Lay of The Land

Michael and Tory Waxman — the founders of Sundays for Dogs, the Cleveland-based company designed to make dog parents’ lives easy.What began with their own dog, Mabel, and a simple but powerful question — why does feeding dogs well have to be so difficult? — has grown into one of the most exciting consumer companies to emerge from Ohio. Led by loving dog parents Dr. Tory Waxman, a veterinarian, and Michael Waxman, a serial entrepreneur, Sundays pioneered human-grade, air-dried, zero-synthetics dog food designed to be healthier than kibble and easier than refrigerated alternatives.Since our last recorded conversation in 2023 (Lay of The Land Episode #123), Sundays has scaled dramatically. Having raised more than $55 million in capital and built out a Cleveland-based R&D Test Kitchen — where our conversation today took place — Sundays has grown from a direct-to-consumer upstart into a nationally recognized brand preparing for omni-channel distribution, creating a product that dogs love while positioning themselves at the forefront of the booming pet food market and the emerging ambient fresh movement.In our conversation, Michael and Tory share how they’ve navigated multiple chapters of scaling — including customer acquisition and brand evolution, balancing supply and demand, investing deeply in product innovation, and building a senior leadership team — while staying grounded in the mission that inspired Sundays from the start: making it easier to be an awesome dog parent. They also discuss what excites them most about the future and what comes next for Sundays as the company continues to grow.00:00:00 - "The World's Best Dog Food is Made in Cleveland"00:00:25 - Introduction: Sundays for Dogs00:05:20 - Building an In-House R&D Test Kitchen in Cleveland00:10:06 - Most Dogs Still Eat Kibble (And Why That's Changing)00:15:09 - Marketing Evolution: How Does Sundays for Dogs Stand Out?00:20:18 - New Recipe Launch Preview (From the Test Kitchen!)00:21:33 - Ohio: The Surprising Dog Food Capital of America00:25:36 - Supply Chain Stories & Lessons Learned00:30:39 - When Demand Outpaces Supply: A Good Problem?00:32:59 - Beyond DTC: Omnichannel Distribution Strategy00:38:21 - How AI Will Transform How People Buy Dog Food00:41:34 - Dogs as Family: Where Is Society Headed?00:46:44 - Building Company Culture at Sundays00:52:13 - The Vision: Making Sundays a Household Name00:55:18 - Where to Find Sundays for Dogs-----LINKS:https://sundaysfordogs.com/https://www.linkedin.com/in/michaelewaxmanhttps://www.linkedin.com/in/tory-waxman-87781b176/https://www.layoftheland.fm/123-tory-michael-waxman-sundays/-----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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Today’s episode was recorded live at Ohio VC Fest, where I hosted a panel on AI, joined by an incredible group of investors, including:Peggy Roberts, Managing Partner at The Riverside Company;Candice Matthews Brackeen, Founding Partner at Lightship Capital;Hardik Desai, Managing Partner at JumpStart Ventures;Jamie Weston, Managing Director at Spring Mountain Capital.Together, we walk through where real value is being created with AI, how founders can best leverage it in their business and in raising capital, and explore the vast opportunities and downstream implications of AI looking forward!00:00:00 Introduction to AI Investment Perspectives00:04:27 Understanding the AI Hype Cycle00:06:44 AI in Startups vs. Established Companies00:09:21 Defensibility and Team Dynamics in AI Investments00:12:25 AI's Impact on Business Operations00:15:15 Fundraising Strategies in the AI Landscape00:18:12 Evaluating AI Companies: Metrics and Expectations00:21:08 The Role of Education and Training in AI Adoption00:23:45 Future Predictions for AI in Various Industries00:26:27 Staying abreast AI's Evolution00:43:34 Closing Thoughts on AI-----LINKS:https://ohiovcfest.com/https://www.riversidecompany.com/https://www.lightship.capital/https://jumpstart.vc/https://www.springmountaincapital.com/https://jumpstartinc.org/https://www.linkedin.com/in/peggyrhttps://www.linkedin.com/in/candicebrackeen/https://www.linkedin.com/in/hardikadesai/https://www.linkedin.com/in/jamie-weston-75136a2/-----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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Craig Newmark is the