactly the brightest time in our history, but I think it was a great story to tell to really help the rest of the world understand what Benedictine is and what they're about and why they are such a big part of Cleveland and our community.

 

Jeffrey Stern [00:07:22]:
So what inspired you wanting to tell this story?

 

Jim McCarthy [00:07:27]:
Sure. Yeah. And that's it right there. So we play in two state championships. The second one we win, Ray Williams gets named Mr. Ohio, you know, the Heisman of high school football in Ohio. And, you know, we're the toast of the town. We are all over the newspapers and media kind of felt like local celebrities, right? And then this tragedy occurs and before we know it, two of my teammates are on trial for my other teammate's murder.

 

Jim McCarthy [00:08:01]:
And we went from being the toast of the town to we're being called criminals and the media is putting handcuffs over our school crest. And you know, we were just, were immediately labeled as bad kids. And this, you know, almost like we deserved what we got kind of a thing. And if you can imagine how difficult it was to bury your 15 year old teammate and then in a matter of days you see your other two teammates walking out of school in handcuffs while you've got two siblings of one of those guys still at school with you and on the football team that that bad course of events and the ripple effects of all of that just continued for quite a long time, and it just left a really bad taste in all of our mouths. And there was hardly a few weeks or months that go by that you don't run into somebody that says, oh, you went to Benedictine, and, yeah, you. You went to high school with. With that kid that shot and killed and murdered his own teammates, or that the memories and. And kind of what people think they know about that story, it just is, frankly, it's false because the story had never been told before.

 

Jim McCarthy [00:09:15]:
So I think once you. Once you hear these things about your family and your family's kind of run through the mud over and over again, and you just get to a point where you're like, enough's enough. We need to tell this story. And thank God we got the chance to release it last week.

 

Jeffrey Stern [00:09:35]:
So, Dave, it's not every day that a real estate entrepreneur, an executive like yourself, appears in the credits of a film like this. And, you know, your background as an entrepreneur is an amazing story in and of itself that we can dive into in a little bit. But I'd love to understand where your and Jimmy's path crossed and what resonated with you about this film and the story that.

 

Jeffrey Stern [00:10:01]:
That Jimmy's trying to tell.

 

Davis Conwill [00:10:03]:
Wow. Well. Well, thank you very much. Those are lofty, lofty praise. And yeah, not every day does a real estate entrepreneur get credits in a documentary. But not every. Not every day do you get an opportunity to work alongside exceptional, extraordinary people like Jimmy McCarthy. So, for me, first and foremost, Jimmy and I are super close friends.

 

Davis Conwill [00:10:35]:
We've built a friendship over the last 10 plus years. And it's just interesting, sort of the how, you know, the building blocks of life and the road, the path that we take. I had no clue of Jimmy's background, what he went through at Benedictine. I didn't know this story at all. And, you know, one day I got a phone call. Jimmy asked me to come to his office, and, you know, he handed me a screenplay. And I said, you know, okay, what's this? He said, I. I wrote a screenplay.

 

Davis Conwill [00:11:14]:
I had no idea that Jimmy was capable of writing a screenplay. I was, you know, not, you know, he's an extraordinary individual, but that was exceeding my, at that point, my knowledge of. Of what, of who Jimmy is and what he's capable of. But anyhow, read the screenplay was blown away. It invoked a lot of emotion. It was well written. And when he, when he explained that this is a story that, you know, based on true events that he lived through during high school and the story of his time at Benedictine, it became even more, resonated even more with me and asked me if I wanted to maybe work alongside with him and kind of partner up on helping him make the film. And I gave an enthusiastic yes to that.

 

Davis Conwill [00:12:15]:
And from then on, you know, I was, you know, along, you know, along his side the whole way. As an investor, as a counselor, I know nothing about filmmaking. Zilch. Know a little bit about real estate, a little bit about finance and you know, being an entrepreneur, but, you know, and also from my perspective, you know, I'm kind of a habitual lifelong learner. Love to get into deals and opportunities and learn new things. So for me it was a no brainer.

 

Jeffrey Stern [00:12:51]:
If you'll indulge the entrepreneurial detour for a moment, just you've been with Redwood for over two decades, wore many hats over the tens of thousands of homes developed and billions of dollars invested there. Ultimately as CEO for a chapter of it. Just what is Redwood Living? And kind of take us through the, the arc of your career and kind of the little bit of real estate knowledge, as you modestly put it.

