Lay of The Land

On this special episode of Lay of the Land, I’m joined—for the first time—by the two co-founders of The O.H.I.O. Fund, Mark Kvamme and Ray Leach, as well as the fund’s two founding partners, Jill Meyer and Mike Venerable, to share the inside story of how a bold idea became reality.We explore the inspiration and origins behind a first-of-its-kind strategy designed to generate returns while accelerating prosperity and shaping Ohio’s future. We discuss how, in our first year, we closed on over $230 million in capital from investors and deployed more than $130 million into 19 sector-diverse investments across Ohio’s economy. We also cover what it has taken to build momentum, forge the most powerful network of investors, founders, and operators across the state, and why Ohio’s moment is now—along with the urgency this opportunity demands.———For more on The O.H.I.O. Fund: check out www.theohiofund.com———00:00:00 - The Birth of the Ohio Fund 00:04:08 - Ohio's Economic Landscape and Historical Context 00:07:06 - The Vision Behind the Ohio Fund 00:09:59 - Building a Collaborative Network 00:13:11 - The Urgency of Now: Why Timing Matters 00:15:53 - Capitalizing on Opportunities in Ohio 00:19:17 - The Role of AI and Innovation 00:22:05 - Success Stories and Impact Investments 00:25:08 - Creating a Unified Ohio 00:27:50 - The Future of the Ohio Fund 00:30:55 - Personal Motivations and Collective Ambition 00:35:10 - Reflecting on Progress and Future Aspirations 00:40:16 - Surprises and Insights from the Ohio Fund's First Year 00:51:07 - Looking Ahead: Opportunities and Growth in Ohio 00:55:06 - Embracing Change and Building a New Future-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

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 Football00:09:35 - The Journey of Telling a Story00:17:08 - From Real Estate to Film00:17:59 - The Process of Creating a Film00:22:15 - Healing Through Storytelling00:26:36 - Messages and Takeaways from the Film00:29:54 - Challenges in Documentary Filmmaking00:33:40 - Building from Scratch: The Documentary Process00:35:02 - Pivots and Perspectives: The Evolution of the Script00:39:50 - A Cleveland Story: Local Roots and Universal Themes00:42:06 - The Release Journey: Reactions and Reflections00:44:40 - Looking Ahead: Future Projects and Aspirations00:50:46 - Lessons Learned: Overcoming Doubts and Challenges00:52:44 - Honoring Legacy: Memorials and Scholarships00:55:56 - Hidden Gem-----LINKS:https://www.linkedin.com/in/david-conwill-b099434/https://tv.apple.com/us/movie/mr-football/umc.cmc.4bj5i7tx1hef4shqkmk16asw0https://www.primevideo.com/detail/Mr-Football/0U57SLRHOHWDVTTCP6XMQ56SRZ-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Ivy Zelman is one of the most respected voices in American housing, co-founder of Zelman & Associates, and now Executive Vice President at Walker & Dunlop, which acquired her firm in 2021 as the leading institutional research, advisory, and investment banking firm dedicated exclusively to the U.S. housing industry.Over the last three decades, Ivy has built a reputation for bold, contrarian analysis—famously calling the top of the housing market in 2005 and the bottom in 2012—moments that cemented her as a rare analyst unafraid to speak truth to consensus. That conviction has earned her numerous accolades, including recognition in Barron’s 100 Most Influential Women in U.S. Finance for four consecutive years and induction into the California Homebuilding Foundation’s Hall of Fame.In our conversation, we trace Ivy’s journey from falling into equity research to taking the entrepreneurial leap in 2007, founding Zelman & Associates amid the looming financial crisis. We explore her approach to research and analysis—blending proprietary surveys with a nationwide network of builders, brokers, and lenders—to consistently separate signal from noise.We reflect on her evolution as a leader and entrepreneur, the culture she has cultivated with a team that has stayed by her side for decades, her love of Cleveland, and what it means to pay it forward today through teaching and mentorship as an Adjunct Professor of Finance at Case Western Reserve University, her memoir Gimme Shelter, and much more.00:00:00 - Catalytic Moments in Finance00:08:25 - Recognizing Blind Spots in Research00:11:27 - The Entrepreneurial Inclination00:11:55 - Building Conviction and Confidence00:15:54 - Vision for Success00:17:21 - Detective Work in Research00:18:45 - Cultivating a Strong Network00:22:20 - The Importance of Asking the Right Questions00:25:13 - Reconciliation with Reality00:26:35 - Navigating Market Sentiment00:28:13 - The Evolution of Zellman Associates00:30:38 - Personal Growth as an Entrepreneur00:34:06 - Leadership and Team Development00:36:01 - Maintaining Intellectual Honesty Post-Acquisition00:37:39 - Understanding the Value of Research00:39:15 - Cleveland's Unique Perspective00:42:10 - Paying It Forward and Mentorship00:45:38 - Lessons for the Next Generation00:47:23 - Contrarian