Lay of The Land #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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SPONSOR:
Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.
Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.
Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.
Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.
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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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