 

Davis Conwill [00:13:23]:
Sure. Well, you know, I come from humble beginnings for the most part. Raised in Northeast Ohio, Medina caught a lucky break when I was in high school and my mother went to work for a company called Pride One as a receptionist, secretary and she came home one day and asked if I was interested in working as a laborer on the job site. I was 15 years old, didn't even know what that meant. You know, at that point we, you know, we're kind of lower middle class. So if I wanted money or I wanted to buy something, I would have to work and know, do odds and ends jobs. I think at that point I was working at a car wash delivering newspapers. So, you know, it was a, it was a great opportunity.

 

Davis Conwill [00:14:15]:
So I went to work at Pride 1. And make a very long story short, my career path emanated at Pride 1 when I was in high school and really kind of takes us to present day. Worked there through college. Upon graduating from the University of Akron, I was offered a full time job working inside the office. I think I initially started in the accounting department, eventually became a project manager working in land development. I had the unbelievable blessing of working alongside some amazing entrepreneurs, notably Doug Lair, Jerry Fumey, who were the two co founders of Pride 1. Taught me an incredible amount of, you know, I call it the school of hard knocks. You know, I didn't go to college for real estate or finance, actually have a degree in hr Management because I, I always wanted to get involved in solving people problems and.

 

Davis Conwill [00:15:22]:
But never once actually had a job in hr. Formerly hr. So anyhow worked at Pride One. Pride one eventually partnered up with Red the Redwood founder, who's Steve Kimmelman and Pride One and Redwood partnered and developed in excess of 10,000 units over the course of 10,000 apartment units over the course of 15, 20 years. And so you know, through that partnership, that was the segue that eventually got me into more full time with Redwood where I focus 100% of my time and energy on developing the Redwood platform and had various roles throughout the years, including a few years as CEO of the company and I am now currently serving as the vice chairman of the company. So predominantly overseeing capital, raising, finance, various other sort of strategic matters. Not so much in the day to day operational aspect, but more finance and capital. So the interesting part of, of that transition is it's kind of, you know, open up doors and, and allowed me to have more time to invest time and maybe a little bit of money into other projects and ventures, including this film with Jimmy.

 

Jeffrey Stern [00:17:01]:
Yeah, so that's a, It's a perfect seg.

 

Jeffrey Stern [00:17:03]:
Back shifting gears to, to Mr. Football.

 

Jeffrey Stern [00:17:07]:
So neither of you have kind of a background in, in film. You know, it was, it was news to you, Dave, that, that Jimmy could put together the, the script. But I love to understand what the actual process of creating this film was like before we turned on the mic here. It's just kind of fun to understand and know that Transition Studios was involved here. Sean Reck came on the podcast, I believe he was episode 85 so many years ago. And Ryan Kelly, who's on most recently episode 221, shared his story. So anyone who wants to learn more about the production studios and people behind the film can learn more about their stories respectively. But this is both of your first foray into this world.

 

Jeffrey Stern [00:17:56]:
How do you go about getting started?

 

Jim McCarthy [00:17:59]:
Great question. So both Dave and I, I think one of the things that kind of bonded us and helped us build our close friendship is our love of film. You know, that was, I think one of the first things we really bonded over so many years ago when we became friends was our love of film. And even still to this day we try to keep, we try to make it a regular thing at least maybe once a month where we'll just meet at the theater and catch a movie together and kind of gives us a little bit of time to maybe turn off what's going on outside of that theater and kind of just gives Us a little bit of a safe place to, you know, enjoy our friendship, but just enjoy, enjoy a film and you know, have the chance to talk and reflect on and I think it's just a good, it's a good thing that we have a regular thing we try to do and so have. So having that background, you know. Myself, I have been a student of film as long as I can remember, as long as I was a little kid. And so, you know, co directing a film is truly a dream come true for me. It's just been an incredible experience.

 

Jim McCarthy [00:19:06]:
But. But to kind of answer your question, you know, as Dave mentioned, I. When I was a senior at Cleveland State, I took a screen. It was actually the last semester of my senior year, I took a screenwriting class and, and I decided that I needed to use this story to write my screenplay and you know, to pass the class. But I had never talked about it before. I really had never gotten this off my chest. And so I found it to be really cathartic for me. And I felt pretty good about the script after it was finished and got.

