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Lay of The Land

Lay of The Land

Di: Jeffrey Stern
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A proposito di questo titolo

 Telling the stories of entrepreneurship and builders in Cleveland and throughout Northeast Ohio. Every Thursday, Jeffrey Stern helps map the Cleveland/NEO business ecosystem by talking to founders, investors, and community builders to learn what makes Cleveland/NEO special.© 2024 Lay of The Land Economia Gestione e leadership Leadership
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/
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    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/
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    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/
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    1 ora e 10 min
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