Bryan Stolz, CEO of Winterberry (Southington, CT), shares his journey from being a junior garden designer to running the company. Winterberry is a diversified company that offers maintenance, fertilization, irrigation services, landscape design, and golf course irrigation installation. They have grown from a $10 million company when they were first my client, to a $33.5 million company with 240 employees. The ownership team consists of three partners who have different skill sets and work well together. Winterberry made the decision to close their retail garden center due to competition from big box stores and a shift in their target market. They have focused on systematizing their processes while still allowing room for entrepreneurialism. The company has experienced significant growth, with departments like seasonal color becoming independent and generating $1.2 million in revenue. The conversation explores the organizational structure and culture of the company, focusing on the matrix org chart, dotted line relationships, and the balance between creativity and accountability. We also discuss the importance of crafting roles to fit people’s strengths, the challenges of communication and involving employees in the decision-making process, and the mistakes and struggles faced by the company. The future plans include regional expansion, acquisitions, and continuous personal and professional development. Takeaways * Opportunities and leaps of faith are important for growth * Systematizing processes can help manage chaos and allow for scalability * Closing a retail division can be a strategic decision to focus on core services * Entrepreneurial spirit can be nurtured within a structured framework * Departmental growth can be driven by individual initiative The matrix org chart and dotted line relationships can create a loose framework culture that allows for creativity but can be inefficient and less effective at holding people accountable. * Crafting roles to fit people’s strengths and interests can lead to greater job satisfaction and upward mobility within the company. * Effective communication and involvement of employees in decision-making processes are crucial for maintaining trust and alignment within the organization. * Learning from mistakes and being open to change are essential for growth and success. * Regional expansion and strategic acquisitions are part of the company’s future plans. * Continuous personal and professional development, including seeking external knowledge and learning skills for the next level, is important for career advancement.