 

Jim McCarthy [00:19:42]:
Obviously got a pretty good grade on it. And I just told myself that at 20 years old or 21 years old, I'm not really sure what I'm going to do with the rest of my life and I'm just starting to build connections and all of that. But I knew that at some point, once I was a little more established in my career, et cetera, that I needed to circle back on this. And so fast forward to about four years ago. Dave mentioned he was the first, first phone call I made after, after I had, I had made a few connections, decided that it was time to, to share the script. I was really just looking for someone to help me just polish it up a little bit because I written it without any background as a, as a college kid. And before I knew it, it got shared around and I had producers calling me and so I, I called Dave use that first phone call and we talked and we just decided that we, if we were going to do this, we needed to do our due diligence and really kind of turn over every rock and just know what our options were and, and just decide, you know, just like I think what Dave does amazing in, in the Redwood real estate world is he's very good at being dialed in with the details and really understanding what, what he's, what cards he has to play with. And then he, you know, and he, he makes sure that he has the most data available to him to make those right decisions.

 

Jim McCarthy [00:21:10]:
And so we. We felt like we needed to do the same thing, that we needed to have a few different conversations and see who we gravitated towards and, you know, what was the best fit. And so we ended up getting referred to Sean Rec, who's the president of Transition Studios here in Cleveland. It is an absolute hidden gem here. They've had quite a few hits that have gone onto the big streamers. And so we had a few conversations with Sean and his team, and, you know, we quickly realized that a documentary was probably the right approach to this story, at least from the first iteration of it, and. And just feeling like Sean and Transition really understood the true crime genre and he knew what. What.

 

Jim McCarthy [00:21:58]:
What our vision was. And once those things start to. To. To fit, you know, it becomes just more of a feeling and a gut. Gut call, you know. You know, we're both glad that we, you know, we went through that process to find the right. The right team and the right studio.

 

Jeffrey Stern [00:22:15]:
Yeah, absolutely. As much as it was a cathartic journey for yourself, and one thing that's very clear in the film, just listening to people reflect on it, is how cathartic I think it was for everyone involved. Documentaries, you know, always kind of rely on candid, open, unfettered interviews. And I was just kind of curious what it was like to get people like Ray to participate and open up on camera and just people's willingness to participate in this story, to kind of relive the past and then at the same time, having big names like Jim Trestle as part of the story, just the process of reaching out to people, having those conversations. Anything that surprised you about that part of the process?

 

Jim McCarthy [00:23:11]:
Yeah. So, I mean, what I had going for me was I literally have been thinking this through in my head for 20 years. And so the good thing is, is coming out of the gate, I'd already thought about all these things really obsessively, and I thought about, you know, what am I going to say to my teammates and to Ray Williams and to the Huddleston family when I sit down and talk about wanting to do this? So I will say I felt prepared because I thought about it for so long, but I think we had to come up with a very clear set of goals. Telling the story from just a factual basis, trying to tell the most factual, true side of the story as possible, but really trying to have the most positive outcomes for every party involved. And so once we really dialed our vision in and what our main goals were, it really helped. All of those tough conversations, it changed those into positive conversations very quickly. And so that was really just. That was the momentum we kind of took after each conversation.

 

Jim McCarthy [00:24:26]:
And, you know, Coach Tressel was one of those. You know, he kind of wanted to. To do an interview with me, even though we had worked a little bit in the past together, and he sort of knew me a little bit. Benedictine was a place that's really close to his heart, and he wanted to make sure if he was going to participate in this, it was for the right reasons. And the list goes on and on. Terry Pluto is in the film hall of Fame, sports writer from Cleveland. Once you had those conversations and you try to help them understand what your goals were, it. They became easy conversations pretty quick.

 

Jim McCarthy [00:25:02]:
And then. And then just to kind of answer the second part of your question, I knew. I knew that this most likely was a story that, for the most part, had never been told, because I knew that I had never talked about it and for the most part, hadn't really talked much with my teammates about it. But when I sat down with Ray Williams and then I sat down with John Huddleston, his two brothers, I realized that they had never talked about it with each other. So even these brothers had never sat down and never had talked about this with each other, with each other before. So that really then opened our eyes to how important the story is, how methodical we need to take it as we start to produce the film. And then as the interviews went on and we started to get, you know, midway through the film, I realized that after every interview, you could see this healing taking place with each person we were interviewing, because it was their first time to finally talk about it and get it off their chest. So there's almost a story within the story there, because the healing that it's brought to everybody involved, parents, obviously my teammates, faculty, it's been incredible.

 

Jim McCarthy [00:26:18]:
It really has.

 

Jeffrey Stern [00:26:19]:
What do you hope people take away from the film? You know, now. Now that it's. It's out there, what. What is the. The message that. That you wish people take from it? People who might be familiar with the story, but also people whom. Who may not be?

 

Jim McCarthy [00:26:36]:
Yeah. Well, when we. When we. When I mentioned. We sat down and. And we kind of put together those core goals that we had for the project, specifically John Huddleston and Ray Williams. They. They both wanted to really target the youth with this project.