founder of Craigslist and someone whose work has shaped the modern internet as we know it.Long before Craigslist became one of the most enduring, important, and frequented platforms on the web, long before the internet even connected all of us, Craig was a computer science student here in Cleveland at Case Western Reserve University — tinkering with early programming languages, studying neural networks and AI, and exploring the frontier of software engineering.The rest is history — an amazing history which we’ll cover in our conversation today, how Craig became the accidental entrepreneur behind one of the most legendary companies of our time, and a driving force of the internet itself. Our conversation spans his path to Silicon Valley, the creation and stewardship of Craigslist, the moral compass that has guided his decision making along the way, his growth as an entrepreneur and leader, the implications and consequences of building one of the largest platforms of all time, and the work he’s now doing to help meliorate the internet and country through his philanthropic initiatives with veterans, journalism, cybersecurity, and lots more.This was a truly special conversation, and I’m grateful to share it with you today — please enjoy this awesome discussion with Craig Newmark, the founder of Craigslist.00:00:00 Craig Newmark on Building Craigslist and the Early Internet00:03:52 From Case Western to Craigslist: Craig Newmark’s Origin Story00:07:21 Why Craigslist Was an Accidental Startup, Not a Planned Company00:12:18 How Craigslist Helped Democratize the Internet for Everyday People00:15:28 The Birth of Craigslist: From Email List to Iconic Website00:18:31 Monetizing Craigslist Without Selling Out Users or Trust00:20:23 Turning Down Billions: Craig Newmark’s Moral Compass at Craigslist00:23:39 Why Craigslist’s Simple Design Beat Venture-Backed Competitors00:25:50 How Craigslist Survived While Startups Tried to Unbundle It00:30:22 What Craigslist Taught Craig Newmark About Human Behavior00:31:58 Balancing Crime Prevention and Civil Liberties on Craigslist00:36:00 Why Craigslist Became One of the Most Trusted Platforms Online00:41:12 The Craigslist Design Philosophy: Simple, Fast, and Human00:44:01 From Craigslist to Philanthropy: Craig Newmark’s Next Chapter00:55:58 Craig Newmark’s Advice for Founders-----LINKS:https://www.craigslist.org/https://craignewmarkphilanthropies.org/https://www.linkedin.com/in/craignewmark/https://pausetake9.org/-----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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Brad DeHays — Founder and CEO of Connect Real Estate and Connect Housing Blocks.Brad’s journey spans from buying small distressed properties while still in college to leading one of the most ambitious housing manufacturing platforms in the country. Through Connect Real Estate, Brad has revitalized some of Ohio’s most overlooked landmarks — transforming abandoned power plants, trolley barns, and historic buildings into vibrant new community anchors.That same entrepreneurial vision inspired him to launch Connect Housing Blocks (CHB), a 630,000-square-foot modular housing facility anchored in Ohio, now one of the largest modular housing factories in the world. Using state-of-the-art equipment and prefabrication methods, CHB produces high-quality apartments from start to finish, eliminating nearly all measuring, cutting, and heavy lifting—the result: faster, more consistent, and more affordable housing production at scale.In our conversation, which took place on site at CHB, Brad shares how he’s navigated multiple chapters of starting and scaling Connect, the founding insight that drove him to take on industrial-scale modular housing, how he engages communities and leverages public–private partnerships, his unique approach to talent and culture, and his vision for solving the housing crisis by massively scaling up production capability.00:00:00 - The Birth of an Innovative Solution00:04:50 - Understanding the Housing Crisis00:09:56 - Reinventing Construction Processes00:15:59 - Scaling Modular Housing Production00:21:55 - Transforming the Construction Timeline00:32:46 - Vision for the Future of Housing00:36:43 - Scaling Modular Construction: A Game Changer00:42:34 - The Future of Modular Housing: Opportunities and Challenges00:47:17 - Design and Aesthetics in