Views on Market Trends00:49:17 - Balancing Work and Family Life00:51:20 - Hidden Gem-----LINKS:https://www.linkedin.com/in/ivy-zelman-64304616b/https://www.zelmanassociates.com/https://www.amazon.com/Gimme-Shelter-Skills-Street-Trailblazer/dp/1737709929-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Ryan Kelly is a filmmaker, entrepreneur, and partner of Substance, a film and television production company based in Cleveland.What if Northeast Ohio had the infrastructure to support large-scale film productions? That question first took root when Ryan found himself on the set of Cherry—a feature film shot in Cleveland by the Russo Brothers, the acclaimed Cleveland-born directors behind Avengers and Captain America—soaking in the experience of working alongside Hollywood heavyweights in his hometown.What followed was Ryan’s relentless pursuit of that vision and his work to build up Northeast Ohio’s film industry.Before founding Substance, Ryan co-founded TRG Sound & Vision alongside industry veterans Adam Wilde and Geoff Yaw. TRG boasts one of the largest sound stages in the Midwest: 160,000 square feet of studio space, a Virtual Production Wall, a 40' by 60' cyclorama wall, and 40 semi-permanent sets staffed by skilled industry professionals to meet the demands of large productions.As a filmmaker, Ryan is the director and producer of the docuseries WrestleHer, which tells the story behind sanctioning high school girls’ wrestling in Ohio and the generation of athletes growing the sport.Ryan’s journey is a powerful blend of artistic conviction and entrepreneurial grit. In our conversation, we explore how he carved a path into the film industry from scratch as a touring musician and drummer, what he learned from working alongside others in the industry—like Transition Studios, whose story was shared by Shawn Rech in Episode 85 of Lay of The Land—and how he approaches creative risk, storytelling, and making Cleveland a true contender on the national production map.00:00:00 - From Punk Rock to Filmmaking: A Journey of Artistry00:08:08 - Navigating the Filmmaking Landscape: Players and Perspectives00:13:16 - The Evolution of TRG: A Hub for Creative Production00:21:11 - The Artist-Entrepreneur Duality: Balancing Creativity and Business00:28:19 - Cleveland's Potential: A Production Hub in the Making00:33:35 - The Birth of Substance: A New Identity00:40:51 - The Multifaceted Role of a Filmmaker00:47:36 - Inspiring Projects and Personal Connections00:55:00 - Hidden Gem-----LINKS:https://www.linkedin.com/in/rjk216/https://www.thisissubstance.com/https://www.linkedin.com/in/rjk216/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Andrew Hurst is the founder and CEO of Delivered, a fast-scaling logistics platform revolutionizing parcel shipping with faster, more reliable deliveries at lower costs.He also serves as CEO of Ark Transportation, where he led a fivefold revenue increase in just five years, and is the founder of Veroot, a compliance platform now trusted by thousands of logistics teams nationwide.Under his leadership, and across all three companies, Andrew is bringing an entrepreneurial lens to the freight industry he grew up in—challenging the status quo, disrupting legacy giants, and redefining how parcel shippers move goods across the country.This was a ton of fun. First off, we set up shop right on the warehouse floor where Andrew has built all three of these companies. The industrial-scale freight equipment and thousands of parcels and packages provided an incredible backdrop for the conversation—one that reflects Andrew’s life’s work, calling, and ambition to transform an entire industry. For those who’d prefer to see it, I encourage you to watch our conversation on YouTube.We talk about the advantages and pride of building in Cleveland, how he’s raising a family of 11 children while scaling all three companies, what it’s like competing against Goliaths like FedEx and UPS, and what he believes the future of logistics will look like. Andrew’s clarity of thought, humility, and commitment to creating enduring impact are inspiring—it’s not surprising he’s been recognized with the Vistage Excellence in Leadership Award and named a Smart Business Dealmaker of the Year in 2023.-----LINKS:https://shipdelivered.com/en/https://www.linkedin.com/in/hurstandrew/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Dale Wollschleger is the Founder and former CEO of Cleveland-based ExactCare Pharmacy and the developer of the ExactPack™—a patient-specific medication packaging system designed to simplify complex medication regimens.This conversation with Dale dives into the unlikely journey of a pharmacist-turned-entrepreneur who started in the back of a small Cleveland pharmacy and built a billion-dollar organization serving patients across the country.ExactCare’s meteoric growth—from inception to a multi-hundred-million-dollar (revenue) business in under a decade—has earned it repeated recognition as an Inc. 5000 fastest-growing company; Dale