Episodios

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

    #239: Akram Boutros (Nexus Bedside) — The Future of Healthcare and Nursing
    Feb 5 2026
    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 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/5f0c1e28faConnect 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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    55 m
  • #238 Tyler Dunagin (TurnServ) — Curiosity, Leadership, and Entrepreneurship in Multifamily

    #238 Tyler Dunagin (TurnServ) — Curiosity, Leadership, and Entrepreneurship in Multifamily
    Jan 29 2026
    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 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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    1 h y 10 m
  • #237: Tory & Michael Waxman (Sundays For Dogs) — Making the World’s Best Dog Food in Cleveland

    #237: Tory & Michael Waxman (Sundays For Dogs) — Making the World’s Best Dog Food in Cleveland
    Jan 22 2026
    Michael and Tory Waxman — the founders of Sundays for Dogs, the Cleveland-based company designed to make dog parents’ lives easy.What began with their own dog, Mabel, and a simple but powerful question — why does feeding dogs well have to be so difficult? — has grown into one of the most exciting consumer companies to emerge from Ohio. Led by loving dog parents Dr. Tory Waxman, a veterinarian, and Michael Waxman, a serial entrepreneur, Sundays pioneered human-grade, air-dried, zero-synthetics dog food designed to be healthier than kibble and easier than refrigerated alternatives.Since our last recorded conversation in 2023 (Lay of The Land Episode #123), Sundays has scaled dramatically. Having raised more than $55 million in capital and built out a Cleveland-based R&D Test Kitchen — where our conversation today took place — Sundays has grown from a direct-to-consumer upstart into a nationally recognized brand preparing for omni-channel distribution, creating a product that dogs love while positioning themselves at the forefront of the booming pet food market and the emerging ambient fresh movement.In our conversation, Michael and Tory share how they’ve navigated multiple chapters of scaling — including customer acquisition and brand evolution, balancing supply and demand, investing deeply in product innovation, and building a senior leadership team — while staying grounded in the mission that inspired Sundays from the start: making it easier to be an awesome dog parent. They also discuss what excites them most about the future and what comes next for Sundays as the company continues to grow.00:00:00 - "The World's Best Dog Food is Made in Cleveland"00:00:25 - Introduction: Sundays for Dogs00:05:20 - Building an In-House R&D Test Kitchen in Cleveland00:10:06 - Most Dogs Still Eat Kibble (And Why That's Changing)00:15:09 - Marketing Evolution: How Does Sundays for Dogs Stand Out?00:20:18 - New Recipe Launch Preview (From the Test Kitchen!)00:21:33 - Ohio: The Surprising Dog Food Capital of America00:25:36 - Supply Chain Stories & Lessons Learned00:30:39 - When Demand Outpaces Supply: A Good Problem?00:32:59 - Beyond DTC: Omnichannel Distribution Strategy00:38:21 - How AI Will Transform How People Buy Dog Food00:41:34 - Dogs as Family: Where Is Society Headed?00:46:44 - Building Company Culture at Sundays00:52:13 - The Vision: Making Sundays a Household Name00:55:18 - Where to Find Sundays for Dogs-----LINKS:https://sundaysfordogs.com/https://www.linkedin.com/in/michaelewaxmanhttps://www.linkedin.com/in/tory-waxman-87781b176/https://www.layoftheland.fm/123-tory-michael-waxman-sundays/-----SPONSOR:Roundstone InsuranceRoundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/
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    1 h y 2 m
  • [Bonus] Ohio VC Fest — Investing and Building with AI

    [Bonus] Ohio VC Fest — Investing and Building with AI
    Jan 15 2026

    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 Perspectives
    00:04:27 Understanding the AI Hype Cycle
    00:06:44 AI in Startups vs. Established Companies
    00:09:21 Defensibility and Team Dynamics in AI Investments
    00:12:25 AI's Impact on Business Operations
    00:15:15 Fundraising Strategies in the AI Landscape
    00:18:12 Evaluating AI Companies: Metrics and Expectations
    00:21:08 The Role of Education and Training in AI Adoption
    00:23:45 Future Predictions for AI in Various Industries
    00:26:27 Staying abreast AI's Evolution
    00:43:34 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/peggyr
    https://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/
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    45 m
  • #235: Craig Newmark — Craigslist