 

Jim McCarthy [00:26:53]:
And once. Once we released it, we really. They really wanted to have a plan for us to really get in front of as many youth as we could to show the film and Then talk with them and answer questions. So there definitely is a cautionary tale that we, we really want to get as in front of as many kids as possible. We think that even if they, if it teaches them to think twice before making that split decision that could possibly ruin their, or ruin their life or, or cause a lot of harm to their life and others in a matter of seconds. So that is definitely a big core part of that. But I would say what really motivated me to do this overall and really feeling like this was that right time is just, we just so divided right now as a country and as a people and you know, and I feel like we're empathy is at almost at an all time low. And once again going back to the spirit of Benedictine, I mean, we were, we were a, at the time, a group of ragtag blue collar kids from all over the city of Cleveland, all different races, all different backgrounds.

 

Jim McCarthy [00:28:10]:
And so what we did at Benedictine freshman year, the first day we left all of our differences at, at the door. And so when we walked into Benedictine as freshmen that first day, it was all about what, what are the common things that we can learn about each other and what are the common goals then that we can learn together and bond over and then have success throughout our high school careers and then into our lives. And so I just really think, I really wanted to make sure we captured the spirit of Benedictine because I just think if we can just as a people, if it just gives us the ability to just stop and just try to understand each other just a little bit more, I just think we would just be so much better off because of it.

 

Jeffrey Stern [00:29:02]:
It's certainly a platform that seems to facilitate having those kinds of conversations that in the absence of the film, I mean, obviously it didn't happen for 20 years, those conversations. So in a lot of ways, from the outside looking in, it feels the journey of creating a film is very much an entrepreneurial one, generally comes with some very difficult challenges, some lows, some highs in the process itself. When you reflect on the experience of actually bringing this to fruition, what sticks out to you as some of the greatest hurdles, challenges overcome. But more on the process of bringing this and making it a reality.

 

Jim McCarthy [00:29:54]:
One of the big ones was with any other project that I've ever worked on in my whole career, there was a very clear start and end to that project. Right. And usually there's a deadline that is kind of driving that project. Right. This was a whole new world for me because it was, there's no, obviously you want to get it finished as quickly as possible, but you needed to kind of let the Tory story tell itself. And so it took you maybe in some directions you weren't expecting. And you know, you get down to maybe you're like, all right, we're on our, our 50th interview. This is probably going to be the last one.

 

Jim McCarthy [00:30:32]:
And then all of a sudden that interview tells a story and you're like, whoa, I wasn't expecting that. Now we got to go talk to this other person, because this is pretty important. And so just not really having a clear defined finish was really difficult for me because, you know, you kind of, I think in, in my, my working career, it's like you always need to know where that end of the, the goal line is. And so not having that was really tough for me. And then, and I, I just think learning a new medium, learning something brand new and try to, and try to execute it, it's a humbling experience. And so it just really reinstilled in me how the people that you work with are so important. And you gotta be, you gotta be a good teammate and you gotta inspire that, that team, good team camaraderie. And this film only would have been as good as kind of the reflection of, of the team that was put together to do this.

 

Jim McCarthy [00:31:35]:
So really, once again, just so thankful that we had the right people fall in the place that really cared about this and had their heart so closely tied to it and, and thankfully it was, it felt like climbing a mountain at times. It really did. And sometimes you felt like not sure you're going to get to the top, but we just kept pushing, right, you just kind of kept pushing through it and you know, finally we got, we got to the end of the tunnel and it's been, it's been wonderful. So, so really thankful.

 

Jeffrey Stern [00:32:06]:
When you reflect on both building a company like Redwood and now having experience the production of a film, what do you feel are kind of the cross disciplinary insights between those two worlds?

 

Davis Conwill [00:32:19]:
Well, yeah, just to kind of expound on what Jamie was describing as far as the process, especially the process of making a documentary. It's kind of like a sculpture and there's, there's technical expertise that you're bringing to bear and you're, you're inputting into the, into the overall process. But so much of it is, is artistic creating something from scratch. You have to let the story kind of avail itself as, as you get into it because it's kind of a. Yeah, there's a general, obviously overview of the story, but it's it's. It's unscripted. And you know, I guess the. Yeah, that's sort of like the correlation back to the, you know, building a company.

 

Davis Conwill [00:33:06]:
And specifically in the Redwood world, the, the early on sort of entrepreneurial aspects of, you know, the DNA and the. In the business, it was just more I describe as entrepreneurial naivety. You don't know what you don't know and you just gotta jump in and try to figure it out. And then you build structure. And now Redwood is obviously much more of a. You know, it's a larger organization with, with as an operating platform, systems and processes, outstanding people. But you gotta build it and, you know, you're kind of building it from scratch. So a lot of correlations to.

