In this episode, Jason and Makenzie walk listeners through the step-by-step process of an ESOP transaction, breaking down what can often feel like a complex and overwhelming journey into a clear, approachable roadmap. They cover common questions business owners often ask at the start of the process, including: How do I know if my company is a good fit for an ESOP? and who should be involved? From evaluating readiness to understanding the key players involved, Jason and Makenzie share practical insights on who to engage first, what steps to expect, and how to navigate the early stages of exploring employee ownership with confidence.

In this episode, Jason and Makenzie explore what is often one of the most challenging roles in an ESOP transition: frontline management. Immediately after a transition to employee ownership, frontline managers often take on the greatest level of responsibility as they help employees navigate change while keeping the business moving forward. Jason and Makenzie unpack six key threads that can help frontline managers better support their teams and guide the company through a successful transition.

In this episode of the Foundations of Transition Series, Jason and Makenzie focus on the theme of Strategic Direction, asking the critical question: What direction are we moving in, and how are we getting there? Each workshop-style conversation in this series is designed to help business owners think more intentionally about the future of their company and the role they play in shaping it.

This episode challenges owners to step back and “look up” from the day-to-day demands of running a business to look ahead. Jason and Makenzie discuss why better questions lead to better strategy, and how defining what you hope to gain from the future of the company can lead to a plan that is both realistic and effective. Through practical insights, they explore how thoughtful strategic direction creates clarity, momentum, and a path forward for both the owner and the organization.