Episodi

  • [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/
    Mostra di più Mostra meno
    45 min
  • #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/
    Mostra di più Mostra meno
    1 ora e 2 min
  • #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/
    Mostra di più Mostra meno
    1 ora e 10 min
  • #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 Slain00:00 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/
    Mostra di più Mostra meno
    51 min
  • #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/
    Mostra di più Mostra meno
    53 min
  • #231: Perry Stancato (Signature Sauces) — The Secret Sauce of Sauces

    #231: Perry Stancato (Signature Sauces) — The Secret Sauce of Sauces
    Nov 20 2025
    Perry Stancato is the founder and CEO of Signature Sauces and a third-generation operator of the beloved Cleveland institution, Stancato’s Italian Restaurant.This conversation with Perry explores the entrepreneurial journey of someone who grew up in the family restaurant — from standing on a milk crate as a kid making waffles for Sunday brunch to running Stancato’s today while simultaneously building Signature Sauces into a premier national food manufacturing partner.Signature Sauces began in 2005 with a simple idea: to bottle his family’s legendary red sauce after customers kept asking for it. What started as a way to serve Stancato’s loyal patrons quickly evolved into something much larger. Perry discovered that while retail was cutthroat and unforgiving, his passion and true product-market fit lay in foodservice — helping other restaurants scale their “secret sauces.” Today, Signature Sauces has grown into a company that helps make the products that make others famous, serving clients from local Ohio favorites to national brands like Bob Evans, Momofuku, Benihana, Barrio, and many more.Alongside that manufacturing growth, Perry continues to steward Stancato’s — the restaurant that has been a Cleveland staple for decades. He reflects on the delicate balance of honoring a community legacy while making small, thoughtful changes to stay relevant across generations.In our conversation, Perry shares the challenges of taking nearly ten years to get Signature Sauces off the ground, the resilience it took to keep going, the lessons learned from retail versus foodservice, and what he’s most proud of: seeing team members who started as dishwashers grow into leaders, and knowing his work helps thousands of diners enjoy meals every day. We also dive into his Ohio pride, from the region’s food scene to partnerships like the Ohio State Buckeye Tailgate sauces, and his perspective on what it takes to build a legacy business in Cleveland.00:00:00 - The Legacy of Stancatos: A Family Business Journey00:09:03 - From Family Recipes to Signature Sauces00:12:49 - Navigating the Food Industry: Retail vs. Food Service00:17:15 - Scaling Up: The Art and Science of Sauce Production00:20:39 - The Future of Signature Sauces: Expanding Partnerships00:21:55 - The Entrepreneurial Journey Begins00:23:33 - Vision and Growth of Signature Sauces00:26:10 - Lessons from the Restaurant Industry00:29:10 - Balancing Time and Responsibilities00:31:40 - Building a Legacy in Ohio00:34:30 - Innovation and Technology in Food Production00:37:08 - Trends in the Culinary World00:39:44 - Understanding Risk and Success00:42:22 - Navigating Customer Relationships00:45:20 - Insights for Aspiring Food Entrepreneurs00:45:35 - Reflections on the Journey-----LINKS:https://www.signaturesauces.com/https://www.stancatos.com/https://www.linkedin.com/in/perry-stancato-799b16b/-----SPONSOR:Roundstone InsuranceRoundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/
    Mostra di più Mostra meno
    55 min
  • #230: Kaitie & Kyle Nickel (Cleveland Vibes) — All Things Positive in Cleveland