Modular Construction00:52:56 - Labor Challenges in the Construction Industry00:56:16 - Cultural Dynamics and Employee Empowerment01:01:05 - Looking Ahead: Growth and Future Prospects-----LINKS:https://connecthousingblocks.com/https://www.linkedin.com/in/braddehays/-----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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Chaya Slain is the Founder, President, and Chief Investment Officer at Virtera Partners.After studying mathematics at Columbia University, she discovered her deeper interest in investing at Goldman Sachs. After several years in New York, she returned to Cleveland and joined Parkwood, the Mandel family investment office, where she spent more than a decade immersed in institutional investing. At Parkwood, she developed a disciplined, process-driven investment philosophy; built relationships with leading private equity, hedge fund, and real estate managers; and learned directly from Mort Mandel’s cultural and strategic principles.In 2020, Chaya founded Virtera Partners, a boutique investment firm designed to offer ultra-high-net-worth families the sophistication of a top-tier institutional allocator with the personal attention of a single-family office. Virtera has grown into a platform providing clients access to differentiated public and private market opportunities — supported by deep sourcing, rigorous diligence, and a willingness to do things differently when the data points that way.In our conversation, we trace Chaya’s journey from Wall Street to Cleveland; her early entrepreneurial spark running a deli during her time at Columbia University; the leap from investor to founder; and the empathy and insight that transition has given her when evaluating other entrepreneurs and investment managers. We explore behavioral discipline, portfolio construction in uncertain markets, long-term thinking, and what it means to build with integrity, excellence, and a true sense of stewardship.As someone who loves this intersection of investing and entrepreneurship, it was fun to hear Chaya’s reflections on it and learn from her experience. Please enjoy this great conversation with Chaya Slain--Disclaimer:This podcast is provided for informational and educational purposes only and should not be construed as investment advice, a recommendation, or an offer or solicitation to buy or sell any securities or investment products. The views expressed are those of the speaker as of the date of recording and may change without notice. Investing involves risk, including the potential loss of principal. Investments in private funds and alternative investments are speculative, involve a high degree of risk, are often illiquid, may lack transparency, and are intended for sophisticated investors who are able to bear the risk of loss. Such investments may not be suitable for all investors.--00:00 Chaya's Journey: From Goldman Sachs to Investing08:33 Lessons from Parkwood: Building a Network and Process12:06 The Entrepreneurial Spirit: Transitioning to Founding17:51 Investment Decision-Making: Process and Emotion21:34 Navigating Emotional Biases in Decision Making23:26 Investment Philosophy: Flexibility Over Boxes26:05 Contrarian Investments: The Case for Energy28:42 Cleveland vs. New York: The Advantage of Distance30:27 Lessons from Entrepreneurship: Empathy and Long-Term Thinking34:41 Evolving the Business: From Family Office to Fund37:24 Defining Success: Integrity and Performance38:29 Challenges of Being Different in Investing41:47 Current Market Concerns and Portfolio Construction43:46 The Importance of Alternative Investments-----LINKS:https://www.linkedin.com/in/chaya-slain/https://www.virterapartners.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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Jerry Schill is the founder and CEO of Schill Grounds Management — a company he launched in 1993 with his brother after a chance summer job revealed a passion for landscaping. What began as a two-person side hustle has grown into a large-scale commercial grounds management company, now one of the fastest-growing platforms in the industry.In 2020, Jerry began a bold new chapter—scaling Schill Grounds Management through strategic acquisitions alongside organic growth. Under his leadership, the company has completed more than 16 acquisitions and now