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 Stride
02:46 Introduction and Personal Connection
04:42 The Journey to Tandem Stride
07:15 Identifying Gaps in Injury Care
09:47 Understanding Patient Needs
12:21 Building the Tandem Stride Platform
15:13 Engagement and Outreach Strategies
17:57 Navigating Healthcare Partnerships
20:30 The Business Model and Future Vision
33:39 Engaging in Healthcare Innovation
34:42 Defining the Vision for TandemStride
37:37 Creating a New Category in Injury Care
40:09 Changing Incentives in Healthcare
44:07 Long-Term Policy Initiatives
45:05 Personal Growth as a Leader
48:59 Family Dynamics in Business
51:46 Exciting Developments Ahead
54:53 Embracing Uncertainty in Entrepreneurship
59:21 Outro

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LINKS:
https://www.linkedin.com/in/kalinamatt/
https://www.tandemstride.com/
https://www.amazon.com/Cut-Through-Shortcut-That-Everything/dp/0960083766

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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.

Cerity Partners
Cerity 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/

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 - Introduction
00:03:40 - The Journey of Akram Boutros, MD
00:08:45 - Formative Experiences and Lessons Learned
00:13:57 - The Complexity of Running a Health System
00:19:08 - Defining the Ideal Health System
00:25:42 - The Birth of Nexus Bedside: A New Approach to Nursing
00:30:54 - Optimizing Patient Care Through Technology
00:35:40 - Business Model and Client Success
00:42:10 - Entrepreneurial Lessons in Healthcare
00:46:44 - Building Nexus in Cleveland
00:52:12 - Reflections on the Journey

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LINKS:
https://www.linkedin.com/in/akramboutrosmd/

https://nexus-rn.com/

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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 Partners
Cerity 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/

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 Rebellion
05:22 From Sports to Entrepreneurship: A Life Change
08:34 Curiosity in Real Estate: Finding a Path
11:17 Building TurnServe: Addressing Market Needs
14:19 Identifying Problems: The Birth of Liquid Liner
16:55 Innovating Solutions: The Refinishing Journey
20:06 Scaling Up: The Growth of TurnServe
22:52 The Evolution of Products: From Painters to Liquid Liner
25:39 The Chemistry of Success: Creating Liquid Liner
28:50 Reflecting on Growth: The Vision for TurnServe
31:23 Funding the Future: Capital and Growth Strategies
34:02 Breaking Barriers: Entering the Market
38:59 Navigating Growth Capital: Lessons Learned
43:54 Evolving Perspectives on Success
48:32 Leadership Transformation: From Selfish to Selfless
51:53 Convenience as a Driving Force
57:38 The Future of Multifamily: Automation and Innovation
01:02:29 Community Pride: Building in Northeast Ohio

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LINKS:
https://www.linkedin.com/in/tylerdunagin/
https://www.turnserv.com/
ApartmentFlooring.com
ApartmentPainters.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/

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 Dogs
00:05:20 - Building an In-House R&D Test Kitchen in Cleveland
00:10:06 - 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 America
00:25:36 - Supply Chain Stories & Lessons Learned
00:30:39 - When Demand Outpaces Supply: A Good Problem?
00:32:59 - Beyond DTC: Omnichannel Distribution Strategy
00:38:21 - How AI Will Transform How People Buy Dog Food
00:41:34 - Dogs as Family: Where Is Society Headed?
00:46:44 - Building Company Culture at Sundays
00:52:13 - The Vision: Making Sundays a Household Name
00:55:18 - Where to Find Sundays for Dogs

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LINKS:
https://sundaysfordogs.com/
https://www.linkedin.com/in/michaelewaxman
https://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/

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

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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/

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 Internet
00:03:52 From Case Western to Craigslist: Craig Newmark’s Origin Story
00:07:21 Why Craigslist Was an Accidental Startup, Not a Planned Company
00:12:18 How Craigslist Helped Democratize the Internet for Everyday People
00:15:28 The Birth of Craigslist: From Email List to Iconic Website
00:18:31 Monetizing Craigslist Without Selling Out Users or Trust
00:20:23 Turning Down Billions: Craig Newmark’s Moral Compass at Craigslist
00:23:39 Why Craigslist’s Simple Design Beat Venture-Backed Competitors
00:25:50 How Craigslist Survived While Startups Tried to Unbundle It
00:30:22 What Craigslist Taught Craig Newmark About Human Behavior
00:31:58 Balancing Crime Prevention and Civil Liberties on Craigslist
00:36:00 Why Craigslist Became One of the Most Trusted Platforms Online
00:41:12 The Craigslist Design Philosophy: Simple, Fast, and Human
00:44:01 From Craigslist to Philanthropy: Craig Newmark’s Next Chapter
00:55:58 Craig Newmark’s Advice for Founders

