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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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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