operates across six states and Ontario, Canada. With a growing family of nine brands and more than 1,400 team members, Schill Grounds Management is recognized as a national leader built on consistency, performance, and a people-first culture — and Jerry is still very much in building mode.Beyond the business, Jerry is an active contributor to several industry associations, including the National Association of Landscape Professionals, the Accredited Snow Contractors Association, and the Ohio Landscape Association. He also founded Holiday Feast — an annual charitable tradition that has served thousands of free meals to families in need throughout the Cleveland community.Throughout our awesome conversation, Jerry reflects on entrepreneurship, drive, discipline, humility, ambition, what it means to build something that lasts, and lots more.00:00 Introduction to Jerry Schill and His Journey00:59 The Impact of Family and Early Influences01:49 The Leap into Entrepreneurship03:54 The Evolution of Show Landscape07:21 Understanding the Landscaping Industry13:08 Leadership Evolution and Personal Growth19:04 The Importance of Peer Networks20:58 Scaling the Business and Maintaining Culture24:32 The Shift to Acquisitions for Growth27:47 Integrating Acquired Companies Successfully31:38 The Role of Technology in Landscaping34:47 Motivation and Future Vision for SGM38:09 Lessons Learned from the Journey39:55 Curiosity and Lifelong Learning41:13 The Holiday Feast Initiative44:08 Aiming for a Billion-Dollar Company45:46 Advice to Younger Self46:56 Hidden Gems in Cleveland-----LINKS:https://schilllandscaping.com/abouthttps://www.linkedin.com/in/jerry-schill-2b010b1a/Referenced Episode — Sanjay Singh: https://www.layoftheland.fm/218-sanjay-singh-macer-get-good-at-hard-things/-----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.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

Perry Stancato is the founder and CEO of Signature Sauces and a third-generation operator of the beloved Cleveland institution, Stancato’s Italian Restaurant.This conversation with Perry explores the entrepreneurial journey of someone who grew up in the family restaurant — from standing on a milk crate as a kid making waffles for Sunday brunch to running Stancato’s today while simultaneously building Signature Sauces into a premier national food manufacturing partner.Signature Sauces began in 2005 with a simple idea: to bottle his family’s legendary red sauce after customers kept asking for it. What started as a way to serve Stancato’s loyal patrons quickly evolved into something much larger. Perry discovered that while retail was cutthroat and unforgiving, his passion and true product-market fit lay in foodservice — helping other restaurants scale their “secret sauces.” Today, Signature Sauces has grown into a company that helps make the products that make others famous, serving clients from local Ohio favorites to national brands like Bob Evans, Momofuku, Benihana, Barrio, and many more.Alongside that manufacturing growth, Perry continues to steward Stancato’s — the restaurant that has been a Cleveland staple for decades. He reflects on the delicate balance of honoring a community legacy while making small, thoughtful changes to stay relevant across generations.In our conversation, Perry shares the challenges of taking nearly ten years to get Signature Sauces off the ground, the resilience it took to keep going, the lessons learned from retail versus foodservice, and what he’s most proud of: seeing team members who started as dishwashers grow into leaders, and knowing his work helps thousands of diners enjoy meals every day. We also dive into his Ohio pride, from the region’s food scene to partnerships like the Ohio State Buckeye Tailgate sauces, and his perspective on what it takes to build a legacy business in Cleveland.00:00:00 - The Legacy of Stancatos: A Family Business Journey00:09:03 - From Family Recipes to Signature Sauces00:12:49 - Navigating the Food Industry: Retail vs. Food Service00:17:15 - Scaling Up: The Art and Science of Sauce Production00:20:39 - The Future of Signature Sauces: Expanding Partnerships00:21:55 - The Entrepreneurial Journey Begins00:23:33 - Vision and Growth of Signature Sauces00:26:10 - Lessons from the Restaurant Industry00:29:10 - Balancing Time and Responsibilities00:31:40 - Building a Legacy in Ohio00:34:30 - Innovation and Technology in Food Production00:37:08 - Trends in the Culinary World00:39:44 - Understanding Risk and Success00:42:22 - Navigating Customer Relationships00:45:20 - Insights for Aspiring Food Entrepreneurs00:45:35 - Reflections on the Journey-----LINKS:https://www.signaturesauces.com/https://www.stancatos.com/https://www.linkedin.com/in/perry-stancato-799b16b/-----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/

