Lay of The Land

Jeffrey Stern
  • 5.0 (36)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. #237: Tory & Michael Waxman (Sundays For Dogs) — Making the World’s Best Dog Food in Cleveland

    4D AGO

    #237: Tory & Michael Waxman (Sundays For Dogs) — Making the World’s Best Dog Food in Cleveland

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

    1h 2m
  2. [Bonus] Ohio VC Fest — Investing and Building with AI

    JAN 15

    [Bonus] Ohio VC Fest — Investing and Building with AI

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

    45 min
  3. #235: Craig Newmark — Craigslist

    JAN 8

    #235: Craig Newmark — Craigslist

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

    1h 2m
  4. #234: Brad DeHays (Connect Housing Blocks) — Building the Future of Housing, Construction, and Modular’s Potential

    12/18/2025

    #234: Brad DeHays (Connect Housing Blocks) — Building the Future of Housing, Construction, and Modular’s Potential

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

    1h 10m
  5. #233: Chaya Slain (Virtera Partners) — Dare To Be Different, Dare To Be Great

    12/11/2025

    #233: Chaya Slain (Virtera Partners) — Dare To Be Different, Dare To Be Great

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

    51 min
  6. #232: Jerry Schill (Schill Grounds Management) — Embrace the Change

    12/04/2025

    #232: Jerry Schill (Schill Grounds Management) — Embrace the Change

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

    53 min
  7. #231: Perry Stancato (Signature Sauces) — The Secret Sauce of Sauces

    11/20/2025

    #231: Perry Stancato (Signature Sauces) — The Secret Sauce of Sauces

    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 Insurance Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership. Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings. Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs. Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here. Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs. Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/ Follow Lay of The Land on X @podlayoftheland https://www.jeffreys.page/

    55 min
  8. #230: Kaitie & Kyle Nickel (Cleveland Vibes) — All Things Positive in Cleveland

    11/13/2025

    #230: Kaitie & Kyle Nickel (Cleveland Vibes) — All Things Positive in Cleveland

    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 Insurance Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership. Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings. Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs. Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here. Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs. Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/ Follow Lay of The Land on X @podlayoftheland https://www.jeffreys.page/

    1h 1m
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5
out of 5
36 Ratings

About

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.

Information

  • Creator
    Jeffrey Stern
  • Years Active
    2020 - 2026
  • Episodes
    244
  • Rating
    Clean
  • Copyright
    © 2024 Lay of The Land
  • Show Website
    Lay of The Land

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