 

Davis Conwill [00:33:52]:
To make it, you know, from building a company to make a documentary. And, and what I was going to add on to what Jimmy was describing without having kind of an end date. You're. You're scheduling and you're meeting with people and you're producing as you're creating the film, it's all iterative. You're iterating, you're iterating and kind of the telling the story as you go. And then as you're telling the story, you're. You're producing, you're calling people, you're scheduling interviews, you're traveling to locations across the country. This person makes a comment, okay, that triggers a response where you need to call this person back or maybe interview this person.

 

Davis Conwill [00:34:42]:
And okay, this new individual is kind of a new character that's emerging from some dialogue. So it's interesting. It's like nothing that I've ever been a part of. And again, it was an absolutely amazing experience.

 

Jeffrey Stern [00:35:02]:
It seems to me one of the other kind of parallels there between maybe the film and entrepreneurship world might be the idea of pivots in some way. And I'm curious, from your perspective, Jimmy, when you drafted the script, how much has it deviated from that? Are there themes or topics or ideas that you thought would be central to the film? And what did you learn about what was included, what was not included, and just kind of following the signal from the conversations you were actually having?

 

Jim McCarthy [00:35:39]:
Yeah, that's a great question and one that I haven't been asked yet, to be honest with you. And that's a. It's a. It's a good question. It's something I think about actually quite a bit, even now that we're kind of. That we are a week out of releasing this film. If you can kind of imagine I was 16 when this happened, 16, 17. I was a captain on the football team.

 

Jim McCarthy [00:36:08]:
So I was one of only just a handful of guys that was pulled into a room, closed the door and really got to know at least a decent part of what actually happened. And then I was there for the following season as well. So I write the script a couple years later when I'm two or three years later, I'm a senior in college.

 

Davis Conwill [00:36:33]:
And.

 

Jim McCarthy [00:36:36]:
The way that I wrote it back then is definitely not the end result. I would say most of it is there. I mean, it's. We didn't, we didn't have to deviate much, but it shows you the perspective of what maybe what a 21 year old kid has at the time. And then it allowed me to look and say, okay, as I started to get older and I started to look back and say, okay, maybe I'm. Maybe I was hard with this person and maybe now that I'm a little bit older and I have a little bit better perspective that maybe that was just, that was kind of just a kid not understanding and just kind of angry and sad and, and so I was able to kind of go through it over the years and sort of update it a little bit after I had some perspective. And then having kids is a whole nother thing, right? Like, you start to get older and you realize like, wait a second, we didn't know what we were doing. We were kids.

 

Jim McCarthy [00:37:30]:
This really could have happened to anybody because I know, I knew my teammates were good, good guys. This was not something they were doing on a regular basis. It's not any of us were doing. We were good kids. We were almost in a bubble in a way. And so I will tell you, like in my original script, Rodney, the, the drug dealer, the shooter, he's kind of the, he's sort of the villain of the story. And, and so for so long I had really blamed him and said, obviously he's. He's this drug dealer that shot and killed my teammate.

 

Jim McCarthy [00:38:04]:
And then, you know, a few years later he ends up committing another murder and now he's in prison for the rest of his life. And so it was really easy to pinpoint him as the bad guy and kind of make him the antagonist. But once I started to then finally dig into the story and I started to get the truth of it, I realized that he was just another casualty in this, that he was really only defending himself because he had gotten jumped a couple weeks earlier and wasn't able to defend himself. And so I quickly realized that he's Just another innocent victim in this, because I found out that it really put. He got. He became really guilty, and it really put him in a dark place, and it. It kind of pushed him into a. Kind of on a bad path to.

 

Jim McCarthy [00:38:54]:
To where he ending up in prison. So that's just an example of how I think my perspective as a kid changed over the years. And I was, you know, so thankful that I did wait, obviously, to. To make sure I was able to flesh some of those things out and then obviously get to the bottom of the story, because when I wrote the script, I only knew what I knew. But obviously now I have the context of being able to talk to everybody and get. Get everything out.

 

Jeffrey Stern [00:39:20]:
You kind of alluded to this in your. In your answer there. I mean, obviously this is authentically a Cleveland story. But. But do you see the story of Mr. Football as a Cleveland story? I mean, obviously it resonates across communities nationwide, but just what aspects do you feel uniquely about this place and which parts more broadly universal?

 

Davis Conwill [00:39:54]:
Yeah, for sure.