    #235: Craig Newmark — Craigslist
    Jan 8 2026
    Craig Newmark is the founder of Craigslist and someone whose work has shaped the modern internet as we know it.Long before Craigslist became one of the most enduring, important, and frequented platforms on the web, long before the internet even connected all of us, Craig was a computer science student here in Cleveland at Case Western Reserve University — tinkering with early programming languages, studying neural networks and AI, and exploring the frontier of software engineering.The rest is history — an amazing history which we’ll cover in our conversation today, how Craig became the accidental entrepreneur behind one of the most legendary companies of our time, and a driving force of the internet itself. Our conversation spans his path to Silicon Valley, the creation and stewardship of Craigslist, the moral compass that has guided his decision making along the way, his growth as an entrepreneur and leader, the implications and consequences of building one of the largest platforms of all time, and the work he’s now doing to help meliorate the internet and country through his philanthropic initiatives with veterans, journalism, cybersecurity, and lots more.This was a truly special conversation, and I’m grateful to share it with you today — please enjoy this awesome discussion with Craig Newmark, the founder of Craigslist.00:00:00 Craig Newmark on Building Craigslist and the Early Internet00:03:52 From Case Western to Craigslist: Craig Newmark’s Origin Story00:07:21 Why Craigslist Was an Accidental Startup, Not a Planned Company00:12:18 How Craigslist Helped Democratize the Internet for Everyday People00:15:28 The Birth of Craigslist: From Email List to Iconic Website00:18:31 Monetizing Craigslist Without Selling Out Users or Trust00:20:23 Turning Down Billions: Craig Newmark’s Moral Compass at Craigslist00:23:39 Why Craigslist’s Simple Design Beat Venture-Backed Competitors00:25:50 How Craigslist Survived While Startups Tried to Unbundle It00:30:22 What Craigslist Taught Craig Newmark About Human Behavior00:31:58 Balancing Crime Prevention and Civil Liberties on Craigslist00:36:00 Why Craigslist Became One of the Most Trusted Platforms Online00:41:12 The Craigslist Design Philosophy: Simple, Fast, and Human00:44:01 From Craigslist to Philanthropy: Craig Newmark’s Next Chapter00:55:58 Craig Newmark’s Advice for Founders-----LINKS:https://www.craigslist.org/https://craignewmarkphilanthropies.org/https://www.linkedin.com/in/craignewmark/https://pausetake9.org/-----SPONSOR:Roundstone InsuranceRoundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/
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    1 h y 2 m
  • #234: Brad DeHays (Connect Housing Blocks) — Building the Future of Housing, Construction, and Modular’s Potential

    #234: Brad DeHays (Connect Housing Blocks) — Building the Future of Housing, Construction, and Modular’s Potential
    Dec 18 2025

    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 Solution
    00:04:50 - Understanding the Housing Crisis
    00:09:56 - Reinventing Construction Processes
    00:15:59 - Scaling Modular Housing Production
    00:21:55 - Transforming the Construction Timeline
    00:32:46 - Vision for the Future of Housing
    00:36:43 - Scaling Modular Construction: A Game Changer
    00:42:34 - The Future of Modular Housing: Opportunities and Challenges
    00:47:17 - Design and Aesthetics in Modular Construction
    00:52:56 - Labor Challenges in the Construction Industry
    00:56:16 - Cultural Dynamics and Employee Empowerment
    01:01:05 - 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/
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    1 h y 10 m
  • #233: Chaya Slain (Virtera Partners) — Dare To Be Different, Dare To Be Great

