Podcast
Lay of The Land
Hosted by Jeffrey Stern · EN
Telling the stories of entrepreneurship and builders in Cleveland and throughout Northeast Ohio. Every Thursday, Jeffrey Stern helps map the Cleveland/NEO business ecosystem by talking to founders, investors, and community builders to learn what makes Cleveland/NEO special.
37episodes
Episodes
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#238 Tyler Dunagin (TurnServ) — Curiosity, Leadership, and Entrepreneurship in Multifamily
Jan 2901:09:40Tap to summarizeTyler Dunagin is the founder and CEO of Turnserv, a Northeast Ohio–based platform company behind brands like ApartmentPainters.com, ApartmentFlooring.com, and Liquid Liner — each rethinking a critical piece of the residential turnover and value-add process for property owners and operators.In our conversation, Tyler traces his journey from early curiosity in real estate and the unlocking of his entrepreneurial spirit, to building a multi-brand platform that now partners with some of the largest property managers in the country, which has earned Turnserv a place on the Inc. 5000 list of America’s fastest-growing companies, as it continues to expand its product-market fit across Ohio and beyond in this highly fragmented industry.We explore why speed and convenience matter more than ever in multifamily — and how a chance encounter in an apartment bathroom led Tyler down an unexpected path: learning chemistry, working with labs, and ultimately inventing Liquid Liner, a patented surface-restoration coating that’s 30 times thicker than traditional sprays and now used at scale to renew bathtubs, tile, cabinets, and countertops — without replacement or specialized tools.We also dig into Tyler’s evolution as a leader — from owner-operator to coach; from pure growth to purpose, culture, capital, and long-term value creation; and his deep pride in building from Northeast Ohio.Tyler brings a wonderful mix of humility, ambition, and thoughtfulness to everything he’s building, and I had a great time learning from him in this awesome conversation — so please enjoy my discussion with Tyler Dunagin.00:00 The Journey Begins: Curiosity and Rebellion05:22 From Sports to Entrepreneurship: A Life Change08:34 Curiosity in Real Estate: Finding a Path11:17 Building TurnServe: Addressing Market Needs14:19 Identifying Problems: The Birth of Liquid Liner16:55 Innovating Solutions: The Refinishing Journey20:06 Scaling Up: The Growth of TurnServe22:52 The Evolution of Products: From Painters to Liquid Liner25:39 The Chemistry of Success: Creating Liquid Liner28:50 Reflecting on Growth: The Vision for TurnServe31:23 Funding the Future: Capital and Growth Strategies34:02 Breaking Barriers: Entering the Market38:59 Navigating Growth Capital: Lessons Learned43:54 Evolving Perspectives on Success48:32 Leadership Transformation: From Selfish to Selfless51:53 Convenience as a Driving Force57:38 The Future of Multifamily: Automation and Innovation01:02:29 Community Pride: Building in Northeast Ohio-----LINKS:https://www.linkedin.com/in/tylerdunagin/https://www.turnserv.com/ApartmentFlooring.comApartmentPainters.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/
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#237: Tory & Michael Waxman (Sundays For Dogs) — Making the World’s Best Dog Food in Cleveland
Jan 2201:02:27Tap to summarizeMichael 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/
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[Bonus] Ohio VC Fest — Investing and Building with AI
Jan 1500:44:50Tap to summarizeToday’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/
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#235: Craig Newmark — Craigslist
Jan 801:02:01Tap to summarizeCraig 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/
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#234: Brad DeHays (Connect Housing Blocks) — Building the Future of Housing, Construction, and Modular’s Potential
Dec 1801:10:06Tap to summarizeBrad 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/
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#233: Chaya Slain (Virtera Partners) — Dare To Be Different, Dare To Be Great
Dec 1100:50:44Tap to summarizeChaya 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/
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#222: Ivy Zelman (Zelman & Associates) — Non-Consensus and Correct in The Housing Industry
Sep 400:54:41Tap to summarizeIvy 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/
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#221: Ryan Kelly (Substance) — Building Cleveland’s Film Industry
Aug 2800:58:40Tap to summarizeRyan 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/
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#220: Andrew Hurst (Delivered) — The Business of Moving Things
Aug 1401:09:21Tap to summarizeAndrew 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/
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#219: Dale Wollschleger (ExactCare) — From Pharmacist to Building a Billion-Dollar Pharmacy Care Company (TOF Report)
Jul 31, 202500:52:49Tap to summarizeDale 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/
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