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 Insurance

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.

-----

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 @podlayoftheland

https://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 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

-----

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

-----

SPONSOR:

Roundstone Insurance

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.

-----

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 @podlayoftheland

https://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 Finance
00:08:25 - Recognizing Blind Spots in Research
00:11:27 - The Entrepreneurial Inclination
00:11:55 - Building Conviction and Confidence
00:15:54 - Vision for Success
00:17:21 - Detective Work in Research
00:18:45 - Cultivating a Strong Network
00:22:20 - The Importance of Asking the Right Questions
00:25:13 - Reconciliation with Reality
00:26:35 - Navigating Market Sentiment
00:28:13 - The Evolution of Zellman Associates
00:30:38 - Personal Growth as an Entrepreneur
00:34:06 - Leadership and Team Development
00:36:01 - Maintaining Intellectual Honesty Post-Acquisition
00:37:39 - Understanding the Value of Research
00:39:15 - Cleveland's Unique Perspective
00:42:10 - Paying It Forward and Mentorship
00:45:38 - Lessons for the Next Generation
00:47:23 - Contrarian Views on Market Trends
00:49:17 - Balancing Work and Family Life
00:51:20 - 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 Insurance

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.

-----

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 @podlayoftheland

https://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 Artistry
00:08:08 - Navigating the Filmmaking Landscape: Players and Perspectives
00:13:16 - The Evolution of TRG: A Hub for Creative Production
00:21:11 - The Artist-Entrepreneur Duality: Balancing Creativity and Business
00:28:19 - Cleveland's Potential: A Production Hub in the Making
00:33:35 - The Birth of Substance: A New Identity
00:40:51 - The Multifaceted Role of a Filmmaker
00:47:36 - Inspiring Projects and Personal Connections
00:55:00 - Hidden Gem

-----

LINKS:
https://www.linkedin.com/in/rjk216/
https://www.thisissubstance.com/
https://www.linkedin.com/in/rjk216/

-----

SPONSOR:

Roundstone Insurance

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.

-----

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 @podlayoftheland

https://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 Insurance

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.

-----

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 @podlayoftheland

https://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 Entrepreneur
14:34 - Building ExactCare: Addressing Complex Patient Needs
24:18 - The Evolution and Vision of ExactCare
31:07 - Entrepreneurial Spirit in Pharmacy
38:59 - Understanding the Pharmacy Industry
43:24 - 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 Insurance

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.

-----

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 @podlayoftheland

https://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 Insurance

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.

-----

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 @podlayoftheland

https://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 Insurance

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.

-----

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 @podlayoftheland

https://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 Success
00:46:50 - Hidden Gem

-----

LINKS:
https://www.linkedin.com/in/tj-dembinski/
https://www.eagleelectronics.com/
https://theohiofund.com/

-----

SPONSOR:

Roundstone Insurance

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.

-----

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 @podlayoftheland

https://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 Insurance

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.

-----

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 @podlayoftheland

https://www.jeffreys.page/