himself was named an Ernst & Young Entrepreneur of the Year.Ultimately, Dale’s remarkable journey stems from an observation he made as a pharmacist: that pharmacists have the opportunity to play a more integral role in clinical care—and that their responsibility doesn’t end when the patient leaves the store. Many patients could live healthier, more independent lives if only they took the right medications at the right times.In our conversation, Dale shares how he navigated the many chapters of scaling a healthcare business: bringing in private equity and outside capital, evolving his leadership, and balancing high-growth expectations with a deep commitment to patient outcomes, company culture, family—and much more.00:00 - The Journey of a Pharmacist Turned Entrepreneur14:34 - Building ExactCare: Addressing Complex Patient Needs24:18 - The Evolution and Vision of ExactCare31:07 - Entrepreneurial Spirit in Pharmacy38:59 - Understanding the Pharmacy Industry43:24 - Pride in Building in Cleveland-----For more on The O.H.I.O. Fund: check out & subscribe to future content @ www.theohiofund.com-----LINKS:https://www.exactcarepharmacy.com/https://www.linkedin.com/in/dale-wollschleger/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Sanjay Singh is a thoughtful strategist, seasoned executive, and business philosopher whose journey to leading the iconic Cleveland brand Mace Security—and his reflections on it—are remarkable.Sanjay’s story weaves together a deep appreciation for manufacturing and a career shaped by curiosity, resilience, and a knack for doing hard things—ultimately culminating in a personal philosophy grounded in introspection and presence.From navigating activist shareholders during a turnaround at Mace to developing frameworks around fear, ego, inquiry, and deep intuition, Sanjay offers a unique lens into what it means to lead with vulnerability and intention.This conversation leans more philosophical than most Lay of The Land episodes—a reflection of Sanjay’s clarity of thought, deep presence, and his insights into consciousness and awareness. His perspective on leadership elevates the discussion far beyond the business realm, offering thoughtful takeaways for both work and life.Sanjay also serves on the boards of MAGNET—whose story was shared by Ethan Karp in Episode 139—and The Nature Center at Shaker Lakes. He’s married to Erin Singh, CEO of Options Naturopathic, who joined us on Episode 147 to share her own journey.Sanjay is a true student of the world, of people, and of business. It was a real joy for me to try to distill the many conversations we’ve had about his perspective into this one here today.00:00:00 - Sanjay's Unlikely Journey  00:11:40 - Frameworks for Success  00:19:18 - The Story of Mace  00:32:58 - Vulnerability as an Equalizer  00:39:10 - Turning Companies Around: Key Ingredients  00:47:16 - Balancing Intuition and Intellect  00:54:50 - Defining Success and Impact  01:01:30 - Hidden Gem-----LINKS:https://www.linkedin.com/in/sanjaysinghdrivingexcellence/https://www.mace.com/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Kelcey Lehrich is the Co-Founder and CEO of 365 Holdings, based in Akron, Ohio. 365 Holdings acquires and operates consumer products companies, with a focus on eCommerce and a goal of long-term ownership.In our conversation, Kelcey shares his path to entrepreneurship and his evolution from making his first acquisition to becoming a seasoned operator. He weaves in lessons from challenging ventures, unconventional acquisitions, and the earned wisdom of building durable businesses in the competitive world of e-commerce.We unpack how Kelcey thinks about demand creation versus demand capture, what it takes to build a resilient holding company, the tradeoffs between a centralized shared-services model and a decentralized structure, and how to create the best long-term home for brands. He also shares wisdom on what makes a company worth buying in the first place, lessons learned from organizing the HoldCo Conference — the un-conference of Micro Private Equity — here in Cleveland, and much more.Kelcey offers valuable insight for anyone exploring entrepreneurship through acquisition — or simply curious about how to thoughtfully scale something of quality over time. Please enjoy!00:00:00 - The Entrepreneurial Spirit Unlocked  00:05:32 - Navigating Early Entrepreneurial Ventures  00:08:28 - The Birth of 365 Holdings  00:11:18 - E-Commerce Evolution and Insights  00:14:36 - Acquisition Strategies and Lessons Learned  00:17:37 - Understanding Distressed M&A  00:20:13 - The Rise of Entrepreneurship Through Acquisition  00:35:33 - Evolving Business Strategies  00:38:30 - Defining Success in Business  00:39:46 - Core Values and Company Culture  00:40:58 - Raising the Quality Bar  00:42:59 - The HoldCo Conference  00:45:20 - The Mindset of a HoldCo Entrepreneur  00:47:01 - Incentives and Profit Sharing  00:49:30 - Inspirations and Aspirations  00:50:16 - The Future of E-Commerce  00:52:12 - Opportunistic Acquisitions  00:53:19 - Building in Northeast Ohio  00:55:00 - Hidden Gem-----LINKS:https://365-holdings.com/https://www.linkedin.com/in/kelceylehrich/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