Kaitie and Kyle Nickel are entrepreneurs, storytellers, and community builders based in Cleveland. They have grown beloved brands such as Cleveland Vibes, The Cleveland Market, and Cleve or Leave to reach hundreds of thousands of followers and many millions of people. Their work is driven by a shared goal: to connect people, celebrate local culture, and inspire growth. Passionate about empowering small businesses and shaping Cleveland’s cultural identity, Kaitie and Kyle have built a family business that blends storytelling, innovation, and community into something uniquely impactful.In our conversation, we discuss the origins of Cleveland Vibes and how it became a platform for positive storytelling. We explore how the couple is reframing Cleveland’s narrative and brand for a new generation, and how their work has evolved from social media into events, agency projects, and viral cultural moments. We also talk about what it means to build a family business and define success through community impact.Kaitie and Kyle are doing incredible work telling Cleveland’s story, and I’m excited to share our conversation with you today.00:00:00 - Introduction and Setting the Stage00:02:53 - Discovering Cleveland: A New Perspective00:05:36 - Kaitie’s Journey: From Nursing to Creative Storytelling00:08:00 - The Storytelling Challenge: Changing Perceptions of Cleveland00:12:20 - The Birth of Cleveland Vibes: A Community Movement00:17:04 - Cleveland Vibes Today: More Than Just Social Media00:18:18 - Building an Audience: The Power of Community00:23:43 - Entrepreneurial Lessons: Building Together00:27:10 - Cleve or Leave: A New Brand Emerges00:29:52 - Creative Process: Froggy’s Journey to Fame00:33:52 - Preparing for Viral Moments00:37:59 - The Creative Playground00:39:43 - Defining Success and Vision00:44:42 - Changing Perceptions of Cleveland00:49:02 - The Brand of Cleveland00:51:37 - Hidden Gems-----LINKS:https://clevelandvibes.com/https://www.facebook.com/clevelandvibes/-----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/

Nearly a year and a half after our conversation first aired in 2024, Lost & Found in Cleveland is ready to make its way to theaters nationwide on November 7, 2025.When I first sat down with Keith Gerchak and Marisa Guterman, the creative forces behind the film, we explored the decade-long journey that brought this story to life—from writing and directing this cinematic love letter to Cleveland, to raising capital, recruiting a star-studded cast featuring Martin Sheen, Dennis Haysbert, June Squibb, Stacy Keach, and many others, and filming across Cleveland’s iconic landscapes.With the film’s theatrical debut now just around the corner, this feels like the perfect moment to revisit their remarkable story.So, with that exciting update, please enjoy this encore conversation from the Lay of The Land archives with Keith Gerchak and Marisa Guterman, the filmmakers behind Lost & Found in Cleveland, airing in theaters across Cleveland starting November 7, 2025.Tickets are now on sale at https://tickets.lostandfoundincleveland.com/! More theaters are being added daily. 00:00:00 - The American Dream in Cleveland 00:05:56 - The Journey of Filmmaking 00:19:10 - Character Development and Storytelling 00:32:39 - Challenges and Triumphs in Production 00:42:44 - The Journey of Filmmaking: Vision and Execution 00:44:44 - Challenges of Fundraising in Cleveland 00:46:31 - The Economic Impact of Local Filmmaking 00:49:15 - Building a Sustainable Film Industry in Cleveland 00:51:33 - Changing the Narrative: Cleveland's Film Identity 00:54:53 - Casting Challenges and Triumphs 01:01:38 - Overcoming On-Set Challenges 01:09:21 - The Message of Hope in Film-----LINKS:Lost & Found in Cleveland IMDB: https://www.imdb.com/title/tt4601732/Connect with Keith Gerchak: https://www.linkedin.com/in/keithgerchak/Connect with Marisa Guterman: https://www.linkedin.com/in/marisa-guterman-187677a9/Double G Films: https://www.doublegfilms.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/

