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. #242 Scot Lowry (PromiseONE) — The Right to Win in Entrepreneurship Through Acquisition

    2D AGO

    #242 Scot Lowry (PromiseONE) — The Right to Win in Entrepreneurship Through Acquisition

    Scot Lowry — Managing Partner and Co-Founder of PromiseONE Companies Scot is the Managing Partner and Co-Founder of PromiseONE Companies, a Cleveland-based investment firm that helps purpose-driven entrepreneurs acquire and grow established businesses through Entrepreneurship Through Acquisition, or ETA. Prior to launching PromiseONE, Scot acquired and led Fathom, a digital marketing firm he grew more than 450% over a decade — an experience that became both the financial engine and talent incubator behind PromiseONE’s long-term portfolio strategy. Today, Scot also serves as the Richard Osborne Professor of Entrepreneurship at Case Western Reserve University, where he teaches acquisition entrepreneurship and helps steward one of the nation’s longest-standing ETA programs. In our conversation, Scot and I explore Cleveland’s unique “right to win” in ETA and the decades-long lineage that traces back to his mentor, Richard Osborne. We talk about what it truly means to become a credible buyer, how to earn the trust of legacy sellers, and why understanding what matters most to them is the foundation of great dealmaking. We unpack the evolution of PromiseONE’s patient capital model, the philosophy of “your dream is my dream,” and how Scot has helped multiple operators transition from employee to business owner. We also discuss negotiation, long-term ownership versus traditional private equity, mentorship, and a deeply personal crucible moment that reshaped Scot’s leadership philosophy and sense of purpose. Scot is a thoughtful entrepreneur, investor, and teacher, and this was a really meaningful conversation — please enjoy. 00:00 Introduction to Promise Partners and Scott Lowry03:08 Cleveland's Right to Win in Entrepreneurship05:51 The Role of Richard Osborne and Promise Partners08:57 Building Credibility as a Buyer12:07 The Evolution of Promise One Companies14:55 Understanding Legacy Sellers18:04 The Importance of Relationships in Deal Making20:55 Navigating the Acquisition Process23:48 Lessons from Fathom's Growth and Leadership27:06 The Philosophy Behind Promise One's Model37:56 Choosing the Path of Entrepreneurship40:06 Building a Community of Entrepreneurs43:13 Incubating New Business Ideas46:04 The Promise Partners Model48:46 Long-Term Vision and Patient Capital51:53 The Art of Deal Making56:03 Teaching and Mentoring Future Entrepreneurs01:00:13 Reflections on Personal Growth and Purpose ----- LINKS:https://promiseone.com/about-us/ https://case.edu/weatherhead/academics/entrepreneurship-through-acquisition https://www.linkedin.com/in/scotlowry/ ----- SPONSOR:Roundstone Insurance — https://roundstoneinsurance.com/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. Cerity PartnersCerity Partners, a full-service investment and wealth management firm serving high-net-worth individuals, entrepreneurs, and business owners, is proud to sponsor Lay of The Land. The firm has local roots in Cleveland and across Ohio, and like this podcast, Cerity Partners advisors specialize in serving the interests of local entrepreneurs and business leaders. They understand how to manage the total picture of wealth, both personal and professional. Cerity Partners has a unified team of specialists who collaborate on almost every aspect of a client’s financial life, including business ownership. The firm’s national presence means it can offer the resources and specialized knowledge of the largest institutions with the independence and service of a neighbor. The Cerity Partners Cleveland team understands the complexity that comes with wealth, and they adhere to fiduciary standards. Discover the financial lay of your land. Learn more at ceritypartners.com/NPR or call 216-464-6266. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here: https://layoftheland.ck.page/5f0c1e28fa 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 14m
  2. #241 Chad Delligatti (InnoSource) — Staffing, AI, and the Future of Talent