TJ Dembinski is the co-founder and CEO of Eagle Electronics, dedicated to on-shoring America’s critical technology supply chain, starting with the IoT and automotive-grade cellular modules!This journey traces a fascinating arc — one that begins with the macro and geopolitical forces shaping global commerce and lands in a Northeast Ohio advanced micro-electronic manufacturing floor where Eagle Electronics is domestically building one of the most critical pieces of our digital infrastructure: the cellular module.TJ's story, and the founding of Eagle, is deeply embedded in these broader structural shifts — from the decoupling of U.S. global supply chains to the bipartisan momentum around domestic manufacturing and deindustrialization, to the evolving national security concerns that now govern the production of connected technologies.We also talk about the nuances of reshoring, what onshoring looks like in practice, what cellular modules are, and why Ohio — of all places — is emerging as the epicenter of America’s next industrial chapter. From partnerships to cutting-edge automation, from regulatory and security considerations to hard-earned insights about what it actually takes to build something physical at scale — TJ brings an insightful clarity to one of the most exciting, complex, and important entrepreneurial movements underway today and how Eagle Electronics is positioned to lead within it.00:00:00 - Reviving Domestic Manufacturing  00:05:09 - The Evolution of Eagle Electronics  00:08:11 - Understanding Cellular Modules and Their Importance  00:10:56 - Navigating Regulatory Challenges  00:14:02 - The Role of Trust and Security in Technology  00:16:53 - Building a Skilled Workforce in Ohio  00:20:00 - Funding and Capital Landscape in Ohio  00:23:04 - The Future of Onshoring and Manufacturing  00:26:02 - Lessons Learned as a Founder  00:29:04 - The Importance of Nuance in Global Supply Chains  00:37:00 - Requirements for Success00:46:50 - Hidden Gem-----LINKS:https://www.linkedin.com/in/tj-dembinski/https://www.eagleelectronics.com/https://theohiofund.com/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Ibrahim Mohmed is the founder of CourtSide Media Group and the co-founder & CEO of Taja AI. His entrepreneurial journey began right here in Ohio, where he launched CourtSide Media, a digital media agency that serves influencers with audiences ranging from 1 million to 75 million followers across various social platforms. Through CourtSide Media, Ibrahim has collaborated with high-profile clients including NBA legend Kevin Garnett, Cleveland’s FutureLAND annual conference, and prominent influencer Lauren Fitzmaurice—effectively amplifying their reach and impact through strategic, organic growth.Building on his success with CourtSide, Ibrahim co-founded Taja AI—a platform designed specifically to empower small businesses and content creators. TAJA AI automates content workflows by optimizing, repurposing, and scheduling content, significantly saving time for thousands of creators while maximizing their audience engagement and discoverability.Beyond his entrepreneurial ventures, Ibrahim is deeply committed to social impact through his organization, Nile Nights, which curates events to raise awareness and funds for individuals and communities affected by the ongoing conflict in Sudan.As a founder at the forefront of media and AI, Ibrahim offers powerful insight into where the space is headed and what it takes to succeed within it—please enjoy this fascinating conversation with Ibrahim Mohmed.00:00:00 - The Shift to Video Podcasting  00:04:06 - Understanding Taja AI  00:06:03 - The Entrepreneurial Journey Begins  00:08:14 - The Drive for Storytelling in Media  00:11:47 - The Power of Technological Leverage  00:13:22 - The Vision and Evolution of Taja AI  00:15:31 - User Experience and Product Functionality  00:17:36 - Building a Scalable Company with AI  00:20:35 - The Changing Landscape of Venture Capital  00:22:10 - Navigating Model Providers in AI  00:23:30 - Navigating Competition in the AI Landscape  00:26:26 - Understanding Vibe Coding and Its Impact  00:27:52 - Product Philosophy and Customer Engagement  00:29:41 - Common Mistakes Creators Make  00:32:34 - The Intersection of AI and Human Creativity  00:35:01 - Sustainable Business Models in Content Creation  00:36:42 - Personal Impact and Future Aspirations  00:37:48 - Embracing Adversity in Entrepreneurship  00:40:28 - Looking Ahead: Growth and Innovation  00:47:00 - Final Thoughts and Hidden Gems in Cleveland-----LINKS:https://www.linkedin.com/in/ibrahim-mohmed-982076110/https://www.courtsidegroup.com/https://www.taja.ai/-----SPONSOR:Roundstone InsuranceRoundstone 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.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/