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LINKS:
https://www.craigslist.org/
https://craignewmarkphilanthropies.org/
https://www.linkedin.com/in/craignewmark/
https://pausetake9.org/

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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/

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

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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/

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 Investing
08:33 Lessons from Parkwood: Building a Network and Process
12:06 The Entrepreneurial Spirit: Transitioning to Founding
17:51 Investment Decision-Making: Process and Emotion
21:34 Navigating Emotional Biases in Decision Making
23:26 Investment Philosophy: Flexibility Over Boxes
26:05 Contrarian Investments: The Case for Energy
28:42 Cleveland vs. New York: The Advantage of Distance
30:27 Lessons from Entrepreneurship: Empathy and Long-Term Thinking
34:41 Evolving the Business: From Family Office to Fund
37:24 Defining Success: Integrity and Performance
38:29 Challenges of Being Different in Investing
41:47 Current Market Concerns and Portfolio Construction
43:46 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/

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

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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/

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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.

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Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/

Follow Lay of The Land on X @podlayoftheland

https://www.jeffreys.page/

Perry Stancato is the founder and CEO of Signature Sauces and a third-generation operator of the beloved Cleveland institution, Stancato’s Italian Restaurant.

This conversation with Perry explores the entrepreneurial journey of someone who grew up in the family restaurant — from standing on a milk crate as a kid making waffles for Sunday brunch to running Stancato’s today while simultaneously building Signature Sauces into a premier national food manufacturing partner.

Signature Sauces began in 2005 with a simple idea: to bottle his family’s legendary red sauce after customers kept asking for it. What started as a way to serve Stancato’s loyal patrons quickly evolved into something much larger. Perry discovered that while retail was cutthroat and unforgiving, his passion and true product-market fit lay in foodservice — helping other restaurants scale their “secret sauces.” Today, Signature Sauces has grown into a company that helps make the products that make others famous, serving clients from local Ohio favorites to national brands like Bob Evans, Momofuku, Benihana, Barrio, and many more.

Alongside that manufacturing growth, Perry continues to steward Stancato’s — the restaurant that has been a Cleveland staple for decades. He reflects on the delicate balance of honoring a community legacy while making small, thoughtful changes to stay relevant across generations.

In our conversation, Perry shares the challenges of taking nearly ten years to get Signature Sauces off the ground, the resilience it took to keep going, the lessons learned from retail versus foodservice, and what he’s most proud of: seeing team members who started as dishwashers grow into leaders, and knowing his work helps thousands of diners enjoy meals every day. We also dive into his Ohio pride, from the region’s food scene to partnerships like the Ohio State Buckeye Tailgate sauces, and his perspective on what it takes to build a legacy business in Cleveland.

00:00:00 - The Legacy of Stancatos: A Family Business Journey
00:09:03 - From Family Recipes to Signature Sauces
00:12:49 - Navigating the Food Industry: Retail vs. Food Service
00:17:15 - Scaling Up: The Art and Science of Sauce Production
00:20:39 - The Future of Signature Sauces: Expanding Partnerships
00:21:55 - The Entrepreneurial Journey Begins
00:23:33 - Vision and Growth of Signature Sauces
00:26:10 - Lessons from the Restaurant Industry
00:29:10 - Balancing Time and Responsibilities
00:31:40 - Building a Legacy in Ohio
00:34:30 - Innovation and Technology in Food Production
00:37:08 - Trends in the Culinary World
00:39:44 - Understanding Risk and Success
00:42:22 - Navigating Customer Relationships
00:45:20 - Insights for Aspiring Food Entrepreneurs
00:45:35 - Reflections on the Journey

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LINKS:
https://www.signaturesauces.com/
https://www.stancatos.com/
https://www.linkedin.com/in/perry-stancato-799b16b/

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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.

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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/