 

Jim McCarthy [00:39:57]:
I mean, is it a Cleveland story? Yes, it is, because. Takes place in Cleveland. It takes place at, like, I mentioned, Benedictine High School, which is such a pillar of this community for almost a hundred years now. So is it a Cleveland story? Yes, but I never looked at this as being, you know, we're just keeping this to Cleveland or it's only relevant to Clevelanders and Ohio people from Ohio. Completely the. The opposite. I mean, the driving force behind this was to get this in front of the whole world because we do think that we can change the lives of kids all over the world and hopefully, like I said, inject a little empathy into it, because I feel like James Gunn just did that on a commercial level with Superman, how he was able to infuse empathy and into that blockbuster movie. And walking out, I just had this.

 

Jim McCarthy [00:40:52]:
I had this little pep in my step walking out of the theater after watching Superman. Like, I want to go hold the door for the guy that's walking in the theater. You know, it made me want to just do. Be extra nice that day. And. And so I hope that. That we can provide a little bit of that magic that James Gunn was able to inject in the Superman. Definitely.

 

Jim McCarthy [00:41:12]:
This is a. This is a story that's relevant worldwide. It's a good mixture of true crime and sports. Right. And so, I mean, I think, you know, as Americans, we love. We love football, and I think the rest of the world is pretty intrigued by American football. And then I think true crime is one of the biggest genres and in all over the world. So I think we've got.

 

Jim McCarthy [00:41:36]:
We're pretty well set up for something that's universal to everybody.

 

Jeffrey Stern [00:41:43]:
You mentioned the light at the end of the tunnel. Having reached it and emerged into the world. And on the other side, what has it been like? How has it resonated? What has surprised you about the release and distribution of the film? Obviously, there is a certain indefinite time to the process, but seems like a clear demarcation of something accomplished along the way. So just gotta speak to releasing it.

 

Jim McCarthy [00:42:14]:
And this is where that. Yeah, right. And this is where that sort of. You need to have a good tag team of creative entrepreneur with traditional entrepreneur. Right. Because I really looked like mine. The core. My core job in all of this was to create something that was as good as it possibly could be and.

 

Jim McCarthy [00:42:34]:
And to get it out into the world. And so last Tuesday was really kind of that getting to the top of the mountain for me. And so I feel like I'm so happy with how it turned out. It really, you know, like I said, after thinking about it for 20, 21 years, you don't. You kind of don't anticipate it to meet your expectations, and it did. So I'm so happy and so thrilled, and it's been just a whirlwind. I don't really have a way to describe how the last week has been. I mentioned before we got on, there's been a few times where I've had to pinch myself just to remind myself that I'm still awake, because it does feel that way.

 

Jim McCarthy [00:43:13]:
But it's great hearing that people enjoy it and hearing those things is so incredible. But I think what's the biggest thing for me is I want to show this to my kid. And I've already had some. Some people reach out to me. They've sat their kids down and they've watched it, and the kids really enjoyed it. And they had a bunch of questions after it, like those. Hearing those things is so awesome. And then the other part of it is hearing everybody from Benedictine feel like we've made them proud.

 

Jim McCarthy [00:43:44]:
Because Benedictine, like I keep saying, is such. So important to the city, to this community, but it's so important to thousands of families all over the country now that have. Have been a part of that family. So hearing that from the. At least so far from the Benedictine community, that something that they can be proud of and. And hopefully start to share what's so special about Benedict and to the rest of the world. So that's what's been so Incredible to me and my sort of reactions. But now it's kind of.

 

Jim McCarthy [00:44:16]:
We're passing that, that entrepreneurial baton a little bit where Dave's really great at scaling and, and getting us in front of the right people to really take this from a distribution standpoint to its highest point. So we're kind of like that perfect tag team and wanting to make sure this is as big and as great as it possibly can be.

 

Davis Conwill [00:44:39]:
You know, I'll just add a quick comment. You know, I think this is just the tip of the spear. This is Jimmy's life. I'm just a passenger on his, his, his train here and, and I'm, I'm, you know, an enthusiastic supporter. As I said, to the extent that Jimmy wishes to do more projects or making films, telling people stories, even sticking with sort of the Mr. Football nomenclature and this, this, you know, the style, the genre, you know, I'm sure there's a lot of stories that we could tell across the country that are worthy of, of being told, you know, and do it well. And those individuals and in those particular situations, this, this is now validating empirically for, for Jimmy as a, as a filmmaker and those particular individuals can, can trust their sort of precious stories that are so close to their hearts and they live through with. In Jimmy's.