    FEB 27

    #241 Chad Delligatti (InnoSource) — Staffing, AI, and the Future of Talent

    Chad Delligatti — CEO of InnoSource Chad Delligatti is the CEO of InnoSource — a more than two-decade-old, Ohio-based company that has grown into a national workforce solutions platform serving Fortune 500 and midsized organizations across the country. Since joining InnoSource in 2000 as one of its earliest employees, Chad has devoted his entire professional career to building the company — helping it evolve from a regional staffing firm into the leading HR, talent, outsourcing, and data solutions partner it is today, employing more than 2,000 associates across North America, partnering with clients to deliver highly customized recruiting and workforce management solutions. But this isn’t just a story about staffing…From sweeping neighbors’ floors in Bexley as a child, to running a lawn care business in Granville, to flipping Beanie Babies in college, Chad’s entrepreneurial drive showed up early. And when faced with the choice between joining a large corporation or becoming one of the first employees at a small, fledgling company called InnoSource, he chose the entrepreneurial path — a decision that shaped the next 25 years of his life. In our conversation, Chad reflects on what it means to dedicate decades to building one company — the evolution of the staffing and outsourcing industry from newspaper classifieds to job boards to AI-driven recruiting — and how InnoSource is now entering a new chapter powered by technology. We unpack how the implementation of AI is reshaping hiring funnels, reducing time-to-offer, improving tenure, and fundamentally transforming how workforce solutions are delivered. We also explore what hasn’t changed: the company’s cultural anchors, leadership principles, and Chad’s conviction that technology must enhance — not replace — the human touch. This conversation was a lot of fun — chad exudes passion for his work and it comes through in spades. Please So please enjoy this awesome discussion with Chad Delligatti. 00:00 The Journey of InnoSource: A Personal Story15:07 InnoSource Today: Services and Innovations19:26 Evolution of the Staffing Industry: Adapting to Change26:47 AI in Recruitment: Transforming the Landscape31:20 The Human Touch: Balancing AI and Personal Connection33:13 Embracing Change in Recruitment37:22 Leadership Lessons from Experience46:59 Core Values and Company Culture55:24 Defining Success and Motivation01:01:21 Upskilling for Future Opportunities01:05:10 Outro ----- LINKS:https://innosource.com/ https://www.linkedin.com/in/chad-delligatti-621bba2/ ----- 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. Cerity PartnersCerity Partners, a full-service investment and wealth management firm serving high-net-worth individuals, entrepreneurs, and business owners, is proud to sponsor Lay of The Land. The firm has local roots in Cleveland and across Ohio, and like this podcast, Cerity Partners advisors specialize in serving the interests of local entrepreneurs and business leaders. They understand how to manage the total picture of wealth, both personal and professional. Cerity Partners has a unified team of specialists who collaborate on almost every aspect of a client’s financial life, including business ownership. The firm’s national presence means it can offer the resources and specialized knowledge of the largest institutions with the independence and service of a neighbor. The Cerity Partners Cleveland team understands the complexity that comes with wealth, and they adhere to fiduciary standards. Discover the financial lay of your land. Learn more at ceritypartners.com/NPR or call 216-464-6266. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here: https://layoftheland.ck.page/5f0c1e28fa 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 6m
  3. #240 Matt Kalina (TandemStride) — The Business of Trauma Recovery

    FEB 12

    #240 Matt Kalina (TandemStride) — The Business of Trauma Recovery

    Matt Kalina — Founder and CEO of TandemStride Matt Kalina is the Founder and CEO of TandemStride, a healthcare marketplace that connects trauma survivors with peers, care partners, and providers to support long-term recovery. Inspired by his family’s firsthand experience with traumatic injury, Matt is dedicated to building solutions that close the gap between emergency care and ongoing support. With his leadership, TandemStride is advancing a more connected and compassionate model of recovery. In our conversation, Matt and I explore the often-overlooked realities of life after traumatic injury, why peer support is such a powerful layer of care, how his family adapted to his brother’s traumatic loss of his both his legs in 2012 and have come together through TandemStride to  building the support platform they wish had existed by meeting people in moments of real crisis, not months later. We also talk about Matt’s evolution as a leadership, his Ohio go-to-market strategy, the power of incentives, the business of trauma, working with his family in the company, empathy, and coming into your life’s work.  Matt is an inspiring entrepreneur and this was a really special conversation – please enjoy. 00:00 Introduction to Tandem Stride02:46 Introduction and Personal Connection04:42 The Journey to Tandem Stride07:15 Identifying Gaps in Injury Care09:47 Understanding Patient Needs12:21 Building the Tandem Stride Platform15:13 Engagement and Outreach Strategies17:57 Navigating Healthcare Partnerships20:30 The Business Model and Future Vision33:39 Engaging in Healthcare Innovation34:42 Defining the Vision for TandemStride37:37 Creating a New Category in Injury Care40:09 Changing Incentives in Healthcare44:07 Long-Term Policy Initiatives45:05 Personal Growth as a Leader48:59 Family Dynamics in Business51:46 Exciting Developments Ahead54:53 Embracing Uncertainty in Entrepreneurship59:21 Outro ----- LINKS:https://www.linkedin.com/in/kalinamatt/https://www.tandemstride.com/https://www.amazon.com/Cut-Through-Shortcut-That-Everything/dp/0960083766 ----- 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. Cerity PartnersCerity Partners, a full-service investment and wealth management firm serving high-net-worth individuals, entrepreneurs, and business owners, is proud to sponsor Lay of The Land. The firm has local roots in Cleveland and across Ohio, and like this podcast, Cerity Partners advisors specialize in serving the interests of local entrepreneurs and business leaders. They understand how to manage the total picture of wealth, both personal and professional. Cerity Partners has a unified team of specialists who collaborate on almost every aspect of a client’s financial life, including business ownership. The firm’s national presence means it can offer the resources and specialized knowledge of the largest institutions with the independence and service of a neighbor. The Cerity Partners Cleveland team understands the complexity that comes with wealth, and they adhere to fiduciary standards. Discover the financial lay of your land. Learn more at ceritypartners.com/NPR or call 216-464-6266. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here: https://layoftheland.ck.page/5f0c1e28fa 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
  4. #239: Akram Boutros (Nexus Bedside) — The Future of Healthcare and Nursing