    #233: Chaya Slain (Virtera Partners) — Dare To Be Different, Dare To Be Great
    Dec 11 2025
    Chaya Slain is the Founder, President, and Chief Investment Officer at Virtera Partners.After studying mathematics at Columbia University, she discovered her deeper interest in investing at Goldman Sachs. After several years in New York, she returned to Cleveland and joined Parkwood, the Mandel family investment office, where she spent more than a decade immersed in institutional investing. At Parkwood, she developed a disciplined, process-driven investment philosophy; built relationships with leading private equity, hedge fund, and real estate managers; and learned directly from Mort Mandel’s cultural and strategic principles.In 2020, Chaya founded Virtera Partners, a boutique investment firm designed to offer ultra-high-net-worth families the sophistication of a top-tier institutional allocator with the personal attention of a single-family office. Virtera has grown into a platform providing clients access to differentiated public and private market opportunities — supported by deep sourcing, rigorous diligence, and a willingness to do things differently when the data points that way.In our conversation, we trace Chaya’s journey from Wall Street to Cleveland; her early entrepreneurial spark running a deli during her time at Columbia University; the leap from investor to founder; and the empathy and insight that transition has given her when evaluating other entrepreneurs and investment managers. We explore behavioral discipline, portfolio construction in uncertain markets, long-term thinking, and what it means to build with integrity, excellence, and a true sense of stewardship.As someone who loves this intersection of investing and entrepreneurship, it was fun to hear Chaya’s reflections on it and learn from her experience. Please enjoy this great conversation with Chaya Slain--Disclaimer:This podcast is provided for informational and educational purposes only and should not be construed as investment advice, a recommendation, or an offer or solicitation to buy or sell any securities or investment products. The views expressed are those of the speaker as of the date of recording and may change without notice. Investing involves risk, including the potential loss of principal. Investments in private funds and alternative investments are speculative, involve a high degree of risk, are often illiquid, may lack transparency, and are intended for sophisticated investors who are able to bear the risk of loss. Such investments may not be suitable for all investors.--00:00 Chaya's Journey: From Goldman Sachs to Investing08:33 Lessons from Parkwood: Building a Network and Process12:06 The Entrepreneurial Spirit: Transitioning to Founding17:51 Investment Decision-Making: Process and Emotion21:34 Navigating Emotional Biases in Decision Making23:26 Investment Philosophy: Flexibility Over Boxes26:05 Contrarian Investments: The Case for Energy28:42 Cleveland vs. New York: The Advantage of Distance30:27 Lessons from Entrepreneurship: Empathy and Long-Term Thinking34:41 Evolving the Business: From Family Office to Fund37:24 Defining Success: Integrity and Performance38:29 Challenges of Being Different in Investing41:47 Current Market Concerns and Portfolio Construction43:46 The Importance of Alternative Investments-----LINKS:https://www.linkedin.com/in/chaya-slain/https://www.virterapartners.com/-----SPONSOR:Roundstone InsuranceRoundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/
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    51 m
  • #232: Jerry Schill (Schill Grounds Management) — Embrace the Change

    #232: Jerry Schill (Schill Grounds Management) — Embrace the Change
    Dec 4 2025

    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 Journey
    00:59 The Impact of Family and Early Influences
    01:49 The Leap into Entrepreneurship
    03:54 The Evolution of Show Landscape
    07:21 Understanding the Landscaping Industry
    13:08 Leadership Evolution and Personal Growth
    19:04 The Importance of Peer Networks
    20:58 Scaling the Business and Maintaining Culture
    24:32 The Shift to Acquisitions for Growth
    27:47 Integrating Acquired Companies Successfully
    31:38 The Role of Technology in Landscaping
    34:47 Motivation and Future Vision for SGM
    38:09 Lessons Learned from the Journey
    39:55 Curiosity and Lifelong Learning
    41:13 The Holiday Feast Initiative
    44:08 Aiming for a Billion-Dollar Company
    45:46 Advice to Younger Self
    46:56 Hidden Gems in Cleveland

    -----


    LINKS:
    https://schilllandscaping.com/about
    https://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/
    Más Menos
    53 m