What happens when an entrepreneur stops chasing every opportunity and commits fully to one clear path? In a recent appearance on The Turn, Landscape Collective Founder and CEO Jerry Schill shared the honest story of how focus, discipline, and long-term thinking helped transform a local landscaping company into one of the industry’s leading growth platforms.
Jerry reflects on spending nearly 20 years building a business with his brother, pursuing a mix of design-build, residential, and creative work. Like many growing companies, success came with complexity. Eventually, the business split, and Jerry took over the maintenance side of the company, rolling revenue back to approximately $3 million. He openly shares that the moment was uncertain and intimidating, but it also became the turning point that changed everything.
Instead of rebuilding the same way, Jerry made a bold decision to simplify and specialise. He exited residential work, focused on recurring commercial maintenance revenue, and built what he describes as a “business in a box” model designed to scale. Between 2012 and 2019, the company grew from 0% recurring revenue to 93%, laying the operational foundation for the next phase of expansion.
That discipline eventually led to strategic partnerships, accelerated growth, and the creation of today’s Landscape Collective network. What began as a reset became a platform spanning dozens of locations, more than 1,600 team members, multiple states, and nearly $200 million in revenue.
Throughout the conversation, Jerry also speaks candidly about leadership lessons that resonate far beyond landscaping: overcoming imposter syndrome, learning to surround yourself with smarter people, understanding the difference between an expense and an investment, and building every business as if it could one day be sold.
Topics Covered
- Starting a company with family and navigating a business split
- Rebuilding from $3 million with a sharper strategy
- Growing recurring revenue from 0% to 93%
- Why he eliminated the residential division
- Creating a scalable operating model
- Joining Vistage and learning from other leaders
- Why traditional financing said no, and what came next
- Partnering with private equity for growth
- Scaling from 4 locations to 37
- Leading through rapid expansion
- Why every business should be built to sell
Why This Story Matters
Jerry’s story is a reminder that growth is not always about doing more. Sometimes it comes from doing fewer things exceptionally well. Focus, discipline, and the courage to change direction can create extraordinary outcomes.
Watch the Full Episode
Watch Jerry Schill’s full appearance on The Turn here: Watch the Episode