    FEB 5

    #239: Akram Boutros (Nexus Bedside) — The Future of Healthcare and Nursing

    Akram Boutros — Founder and CEO of Nexus Bedside. Akram brings more than 30 years of experience as a healthcare leader, executive, and clinician. He previously served as CEO of The MetroHealth System in Cleveland from 2013 to 2022, where he led a team of more than 6,000 employees and 3,500 medical staff, overseeing a nearly billion-dollar revenue operation and the complete transformation of the MetroHealth campus and care model. Prior to that, Akram held senior leadership roles at multiple health systems across the country, and he began his career as a physician, earning his Doctor of Medicine from SUNY Downstate Health Sciences. Akram is also a serial entrepreneur. In 2025, he raised a few million dollars of seed capital to found Nexus Bedside—a company reimagining inpatient nursing staffing and working to fundamentally improve outcomes for patients, nurses, and health systems overall. In this conversation, Akram and I unpack his full journey and perspective on healthcare and entrepreneurship—from immigrating to the U.S. and becoming a physician, to his decade leading MetroHealth, to navigating a public and controversial departure from the public health system, and ultimately experiencing the healthcare system as a patient himself. We explore how these experiences shaped his decision to start and build Nexus Bedside, his philosophy on leadership, lessons learned as an entrepreneur, the massive opportunity for AI in healthcare, and what he believes the future of inpatient care and nursing should be. Please enjoy this awesome conversation with Akram. 00:00:00 - Introduction00:03:40 - The Journey of Akram Boutros, MD00:08:45 - Formative Experiences and Lessons Learned00:13:57 - The Complexity of Running a Health System00:19:08 - Defining the Ideal Health System00:25:42 - The Birth of Nexus Bedside: A New Approach to Nursing00:30:54 - Optimizing Patient Care Through Technology00:35:40 - Business Model and Client Success00:42:10 - Entrepreneurial Lessons in Healthcare00:46:44 - Building Nexus in Cleveland00:52:12 - Reflections on the Journey ----- LINKS:https://www.linkedin.com/in/akramboutrosmd/ https://nexus-rn.com/ ----- SPONSORS: 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. Cerity PartnersCerity Partners, a full-service investment and wealth management firm serving high-net-worth individuals, entrepreneurs, and business owners, is proud to sponsor Lay of The Land. The firm has local roots in Cleveland and across Ohio, and like this podcast, Cerity Partners advisors specialize in serving the interests of local entrepreneurs and business leaders. They understand how to manage the total picture of wealth, both personal and professional. Cerity Partners has a unified team of specialists who collaborate on almost every aspect of a client’s financial life, including business ownership. The firm’s national presence means it can offer the resources and specialized knowledge of the largest institutions with the independence and service of a neighbor. The Cerity Partners Cleveland team understands the complexity that comes with wealth, and they adhere to fiduciary standards. Discover the financial lay of your land. Learn more at ceritypartners.com/NPR or call 216-464-6266. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here: https://layoftheland.ck.page/5f0c1e28fa 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
  5. #238 Tyler Dunagin (TurnServ) — Curiosity, Leadership, and Entrepreneurship in Multifamily

    JAN 29

    #238 Tyler Dunagin (TurnServ) — Curiosity, Leadership, and Entrepreneurship in Multifamily

    Tyler 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 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
  6. #237: Tory & Michael Waxman (Sundays For Dogs) — Making the World’s Best Dog Food in Cleveland

    JAN 22

    #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
  7. [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
  8. #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
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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
    249
  • Rating
    Clean
  • Copyright
    © 2024 Lay of The Land
  • Show Website
    Lay of The Land

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