Nearly a year and a half after our conversation first aired, Aaron Slodov and Atomic Industries have reached an important milestone worth celebrating. Atomic recently announced the close of its $25 million Series A, led by MaC Venture Capital and DTX Ventures, with participation from Narya and others, to accelerate the rollout of its AI-driven manufacturing platform.With this funding, Atomic is expanding its software-defined factory footprint and advancing the AI systems at the heart of its vision—one that has already moved from pilot to production, shipping parts to some of the world’s most demanding OEMs. At its core, Atomic is working to strengthen America’s industrial base by making the manufacturing of physical goods more localized, resilient, and technology-enabled.This felt like the perfect moment to revisit my conversation with Aaron, where we unpack his techno-industrialist philosophy, the deep history of Ohio manufacturing, and why the future of physical production matters so much for our country.So, with that timely update, please enjoy this timeless conversation from the Lay of The Land archives with Aaron Slodov, CEO of Atomic Industries.00:00:00 – The Rise of Techno-Industrialism00:05:56 – The Journey from Bits to Atoms00:10:41 – The Challenges of Manufacturing00:15:47 – Reindustrialization and the Post-Industrial Myth00:20:48 – Atomic Industries: Innovating Manufacturing00:25:42 – Exascaling the Industrial Base00:30:49 – The Future of Manufacturing Talent00:40:46 – The Shift in Manufacturing Careers00:42:50 – Incentivizing the Return to Manufacturing00:44:58 – Cultural Integration of Tech and Manufacturing00:50:38 – Defining Success in Modern Manufacturing00:52:03 – The Importance of a Techno-Industrial Framework00:56:12 – Policy and the Future of Manufacturing01:02:33 – The Potential of Reindustrialization01:05:57 – Storytelling as a Tool for Founders-----LINKS:https://www.linkedin.com/in/abslodov/https://twitter.com/aphysicisthttps://www.atomic.industries/https://www.piratewires.com/p/techno-industrialist-manifestohttps://twitter.com/newindustrials-----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/

Ralph Lazaro, Co-founder & CEO of INaudio, has spent more than two decades leading high-performing teams and driving innovation. His career began in Fortune 500 companies before he joined Findaway in 2012, where he helped transform the business from a physical device company into a $100M+ digital audiobook powerhouse — a journey that ultimately led to Spotify’s acquisition of Findaway.Now, alongside Blake Squires (who shared his own remarkable entrepreneurial story on episode 206 of Lay of the Land), Ralph is carrying that story forward with INaudio, a spinout from Spotify dedicated to powering the global audiobook ecosystem as an independent company.In our conversation, Ralph shares his decision to leave Charlotte, North Carolina, and move to Cleveland to join Findaway — and the culture that convinced him it was the right leap. He reflects on Findaway’s transformation and the lessons learned from co-founder and CEO Mitch Kroll, who shared his story on episode 128. We also discuss Spotify’s acquisition, what it was like integrating into big tech, and the launch of audiobooks to hundreds of millions of listeners. Ralph walks us through the INaudio spinout process — buying back the very business he helped grow inside Spotify — and what it’s been like stepping back into the founder’s seat.From building a new team and intentionally shaping its culture around past lessons and personal philosophies, to navigating the evolving audiobook industry with new competitors and technologies, Ralph offers thoughtful insights into INaudio’s mission as “the world’s audiobook partner.” He also reflects on entrepreneurship, Cleveland as a place to build, and how his definition of success has evolved.Ralph brings incredible energy, humility, and earned wisdom to this conversation, and I’m grateful to share it with you.00:00:00 - The Findaway Journey Begins00:08:42 - Transitioning from Spotify to Findaway 2.000:16:53 - Exploring Opportunities in Audio00:24:31 - The Evolving Audiobook Landscape00:35:55 - Navigating Leadership Transitions00:41:47 - Lessons from Spotify00:46:56 - Optimizing for Growth00:54:25 - The Future of Audiobooks01:03:14 - The Importance of Leadership in Career Growth01:04:40 - Hidden Gem-----LINKS:https://www.linkedin.com/in/ralph-lazaro/https://www.inaudio.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/