 

Davis Conwill [00:45:54]:
Jimmy's hand. So excited to. Excited for the future as far as, you know, what, what comes next. I know we gotta stay, stay in the moment and live the moment and you know, we're, we're, we're perpetuating Mr. Football and, and want to see tremendous success. I just can't help but think ahead. It's just my nature. It's my, my natural propensity to kind of think forward.

 

Davis Conwill [00:46:20]:
And you know, I can, I can sort of visualize 10 years from now, Cat. A catalog of films that have Jimmy's name on it, if that's what he chooses to do. You know, he's got a very successful business and he's got a. Know wonderful family and a lot going on, but he's clearly a very talented film filmmaker. So it's just excited to be part of the, part of the team.

 

Jeffrey Stern [00:46:48]:
What are you most excited about, Jimmy right now?

 

Jim McCarthy [00:46:50]:
I'm just, I'm living the dream. I mean, I'm just trying to soak it all in. And what, what am I most excited about? I'm most excited that I, I've got a guy like this in my corner. I mean, I think what he just said says it all. I don't, I don't really have to expand on it, but just. I'm so blessed. I am so blessed. I am so lucky to have not only Dave Conwell in my corner, but there's more people he's brought into the fold.

 

Jim McCarthy [00:47:20]:
There's, there's other business guys or just connections that, you know, we kind of have this group that we've put together of just really great, great guys that look out for each other that, you know, want to do good, good things and impactful things. And that's what I'm excited about. Because I mean, like we, we kind of joked about before we started here, Jeffrey, the fact that if you can, if you can marry some, something that you love and that you're passionate about with something that can help others and change other people's lives, I don't have anything else that's better than that. I don't think I'll ever come across anything, at least for me, that's better than that. So what I'm excited is that hopefully this can, this continues to do Those things, this Mr. Football and you know, and we'll see if there's another opportunity to do that. I think we'll cross that mountain when we get there.

 

Davis Conwill [00:48:14]:
Yeah, it's like when in the redwood world we close a deal, break ground. Great. We celebrate it. But I'm already thinking about the next deal. The next deal. That's just.

 

Jim McCarthy [00:48:26]:
Yep, yep.

 

Davis Conwill [00:48:28]:
And, and you know, and you, you, you know, you mentioned entrepreneurship and, and an entrepreneur. That word has been said multiple times and a lot of people have ways to define and describe that, but from my definition, it's. It's the intersection of passion and ability. God, God given abilities. And using your, your God given talents, leveraging that with immense passion to, to do great things, bring about amazing results and, and impact people's lives. So this is certainly a very staunch example of, of what being an entrepreneur is all about.

 

Jeffrey Stern [00:49:14]:
Yeah. Beautifully said. When you reflect on this whole journey together, are there particularly salient or important parts of the journey that you wish I had asked about? Is there something that we're missing here? When you think about Mr. Football and the story and the process of making it a reality, I don't think so.

 

Jim McCarthy [00:49:39]:
I just think. I just think that it's easy to tell yourself why something can't happen or why you're not right for this or I don't know how to do this. So yeah, it's so easy to make those excuses. And as humans, it's easy. We naturally can do those things, especially once you let anxiety creep in. Right. But I think it's just that it's a testament to keep pushing, keep learning. You can do it.

 

Jim McCarthy [00:50:09]:
And it took us almost four years, but we figured it out and, you know, we're really proud of the end result. And I think we're both really glad that maybe when we. There were certain times where we were questioning it or not sure if we could keep pushing, we just. We just believed in what we set out to do, and we kept pushing. And thank God we did it and know. So I think that's the lesson for everybody out there. It's don't. Don't tell yourself you can't do it.

 

Jim McCarthy [00:50:35]:
You can. And we're in today's age. We have so much at our disposal to learn and do new things. Take advantage of it.

 

Davis Conwill [00:50:46]:
Well, Jeffrey, my biggest regret about the movie and the time span was Jimmy cutting the film of my flag football intramural league at the University of Akron. I had a highlight reel that was set to. To.

 

Jim McCarthy [00:51:03]:
Well, we didn't want to show up. We didn't want to show up Ray Williams.

 

Davis Conwill [00:51:05]:
Yeah, you know, he has. He has all these highlights of Ray Williams. I think there's some. Some clips of LeBron James running a crossing pattern, but for whatever. Whatever reasons, Jimmy cut my flag football highlight highlight reel from University of Akron intramural squad. So I'm a little bit sad about that, but it's all right. I'll get over it.

 

Jim McCarthy [00:51:30]:
I support you, Dave. I support you, Dan.

 

Jeffrey Stern [00:51:34]:
It's tough to beat the triple return touchdown saga that Ray had. I mean, that's a crazy story to just set the standard of what an athlete he is.

