The Deal Factory
Most entrepreneurs dream about building a business that lasts. Few ever build one capable of attracting multiple private equity partners, completing more than 20 acquisitions, and creating life-changing wealth for employees. In this episode of The Deal Factory, Jeff Harkness sits down with Jerry Shill, Founder & CEO of Schill Landscape Collective, to unpack the 35-year journey from a local landscaping company to one of North America's fastest-growing commercial landscape platforms. Jerry shares the pivotal decisions that changed everything—from splitting the family business and focusing exclusively on recurring maintenance revenue to designing a scalable "business in a box" operating model that ultimately attracted institutional capital. The conversation dives deep into acquisitions, integration, leadership development, value creation, data-driven operations, and what it really takes to build a billion-dollar vision. Whether you're considering private equity, actively acquiring businesses, or simply trying to scale your company, this episode delivers a masterclass from someone who's lived every stage of the journey. Key Discussion Points * Building a maintenance-first business model that scales * Why recurring revenue beats chasing construction projects * Designing a "Business in a Box" operating system * Preparing a company for institutional capital * Lessons from partnering with Argon Capital and TruArc Partners * Scaling from $2M to nearly $31M EBITDA * What Jerry learned completing 21 acquisitions * Why integration—not the deal—is the real challenge * Centralized vs. decentralized leadership models * Data, KPIs and forecasting at scale * Creating wealth through management equity * AI, robotics and the future of commercial landscaping * Why customer issue resolution is a competitive advantage * Building businesses that are designed to sell
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