Terry Coyne is an Executive Vice Chairman of Newmark and Principal of Terry Coyne Properties. Over his 25-plus-year career, Terry has become one of Ohio’s most accomplished commercial real estate leaders, negotiating more than 2,000 transactions totaling over $5 billion in value. In Cleveland alone, over the past five years, he and his team have brokered 250 transactions worth more than $1.2 billion.In our conversation, we cover Terry’s unique philosophy and strategy on real estate, risk, and patience — which have led him to a diverse range of opportunities, from representing companies like GOJO and L’Oréal, to redeveloping the old Chrysler Plant, building the MidTown Tech Park in Cleveland, and now leading the 670+ acre site at Rickenbacker adjacent to Anduril’s new Arsenal 1 Hyperscale Manufacturing Facility.We also break down Terry’s views on Ohio’s regional markets, what he’s learned from his father, the intersection of real estate and entrepreneurship, and his perspective on the future of the state’s economy — from data centers and energy policy to the cultural ambition needed for Ohio to continue its rise.00:00:00 - Introduction to Terry Coyne and His Career00:25:48 - Exploring Ohio's Unique Markets00:30:38 - Land vs. Real Estate: Understanding Value00:37:16 - The Future of Work: Remote vs. In-Office00:42:59 - Taxation and Its Impact on Real Estate00:49:48 - Hidden Gem-----LINKS:https://www.linkedin.com/in/terrycoyne/https://terrycoyne.com/terry-coyne-properties/-----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/

Jeff Berlin is the Founder and President of Bridge Industries & Chairman and CEO of TransTech Energy. Jeff’s journey spans from his early days at Parker Hannifin to helping grow Hawk Corporation from a $20 million single-plant business into a $200 million global operation, and ultimately to founding his own company, Bridge — an industrial holding company anchored by TransTech — that has quietly scaled into a multi-hundred-million-dollar enterprise based in Chagrin Falls.In our conversation, we cover Jeff’s conviction in the importance of American manufacturing and how it shaped his career-long commitment to building enduring businesses; the creation of Bridge Industries and his intentional choice of a permanent holding-company model over traditional private equity; the more than 25-fold scaling of TransTech into a diversified industrial platform with over 700 employees, up from just 35 a decade earlier; and the lessons learned along the way — the resilience and philosophy that guide him, how to weather downturns, usefulness as a true measure of value and success, culture across companies, and much more.00:00:00 - The Roots of American Manufacturing Belief 00:07:35 - Formative Experiences in Leadership 00:09:00 - Transformational Growth at Hawk 00:11:55 - Resilience in Business 00:13:10 - The Birth of Bridge 00:14:14 - Understanding Industrial Holding Companies 00:16:25 - Differentiation from Traditional Private Equity 00:19:00 - The Journey of Bridge 00:20:47 - Strategic Growth and Acquisitions 00:27:31 - Managing Geographic Expansion 00:30:01 - Introducing TransTech 00:31:28 - Building Infrastructure for Energy Solutions 00:35:59 - Strategic Growth and Acquisition Insights 00:38:10 - The Importance of Vertical Integration 00:42:51 - Cultural Dynamics in Business Integration 00:43:43 - The State of American Manufacturing 00:46:30 - Defining Success and Value Creation 00:48:10 - Future Ambitions for Bridge and TransTech 00:49:40 - Mentorship and Leadership Evolution 00:51:22 - Understanding the Nature of Industrial Work 00:54:40 - The Role of Infrastructure in Daily Life 00:55:56 - Excitement for Future Challenges 00:58:07 - Investing in Financial and IT Infrastructure 00:59:52 - Automation and Its Implications 01:01:53 - Guiding Wisdom and Philosophy 01:02:51 - Renewable Natural Gas and Environmental Impact 01:05:51 - Hidden Gem-----LINKS:https://www.linkedin.com/in/jeff-berlin-9b156a12/https://bridgeind.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/

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/