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/

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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/

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.

-----

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/