    #230: Kaitie & Kyle Nickel (Cleveland Vibes) — All Things Positive in Cleveland
    Nov 13 2025
    Kaitie and Kyle Nickel are entrepreneurs, storytellers, and community builders based in Cleveland. They have grown beloved brands such as Cleveland Vibes, The Cleveland Market, and Cleve or Leave to reach hundreds of thousands of followers and many millions of people. Their work is driven by a shared goal: to connect people, celebrate local culture, and inspire growth. Passionate about empowering small businesses and shaping Cleveland’s cultural identity, Kaitie and Kyle have built a family business that blends storytelling, innovation, and community into something uniquely impactful.In our conversation, we discuss the origins of Cleveland Vibes and how it became a platform for positive storytelling. We explore how the couple is reframing Cleveland’s narrative and brand for a new generation, and how their work has evolved from social media into events, agency projects, and viral cultural moments. We also talk about what it means to build a family business and define success through community impact.Kaitie and Kyle are doing incredible work telling Cleveland’s story, and I’m excited to share our conversation with you today.00:00:00 - Introduction and Setting the Stage00:02:53 - Discovering Cleveland: A New Perspective00:05:36 - Kaitie’s Journey: From Nursing to Creative Storytelling00:08:00 - The Storytelling Challenge: Changing Perceptions of Cleveland00:12:20 - The Birth of Cleveland Vibes: A Community Movement00:17:04 - Cleveland Vibes Today: More Than Just Social Media00:18:18 - Building an Audience: The Power of Community00:23:43 - Entrepreneurial Lessons: Building Together00:27:10 - Cleve or Leave: A New Brand Emerges00:29:52 - Creative Process: Froggy’s Journey to Fame00:33:52 - Preparing for Viral Moments00:37:59 - The Creative Playground00:39:43 - Defining Success and Vision00:44:42 - Changing Perceptions of Cleveland00:49:02 - The Brand of Cleveland00:51:37 - Hidden Gems-----LINKS:https://clevelandvibes.com/https://www.facebook.com/clevelandvibes/-----SPONSOR:Roundstone InsuranceRoundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/
    Mostra di più Mostra meno
    1 ora e 1 min
  • #229: Keith Gerchak & Marisa Guterman (Lost & Found In Cleveland) — The Making of a New American Fable on Hope & the Post-Industrial American Dream in the Industrial Midwest (REWIND)

    #229: Keith Gerchak & Marisa Guterman (Lost & Found In Cleveland) — The Making of a New American Fable on Hope & the Post-Industrial American Dream in the Industrial Midwest (REWIND)
    Oct 30 2025
    Nearly a year and a half after our conversation first aired in 2024, Lost & Found in Cleveland is ready to make its way to theaters nationwide on November 7, 2025.When I first sat down with Keith Gerchak and Marisa Guterman, the creative forces behind the film, we explored the decade-long journey that brought this story to life—from writing and directing this cinematic love letter to Cleveland, to raising capital, recruiting a star-studded cast featuring Martin Sheen, Dennis Haysbert, June Squibb, Stacy Keach, and many others, and filming across Cleveland’s iconic landscapes.With the film’s theatrical debut now just around the corner, this feels like the perfect moment to revisit their remarkable story.So, with that exciting update, please enjoy this encore conversation from the Lay of The Land archives with Keith Gerchak and Marisa Guterman, the filmmakers behind Lost & Found in Cleveland, airing in theaters across Cleveland starting November 7, 2025.Tickets are now on sale at https://tickets.lostandfoundincleveland.com/! More theaters are being added daily. 00:00:00 - The American Dream in Cleveland 00:05:56 - The Journey of Filmmaking 00:19:10 - Character Development and Storytelling 00:32:39 - Challenges and Triumphs in Production 00:42:44 - The Journey of Filmmaking: Vision and Execution 00:44:44 - Challenges of Fundraising in Cleveland 00:46:31 - The Economic Impact of Local Filmmaking 00:49:15 - Building a Sustainable Film Industry in Cleveland 00:51:33 - Changing the Narrative: Cleveland's Film Identity 00:54:53 - Casting Challenges and Triumphs 01:01:38 - Overcoming On-Set Challenges 01:09:21 - The Message of Hope in Film-----LINKS:Lost & Found in Cleveland IMDB: https://www.imdb.com/title/tt4601732/Connect with Keith Gerchak: https://www.linkedin.com/in/keithgerchak/Connect with Marisa Guterman: https://www.linkedin.com/in/marisa-guterman-187677a9/Double G Films: https://www.doublegfilms.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.Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/
    Mostra di più Mostra meno
    1 ora e 17 min