 

Davis Conwill [00:51:49]:
Yeah. I mean, but in all honesty and truthfulness, I would have loved to have seen. I want to give away too much of the film, but I. I would have loved to seen more of the, you know, one of the. The main characters in high school and college and beyond Lorenzo. He was a. An amazing talent. I mean, he had a blend of hands and quickness, physical.

 

Davis Conwill [00:52:16]:
Physicality, height. I mean, he had all the physical attributes. Seem to really understand the game as well. So, you know, obviously there's bigger things in football, in life, but from a football perspective, we'd love to have seen his career take off as well.

 

Jim McCarthy [00:52:35]:
What this film has done is it's allowed us to kind of come up with a. A memorial for Lorenzo that. That's been installed at Benedictine. So, I mean, after 20 years, it's really awesome that we finally have something physical there to remember Lorenzo and for all the other kids. Going forward to know who he was and what he was all about. But, but then now we've established a scholarship. So Lorenzo Hunter Scholarship is at Benedict and now at least one kid will be able to take advantage of it every year. We're hoping that to grow it and be able to use it on multiple kids.

 

Jim McCarthy [00:53:15]:
But thank you for mentioning Lorenzo, Dave. He first and foremost was the main inspiration for this in the first place. And anybody who would like to kind of help contribute. There's a scholarship in his name at Benedictine. And you're more than happy to make a donation we appreciate.

 

Jeffrey Stern [00:53:35]:
Is an important outcome of all this.

 

Jim McCarthy [00:53:38]:
For sure.

 

Jeffrey Stern [00:53:39]:
We'll work to bookend the conversation here. Earlier, Jimmy mentioned the hidden gem of Transition Studios, which is actually the traditional closing question for hidden gems in the area. So perhaps you've already answered it. But Dave, any hidden gems?

 

Davis Conwill [00:53:59]:
I'd say buyrudwood.com but we have almost, probably, I don't know, 30 locations throughout Northeast Ohio. So I'm not sure. And if we're, if we're, if we're a hidden gem, then you know, we probably need to up our game on the marketing side. But our team does an outstanding job of perpetuating Redwood. And I don't know, I mean, here I go again. Pin gem is Jim McCarthy. Here's a guy that has been in marketing and branding his whole career and, and, and yes, he. Transition Studios is, is a, is a fantastic local studio.

 

Davis Conwill [00:54:43]:
But Jimmy, he did a lot of work on this film, a lot of work. And I remember School of Hard Knocks just jumping in without any formal knowledge in real estate, finance, land development. I remember I went to, I went to a library back in early 2000s. You still gathered your data from libraries, not ChatGPT or wherever else people get their information from these days and checked out a book, how to develop real estate developments and I learned, took notes and, and then that alongside my time at Pride 1. But Jimmy has no formal, I mean he's a film connoisseur and he's obviously, you know, watch a lot of films but he's got no formal training and go to, you know, the LA Film Institute or so for a first time filmmaker. I mean how can you not give them an A plus after watching this film? So I think there's.

 

Jeffrey Stern [00:55:56]:
Well, well said. Well, if people wanted to watch it, where would you direct them?

 

Davis Conwill [00:56:04]:
Apple tv. That's the best platform, but it's on most major streaming platforms.

 

Jeffrey Stern [00:56:11]:
Well, thank you guys again, really appreciate taking the time. It's a lot of fun.

 

Davis Conwill [00:56:16]:
Thank you Jeffrey. Great job.

 

Jeffrey Stern [00:56:21]:
That's all for this week. Thank you for listening. We'd love to hear your thoughts on today's show, so if you have any feedback please send over an email to jeffreyofthelandfm or find us on Twitter odleoftheland or Sternhefe. J E F E if you or.

 

Jeffrey Stern [00:56:38]:
Someone you know would make a good.

 

Jeffrey Stern [00:56:39]:
Guest for our show, please reach out as well and let us know. And if you enjoy the podcast, please subscribe and leave a review on itunes or on your preferred podcast player. Your support goes a long way to help us spread the word and continue to bring the Cleveland founders and builders.

 

Jeffrey Stern [00:56:53]:
We love having on the show.

 

Jeffrey Stern [00:56:55]:
We'll be back here next week at the same time to map more of the land. The Lay of the Land podcast was developed in collaboration with the UpCompany LLC at the time of this recording. Unless otherwise indicated, we do not own equity or other financial interests in the company which appear on this show. All opinions expressed by podcast participants are solely their own and do not reflect the opinions of any entity which employs us. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Thank you for listening and we'll talk to you next week.